Flights from Chicago to Philipsburg (ORD to SXM)

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US$173

5:40pm - 2:00pm
Tue Jul 22nd 2025

19h 20m
Chicago (ORD) → Lower Prince's Quarter (SXM)

1 Stop

Tue Jul 22nd 2025 Spirit Airlines · NK 1106 Depart at 5:40pm from Chicago (ORD) Fly for 3h 10m Arrive at 9:50pm in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 13h 0m

Wed Jul 23rd 2025 Spirit Airlines · NK 100 Depart at 10:50am from Fort Lauderdale (FLL) Fly for 3h 10m Arrive at 2:00pm in Lower Prince's Quarter (SXM)
US$183

8:09am - 8:12am
Tue Jul 22nd 2025

23h 3m
Chicago (ORD) → Lower Prince's Quarter (SXM)

2 Stops

Tue Jul 22nd 2025 Spirit Airlines · NK 1101 Depart at 8:09am from Chicago (ORD) Fly for 3h 14m Arrive at 12:23pm in Miami (MIA)

Layover in Miami for 7h 2m

Tue Jul 22nd 2025 Arajet · DM 2105 Depart at 7:25pm from Miami (MIA) Fly for 2h 20m Arrive at 9:45pm in Santo Domingo (SDQ)

Layover in Santo Domingo for 9h 0m

Wed Jul 23rd 2025 Arajet · DM 400 Depart at 6:45am from Santo Domingo (SDQ) Fly for 1h 27m Arrive at 8:12am in Lower Prince's Quarter (SXM)
US$186

4:36pm - 2:00pm
Tue Jul 22nd 2025

20h 24m
Chicago (ORD) → Lower Prince's Quarter (SXM)

2 Stops

Tue Jul 22nd 2025 Spirit Airlines · NK 1370 Depart at 4:36pm from Chicago (ORD) Fly for 2h 47m Arrive at 8:23pm in Orlando (MCO)

Layover in Orlando for 10h 27m

Wed Jul 23rd 2025 Spirit Airlines · NK 1638 Depart at 6:50am from Orlando (MCO) Fly for 1h 10m Arrive at 8:00am in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 2h 50m

Wed Jul 23rd 2025 Spirit Airlines · NK 100 Depart at 10:50am from Fort Lauderdale (FLL) Fly for 3h 10m Arrive at 2:00pm in Lower Prince's Quarter (SXM)
US$189

8:09am - 8:12am
Tue Jul 15th 2025

23h 3m
Chicago (ORD) → Lower Prince's Quarter (SXM)

2 Stops

Tue Jul 15th 2025 Spirit Airlines · NK 1101 Depart at 8:09am from Chicago (ORD) Fly for 3h 14m Arrive at 12:23pm in Miami (MIA)

Layover in Miami for 7h 2m

Tue Jul 15th 2025 Arajet · DM 2105 Depart at 7:25pm from Miami (MIA) Fly for 2h 20m Arrive at 9:45pm in Santo Domingo (SDQ)

Layover in Santo Domingo for 9h 0m

Wed Jul 16th 2025 Arajet · DM 400 Depart at 6:45am from Santo Domingo (SDQ) Fly for 1h 27m Arrive at 8:12am in Lower Prince's Quarter (SXM)
US$193

6:23pm - 5:21pm
Sun Jul 20th 2025

21h 58m
Chicago (ORD) → Lower Prince's Quarter (SXM)

1 Stop

Sun Jul 20th 2025 Spirit Airlines · NK 1635 Depart at 6:23pm from Chicago (ORD) Fly for 4h 43m Arrive at 12:06am in San Juan (SJU)

Layover in San Juan for 16h 12m

Mon Jul 21st 2025 Frontier Airlines · F9 244 Depart at 4:18pm from San Juan (SJU) Fly for 1h 3m Arrive at 5:21pm in Lower Prince's Quarter (SXM)
US$193

6:23pm - 5:21pm
Sun Jul 27th 2025

21h 58m
Chicago (ORD) → Lower Prince's Quarter (SXM)

1 Stop

Sun Jul 27th 2025 Spirit Airlines · NK 1635 Depart at 6:23pm from Chicago (ORD) Fly for 4h 43m Arrive at 12:06am in San Juan (SJU)

Layover in San Juan for 16h 12m

Mon Jul 28th 2025 Frontier Airlines · F9 244 Depart at 4:18pm from San Juan (SJU) Fly for 1h 3m Arrive at 5:21pm in Lower Prince's Quarter (SXM)
US$196

5:40pm - 2:00pm
Tue Jul 15th 2025

19h 20m
Chicago (ORD) → Lower Prince's Quarter (SXM)

1 Stop

Tue Jul 15th 2025 Spirit Airlines · NK 1106 Depart at 5:40pm from Chicago (ORD) Fly for 3h 10m Arrive at 9:50pm in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 13h 0m

Wed Jul 16th 2025 Spirit Airlines · NK 100 Depart at 10:50am from Fort Lauderdale (FLL) Fly for 3h 10m Arrive at 2:00pm in Lower Prince's Quarter (SXM)
US$202

5:01am - 5:21pm
Sat Jul 19th 2025

11h 20m
Chicago (ORD) → Lower Prince's Quarter (SXM)

2 Stops

Sat Jul 19th 2025 Frontier Airlines · F9 1596 Depart at 5:01am from Chicago (ORD) Fly for 2h 11m Arrive at 8:12am in Atlanta (ATL)

Layover in Atlanta for 2h 13m

Sat Jul 19th 2025 Frontier Airlines · F9 2082 Depart at 10:25am from Atlanta (ATL) Fly for 3h 53m Arrive at 2:18pm in San Juan (SJU)

Layover in San Juan for 2h 0m

Sat Jul 19th 2025 Frontier Airlines · F9 244 Depart at 4:18pm from San Juan (SJU) Fly for 1h 3m Arrive at 5:21pm in Lower Prince's Quarter (SXM)
US$204

6:23pm - 5:21pm
Fri Jul 25th 2025

21h 58m
Chicago (ORD) → Lower Prince's Quarter (SXM)

1 Stop

Fri Jul 25th 2025 Spirit Airlines · NK 1635 Depart at 6:23pm from Chicago (ORD) Fly for 4h 43m Arrive at 12:06am in San Juan (SJU)

Layover in San Juan for 16h 12m

Sat Jul 26th 2025 Frontier Airlines · F9 244 Depart at 4:18pm from San Juan (SJU) Fly for 1h 3m Arrive at 5:21pm in Lower Prince's Quarter (SXM)
US$215

6:23pm - 5:21pm
Sun Jul 13th 2025

21h 58m
Chicago (ORD) → Lower Prince's Quarter (SXM)

1 Stop

Sun Jul 13th 2025 Spirit Airlines · NK 1635 Depart at 6:23pm from Chicago (ORD) Fly for 4h 43m Arrive at 12:06am in San Juan (SJU)

Layover in San Juan for 16h 12m

Mon Jul 14th 2025 Frontier Airlines · F9 244 Depart at 4:18pm from San Juan (SJU) Fly for 1h 3m Arrive at 5:21pm in Lower Prince's Quarter (SXM)
US$217

6:23pm - 5:21pm
Thu Jul 24th 2025

21h 58m
Chicago (ORD) → Lower Prince's Quarter (SXM)

1 Stop

Thu Jul 24th 2025 Spirit Airlines · NK 1635 Depart at 6:23pm from Chicago (ORD) Fly for 4h 43m Arrive at 12:06am in San Juan (SJU)

Layover in San Juan for 16h 12m

Fri Jul 25th 2025 Frontier Airlines · F9 244 Depart at 4:18pm from San Juan (SJU) Fly for 1h 3m Arrive at 5:21pm in Lower Prince's Quarter (SXM)
US$222

4:36pm - 2:00pm
Tue Jul 15th 2025

20h 24m
Chicago (ORD) → Lower Prince's Quarter (SXM)

2 Stops

Tue Jul 15th 2025 Spirit Airlines · NK 1370 Depart at 4:36pm from Chicago (ORD) Fly for 2h 47m Arrive at 8:23pm in Orlando (MCO)

Layover in Orlando for 10h 27m

Wed Jul 16th 2025 Spirit Airlines · NK 1638 Depart at 6:50am from Orlando (MCO) Fly for 1h 10m Arrive at 8:00am in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 2h 50m

Wed Jul 16th 2025 Spirit Airlines · NK 100 Depart at 10:50am from Fort Lauderdale (FLL) Fly for 3h 10m Arrive at 2:00pm in Lower Prince's Quarter (SXM)
US$222

4:36pm - 2:00pm
Sun Jul 13th 2025

20h 24m
Chicago (ORD) → Lower Prince's Quarter (SXM)

2 Stops

Sun Jul 13th 2025 Spirit Airlines · NK 1370 Depart at 4:36pm from Chicago (ORD) Fly for 2h 47m Arrive at 8:23pm in Orlando (MCO)

Layover in Orlando for 10h 27m

Mon Jul 14th 2025 Spirit Airlines · NK 1638 Depart at 6:50am from Orlando (MCO) Fly for 1h 10m Arrive at 8:00am in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 2h 50m

