Wed Dec 14th 2022 Spirit Airlines · NK 3147 Depart at 10:20 am from San Juan (SJU) Fly for 2h 49m Arrive at 12:09 pm in Miami (MIA)
Layover in Miami for 2h 46m
Wed Dec 14th 2022 Spirit Airlines · NK 3164 Depart at 2:55 pm from Miami (MIA) Fly for 3h 24m Arrive at 5:19 pm in Chicago (ORD)
Tue Dec 20th 2022 Spirit Airlines · NK 143 Depart at 2:58 am from Aguadilla (BQN) Fly for 2h 58m Arrive at 4:56 am in Orlando (MCO)
Layover in Orlando for 1h 54m
Tue Dec 20th 2022 Spirit Airlines · NK 322 Depart at 6:50 am from Orlando (MCO) Fly for 2h 57m Arrive at 8:47 am in Chicago (ORD)
Wed Dec 21st 2022 Spirit Airlines · NK 3319 Depart at 6:40 am from San Juan (SJU) Fly for 3h 8m Arrive at 8:48 am in Orlando (MCO)
Layover in Orlando for 1h 52m
Wed Dec 21st 2022 Spirit Airlines · NK 322 Depart at 10:40 am from Orlando (MCO) Fly for 3h 3m Arrive at 12:43 pm in Chicago (ORD)
Tue Dec 20th 2022 Spirit Airlines · NK 143 Depart at 2:58 am from Aguadilla (BQN) Fly for 2h 58m Arrive at 4:56 am in Orlando (MCO)
Layover in Orlando for 6h 4m
Tue Dec 20th 2022 Frontier Airlines · F9 1022 Depart at 11:00 am from Orlando (MCO) Fly for 2h 49m Arrive at 12:49 pm in Chicago (MDW)
Tue Dec 13th 2022 Frontier Airlines · F9 105 Depart at 3:59 am from San Juan (SJU) Fly for 3h 18m Arrive at 6:17 am in Orlando (MCO)
Layover in Orlando for 4h 43m
Tue Dec 13th 2022 Frontier Airlines · F9 1022 Depart at 11:00 am from Orlando (MCO) Fly for 2h 49m Arrive at 12:49 pm in Chicago (MDW)
Wed Dec 14th 2022 Frontier Airlines · F9 105 Depart at 3:59 am from San Juan (SJU) Fly for 3h 18m Arrive at 6:17 am in Orlando (MCO)
Layover in Orlando for 4h 43m
Wed Dec 14th 2022 Frontier Airlines · F9 1022 Depart at 11:00 am from Orlando (MCO) Fly for 2h 49m Arrive at 12:49 pm in Chicago (MDW)
Wed Dec 14th 2022 Frontier Airlines · F9 105 Depart at 3:59 am from San Juan (SJU) Fly for 3h 18m Arrive at 6:17 am in Orlando (MCO)
Layover in Orlando for 4h 23m
Wed Dec 14th 2022 Spirit Airlines · NK 322 Depart at 10:40 am from Orlando (MCO) Fly for 3h 3m Arrive at 12:43 pm in Chicago (ORD)
Tue Dec 13th 2022 Frontier Airlines · F9 101 Depart at 3:26 pm from San Juan (SJU) Fly for 4h 7m Arrive at 6:33 pm in Atlanta (ATL)
Layover in Atlanta for 2h 52m
Tue Dec 13th 2022 Spirit Airlines · NK 2648 Depart at 9:25 pm from Atlanta (ATL) Fly for 2h 11m Arrive at 10:36 pm in Chicago (ORD)
Wed Dec 14th 2022 Frontier Airlines · F9 101 Depart at 3:26 pm from San Juan (SJU) Fly for 4h 7m Arrive at 6:33 pm in Atlanta (ATL)
Layover in Atlanta for 2h 52m
Wed Dec 14th 2022 Spirit Airlines · NK 2648 Depart at 9:25 pm from Atlanta (ATL) Fly for 2h 11m Arrive at 10:36 pm in Chicago (ORD)
Mon Dec 19th 2022 Spirit Airlines · NK 374 Depart at 3:59 am from Aguadilla (BQN) Fly for 2h 38m Arrive at 5:37 am in Fort Lauderdale (FLL)
Layover in Fort Lauderdale for 1h 58m
Mon Dec 19th 2022 Spirit Airlines · NK 3 Depart at 7:35 am from Fort Lauderdale (FLL) Fly for 3h 14m Arrive at 9:49 am in Chicago (ORD)
Tue Dec 20th 2022 Spirit Airlines · NK 374 Depart at 3:59 am from Aguadilla (BQN) Fly for 2h 38m Arrive at 5:37 am in Fort Lauderdale (FLL)
