Flights from St. John s to Chicago (YYT to ORD)

Discover more affordable dates and routes for flights from St. John s to Chicago (YYT to ORD) within a date range.

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US$342

1:15pm - 4:12pm
Mon Sep 15th 2025

29h 27m
St. John s (YYT) → Chicago (ORD)

3 Stops

Mon Sep 15th 2025 Porter Airlines · PD 296 Depart at 1:15pm from St. John s (YYT) Fly for 3h 1m Arrive at 2:46pm in Ottawa (YOW)

Layover in Ottawa for 1h 19m

Mon Sep 15th 2025 Porter Airlines · PD 2339 Depart at 4:05pm from Ottawa (YOW) Fly for 1h 35m Arrive at 5:40pm in New York (EWR)

Layover in New York for 12h 22m

Tue Sep 16th 2025 Spirit Airlines · NK 1299 Depart at 6:02am from New York (EWR) Fly for 2h 52m Arrive at 8:54am in Orlando (MCO)

Layover in Orlando for 5h 13m

Tue Sep 16th 2025 Spirit Airlines · NK 2410 Depart at 2:07pm from Orlando (MCO) Fly for 3h 5m Arrive at 4:12pm in Chicago (ORD)
US$342

1:15pm - 5:39pm
Mon Sep 15th 2025

30h 54m
St. John s (YYT) → Chicago (ORD)

3 Stops

Mon Sep 15th 2025 Porter Airlines · PD 296 Depart at 1:15pm from St. John s (YYT) Fly for 3h 1m Arrive at 2:46pm in Ottawa (YOW)

Layover in Ottawa for 1h 19m

Mon Sep 15th 2025 Porter Airlines · PD 2339 Depart at 4:05pm from Ottawa (YOW) Fly for 1h 35m Arrive at 5:40pm in New York (EWR)

Layover in New York for 16h 25m

Tue Sep 16th 2025 Spirit Airlines · NK 3124 Depart at 10:05am from New York (EWR) Fly for 3h 13m Arrive at 1:18pm in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 1h 56m

Tue Sep 16th 2025 Spirit Airlines · NK 1225 Depart at 3:14pm from Fort Lauderdale (FLL) Fly for 3h 25m Arrive at 5:39pm in Chicago (ORD)
US$346

3:40pm - 9:58pm
Mon Sep 15th 2025

32h 48m
St. John s (YYT) → Chicago (ORD)

1 Stop

Mon Sep 15th 2025 WestJet · WS 1948 Depart at 3:40pm from St. John s (YYT) Fly for 5h 9m Arrive at 7:19pm in Orlando (MCO)

Layover in Orlando for 24h 31m

Tue Sep 16th 2025 Spirit Airlines · NK 341 Depart at 7:50pm from Orlando (MCO) Fly for 3h 8m Arrive at 9:58pm in Chicago (ORD)
US$358

1:15pm - 5:39pm
Mon Sep 15th 2025

30h 54m
St. John s (YYT) → Chicago (ORD)

3 Stops

Mon Sep 15th 2025 Porter Airlines · PD 296 Depart at 1:15pm from St. John s (YYT) Fly for 3h 1m Arrive at 2:46pm in Ottawa (YOW)

Layover in Ottawa for 1h 19m

Mon Sep 15th 2025 Porter Airlines · PD 2339 Depart at 4:05pm from Ottawa (YOW) Fly for 1h 35m Arrive at 5:40pm in New York (EWR)

Layover in New York for 11h 35m

Tue Sep 16th 2025 Spirit Airlines · NK 540 Depart at 5:15am from New York (EWR) Fly for 2h 27m Arrive at 7:42am in Atlanta (ATL)

Layover in Atlanta for 8h 37m

Tue Sep 16th 2025 Frontier Airlines · F9 1595 Depart at 4:19pm from Atlanta (ATL) Fly for 2h 20m Arrive at 5:39pm in Chicago (ORD)
US$361

3:40pm - 4:12pm
Mon Sep 15th 2025

27h 2m
St. John s (YYT) → Chicago (ORD)

1 Stop

Mon Sep 15th 2025 WestJet · WS 1948 Depart at 3:40pm from St. John s (YYT) Fly for 5h 9m Arrive at 7:19pm in Orlando (MCO)