Mon Jul 14th 2025 Spirit Airlines · NK 100 Depart at 10:50am from Fort Lauderdale (FLL) Fly for 3h 10m Arrive at 2:00pm in Lower Prince's Quarter (SXM)
US$224

5:40pm - 2:00pm
Sun Jul 20th 2025

19h 20m
Chicago (ORD) → Lower Prince's Quarter (SXM)

1 Stop

Sun Jul 20th 2025 Spirit Airlines · NK 1106 Depart at 5:40pm from Chicago (ORD) Fly for 3h 10m Arrive at 9:50pm in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 13h 0m

Mon Jul 21st 2025 Spirit Airlines · NK 100 Depart at 10:50am from Fort Lauderdale (FLL) Fly for 3h 10m Arrive at 2:00pm in Lower Prince's Quarter (SXM)
US$224

5:40pm - 2:00pm
Thu Jul 17th 2025

19h 20m
Chicago (ORD) → Lower Prince's Quarter (SXM)

1 Stop

Thu Jul 17th 2025 Spirit Airlines · NK 1106 Depart at 5:40pm from Chicago (ORD) Fly for 3h 10m Arrive at 9:50pm in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 13h 0m

Fri Jul 18th 2025 Spirit Airlines · NK 100 Depart at 10:50am from Fort Lauderdale (FLL) Fly for 3h 10m Arrive at 2:00pm in Lower Prince's Quarter (SXM)
US$224

5:40pm - 2:00pm
Fri Jul 18th 2025

19h 20m
Chicago (ORD) → Lower Prince's Quarter (SXM)

1 Stop

Fri Jul 18th 2025 Spirit Airlines · NK 1106 Depart at 5:40pm from Chicago (ORD) Fly for 3h 10m Arrive at 9:50pm in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 13h 0m

Sat Jul 19th 2025 Spirit Airlines · NK 100 Depart at 10:50am from Fort Lauderdale (FLL) Fly for 3h 10m Arrive at 2:00pm in Lower Prince's Quarter (SXM)
US$224

5:40pm - 2:00pm
Fri Jul 25th 2025

19h 20m
Chicago (ORD) → Lower Prince's Quarter (SXM)

1 Stop

Fri Jul 25th 2025 Spirit Airlines · NK 1106 Depart at 5:40pm from Chicago (ORD) Fly for 3h 10m Arrive at 9:50pm in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 13h 0m

Sat Jul 26th 2025 Spirit Airlines · NK 100 Depart at 10:50am from Fort Lauderdale (FLL) Fly for 3h 10m Arrive at 2:00pm in Lower Prince's Quarter (SXM)
US$224

7:45am - 2:00pm
Sun Jul 27th 2025

29h 15m
Chicago (ORD) → Lower Prince's Quarter (SXM)

2 Stops

Sun Jul 27th 2025 Frontier Airlines · F9 4064 Depart at 7:45am from Chicago (ORD) Fly for 2h 6m Arrive at 10:51am in Washington, D.C. (BWI)

Layover in Washington, D.C. for 19h 34m

Mon Jul 28th 2025 Spirit Airlines · NK 1042 Depart at 6:25am from Washington, D.C. (BWI) Fly for 2h 36m Arrive at 9:01am in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 1h 49m

Mon Jul 28th 2025 Spirit Airlines · NK 100 Depart at 10:50am from Fort Lauderdale (FLL) Fly for 3h 10m Arrive at 2:00pm in Lower Prince's Quarter (SXM)
US$225

5:51am - 8:12am
Thu Jul 17th 2025

25h 21m
Chicago (ORD) → Lower Prince's Quarter (SXM)

3 Stops

Thu Jul 17th 2025 Spirit Airlines · NK 1176 Depart at 5:51am from Chicago (ORD) Fly for 2h 9m Arrive at 9:00am in New York (LGA)

Layover in New York for 0h 55m

Thu Jul 17th 2025 Spirit Airlines · NK 1177 Depart at 9:55am from New York (LGA) Fly for 3h 17m Arrive at 1:12pm in Miami (MIA)

Layover in Miami for 6h 13m

Thu Jul 17th 2025 Arajet · DM 2105 Depart at 7:25pm from Miami (MIA) Fly for 2h 20m Arrive at 9:45pm in Santo Domingo (SDQ)

Layover in Santo Domingo for 9h 0m

Fri Jul 18th 2025 Arajet · DM 400 Depart at 6:45am from Santo Domingo (SDQ) Fly for 1h 27m Arrive at 8:12am in Lower Prince's Quarter (SXM)
US$226

6:40am - 5:21pm
Sat Jul 19th 2025

9h 41m
Chicago (ORD) → Lower Prince's Quarter (SXM)

1 Stop

Sat Jul 19th 2025 Spirit Airlines · NK 1877 Depart at 6:40am from Chicago (ORD) Fly for 4h 43m Arrive at 12:23pm in San Juan (SJU)

Layover in San Juan for 3h 55m

Sat Jul 19th 2025 Frontier Airlines · F9 244 Depart at 4:18pm from San Juan (SJU) Fly for 1h 3m Arrive at 5:21pm in Lower Prince's Quarter (SXM)
US$226

6:23pm - 5:21pm
Thu Jul 17th 2025

21h 58m
Chicago (ORD) → Lower Prince's Quarter (SXM)

1 Stop

Thu Jul 17th 2025 Spirit Airlines · NK 1635 Depart at 6:23pm from Chicago (ORD) Fly for 4h 43m Arrive at 12:06am in San Juan (SJU)

Layover in San Juan for 16h 12m

Fri Jul 18th 2025 Frontier Airlines · F9 244 Depart at 4:18pm from San Juan (SJU) Fly for 1h 3m Arrive at 5:21pm in Lower Prince's Quarter (SXM)
US$227

4:43pm - 2:00pm
Sun Jul 13th 2025

20h 17m
Chicago (ORD) → Lower Prince's Quarter (SXM)

2 Stops

Sun Jul 13th 2025 Frontier Airlines · F9 2792 Depart at 4:43pm from Chicago (ORD) Fly for 3h 2m Arrive at 8:45pm in Orlando (MCO)

Layover in Orlando for 10h 5m

Mon Jul 14th 2025 Spirit Airlines · NK 1638 Depart at 6:50am from Orlando (MCO) Fly for 1h 10m Arrive at 8:00am in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 2h 50m

Mon Jul 14th 2025 Spirit Airlines · NK 100 Depart at 10:50am from Fort Lauderdale (FLL) Fly for 3h 10m Arrive at 2:00pm in Lower Prince's Quarter (SXM)
US$228

8:09am - 8:12am
Thu Jul 17th 2025

23h 3m
Chicago (ORD) → Lower Prince's Quarter (SXM)

2 Stops

Thu Jul 17th 2025 Spirit Airlines · NK 1101 Depart at 8:09am from Chicago (ORD) Fly for 3h 14m Arrive at 12:23pm in Miami (MIA)

Layover in Miami for 7h 2m

Thu Jul 17th 2025 Arajet · DM 2105 Depart at 7:25pm from Miami (MIA) Fly for 2h 20m Arrive at 9:45pm in Santo Domingo (SDQ)

Layover in Santo Domingo for 9h 0m

Fri Jul 18th 2025 Arajet · DM 400 Depart at 6:45am from Santo Domingo (SDQ) Fly for 1h 27m Arrive at 8:12am in Lower Prince's Quarter (SXM)
US$232

4:26pm - 2:00pm
Fri Jul 25th 2025

20h 34m
Chicago (ORD) → Lower Prince's Quarter (SXM)

2 Stops

Fri Jul 25th 2025 Frontier Airlines · F9 2792 Depart at 4:26pm from Chicago (ORD) Fly for 3h 2m Arrive at 8:28pm in Orlando (MCO)

Layover in Orlando for 10h 22m

Sat Jul 26th 2025 Spirit Airlines · NK 1638 Depart at 6:50am from Orlando (MCO) Fly for 1h 10m Arrive at 8:00am in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 2h 50m

Sat Jul 26th 2025 Spirit Airlines · NK 100 Depart at 10:50am from Fort Lauderdale (FLL) Fly for 3h 10m Arrive at 2:00pm in Lower Prince's Quarter (SXM)
US$233

4:36pm - 2:00pm
Thu Jul 17th 2025

20h 24m
Chicago (ORD) → Lower Prince's Quarter (SXM)

2 Stops

Thu Jul 17th 2025 Spirit Airlines · NK 1370 Depart at 4:36pm from Chicago (ORD) Fly for 2h 47m Arrive at 8:23pm in Orlando (MCO)

Layover in Orlando for 10h 27m

Fri Jul 18th 2025 Spirit Airlines · NK 1638 Depart at 6:50am from Orlando (MCO) Fly for 1h 10m Arrive at 8:00am in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 2h 50m

Fri Jul 18th 2025 Spirit Airlines · NK 100 Depart at 10:50am from Fort Lauderdale (FLL) Fly for 3h 10m Arrive at 2:00pm in Lower Prince's Quarter (SXM)
US$233

4:36pm - 2:00pm
Fri Jul 18th 2025

20h 24m
Chicago (ORD) → Lower Prince's Quarter (SXM)