Layover in Fort Lauderdale for 1h 58m
Tue Dec 20th 2022 Spirit Airlines · NK 3 Depart at 7:35 am from Fort Lauderdale (FLL) Fly for 3h 14m Arrive at 9:49 am in Chicago (ORD)
Wed Dec 21st 2022 Spirit Airlines · NK 111 Depart at 5:25 pm from San Juan (SJU) Fly for 3h 15m Arrive at 7:40 pm in Orlando (MCO)
Layover in Orlando for 3h 27m
Wed Dec 21st 2022 Frontier Airlines · F9 1024 Depart at 11:07 pm from Orlando (MCO) Fly for 2h 49m Arrive at 12:56 am in Chicago (MDW)
Wed Dec 21st 2022 Frontier Airlines · F9 119 Depart at 11:20 am from San Juan (SJU) Fly for 2h 54m Arrive at 1:14 pm in Miami (MIA)
Layover in Miami for 3h 48m
Wed Dec 21st 2022 Frontier Airlines · F9 2650 Depart at 5:02 pm from Miami (MIA) Fly for 3h 12m Arrive at 7:14 pm in Chicago (MDW)
Sat Dec 17th 2022 Frontier Airlines · F9 105 Depart at 3:59 am from San Juan (SJU) Fly for 3h 18m Arrive at 6:17 am in Orlando (MCO)
Layover in Orlando for 4h 14m
Sat Dec 17th 2022 Frontier Airlines · F9 1022 Depart at 10:31 am from Orlando (MCO) Fly for 2h 49m Arrive at 12:20 pm in Chicago (MDW)
Tue Dec 13th 2022 Spirit Airlines · NK 3147 Depart at 10:20 am from San Juan (SJU) Fly for 2h 49m Arrive at 12:09 pm in Miami (MIA)
Layover in Miami for 2h 46m
Tue Dec 13th 2022 Spirit Airlines · NK 3164 Depart at 2:55 pm from Miami (MIA) Fly for 3h 24m Arrive at 5:19 pm in Chicago (ORD)
Tue Dec 20th 2022 Spirit Airlines · NK 3147 Depart at 10:20 am from San Juan (SJU) Fly for 2h 49m Arrive at 12:09 pm in Miami (MIA)
Layover in Miami for 2h 46m
Tue Dec 20th 2022 Spirit Airlines · NK 3164 Depart at 2:55 pm from Miami (MIA) Fly for 3h 24m Arrive at 5:19 pm in Chicago (ORD)
Sat Dec 17th 2022 Frontier Airlines · F9 117 Depart at 1:14 pm from San Juan (SJU) Fly for 3h 24m Arrive at 3:38 pm in Orlando (MCO)
Layover in Orlando for 2h 42m
Sat Dec 17th 2022 Spirit Airlines · NK 322 Depart at 6:20 pm from Orlando (MCO) Fly for 3h 4m Arrive at 8:24 pm in Chicago (ORD)
Thu Dec 8th 2022 Frontier Airlines · F9 139 Depart at 9:25 pm from Aguadilla (BQN) Fly for 3h 7m Arrive at 11:32 pm in Orlando (MCO)
Layover in Orlando for 7h 3m
Fri Dec 9th 2022 Frontier Airlines · F9 1154 Depart at 6:35 am from Orlando (MCO) Fly for 3h 15m Arrive at 8:50 am in Chicago (ORD)
Tue Dec 20th 2022 Frontier Airlines · F9 101 Depart at 3:26 pm from San Juan (SJU) Fly for 4h 7m Arrive at 6:33 pm in Atlanta (ATL)
Layover in Atlanta for 2h 52m
Tue Dec 20th 2022 Spirit Airlines · NK 2648 Depart at 9:25 pm from Atlanta (ATL) Fly for 2h 11m Arrive at 10:36 pm in Chicago (ORD)
Fri Dec 16th 2022 Spirit Airlines · NK 3147 Depart at 10:20 am from San Juan (SJU) Fly for 2h 49m Arrive at 12:09 pm in Miami (MIA)
Layover in Miami for 2h 46m
Fri Dec 16th 2022 Spirit Airlines · NK 3164 Depart at 2:55 pm from Miami (MIA) Fly for 3h 24m Arrive at 5:19 pm in Chicago (ORD)
Thu Dec 15th 2022 Spirit Airlines · NK 3147 Depart at 10:20 am from San Juan (SJU) Fly for 2h 49m Arrive at 12:09 pm in Miami (MIA)
Layover in Miami for 2h 46m
Thu Dec 15th 2022 Spirit Airlines · NK 3164 Depart at 2:55 pm from Miami (MIA) Fly for 3h 24m Arrive at 5:19 pm in Chicago (ORD)