Layover in Orlando for 18h 48m

Tue Sep 16th 2025 Spirit Airlines · NK 2410 Depart at 2:07pm from Orlando (MCO) Fly for 3h 5m Arrive at 4:12pm in Chicago (ORD)
US$364

3:40pm - 10:52am
Mon Sep 15th 2025

21h 42m
St. John s (YYT) → Chicago (ORD)

2 Stops

Mon Sep 15th 2025 WestJet · WS 1948 Depart at 3:40pm from St. John s (YYT) Fly for 5h 9m Arrive at 7:19pm in Orlando (MCO)

Layover in Orlando for 11h 12m

Tue Sep 16th 2025 Spirit Airlines · NK 2205 Depart at 6:31am from Orlando (MCO) Fly for 1h 9m Arrive at 7:40am in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 0h 47m

Tue Sep 16th 2025 Spirit Airlines · NK 1379 Depart at 8:27am from Fort Lauderdale (FLL) Fly for 3h 25m Arrive at 10:52am in Chicago (ORD)
US$369

5:00am - 10:53am
Mon Sep 15th 2025

8h 23m
St. John s (YYT) → Chicago (ORD)

1 Stop

Mon Sep 15th 2025 United Airlines · UA 8424 Depart at 5:00am from St. John s (YYT) Fly for 3h 30m Arrive at 7:00am in Toronto (YYZ)

Layover in Toronto for 3h 0m

Mon Sep 15th 2025 United Airlines · UA 8278 Depart at 10:00am from Toronto (YYZ) Fly for 1h 53m Arrive at 10:53am in Chicago (ORD)
US$375

1:15pm - 5:39pm
Mon Sep 15th 2025

30h 54m
St. John s (YYT) → Chicago (ORD)

3 Stops

Mon Sep 15th 2025 Porter Airlines · PD 296 Depart at 1:15pm from St. John s (YYT) Fly for 3h 1m Arrive at 2:46pm in Ottawa (YOW)

Layover in Ottawa for 1h 19m

Mon Sep 15th 2025 Porter Airlines · PD 2339 Depart at 4:05pm from Ottawa (YOW) Fly for 1h 35m Arrive at 5:40pm in New York (EWR)

Layover in New York for 12h 30m

Tue Sep 16th 2025 Spirit Airlines · NK 2115 Depart at 6:10am from New York (EWR) Fly for 3h 5m Arrive at 9:15am in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 5h 59m

Tue Sep 16th 2025 Spirit Airlines · NK 1225 Depart at 3:14pm from Fort Lauderdale (FLL) Fly for 3h 25m Arrive at 5:39pm in Chicago (ORD)
US$383

3:40pm - 5:39pm
Mon Sep 15th 2025

28h 29m
St. John s (YYT) → Chicago (ORD)

2 Stops

Mon Sep 15th 2025 WestJet · WS 1948 Depart at 3:40pm from St. John s (YYT) Fly for 5h 9m Arrive at 7:19pm in Orlando (MCO)

Layover in Orlando for 11h 12m

Tue Sep 16th 2025 Spirit Airlines · NK 2205 Depart at 6:31am from Orlando (MCO) Fly for 1h 9m Arrive at 7:40am in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 7h 34m

Tue Sep 16th 2025 Spirit Airlines · NK 1225 Depart at 3:14pm from Fort Lauderdale (FLL) Fly for 3h 25m Arrive at 5:39pm in Chicago (ORD)
US$387

6:00am - 9:58pm
Mon Sep 15th 2025

18h 28m
St. John s (YYT) → Chicago (ORD)

2 Stops

Mon Sep 15th 2025 Porter Airlines · PD 234 Depart at 6:00am from St. John s (YYT) Fly for 3h 32m Arrive at 8:02am in Toronto (YYZ)

Layover in Toronto for 1h 48m

Mon Sep 15th 2025 Porter Airlines · PD 503 Depart at 9:50am from Toronto (YYZ) Fly for 2h 52m Arrive at 12:42pm in Orlando (MCO)