2 Stops

Fri Jul 18th 2025 Spirit Airlines · NK 1370 Depart at 4:36pm from Chicago (ORD) Fly for 2h 47m Arrive at 8:23pm in Orlando (MCO)

Layover in Orlando for 10h 27m

Sat Jul 19th 2025 Spirit Airlines · NK 1638 Depart at 6:50am from Orlando (MCO) Fly for 1h 10m Arrive at 8:00am in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 2h 50m

Sat Jul 19th 2025 Spirit Airlines · NK 100 Depart at 10:50am from Fort Lauderdale (FLL) Fly for 3h 10m Arrive at 2:00pm in Lower Prince's Quarter (SXM)
US$237

6:40am - 5:21pm
Sat Jul 26th 2025

9h 41m
Chicago (ORD) → Lower Prince's Quarter (SXM)

1 Stop

Sat Jul 26th 2025 Spirit Airlines · NK 1877 Depart at 6:40am from Chicago (ORD) Fly for 4h 43m Arrive at 12:23pm in San Juan (SJU)

Layover in San Juan for 3h 55m

Sat Jul 26th 2025 Frontier Airlines · F9 244 Depart at 4:18pm from San Juan (SJU) Fly for 1h 3m Arrive at 5:21pm in Lower Prince's Quarter (SXM)
US$244

4:43pm - 2:00pm
Sun Jul 27th 2025

20h 17m
Chicago (ORD) → Lower Prince's Quarter (SXM)

2 Stops

Sun Jul 27th 2025 Frontier Airlines · F9 2792 Depart at 4:43pm from Chicago (ORD) Fly for 3h 2m Arrive at 8:45pm in Orlando (MCO)

Layover in Orlando for 10h 5m

Mon Jul 28th 2025 Spirit Airlines · NK 1638 Depart at 6:50am from Orlando (MCO) Fly for 1h 10m Arrive at 8:00am in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 2h 50m

Mon Jul 28th 2025 Spirit Airlines · NK 100 Depart at 10:50am from Fort Lauderdale (FLL) Fly for 3h 10m Arrive at 2:00pm in Lower Prince's Quarter (SXM)
US$246

4:26pm - 5:21pm
Fri Jul 11th 2025

23h 55m
Chicago (ORD) → Lower Prince's Quarter (SXM)

2 Stops

Fri Jul 11th 2025 Frontier Airlines · F9 2792 Depart at 4:26pm from Chicago (ORD) Fly for 3h 2m Arrive at 8:28pm in Orlando (MCO)

Layover in Orlando for 0h 58m

Fri Jul 11th 2025 Frontier Airlines · F9 1746 Depart at 9:26pm from Orlando (MCO) Fly for 3h 6m Arrive at 12:32am in San Juan (SJU)

Layover in San Juan for 15h 46m

Sat Jul 12th 2025 Frontier Airlines · F9 244 Depart at 4:18pm from San Juan (SJU) Fly for 1h 3m Arrive at 5:21pm in Lower Prince's Quarter (SXM)
US$250

5:01am - 5:21pm
Mon Jul 28th 2025

11h 20m
Chicago (ORD) → Lower Prince's Quarter (SXM)

2 Stops

Mon Jul 28th 2025 Frontier Airlines · F9 1596 Depart at 5:01am from Chicago (ORD) Fly for 2h 11m Arrive at 8:12am in Atlanta (ATL)

Layover in Atlanta for 2h 13m

Mon Jul 28th 2025 Frontier Airlines · F9 2082 Depart at 10:25am from Atlanta (ATL) Fly for 3h 53m Arrive at 2:18pm in San Juan (SJU)

Layover in San Juan for 2h 0m

Mon Jul 28th 2025 Frontier Airlines · F9 244 Depart at 4:18pm from San Juan (SJU) Fly for 1h 3m Arrive at 5:21pm in Lower Prince's Quarter (SXM)
US$251

5:01am - 5:21pm
Fri Jul 18th 2025

11h 20m
Chicago (ORD) → Lower Prince's Quarter (SXM)

2 Stops

Fri Jul 18th 2025 Frontier Airlines · F9 1596 Depart at 5:01am from Chicago (ORD) Fly for 2h 11m Arrive at 8:12am in Atlanta (ATL)

Layover in Atlanta for 2h 13m

Fri Jul 18th 2025 Frontier Airlines · F9 2082 Depart at 10:25am from Atlanta (ATL) Fly for 3h 53m Arrive at 2:18pm in San Juan (SJU)

Layover in San Juan for 2h 0m

Fri Jul 18th 2025 Frontier Airlines · F9 244 Depart at 4:18pm from San Juan (SJU) Fly for 1h 3m Arrive at 5:21pm in Lower Prince's Quarter (SXM)
US$257

5:40pm - 2:00pm
Thu Jul 24th 2025

19h 20m
Chicago (ORD) → Lower Prince's Quarter (SXM)

1 Stop

Thu Jul 24th 2025 Spirit Airlines · NK 1106 Depart at 5:40pm from Chicago (ORD) Fly for 3h 10m Arrive at 9:50pm in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 13h 0m

Fri Jul 25th 2025 Spirit Airlines · NK 100 Depart at 10:50am from Fort Lauderdale (FLL) Fly for 3h 10m Arrive at 2:00pm in Lower Prince's Quarter (SXM)
US$258

11:32am - 5:21pm
Fri Jul 4th 2025

28h 49m
Chicago (ORD) → Lower Prince's Quarter (SXM)

2 Stops

Fri Jul 4th 2025 Frontier Airlines · F9 3352 Depart at 11:32am from Chicago (ORD) Fly for 2h 4m Arrive at 2:36pm in Raleigh (RDU)

Layover in Raleigh for 6h 39m

Fri Jul 4th 2025 Frontier Airlines · F9 1226 Depart at 9:15pm from Raleigh (RDU) Fly for 3h 25m Arrive at 12:40am in San Juan (SJU)

Layover in San Juan for 15h 38m

Sat Jul 5th 2025 Frontier Airlines · F9 244 Depart at 4:18pm from San Juan (SJU) Fly for 1h 3m Arrive at 5:21pm in Lower Prince's Quarter (SXM)
US$265

9:10pm - 2:00pm
Thu Jul 17th 2025

15h 50m
Chicago (ORD) → Lower Prince's Quarter (SXM)

2 Stops

Thu Jul 17th 2025 Spirit Airlines · NK 1180 Depart at 9:10pm from Chicago (ORD) Fly for 2h 49m Arrive at 11:59pm in Houston (IAH)

Layover in Houston for 5h 1m

Fri Jul 18th 2025 Spirit Airlines · NK 1498 Depart at 5:00am from Houston (IAH) Fly for 2h 24m Arrive at 8:24am in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 2h 26m

Fri Jul 18th 2025 Spirit Airlines · NK 100 Depart at 10:50am from Fort Lauderdale (FLL) Fly for 3h 10m Arrive at 2:00pm in Lower Prince's Quarter (SXM)
US$265

9:10pm - 2:00pm
Fri Jul 18th 2025

15h 50m
Chicago (ORD) → Lower Prince's Quarter (SXM)

2 Stops

Fri Jul 18th 2025 Spirit Airlines · NK 1180 Depart at 9:10pm from Chicago (ORD) Fly for 2h 49m Arrive at 11:59pm in Houston (IAH)

Layover in Houston for 5h 1m

Sat Jul 19th 2025 Spirit Airlines · NK 1498 Depart at 5:00am from Houston (IAH) Fly for 2h 24m Arrive at 8:24am in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 2h 26m

Sat Jul 19th 2025 Spirit Airlines · NK 100 Depart at 10:50am from Fort Lauderdale (FLL) Fly for 3h 10m Arrive at 2:00pm in Lower Prince's Quarter (SXM)
US$265

6:23pm - 5:21pm
Fri Jul 11th 2025

21h 58m
Chicago (ORD) → Lower Prince's Quarter (SXM)

1 Stop

Fri Jul 11th 2025 Spirit Airlines · NK 1635 Depart at 6:23pm from Chicago (ORD) Fly for 4h 43m Arrive at 12:06am in San Juan (SJU)

Layover in San Juan for 16h 12m

Sat Jul 12th 2025 Frontier Airlines · F9 244 Depart at 4:18pm from San Juan (SJU) Fly for 1h 3m Arrive at 5:21pm in Lower Prince's Quarter (SXM)
US$265

6:23pm - 5:21pm
Thu Jul 10th 2025

21h 58m
Chicago (ORD) → Lower Prince's Quarter (SXM)

1 Stop

Thu Jul 10th 2025 Spirit Airlines · NK 1635 Depart at 6:23pm from Chicago (ORD) Fly for 4h 43m Arrive at 12:06am in San Juan (SJU)

Layover in San Juan for 16h 12m

Fri Jul 11th 2025 Frontier Airlines · F9 244 Depart at 4:18pm from San Juan (SJU) Fly for 1h 3m Arrive at 5:21pm in Lower Prince's Quarter (SXM)
US$270

5:01am - 5:21pm
Mon Jul 14th 2025

11h 20m
Chicago (ORD) → Lower Prince's Quarter (SXM)