Tue Dec 20th 2022 Frontier Airlines · F9 119 Depart at 11:20 am from San Juan (SJU) Fly for 2h 54m Arrive at 1:14 pm in Miami (MIA)
Layover in Miami for 2h 46m
Tue Dec 20th 2022 United Airlines · UA 1393 Depart at 4:00 pm from Miami (MIA) Fly for 3h 27m Arrive at 6:27 pm in Chicago (ORD)
Fri Dec 16th 2022 Frontier Airlines · F9 111 Depart at 4:32 pm from San Juan (SJU) Fly for 3h 22m Arrive at 6:54 pm in Orlando (MCO)
Layover in Orlando for 4h 13m
Fri Dec 16th 2022 Frontier Airlines · F9 1024 Depart at 11:07 pm from Orlando (MCO) Fly for 2h 49m Arrive at 12:56 am in Chicago (MDW)
Fri Dec 9th 2022 Frontier Airlines · F9 111 Depart at 4:32 pm from San Juan (SJU) Fly for 3h 22m Arrive at 6:54 pm in Orlando (MCO)
Layover in Orlando for 4h 13m
Fri Dec 9th 2022 Frontier Airlines · F9 1024 Depart at 11:07 pm from Orlando (MCO) Fly for 2h 49m Arrive at 12:56 am in Chicago (MDW)
Fri Dec 9th 2022 Frontier Airlines · F9 105 Depart at 3:59 am from San Juan (SJU) Fly for 3h 18m Arrive at 6:17 am in Orlando (MCO)
Layover in Orlando for 4h 43m
Fri Dec 9th 2022 Frontier Airlines · F9 1022 Depart at 11:00 am from Orlando (MCO) Fly for 2h 49m Arrive at 12:49 pm in Chicago (MDW)
Thu Dec 8th 2022 Frontier Airlines · F9 111 Depart at 4:42 pm from San Juan (SJU) Fly for 3h 22m Arrive at 7:04 pm in Orlando (MCO)
Layover in Orlando for 4h 4m
Thu Dec 8th 2022 Frontier Airlines · F9 1024 Depart at 11:08 pm from Orlando (MCO) Fly for 2h 49m Arrive at 12:57 am in Chicago (MDW)
Thu Dec 8th 2022 Frontier Airlines · F9 105 Depart at 3:52 am from San Juan (SJU) Fly for 3h 18m Arrive at 6:10 am in Orlando (MCO)
Layover in Orlando for 4h 21m
Thu Dec 8th 2022 Frontier Airlines · F9 1022 Depart at 10:31 am from Orlando (MCO) Fly for 2h 49m Arrive at 12:20 pm in Chicago (MDW)
Wed Dec 21st 2022 Spirit Airlines · NK 893 Depart at 1:31 pm from San Juan (SJU) Fly for 3h 11m Arrive at 3:42 pm in Orlando (MCO)
Layover in Orlando for 1h 53m
Wed Dec 21st 2022 Spirit Airlines · NK 912 Depart at 5:35 pm from Orlando (MCO) Fly for 3h 3m Arrive at 7:38 pm in Chicago (ORD)
Tue Dec 20th 2022 Spirit Airlines · NK 3147 Depart at 10:20 am from San Juan (SJU) Fly for 2h 49m Arrive at 12:09 pm in Miami (MIA)
Layover in Miami for 2h 27m
Tue Dec 20th 2022 United Airlines · UA 1063 Depart at 2:36 pm from Miami (MIA) Fly for 3h 23m Arrive at 4:59 pm in Chicago (ORD)
Tue Dec 13th 2022 Spirit Airlines · NK 374 Depart at 3:59 am from Aguadilla (BQN) Fly for 2h 38m Arrive at 5:37 am in Fort Lauderdale (FLL)
Layover in Fort Lauderdale for 1h 58m
Tue Dec 13th 2022 Spirit Airlines · NK 3 Depart at 7:35 am from Fort Lauderdale (FLL) Fly for 3h 14m Arrive at 9:49 am in Chicago (ORD)
Fri Dec 16th 2022 Spirit Airlines · NK 374 Depart at 3:59 am from Aguadilla (BQN) Fly for 2h 38m Arrive at 5:37 am in Fort Lauderdale (FLL)
Layover in Fort Lauderdale for 1h 58m
Fri Dec 16th 2022 Spirit Airlines · NK 3 Depart at 7:35 am from Fort Lauderdale (FLL) Fly for 3h 14m Arrive at 9:49 am in Chicago (ORD)
Sat Dec 17th 2022 Spirit Airlines · NK 374 Depart at 3:59 am from Aguadilla (BQN) Fly for 2h 38m Arrive at 5:37 am in Fort Lauderdale (FLL)
Layover in Fort Lauderdale for 1h 58m