Layover in Orlando for 7h 8m

Mon Sep 15th 2025 Spirit Airlines · NK 341 Depart at 7:50pm from Orlando (MCO) Fly for 3h 8m Arrive at 9:58pm in Chicago (ORD)
US$393

5:40pm - 9:58pm
Mon Sep 15th 2025

30h 48m
St. John s (YYT) → Chicago (ORD)

3 Stops

Mon Sep 15th 2025 Air Transat · TS 7241 Depart at 5:40pm from St. John s (YYT) Fly for 2h 5m Arrive at 7:15pm in Halifax (YHZ)

Layover in Halifax for 11h 15m

Tue Sep 16th 2025 Porter Airlines · PD 200 Depart at 6:30am from Halifax (YHZ) Fly for 2h 26m Arrive at 7:56am in Toronto (YYZ)

Layover in Toronto for 1h 54m

Tue Sep 16th 2025 Porter Airlines · PD 503 Depart at 9:50am from Toronto (YYZ) Fly for 2h 52m Arrive at 12:42pm in Orlando (MCO)

Layover in Orlando for 7h 8m

Tue Sep 16th 2025 Spirit Airlines · NK 341 Depart at 7:50pm from Orlando (MCO) Fly for 3h 8m Arrive at 9:58pm in Chicago (ORD)
US$396

3:40pm - 1:09pm
Mon Sep 15th 2025

23h 59m
St. John s (YYT) → Chicago (ORD)

2 Stops

Mon Sep 15th 2025 WestJet · WS 1948 Depart at 3:40pm from St. John s (YYT) Fly for 5h 9m Arrive at 7:19pm in Orlando (MCO)

Layover in Orlando for 11h 26m

Tue Sep 16th 2025 Spirit Airlines · NK 806 Depart at 6:45am from Orlando (MCO) Fly for 2h 39m Arrive at 8:24am in Houston (IAH)

Layover in Houston for 1h 59m

Tue Sep 16th 2025 Spirit Airlines · NK 690 Depart at 10:23am from Houston (IAH) Fly for 2h 46m Arrive at 1:09pm in Chicago (ORD)
US$405

3:40pm - 10:40am
Mon Sep 15th 2025

21h 30m
St. John s (YYT) → Chicago (ORD)

2 Stops

Mon Sep 15th 2025 WestJet · WS 1948 Depart at 3:40pm from St. John s (YYT) Fly for 5h 9m Arrive at 7:19pm in Orlando (MCO)

Layover in Orlando for 2h 44m

Mon Sep 15th 2025 Spirit Airlines · NK 1810 Depart at 10:03pm from Orlando (MCO) Fly for 2h 56m Arrive at 11:59pm in Dallas (DFW)

Layover in Dallas for 8h 1m

Tue Sep 16th 2025 Frontier Airlines · F9 1342 Depart at 8:00am from Dallas (DFW) Fly for 2h 40m Arrive at 10:40am in Chicago (ORD)
US$408

3:40pm - 4:51pm
Mon Sep 15th 2025

27h 41m
St. John s (YYT) → Chicago (ORD)

2 Stops

Mon Sep 15th 2025 WestJet · WS 1948 Depart at 3:40pm from St. John s (YYT) Fly for 5h 9m Arrive at 7:19pm in Orlando (MCO)

Layover in Orlando for 11h 6m

Tue Sep 16th 2025 Spirit Airlines · NK 800 Depart at 6:25am from Orlando (MCO) Fly for 2h 35m Arrive at 9:00am in New York (LGA)

Layover in New York for 6h 13m

Tue Sep 16th 2025 Spirit Airlines · NK 494 Depart at 3:13pm from New York (LGA) Fly for 2h 38m Arrive at 4:51pm in Chicago (ORD)
US$415

6:25pm - 5:39pm
Mon Sep 15th 2025

25h 44m
St. John s (YYT) → Chicago (ORD)

2 Stops

Mon Sep 15th 2025 Porter Airlines · PD 236 Depart at 6:25pm from St. John s (YYT) Fly for 3h 32m Arrive at 8:27pm in Toronto (YYZ)

Layover in Toronto for 10h 3m

Tue Sep 16th 2025 Flair Airlines · F8 1600 Depart at 6:30am from Toronto (YYZ) Fly for 3h 20m Arrive at 9:50am in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 5h 24m