2 Stops

Mon Jul 14th 2025 Frontier Airlines · F9 1596 Depart at 5:01am from Chicago (ORD) Fly for 2h 11m Arrive at 8:12am in Atlanta (ATL)

Layover in Atlanta for 2h 13m

Mon Jul 14th 2025 Frontier Airlines · F9 2082 Depart at 10:25am from Atlanta (ATL) Fly for 3h 53m Arrive at 2:18pm in San Juan (SJU)

Layover in San Juan for 2h 0m

Mon Jul 14th 2025 Frontier Airlines · F9 244 Depart at 4:18pm from San Juan (SJU) Fly for 1h 3m Arrive at 5:21pm in Lower Prince's Quarter (SXM)
US$271

3:35pm - 1:15pm
Sat Jul 12th 2025

20h 40m
Chicago (ORD) → Lower Prince's Quarter (SXM)

2 Stops

Sat Jul 12th 2025 Air Canada · AC 8964 Depart at 3:35pm from Chicago (ORD) Fly for 2h 15m Arrive at 6:50pm in Montreal (YUL)

Layover in Montreal for 1h 25m

Sat Jul 12th 2025 Air Canada · AC 427 Depart at 8:15pm from Montreal (YUL) Fly for 1h 29m Arrive at 9:44pm in Toronto (YYZ)

Layover in Toronto for 10h 46m

Sun Jul 13th 2025 WestJet · WS 2276 Depart at 8:30am from Toronto (YYZ) Fly for 4h 45m Arrive at 1:15pm in Lower Prince's Quarter (SXM)
US$271

10:00am - 7:30pm
Sat Jul 26th 2025

32h 30m
Chicago (ORD) → Lower Prince's Quarter (SXM)

3 Stops

Sat Jul 26th 2025 Spirit Airlines · NK 1113 Depart at 10:00am from Chicago (ORD) Fly for 2h 44m Arrive at 1:44pm in Orlando (MCO)

Layover in Orlando for 5h 29m

Sat Jul 26th 2025 Spirit Airlines · NK 1729 Depart at 7:13pm from Orlando (MCO) Fly for 2h 47m Arrive at 10:00pm in New York (EWR)

Layover in New York for 14h 0m

Sun Jul 27th 2025 Arajet · DM 2311 Depart at 12:00pm from New York (EWR) Fly for 4h 30m Arrive at 4:30pm in Santo Domingo (SDQ)

Layover in Santo Domingo for 1h 33m

Sun Jul 27th 2025 Arajet · DM 400 Depart at 6:03pm from Santo Domingo (SDQ) Fly for 1h 27m Arrive at 7:30pm in Lower Prince's Quarter (SXM)
US$278

9:10pm - 2:00pm
Tue Jul 22nd 2025

15h 50m
Chicago (ORD) → Lower Prince's Quarter (SXM)

2 Stops

Tue Jul 22nd 2025 Spirit Airlines · NK 1180 Depart at 9:10pm from Chicago (ORD) Fly for 2h 49m Arrive at 11:59pm in Houston (IAH)

Layover in Houston for 5h 1m

Wed Jul 23rd 2025 Spirit Airlines · NK 1498 Depart at 5:00am from Houston (IAH) Fly for 2h 24m Arrive at 8:24am in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 2h 26m

Wed Jul 23rd 2025 Spirit Airlines · NK 100 Depart at 10:50am from Fort Lauderdale (FLL) Fly for 3h 10m Arrive at 2:00pm in Lower Prince's Quarter (SXM)
US$283

9:10pm - 2:00pm
Tue Jul 15th 2025

15h 50m
Chicago (ORD) → Lower Prince's Quarter (SXM)

2 Stops

Tue Jul 15th 2025 Spirit Airlines · NK 1180 Depart at 9:10pm from Chicago (ORD) Fly for 2h 49m Arrive at 11:59pm in Houston (IAH)

Layover in Houston for 5h 1m

Wed Jul 16th 2025 Spirit Airlines · NK 1498 Depart at 5:00am from Houston (IAH) Fly for 2h 24m Arrive at 8:24am in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 2h 26m

Wed Jul 16th 2025 Spirit Airlines · NK 100 Depart at 10:50am from Fort Lauderdale (FLL) Fly for 3h 10m Arrive at 2:00pm in Lower Prince's Quarter (SXM)
US$283

9:10pm - 2:00pm
Fri Jul 25th 2025

15h 50m
Chicago (ORD) → Lower Prince's Quarter (SXM)

2 Stops

Fri Jul 25th 2025 Spirit Airlines · NK 1180 Depart at 9:10pm from Chicago (ORD) Fly for 2h 49m Arrive at 11:59pm in Houston (IAH)

Layover in Houston for 5h 1m

Sat Jul 26th 2025 Spirit Airlines · NK 1498 Depart at 5:00am from Houston (IAH) Fly for 2h 24m Arrive at 8:24am in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 2h 26m

Sat Jul 26th 2025 Spirit Airlines · NK 100 Depart at 10:50am from Fort Lauderdale (FLL) Fly for 3h 10m Arrive at 2:00pm in Lower Prince's Quarter (SXM)
US$296

5:40pm - 2:00pm
Thu Jul 10th 2025

19h 20m
Chicago (ORD) → Lower Prince's Quarter (SXM)

1 Stop

Thu Jul 10th 2025 Spirit Airlines · NK 1106 Depart at 5:40pm from Chicago (ORD) Fly for 3h 10m Arrive at 9:50pm in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 13h 0m

Fri Jul 11th 2025 Spirit Airlines · NK 100 Depart at 10:50am from Fort Lauderdale (FLL) Fly for 3h 10m Arrive at 2:00pm in Lower Prince's Quarter (SXM)
US$296

3:35pm - 1:15pm
Sat Jul 26th 2025

20h 40m
Chicago (ORD) → Lower Prince's Quarter (SXM)

2 Stops

Sat Jul 26th 2025 Air Canada · AC 8964 Depart at 3:35pm from Chicago (ORD) Fly for 2h 15m Arrive at 6:50pm in Montreal (YUL)

Layover in Montreal for 3h 0m

Sat Jul 26th 2025 Air Canada · AC 429 Depart at 9:50pm from Montreal (YUL) Fly for 1h 29m Arrive at 11:19pm in Toronto (YYZ)

Layover in Toronto for 9h 11m

Sun Jul 27th 2025 WestJet · WS 2276 Depart at 8:30am from Toronto (YYZ) Fly for 4h 45m Arrive at 1:15pm in Lower Prince's Quarter (SXM)
US$302

4:36pm - 2:00pm
Fri Jul 11th 2025

20h 24m
Chicago (ORD) → Lower Prince's Quarter (SXM)

2 Stops

Fri Jul 11th 2025 Spirit Airlines · NK 1370 Depart at 4:36pm from Chicago (ORD) Fly for 2h 47m Arrive at 8:23pm in Orlando (MCO)

Layover in Orlando for 10h 27m

Sat Jul 12th 2025 Spirit Airlines · NK 1638 Depart at 6:50am from Orlando (MCO) Fly for 1h 10m Arrive at 8:00am in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 2h 50m

Sat Jul 12th 2025 Spirit Airlines · NK 100 Depart at 10:50am from Fort Lauderdale (FLL) Fly for 3h 10m Arrive at 2:00pm in Lower Prince's Quarter (SXM)
US$304

6:40am - 5:21pm
Sat Jul 12th 2025

9h 41m
Chicago (ORD) → Lower Prince's Quarter (SXM)

1 Stop

Sat Jul 12th 2025 Spirit Airlines · NK 1877 Depart at 6:40am from Chicago (ORD) Fly for 4h 43m Arrive at 12:23pm in San Juan (SJU)

Layover in San Juan for 3h 55m

Sat Jul 12th 2025 Frontier Airlines · F9 244 Depart at 4:18pm from San Juan (SJU) Fly for 1h 3m Arrive at 5:21pm in Lower Prince's Quarter (SXM)
US$304

8:09am - 8:12am
Thu Jul 10th 2025

23h 3m
Chicago (ORD) → Lower Prince's Quarter (SXM)

2 Stops

Thu Jul 10th 2025 Spirit Airlines · NK 1101 Depart at 8:09am from Chicago (ORD) Fly for 3h 14m Arrive at 12:23pm in Miami (MIA)

Layover in Miami for 7h 2m

Thu Jul 10th 2025 Arajet · DM 2105 Depart at 7:25pm from Miami (MIA) Fly for 2h 20m Arrive at 9:45pm in Santo Domingo (SDQ)

Layover in Santo Domingo for 9h 0m

Fri Jul 11th 2025 Arajet · DM 400 Depart at 6:45am from Santo Domingo (SDQ) Fly for 1h 27m Arrive at 8:12am in Lower Prince's Quarter (SXM)
US$308

5:01am - 8:12am
Tue Jul 8th 2025

26h 11m
Chicago (ORD) → Lower Prince's Quarter (SXM)

3 Stops

Tue Jul 8th 2025 Frontier Airlines · F9 1596 Depart at 5:01am from Chicago (ORD) Fly for 2h 11m Arrive at 8:12am in Atlanta (ATL)