Sat Dec 17th 2022 Spirit Airlines · NK 3 Depart at 7:35 am from Fort Lauderdale (FLL) Fly for 3h 14m Arrive at 9:49 am in Chicago (ORD)
Wed Dec 14th 2022 Spirit Airlines · NK 374 Depart at 3:59 am from Aguadilla (BQN) Fly for 2h 38m Arrive at 5:37 am in Fort Lauderdale (FLL)
Layover in Fort Lauderdale for 1h 58m
Wed Dec 14th 2022 Spirit Airlines · NK 3 Depart at 7:35 am from Fort Lauderdale (FLL) Fly for 3h 14m Arrive at 9:49 am in Chicago (ORD)
Thu Dec 15th 2022 Spirit Airlines · NK 374 Depart at 3:59 am from Aguadilla (BQN) Fly for 2h 38m Arrive at 5:37 am in Fort Lauderdale (FLL)
Layover in Fort Lauderdale for 1h 58m
Thu Dec 15th 2022 Spirit Airlines · NK 3 Depart at 7:35 am from Fort Lauderdale (FLL) Fly for 3h 14m Arrive at 9:49 am in Chicago (ORD)
Sun Dec 18th 2022 Spirit Airlines · NK 374 Depart at 3:59 am from Aguadilla (BQN) Fly for 2h 38m Arrive at 5:37 am in Fort Lauderdale (FLL)
Layover in Fort Lauderdale for 1h 58m
Sun Dec 18th 2022 Spirit Airlines · NK 3 Depart at 7:35 am from Fort Lauderdale (FLL) Fly for 3h 14m Arrive at 9:49 am in Chicago (ORD)
Thu Dec 8th 2022 Frontier Airlines · F9 121 Depart at 1:29 pm from San Juan (SJU) Fly for 3h 15m Arrive at 3:44 pm in Tampa (TPA)
Layover in Tampa for 6h 29m
Thu Dec 8th 2022 Frontier Airlines · F9 2594 Depart at 10:13 pm from Tampa (TPA) Fly for 2h 46m Arrive at 11:59 pm in Chicago (MDW)
Sun Dec 18th 2022 Spirit Airlines · NK 3147 Depart at 10:20 am from San Juan (SJU) Fly for 2h 49m Arrive at 12:09 pm in Miami (MIA)
Layover in Miami for 2h 46m
Sun Dec 18th 2022 Spirit Airlines · NK 3164 Depart at 2:55 pm from Miami (MIA) Fly for 3h 24m Arrive at 5:19 pm in Chicago (ORD)
Mon Dec 12th 2022 Spirit Airlines · NK 3147 Depart at 10:20 am from San Juan (SJU) Fly for 2h 49m Arrive at 12:09 pm in Miami (MIA)
Layover in Miami for 2h 46m
Mon Dec 12th 2022 Spirit Airlines · NK 3164 Depart at 2:55 pm from Miami (MIA) Fly for 3h 24m Arrive at 5:19 pm in Chicago (ORD)
Sun Dec 25th 2022 Spirit Airlines · NK 374 Depart at 3:59 am from Aguadilla (BQN) Fly for 2h 38m Arrive at 5:37 am in Fort Lauderdale (FLL)
Layover in Fort Lauderdale for 1h 58m
Sun Dec 25th 2022 Spirit Airlines · NK 3 Depart at 7:35 am from Fort Lauderdale (FLL) Fly for 3h 14m Arrive at 9:49 am in Chicago (ORD)
Wed Dec 21st 2022 Spirit Airlines · NK 374 Depart at 3:59 am from Aguadilla (BQN) Fly for 2h 38m Arrive at 5:37 am in Fort Lauderdale (FLL)
Layover in Fort Lauderdale for 1h 58m
Wed Dec 21st 2022 Spirit Airlines · NK 3 Depart at 7:35 am from Fort Lauderdale (FLL) Fly for 3h 14m Arrive at 9:49 am in Chicago (ORD)
Tue Dec 20th 2022 Spirit Airlines · NK 3319 Depart at 6:40 am from San Juan (SJU) Fly for 3h 8m Arrive at 8:48 am in Orlando (MCO)
Layover in Orlando for 2h 12m
Tue Dec 20th 2022 Frontier Airlines · F9 1022 Depart at 11:00 am from Orlando (MCO) Fly for 2h 49m Arrive at 12:49 pm in Chicago (MDW)
Sat Dec 17th 2022 Spirit Airlines · NK 111 Depart at 9:50 am from San Juan (SJU) Fly for 3h 9m Arrive at 11:59 am in Orlando (MCO)
Layover in Orlando for 0h 31m
Sat Dec 17th 2022 Spirit Airlines · NK 2056 Depart at 12:30 pm from Orlando (MCO) Fly for 3h 4m Arrive at 2:34 pm in Chicago (ORD)