Tue Sep 16th 2025 Spirit Airlines · NK 1225 Depart at 3:14pm from Fort Lauderdale (FLL) Fly for 3h 25m Arrive at 5:39pm in Chicago (ORD)
US$422

6:00am - 7:44pm
Mon Sep 15th 2025

16h 14m
St. John s (YYT) → Chicago (ORD)

2 Stops

Mon Sep 15th 2025 Porter Airlines · PD 234 Depart at 6:00am from St. John s (YYT) Fly for 3h 32m Arrive at 8:02am in Toronto (YYZ)

Layover in Toronto for 1h 48m

Mon Sep 15th 2025 Porter Airlines · PD 503 Depart at 9:50am from Toronto (YYZ) Fly for 2h 52m Arrive at 12:42pm in Orlando (MCO)

Layover in Orlando for 4h 42m

Mon Sep 15th 2025 Frontier Airlines · F9 3043 Depart at 5:24pm from Orlando (MCO) Fly for 3h 20m Arrive at 7:44pm in Chicago (ORD)
US$423

6:00am - 12:10am
Mon Sep 15th 2025

20h 40m
St. John s (YYT) → Chicago (ORD)

3 Stops

Mon Sep 15th 2025 Porter Airlines · PD 234 Depart at 6:00am from St. John s (YYT) Fly for 3h 32m Arrive at 8:02am in Toronto (YYZ)

Layover in Toronto for 1h 48m

Mon Sep 15th 2025 Porter Airlines · PD 503 Depart at 9:50am from Toronto (YYZ) Fly for 2h 52m Arrive at 12:42pm in Orlando (MCO)

Layover in Orlando for 5h 50m

Mon Sep 15th 2025 Spirit Airlines · NK 2245 Depart at 6:32pm from Orlando (MCO) Fly for 1h 40m Arrive at 8:12pm in Atlanta (ATL)

Layover in Atlanta for 2h 46m

Mon Sep 15th 2025 Frontier Airlines · F9 3397 Depart at 10:58pm from Atlanta (ATL) Fly for 2h 12m Arrive at 12:10am in Chicago (ORD)
US$429

8:45am - 1:14pm
Mon Sep 15th 2025

6h 59m
St. John s (YYT) → Chicago (ORD)

1 Stop

Mon Sep 15th 2025 United Airlines · UA 8654 Depart at 8:45am from St. John s (YYT) Fly for 3h 31m Arrive at 10:46am in Toronto (YYZ)

Layover in Toronto for 1h 34m

Mon Sep 15th 2025 United Airlines · UA 8694 Depart at 12:20pm from Toronto (YYZ) Fly for 1h 54m Arrive at 1:14pm in Chicago (ORD)
US$432

6:25pm - 5:39pm
Mon Sep 15th 2025

25h 44m
St. John s (YYT) → Chicago (ORD)

3 Stops

Mon Sep 15th 2025 Porter Airlines · PD 236 Depart at 6:25pm from St. John s (YYT) Fly for 3h 32m Arrive at 8:27pm in Toronto (YYZ)

Layover in Toronto for 10h 48m

Tue Sep 16th 2025 Porter Airlines · PD 603 Depart at 7:15am from Toronto (YYZ) Fly for 1h 40m Arrive at 8:55am in New York (LGA)

Layover in New York for 2h 4m

Tue Sep 16th 2025 Spirit Airlines · NK 374 Depart at 10:59am from New York (LGA) Fly for 3h 10m Arrive at 2:09pm in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 1h 5m

Tue Sep 16th 2025 Spirit Airlines · NK 1225 Depart at 3:14pm from Fort Lauderdale (FLL) Fly for 3h 25m Arrive at 5:39pm in Chicago (ORD)
US$448

6:25pm - 4:51pm
Mon Sep 15th 2025

24h 56m
St. John s (YYT) → Chicago (ORD)

2 Stops

Mon Sep 15th 2025 Porter Airlines · PD 236 Depart at 6:25pm from St. John s (YYT) Fly for 3h 32m Arrive at 8:27pm in Toronto (YYZ)