Layover in Atlanta for 1h 9m

Tue Jul 8th 2025 Frontier Airlines · F9 4406 Depart at 9:21am from Atlanta (ATL) Fly for 1h 59m Arrive at 11:20am in Miami (MIA)

Layover in Miami for 8h 5m

Tue Jul 8th 2025 Arajet · DM 2105 Depart at 7:25pm from Miami (MIA) Fly for 2h 20m Arrive at 9:45pm in Santo Domingo (SDQ)

Layover in Santo Domingo for 9h 0m

Wed Jul 9th 2025 Arajet · DM 400 Depart at 6:45am from Santo Domingo (SDQ) Fly for 1h 27m Arrive at 8:12am in Lower Prince's Quarter (SXM)
US$311

12:03pm - 2:00pm
Tue Jul 8th 2025

24h 57m
Chicago (ORD) → Lower Prince's Quarter (SXM)

2 Stops

Tue Jul 8th 2025 Spirit Airlines · NK 2535 Depart at 12:03pm from Chicago (ORD) Fly for 4h 44m Arrive at 5:47pm in San Juan (SJU)

Layover in San Juan for 2h 37m

Tue Jul 8th 2025 Spirit Airlines · NK 2222 Depart at 8:24pm from San Juan (SJU) Fly for 2h 48m Arrive at 11:12pm in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 11h 38m

Wed Jul 9th 2025 Spirit Airlines · NK 100 Depart at 10:50am from Fort Lauderdale (FLL) Fly for 3h 10m Arrive at 2:00pm in Lower Prince's Quarter (SXM)
US$313

5:40pm - 4:30pm
Wed Jul 23rd 2025

21h 50m
Chicago (ORD) → Lower Prince's Quarter (SXM)

2 Stops

Wed Jul 23rd 2025 Spirit Airlines · NK 1106 Depart at 5:40pm from Chicago (ORD) Fly for 3h 10m Arrive at 9:50pm in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 9h 50m

Thu Jul 24th 2025 Spirit Airlines · NK 145 Depart at 7:40am from Fort Lauderdale (FLL) Fly for 2h 10m Arrive at 9:50am in Santo Domingo (SDQ)

Layover in Santo Domingo for 5h 13m

Thu Jul 24th 2025 Arajet · DM 400 Depart at 3:03pm from Santo Domingo (SDQ) Fly for 1h 27m Arrive at 4:30pm in Lower Prince's Quarter (SXM)
US$318

5:40pm - 2:00pm
Fri Jul 11th 2025

19h 20m
Chicago (ORD) → Lower Prince's Quarter (SXM)

1 Stop

Fri Jul 11th 2025 Spirit Airlines · NK 1106 Depart at 5:40pm from Chicago (ORD) Fly for 3h 10m Arrive at 9:50pm in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 13h 0m

Sat Jul 12th 2025 Spirit Airlines · NK 100 Depart at 10:50am from Fort Lauderdale (FLL) Fly for 3h 10m Arrive at 2:00pm in Lower Prince's Quarter (SXM)
US$318

4:45pm - 2:00pm
Tue Jul 8th 2025

20h 15m
Chicago (ORD) → Lower Prince's Quarter (SXM)

1 Stop

Tue Jul 8th 2025 Spirit Airlines · NK 3187 Depart at 4:45pm from Chicago (ORD) Fly for 3h 10m Arrive at 8:55pm in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 13h 55m

Wed Jul 9th 2025 Spirit Airlines · NK 100 Depart at 10:50am from Fort Lauderdale (FLL) Fly for 3h 10m Arrive at 2:00pm in Lower Prince's Quarter (SXM)
US$318

4:37pm - 5:21pm
Sun Jul 6th 2025

23h 44m
Chicago (ORD) → Lower Prince's Quarter (SXM)

2 Stops

Sun Jul 6th 2025 Frontier Airlines · F9 2792 Depart at 4:37pm from Chicago (ORD) Fly for 3h 2m Arrive at 8:39pm in Orlando (MCO)

Layover in Orlando for 3h 1m

Sun Jul 6th 2025 Frontier Airlines · F9 4726 Depart at 11:40pm from Orlando (MCO) Fly for 2h 59m Arrive at 2:39am in San Juan (SJU)

Layover in San Juan for 13h 39m

Mon Jul 7th 2025 Frontier Airlines · F9 244 Depart at 4:18pm from San Juan (SJU) Fly for 1h 3m Arrive at 5:21pm in Lower Prince's Quarter (SXM)
US$318

5:01am - 8:12am
Tue Jul 1st 2025

26h 11m
Chicago (ORD) → Lower Prince's Quarter (SXM)

3 Stops

Tue Jul 1st 2025 Frontier Airlines · F9 1596 Depart at 5:01am from Chicago (ORD) Fly for 2h 6m Arrive at 8:07am in Atlanta (ATL)

Layover in Atlanta for 7h 0m

Tue Jul 1st 2025 Frontier Airlines · F9 3442 Depart at 3:07pm from Atlanta (ATL) Fly for 2h 8m Arrive at 5:15pm in Miami (MIA)

Layover in Miami for 2h 10m

Tue Jul 1st 2025 Arajet · DM 2105 Depart at 7:25pm from Miami (MIA) Fly for 2h 20m Arrive at 9:45pm in Santo Domingo (SDQ)

Layover in Santo Domingo for 9h 0m

Wed Jul 2nd 2025 Arajet · DM 400 Depart at 6:45am from Santo Domingo (SDQ) Fly for 1h 27m Arrive at 8:12am in Lower Prince's Quarter (SXM)
US$323

7:49pm - 2:00pm
Tue Jul 8th 2025

17h 11m
Chicago (ORD) → Lower Prince's Quarter (SXM)

2 Stops

Tue Jul 8th 2025 Spirit Airlines · NK 2191 Depart at 7:49pm from Chicago (ORD) Fly for 2h 48m Arrive at 11:37pm in Orlando (MCO)

Layover in Orlando for 7h 13m

Wed Jul 9th 2025 Spirit Airlines · NK 1638 Depart at 6:50am from Orlando (MCO) Fly for 1h 10m Arrive at 8:00am in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 2h 50m

Wed Jul 9th 2025 Spirit Airlines · NK 100 Depart at 10:50am from Fort Lauderdale (FLL) Fly for 3h 10m Arrive at 2:00pm in Lower Prince's Quarter (SXM)
US$326

9:10pm - 2:00pm
Thu Jul 24th 2025

15h 50m
Chicago (ORD) → Lower Prince's Quarter (SXM)

2 Stops

Thu Jul 24th 2025 Spirit Airlines · NK 1180 Depart at 9:10pm from Chicago (ORD) Fly for 2h 49m Arrive at 11:59pm in Houston (IAH)

Layover in Houston for 5h 1m

Fri Jul 25th 2025 Spirit Airlines · NK 1498 Depart at 5:00am from Houston (IAH) Fly for 2h 24m Arrive at 8:24am in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 2h 26m

Fri Jul 25th 2025 Spirit Airlines · NK 100 Depart at 10:50am from Fort Lauderdale (FLL) Fly for 3h 10m Arrive at 2:00pm in Lower Prince's Quarter (SXM)
US$326

7:15am - 1:15pm
Wed Jul 9th 2025

29h 0m
Chicago (ORD) → Lower Prince's Quarter (SXM)

2 Stops

Wed Jul 9th 2025 Air Canada · AC 4081 Depart at 7:15am from Chicago (ORD) Fly for 2h 25m Arrive at 10:40am in Montreal (YUL)

Layover in Montreal for 1h 20m

Wed Jul 9th 2025 Air Canada · AC 411 Depart at 12:00pm from Montreal (YUL) Fly for 1h 25m Arrive at 1:25pm in Toronto (YYZ)

Layover in Toronto for 19h 5m

Thu Jul 10th 2025 WestJet · WS 2276 Depart at 8:30am from Toronto (YYZ) Fly for 4h 45m Arrive at 1:15pm in Lower Prince's Quarter (SXM)
US$335

5:20pm - 1:15pm
Sat Jul 26th 2025

18h 55m
Chicago (ORD) → Lower Prince's Quarter (SXM)

2 Stops

Sat Jul 26th 2025 WestJet · WS 7319 Depart at 5:20pm from Chicago (ORD) Fly for 1h 27m Arrive at 7:47pm in Detroit (DTW)

Layover in Detroit for 1h 53m

Sat Jul 26th 2025 WestJet · WS 8714 Depart at 9:40pm from Detroit (DTW) Fly for 1h 18m Arrive at 10:58pm in Toronto (YYZ)

Layover in Toronto for 9h 32m

Sun Jul 27th 2025 WestJet · WS 2276 Depart at 8:30am from Toronto (YYZ) Fly for 4h 45m Arrive at 1:15pm in Lower Prince's Quarter (SXM)
US$341

8:17pm - 5:21pm
Fri Jul 4th 2025

20h 4m
Chicago (ORD) → Lower Prince's Quarter (SXM)

2 Stops

Fri Jul 4th 2025 Frontier Airlines · F9 2112 Depart at 8:17pm from Chicago (ORD) Fly for 2h 27m Arrive at 11:44pm in Philadelphia (PHL)