Fri Dec 16th 2022 Spirit Airlines · NK 111 Depart at 9:50 am from San Juan (SJU) Fly for 3h 9m Arrive at 11:59 am in Orlando (MCO)
Layover in Orlando for 0h 31m
Fri Dec 16th 2022 Spirit Airlines · NK 2056 Depart at 12:30 pm from Orlando (MCO) Fly for 3h 4m Arrive at 2:34 pm in Chicago (ORD)
Sun Dec 18th 2022 Spirit Airlines · NK 111 Depart at 9:50 am from San Juan (SJU) Fly for 3h 9m Arrive at 11:59 am in Orlando (MCO)
Layover in Orlando for 0h 31m
Sun Dec 18th 2022 Spirit Airlines · NK 2056 Depart at 12:30 pm from Orlando (MCO) Fly for 3h 4m Arrive at 2:34 pm in Chicago (ORD)
Sat Dec 17th 2022 Spirit Airlines · NK 2837 Depart at 3:25 pm from San Juan (SJU) Fly for 3h 10m Arrive at 5:35 pm in Orlando (MCO)
Layover in Orlando for 0h 45m
Sat Dec 17th 2022 Spirit Airlines · NK 322 Depart at 6:20 pm from Orlando (MCO) Fly for 3h 4m Arrive at 8:24 pm in Chicago (ORD)
Thu Dec 15th 2022 Spirit Airlines · NK 893 Depart at 1:31 pm from San Juan (SJU) Fly for 3h 11m Arrive at 3:42 pm in Orlando (MCO)
Layover in Orlando for 1h 53m
Thu Dec 15th 2022 Spirit Airlines · NK 912 Depart at 5:35 pm from Orlando (MCO) Fly for 3h 3m Arrive at 7:38 pm in Chicago (ORD)
Fri Dec 16th 2022 Spirit Airlines · NK 893 Depart at 1:31 pm from San Juan (SJU) Fly for 3h 11m Arrive at 3:42 pm in Orlando (MCO)
Layover in Orlando for 1h 53m
Fri Dec 16th 2022 Spirit Airlines · NK 912 Depart at 5:35 pm from Orlando (MCO) Fly for 3h 3m Arrive at 7:38 pm in Chicago (ORD)
Sat Dec 17th 2022 Spirit Airlines · NK 883 Depart at 5:40 am from San Juan (SJU) Fly for 3h 7m Arrive at 7:47 am in Orlando (MCO)
Layover in Orlando for 2h 44m
Sat Dec 17th 2022 Frontier Airlines · F9 1022 Depart at 10:31 am from Orlando (MCO) Fly for 2h 49m Arrive at 12:20 pm in Chicago (MDW)
Mon Dec 19th 2022 Spirit Airlines · NK 111 Depart at 9:50 am from San Juan (SJU) Fly for 3h 9m Arrive at 11:59 am in Orlando (MCO)
Layover in Orlando for 0h 31m
Mon Dec 19th 2022 Spirit Airlines · NK 2056 Depart at 12:30 pm from Orlando (MCO) Fly for 3h 4m Arrive at 2:34 pm in Chicago (ORD)
Sat Dec 17th 2022 Delta Air Lines · DL 1431 Depart at 6:46 pm from San Juan (SJU) Fly for 4h 0m Arrive at 9:46 pm in Atlanta (ATL)
Layover in Atlanta for 0h 57m
Sat Dec 17th 2022 Delta Air Lines · DL 2976 Depart at 10:43 pm from Atlanta (ATL) Fly for 1h 53m Arrive at 11:36 pm in Chicago (ORD)
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Tips to help you find the cheapest flights from Puerto Rico to Chicago (PR to CHI).
As someone who works remotely & travels frequently, I always book one way flights and I'm flexible on my departure dates. I look for the best deals. Most sites require you to enter a specific departure date and clutter the page with uneccessary options, images and ads. I want something simple and minimal which allows me to search by departure date range & display a list of flights with the ability to filter according to my needs. So, I built FlightList to solve my own problem & help other travelers who may have the same frustration. It's how I imagine a flight booking site should be.