Layover in Philadelphia for 8h 16m

Sat Jul 5th 2025 Frontier Airlines · F9 1016 Depart at 8:00am from Philadelphia (PHL) Fly for 3h 54m Arrive at 11:54am in San Juan (SJU)

Layover in San Juan for 4h 24m

Sat Jul 5th 2025 Frontier Airlines · F9 244 Depart at 4:18pm from San Juan (SJU) Fly for 1h 3m Arrive at 5:21pm in Lower Prince's Quarter (SXM)
US$349

12:03pm - 5:21pm
Fri Jul 4th 2025

28h 18m
Chicago (ORD) → Lower Prince's Quarter (SXM)

1 Stop

Fri Jul 4th 2025 Spirit Airlines · NK 2535 Depart at 12:03pm from Chicago (ORD) Fly for 4h 44m Arrive at 5:47pm in San Juan (SJU)

Layover in San Juan for 22h 31m

Sat Jul 5th 2025 Frontier Airlines · F9 244 Depart at 4:18pm from San Juan (SJU) Fly for 1h 3m Arrive at 5:21pm in Lower Prince's Quarter (SXM)
US$351

5:40pm - 2:00pm
Sun Jul 27th 2025

19h 20m
Chicago (ORD) → Lower Prince's Quarter (SXM)

1 Stop

Sun Jul 27th 2025 Spirit Airlines · NK 1106 Depart at 5:40pm from Chicago (ORD) Fly for 3h 10m Arrive at 9:50pm in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 13h 0m

Mon Jul 28th 2025 Spirit Airlines · NK 100 Depart at 10:50am from Fort Lauderdale (FLL) Fly for 3h 10m Arrive at 2:00pm in Lower Prince's Quarter (SXM)
US$351

5:40pm - 2:00pm
Sun Jul 13th 2025

19h 20m
Chicago (ORD) → Lower Prince's Quarter (SXM)

1 Stop

Sun Jul 13th 2025 Spirit Airlines · NK 1106 Depart at 5:40pm from Chicago (ORD) Fly for 3h 10m Arrive at 9:50pm in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 13h 0m

Mon Jul 14th 2025 Spirit Airlines · NK 100 Depart at 10:50am from Fort Lauderdale (FLL) Fly for 3h 10m Arrive at 2:00pm in Lower Prince's Quarter (SXM)
US$360

9:45pm - 2:00pm
Tue Jul 8th 2025

15h 15m
Chicago (ORD) → Lower Prince's Quarter (SXM)

2 Stops

Tue Jul 8th 2025 Spirit Airlines · NK 2274 Depart at 9:45pm from Chicago (ORD) Fly for 2h 49m Arrive at 12:34am in Houston (IAH)

Layover in Houston for 4h 26m

Wed Jul 9th 2025 Spirit Airlines · NK 1498 Depart at 5:00am from Houston (IAH) Fly for 2h 24m Arrive at 8:24am in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 2h 26m

Wed Jul 9th 2025 Spirit Airlines · NK 100 Depart at 10:50am from Fort Lauderdale (FLL) Fly for 3h 10m Arrive at 2:00pm in Lower Prince's Quarter (SXM)
US$362

3:07pm - 11:24am
Thu Jul 24th 2025

19h 17m
Chicago (ORD) → Lower Prince's Quarter (SXM)

1 Stop

Thu Jul 24th 2025 Copa Airlines · CM 229 Depart at 3:07pm from Chicago (ORD) Fly for 5h 28m Arrive at 8:35pm in Panama (PTY)

Layover in Panama for 10h 43m

Fri Jul 25th 2025 Copa Airlines · CM 134 Depart at 7:18am from Panama (PTY) Fly for 3h 6m Arrive at 11:24am in Lower Prince's Quarter (SXM)
US$364

9:25pm - 12:29pm
Mon Jul 28th 2025

14h 4m
Chicago (ORD) → Lower Prince's Quarter (SXM)

1 Stop

Mon Jul 28th 2025 United Airlines · UA 396 Depart at 9:25pm from Chicago (ORD) Fly for 2h 21m Arrive at 12:46am in New York (EWR)

Layover in New York for 7h 31m

Tue Jul 29th 2025 United Airlines · UA 1629 Depart at 8:17am from New York (EWR) Fly for 4h 12m Arrive at 12:29pm in Lower Prince's Quarter (SXM)
US$366

12:03pm - 5:21pm
Sun Jul 6th 2025

28h 18m
Chicago (ORD) → Lower Prince's Quarter (SXM)

1 Stop

Sun Jul 6th 2025 Spirit Airlines · NK 2535 Depart at 12:03pm from Chicago (ORD) Fly for 4h 44m Arrive at 5:47pm in San Juan (SJU)

Layover in San Juan for 22h 31m

Mon Jul 7th 2025 Frontier Airlines · F9 244 Depart at 4:18pm from San Juan (SJU) Fly for 1h 3m Arrive at 5:21pm in Lower Prince's Quarter (SXM)
US$371

12:03pm - 5:16pm
Thu Jul 3rd 2025

28h 13m
Chicago (ORD) → Lower Prince's Quarter (SXM)

1 Stop

Thu Jul 3rd 2025 Spirit Airlines · NK 2535 Depart at 12:03pm from Chicago (ORD) Fly for 4h 44m Arrive at 5:47pm in San Juan (SJU)

Layover in San Juan for 22h 31m

Fri Jul 4th 2025 Frontier Airlines · F9 244 Depart at 4:18pm from San Juan (SJU) Fly for 0h 58m Arrive at 5:16pm in Lower Prince's Quarter (SXM)
US$376

9:10pm - 2:00pm
Fri Jul 11th 2025

15h 50m
Chicago (ORD) → Lower Prince's Quarter (SXM)

2 Stops

Fri Jul 11th 2025 Spirit Airlines · NK 1180 Depart at 9:10pm from Chicago (ORD) Fly for 2h 49m Arrive at 11:59pm in Houston (IAH)

Layover in Houston for 5h 1m

Sat Jul 12th 2025 Spirit Airlines · NK 1498 Depart at 5:00am from Houston (IAH) Fly for 2h 24m Arrive at 8:24am in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 2h 26m

Sat Jul 12th 2025 Spirit Airlines · NK 100 Depart at 10:50am from Fort Lauderdale (FLL) Fly for 3h 10m Arrive at 2:00pm in Lower Prince's Quarter (SXM)
US$379

6:02pm - 4:30pm
Wed Jul 23rd 2025

21h 28m
Chicago (ORD) → Lower Prince's Quarter (SXM)

3 Stops

Wed Jul 23rd 2025 Spirit Airlines · NK 1115 Depart at 6:02pm from Chicago (ORD) Fly for 2h 6m Arrive at 9:08pm in Atlanta (ATL)

Layover in Atlanta for 8h 12m

Thu Jul 24th 2025 Spirit Airlines · NK 1387 Depart at 5:20am from Atlanta (ATL) Fly for 1h 49m Arrive at 7:09am in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 0h 31m

Thu Jul 24th 2025 Spirit Airlines · NK 145 Depart at 7:40am from Fort Lauderdale (FLL) Fly for 2h 10m Arrive at 9:50am in Santo Domingo (SDQ)

Layover in Santo Domingo for 5h 13m

Thu Jul 24th 2025 Arajet · DM 400 Depart at 3:03pm from Santo Domingo (SDQ) Fly for 1h 27m Arrive at 4:30pm in Lower Prince's Quarter (SXM)
US$393

9:10pm - 2:00pm
Sun Jul 27th 2025

15h 50m
Chicago (ORD) → Lower Prince's Quarter (SXM)

2 Stops

Sun Jul 27th 2025 Spirit Airlines · NK 1180 Depart at 9:10pm from Chicago (ORD) Fly for 2h 49m Arrive at 11:59pm in Houston (IAH)

Layover in Houston for 5h 1m

Mon Jul 28th 2025 Spirit Airlines · NK 1498 Depart at 5:00am from Houston (IAH) Fly for 2h 24m Arrive at 8:24am in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 2h 26m

Mon Jul 28th 2025 Spirit Airlines · NK 100 Depart at 10:50am from Fort Lauderdale (FLL) Fly for 3h 10m Arrive at 2:00pm in Lower Prince's Quarter (SXM)
US$394

3:07pm - 11:24am
Sat Jul 26th 2025

19h 17m
Chicago (ORD) → Lower Prince's Quarter (SXM)

1 Stop

Sat Jul 26th 2025 Copa Airlines · CM 229 Depart at 3:07pm from Chicago (ORD) Fly for 5h 28m Arrive at 8:35pm in Panama (PTY)

Layover in Panama for 10h 43m

Sun Jul 27th 2025 Copa Airlines · CM 134 Depart at 7:18am from Panama (PTY) Fly for 3h 6m Arrive at 11:24am in Lower Prince's Quarter (SXM)
US$395

4:37pm - 2:00pm
Sun Jul 6th 2025

20h 23m
Chicago (ORD) → Lower Prince's Quarter (SXM)

2 Stops

Sun Jul 6th 2025 Frontier Airlines · F9 2792 Depart at 4:37pm from Chicago (ORD) Fly for 3h 2m Arrive at 8:39pm in Orlando (MCO)

Layover in Orlando for 11h 46m

Mon Jul 7th 2025 Spirit Airlines · NK 2196 Depart at 8:25am from Orlando (MCO) Fly for 1h 12m Arrive at 9:37am in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 1h 26m

Mon Jul 7th 2025 Spirit Airlines · NK 100 Depart at 11:03am from Fort Lauderdale (FLL) Fly for 2h 57m Arrive at 2:00pm in Lower Prince's Quarter (SXM)
US$408

5:01am - 5:21pm
Mon Jul 7th 2025

11h 20m
Chicago (ORD) → Lower Prince's Quarter (SXM)

2 Stops

Mon Jul 7th 2025 Frontier Airlines · F9 1596 Depart at 5:01am from Chicago (ORD) Fly for 2h 11m Arrive at 8:12am in Atlanta (ATL)

Layover in Atlanta for 2h 13m

Mon Jul 7th 2025 Frontier Airlines · F9 2082 Depart at 10:25am from Atlanta (ATL) Fly for 3h 53m Arrive at 2:18pm in San Juan (SJU)

Layover in San Juan for 2h 0m

Mon Jul 7th 2025 Frontier Airlines · F9 244 Depart at 4:18pm from San Juan (SJU) Fly for 1h 3m Arrive at 5:21pm in Lower Prince's Quarter (SXM)
US$410

1:07am - 11:24am
Sun Jul 13th 2025

9h 17m
Chicago (ORD) → Lower Prince's Quarter (SXM)

1 Stop

Sun Jul 13th 2025 Copa Airlines · CM 846 Depart at 1:07am from Chicago (ORD) Fly for 5h 16m Arrive at 6:23am in Panama (PTY)

Layover in Panama for 0h 55m

Sun Jul 13th 2025 Copa Airlines · CM 134 Depart at 7:18am from Panama (PTY) Fly for 3h 6m Arrive at 11:24am in Lower Prince's Quarter (SXM)
US$419

9:32pm - 12:29pm
Sun Jul 20th 2025

13h 57m
Chicago (ORD) → Lower Prince's Quarter (SXM)

1 Stop

Sun Jul 20th 2025 United Airlines · UA 396 Depart at 9:32pm from Chicago (ORD) Fly for 2h 21m Arrive at 12:53am in New York (EWR)

Layover in New York for 7h 24m

Mon Jul 21st 2025 United Airlines · UA 1629 Depart at 8:17am from New York (EWR) Fly for 4h 12m Arrive at 12:29pm in Lower Prince's Quarter (SXM)
US$419

9:31pm - 12:29pm
Tue Jul 22nd 2025

13h 58m
Chicago (ORD) → Lower Prince's Quarter (SXM)

1 Stop

Tue Jul 22nd 2025 United Airlines · UA 276 Depart at 9:31pm from Chicago (ORD) Fly for 1h 59m Arrive at 12:30am in Washington, D.C. (IAD)

Layover in Washington, D.C. for 7h 47m

Wed Jul 23rd 2025 United Airlines · UA 346 Depart at 8:17am from Washington, D.C. (IAD) Fly for 4h 12m Arrive at 12:29pm in Lower Prince's Quarter (SXM)
US$421

9:10pm - 2:00pm
Sun Jul 13th 2025

15h 50m
Chicago (ORD) → Lower Prince's Quarter (SXM)

2 Stops

Sun Jul 13th 2025 Spirit Airlines · NK 1180 Depart at 9:10pm from Chicago (ORD) Fly for 2h 49m Arrive at 11:59pm in Houston (IAH)

Layover in Houston for 5h 1m

Mon Jul 14th 2025 Spirit Airlines · NK 1498 Depart at 5:00am from Houston (IAH) Fly for 2h 24m Arrive at 8:24am in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 2h 26m

Mon Jul 14th 2025 Spirit Airlines · NK 100 Depart at 10:50am from Fort Lauderdale (FLL) Fly for 3h 10m Arrive at 2:00pm in Lower Prince's Quarter (SXM)
US$431

5:01am - 5:21pm
Fri Jul 11th 2025

11h 20m
Chicago (ORD) → Lower Prince's Quarter (SXM)

2 Stops

Fri Jul 11th 2025 Frontier Airlines · F9 1596 Depart at 5:01am from Chicago (ORD) Fly for 2h 11m Arrive at 8:12am in Atlanta (ATL)

Layover in Atlanta for 2h 13m

Fri Jul 11th 2025 Frontier Airlines · F9 2082 Depart at 10:25am from Atlanta (ATL) Fly for 3h 53m Arrive at 2:18pm in San Juan (SJU)

Layover in San Juan for 2h 0m

Fri Jul 11th 2025 Frontier Airlines · F9 244 Depart at 4:18pm from San Juan (SJU) Fly for 1h 3m Arrive at 5:21pm in Lower Prince's Quarter (SXM)
US$438

9:31pm - 12:29pm
Sat Jul 19th 2025

13h 58m
Chicago (ORD) → Lower Prince's Quarter (SXM)

1 Stop

Sat Jul 19th 2025 United Airlines · UA 276 Depart at 9:31pm from Chicago (ORD) Fly for 1h 59m Arrive at 12:30am in Washington, D.C. (IAD)

Layover in Washington, D.C. for 7h 47m

Sun Jul 20th 2025 United Airlines · UA 346 Depart at 8:17am from Washington, D.C. (IAD) Fly for 4h 12m Arrive at 12:29pm in Lower Prince's Quarter (SXM)
US$443

10:15pm - 2:43pm
Fri Jul 25th 2025

15h 28m
Chicago (ORD) → Lower Prince's Quarter (SXM)

1 Stop

Fri Jul 25th 2025 United Airlines · UA 1289 Depart at 10:15pm from Chicago (ORD) Fly for 2h 33m Arrive at 1:48am in New York (EWR)

Layover in New York for 8h 43m

Sat Jul 26th 2025 United Airlines · UA 1629 Depart at 10:31am from New York (EWR) Fly for 4h 12m Arrive at 2:43pm in Lower Prince's Quarter (SXM)
US$445

9:31pm - 12:29pm
Sat Jul 26th 2025

13h 58m
Chicago (ORD) → Lower Prince's Quarter (SXM)

1 Stop

Sat Jul 26th 2025 United Airlines · UA 276 Depart at 9:31pm from Chicago (ORD) Fly for 1h 59m Arrive at 12:30am in Washington, D.C. (IAD)

Layover in Washington, D.C. for 7h 47m

Sun Jul 27th 2025 United Airlines · UA 346 Depart at 8:17am from Washington, D.C. (IAD) Fly for 4h 12m Arrive at 12:29pm in Lower Prince's Quarter (SXM)
US$458

1:07am - 11:24am
Wed Jul 9th 2025

9h 17m
Chicago (ORD) → Lower Prince's Quarter (SXM)

1 Stop

Wed Jul 9th 2025 Copa Airlines · CM 846 Depart at 1:07am from Chicago (ORD) Fly for 5h 16m Arrive at 6:23am in Panama (PTY)

Layover in Panama for 0h 55m

Wed Jul 9th 2025 Copa Airlines · CM 134 Depart at 7:18am from Panama (PTY) Fly for 3h 6m Arrive at 11:24am in Lower Prince's Quarter (SXM)
US$460

9:10pm - 2:00pm
Thu Jul 10th 2025

15h 50m
Chicago (ORD) → Lower Prince's Quarter (SXM)

2 Stops

Thu Jul 10th 2025 Spirit Airlines · NK 1180 Depart at 9:10pm from Chicago (ORD) Fly for 2h 49m Arrive at 11:59pm in Houston (IAH)

Layover in Houston for 5h 1m

Fri Jul 11th 2025 Spirit Airlines · NK 1498 Depart at 5:00am from Houston (IAH) Fly for 2h 24m Arrive at 8:24am in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 2h 26m

Fri Jul 11th 2025 Spirit Airlines · NK 100 Depart at 10:50am from Fort Lauderdale (FLL) Fly for 3h 10m Arrive at 2:00pm in Lower Prince's Quarter (SXM)
US$465

7:39pm - 2:00pm
Fri Jul 4th 2025

17h 21m
Chicago (ORD) → Lower Prince's Quarter (SXM)

1 Stop

Fri Jul 4th 2025 Spirit Airlines · NK 1986 Depart at 7:39pm from Chicago (ORD) Fly for 3h 12m Arrive at 11:51pm in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 11h 12m

Sat Jul 5th 2025 Spirit Airlines · NK 100 Depart at 11:03am from Fort Lauderdale (FLL) Fly for 2h 57m Arrive at 2:00pm in Lower Prince's Quarter (SXM)
US$466

9:31pm - 12:29pm
Tue Jul 15th 2025

13h 58m
Chicago (ORD) → Lower Prince's Quarter (SXM)

1 Stop

Tue Jul 15th 2025 United Airlines · UA 276 Depart at 9:31pm from Chicago (ORD) Fly for 1h 59m Arrive at 12:30am in Washington, D.C. (IAD)

Layover in Washington, D.C. for 7h 47m

Wed Jul 16th 2025 United Airlines · UA 346 Depart at 8:17am from Washington, D.C. (IAD) Fly for 4h 12m Arrive at 12:29pm in Lower Prince's Quarter (SXM)
US$466

9:25pm - 12:29pm
Sun Jul 13th 2025

14h 4m
Chicago (ORD) → Lower Prince's Quarter (SXM)

1 Stop

Sun Jul 13th 2025 United Airlines · UA 396 Depart at 9:25pm from Chicago (ORD) Fly for 2h 21m Arrive at 12:46am in New York (EWR)

Layover in New York for 7h 31m

Mon Jul 14th 2025 United Airlines · UA 1629 Depart at 8:17am from New York (EWR) Fly for 4h 12m Arrive at 12:29pm in Lower Prince's Quarter (SXM)
US$477

6:00am - 2:43pm
Sat Jul 12th 2025

7h 43m
Chicago (ORD) → Lower Prince's Quarter (SXM)

1 Stop

Sat Jul 12th 2025 United Airlines · UA 1658 Depart at 6:00am from Chicago (ORD) Fly for 2h 13m Arrive at 9:13am in New York (EWR)

Layover in New York for 1h 18m

Sat Jul 12th 2025 United Airlines · UA 1629 Depart at 10:31am from New York (EWR) Fly for 4h 12m Arrive at 2:43pm in Lower Prince's Quarter (SXM)
US$482

6:00am - 2:43pm
Sat Jul 26th 2025

7h 43m
Chicago (ORD) → Lower Prince's Quarter (SXM)

1 Stop

Sat Jul 26th 2025 United Airlines · UA 1658 Depart at 6:00am from Chicago (ORD) Fly for 2h 13m Arrive at 9:13am in New York (EWR)

Layover in New York for 1h 18m

Sat Jul 26th 2025 United Airlines · UA 1629 Depart at 10:31am from New York (EWR) Fly for 4h 12m Arrive at 2:43pm in Lower Prince's Quarter (SXM)
US$482

9:31pm - 12:29pm
Fri Jul 18th 2025

13h 58m
Chicago (ORD) → Lower Prince's Quarter (SXM)

1 Stop

Fri Jul 18th 2025 United Airlines · UA 276 Depart at 9:31pm from Chicago (ORD) Fly for 1h 59m Arrive at 12:30am in Washington, D.C. (IAD)

Layover in Washington, D.C. for 7h 47m

Sat Jul 19th 2025 United Airlines · UA 346 Depart at 8:17am from Washington, D.C. (IAD) Fly for 4h 12m Arrive at 12:29pm in Lower Prince's Quarter (SXM)
US$482

10:15pm - 2:43pm
Fri Jul 18th 2025

15h 28m
Chicago (ORD) → Lower Prince's Quarter (SXM)

1 Stop

Fri Jul 18th 2025 United Airlines · UA 1289 Depart at 10:15pm from Chicago (ORD) Fly for 2h 33m Arrive at 1:48am in New York (EWR)

Layover in New York for 8h 43m

Sat Jul 19th 2025 United Airlines · UA 1629 Depart at 10:31am from New York (EWR) Fly for 4h 12m Arrive at 2:43pm in Lower Prince's Quarter (SXM)
US$505

6:00am - 2:43pm
Wed Jul 23rd 2025

7h 43m
Chicago (ORD) → Lower Prince's Quarter (SXM)

1 Stop

Wed Jul 23rd 2025 United Airlines · UA 1658 Depart at 6:00am from Chicago (ORD) Fly for 2h 13m Arrive at 9:13am in New York (EWR)

Layover in New York for 1h 18m

Wed Jul 23rd 2025 United Airlines · UA 1629 Depart at 10:31am from New York (EWR) Fly for 4h 12m Arrive at 2:43pm in Lower Prince's Quarter (SXM)
US$509

6:00am - 2:43pm
Sun Jul 13th 2025

7h 43m
Chicago (ORD) → Lower Prince's Quarter (SXM)

1 Stop

Sun Jul 13th 2025 United Airlines · UA 1658 Depart at 6:00am from Chicago (ORD) Fly for 2h 13m Arrive at 9:13am in New York (EWR)

Layover in New York for 1h 18m

Sun Jul 13th 2025 United Airlines · UA 1629 Depart at 10:31am from New York (EWR) Fly for 4h 12m Arrive at 2:43pm in Lower Prince's Quarter (SXM)
US$538

1:07am - 11:24am
Wed Jul 23rd 2025

9h 17m
Chicago (ORD) → Lower Prince's Quarter (SXM)

1 Stop

Wed Jul 23rd 2025 Copa Airlines · CM 846 Depart at 1:07am from Chicago (ORD) Fly for 5h 16m Arrive at 6:23am in Panama (PTY)

Layover in Panama for 0h 55m

Wed Jul 23rd 2025 Copa Airlines · CM 134 Depart at 7:18am from Panama (PTY) Fly for 3h 6m Arrive at 11:24am in Lower Prince's Quarter (SXM)
US$645

6:00am - 2:43pm
Sat Jul 19th 2025

7h 43m
Chicago (ORD) → Lower Prince's Quarter (SXM)

1 Stop

Sat Jul 19th 2025 United Airlines · UA 1658 Depart at 6:00am from Chicago (ORD) Fly for 2h 13m Arrive at 9:13am in New York (EWR)

Layover in New York for 1h 18m

Sat Jul 19th 2025 United Airlines · UA 1629 Depart at 10:31am from New York (EWR) Fly for 4h 12m Arrive at 2:43pm in Lower Prince's Quarter (SXM)
US$653

6:00am - 2:43pm
Sun Jul 20th 2025

7h 43m
Chicago (ORD) → Lower Prince's Quarter (SXM)

1 Stop

Sun Jul 20th 2025 United Airlines · UA 1658 Depart at 6:00am from Chicago (ORD) Fly for 2h 13m Arrive at 9:13am in New York (EWR)

Layover in New York for 1h 18m

Sun Jul 20th 2025 United Airlines · UA 1629 Depart at 10:31am from New York (EWR) Fly for 4h 12m Arrive at 2:43pm in Lower Prince's Quarter (SXM)
US$659

6:00am - 2:43pm
Wed Jul 2nd 2025

7h 43m
Chicago (ORD) → Lower Prince's Quarter (SXM)

1 Stop

Wed Jul 2nd 2025 United Airlines · UA 1658 Depart at 6:00am from Chicago (ORD) Fly for 2h 13m Arrive at 9:13am in New York (EWR)

Layover in New York for 1h 18m

Wed Jul 2nd 2025 United Airlines · UA 1629 Depart at 10:31am from New York (EWR) Fly for 4h 12m Arrive at 2:43pm in Lower Prince's Quarter (SXM)
US$808

1:07am - 11:24am
Wed Jul 2nd 2025

9h 17m
Chicago (ORD) → Lower Prince's Quarter (SXM)

1 Stop

Wed Jul 2nd 2025 Copa Airlines · CM 846 Depart at 1:07am from Chicago (ORD) Fly for 5h 16m Arrive at 6:23am in Panama (PTY)

Layover in Panama for 0h 55m

Wed Jul 2nd 2025 Copa Airlines · CM 134 Depart at 7:18am from Panama (PTY) Fly for 3h 6m Arrive at 11:24am in Lower Prince's Quarter (SXM)
US$1020

6:00am - 2:43pm
Wed Jul 16th 2025

7h 43m
Chicago (ORD) → Lower Prince's Quarter (SXM)

1 Stop

Wed Jul 16th 2025 United Airlines · UA 1658 Depart at 6:00am from Chicago (ORD) Fly for 2h 13m Arrive at 9:13am in New York (EWR)

Layover in New York for 1h 18m

Wed Jul 16th 2025 United Airlines · UA 1629 Depart at 10:31am from New York (EWR) Fly for 4h 12m Arrive at 2:43pm in Lower Prince's Quarter (SXM)
US$1342

6:00am - 2:43pm
Sun Jul 27th 2025

7h 43m
Chicago (ORD) → Lower Prince's Quarter (SXM)

1 Stop

Sun Jul 27th 2025 United Airlines · UA 1658 Depart at 6:00am from Chicago (ORD) Fly for 2h 13m Arrive at 9:13am in New York (EWR)

Layover in New York for 1h 18m

Sun Jul 27th 2025 United Airlines · UA 1629 Depart at 10:31am from New York (EWR) Fly for 4h 12m Arrive at 2:43pm in Lower Prince's Quarter (SXM)

Sarah Belizaire

@sarahbb1

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John Ford

@eyupitsjohn

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Roaming Sonaa

@roamingsonaa

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Andy Travels

@andy_travels

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Travel With Bender

@travelwitbender

Did you spot my recent article about how to score cheap one way flights? ✈️ FlightList is my new secret tool for discovering cheap routes, within a departure date range. Plus you can also search by country/region for departures & destinations. Powerful! 💪

Wesley Mergard

@travel.with.wes

One useful tool I've found for evaluating different departure and return dates is called FlightList.io. You can quickly scan different travel date ranges, carriers and one way flight options to easily determine the cheapest flight combinations for your trip.

Flights from Chicago to Philipsburg (ORD to SXM)

Sarah Belizaire

John Ford

Roaming Sonaa

Andy Travels

Travel With Bender

Wesley Mergard

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