Layover in Toronto for 10h 48m

Tue Sep 16th 2025 Porter Airlines · PD 603 Depart at 7:15am from Toronto (YYZ) Fly for 1h 40m Arrive at 8:55am in New York (LGA)

Layover in New York for 6h 18m

Tue Sep 16th 2025 Spirit Airlines · NK 494 Depart at 3:13pm from New York (LGA) Fly for 2h 38m Arrive at 4:51pm in Chicago (ORD)
US$462

6:00am - 10:48pm
Mon Sep 15th 2025

19h 18m
St. John s (YYT) → Chicago (ORD)

2 Stops

Mon Sep 15th 2025 Porter Airlines · PD 234 Depart at 6:00am from St. John s (YYT) Fly for 3h 32m Arrive at 8:02am in Toronto (YYZ)

Layover in Toronto for 5h 28m

Mon Sep 15th 2025 WestJet · WS 1232 Depart at 1:30pm from Toronto (YYZ) Fly for 3h 19m Arrive at 4:49pm in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 3h 36m

Mon Sep 15th 2025 Spirit Airlines · NK 2 Depart at 8:25pm from Fort Lauderdale (FLL) Fly for 3h 23m Arrive at 10:48pm in Chicago (ORD)
US$466

6:00am - 11:20pm
Mon Sep 15th 2025

19h 50m
St. John s (YYT) → Chicago (ORD)

3 Stops

Mon Sep 15th 2025 Porter Airlines · PD 234 Depart at 6:00am from St. John s (YYT) Fly for 3h 32m Arrive at 8:02am in Toronto (YYZ)

Layover in Toronto for 1h 48m

Mon Sep 15th 2025 Porter Airlines · PD 503 Depart at 9:50am from Toronto (YYZ) Fly for 2h 52m Arrive at 12:42pm in Orlando (MCO)

Layover in Orlando for 4h 45m

Mon Sep 15th 2025 Spirit Airlines · NK 2022 Depart at 5:27pm from Orlando (MCO) Fly for 2h 20m Arrive at 7:47pm in Washington, D.C. (BWI)

Layover in Washington, D.C. for 2h 12m

Mon Sep 15th 2025 Frontier Airlines · F9 4063 Depart at 9:59pm from Washington, D.C. (BWI) Fly for 2h 21m Arrive at 11:20pm in Chicago (ORD)
US$477

6:25pm - 4:12pm
Mon Sep 15th 2025

24h 17m
St. John s (YYT) → Chicago (ORD)

2 Stops

Mon Sep 15th 2025 Porter Airlines · PD 236 Depart at 6:25pm from St. John s (YYT) Fly for 3h 32m Arrive at 8:27pm in Toronto (YYZ)

Layover in Toronto for 10h 48m

Tue Sep 16th 2025 WestJet · WS 1226 Depart at 7:15am from Toronto (YYZ) Fly for 2h 54m Arrive at 10:09am in Orlando (MCO)

Layover in Orlando for 3h 58m

Tue Sep 16th 2025 Spirit Airlines · NK 2410 Depart at 2:07pm from Orlando (MCO) Fly for 3h 5m Arrive at 4:12pm in Chicago (ORD)
US$485

6:00am - 11:59pm
Mon Sep 15th 2025

20h 29m
St. John s (YYT) → Chicago (ORD)

3 Stops

Mon Sep 15th 2025 Porter Airlines · PD 234 Depart at 6:00am from St. John s (YYT) Fly for 3h 32m Arrive at 8:02am in Toronto (YYZ)

Layover in Toronto for 1h 48m

Mon Sep 15th 2025 Porter Airlines · PD 503 Depart at 9:50am from Toronto (YYZ) Fly for 2h 52m Arrive at 12:42pm in Orlando (MCO)

Layover in Orlando for 3h 4m

Mon Sep 15th 2025 Frontier Airlines · F9 4919 Depart at 3:46pm from Orlando (MCO) Fly for 4h 9m Arrive at 5:55pm in Denver (DEN)

Layover in Denver for 2h 35m

Mon Sep 15th 2025 Frontier Airlines · F9 3172 Depart at 8:30pm from Denver (DEN) Fly for 2h 29m Arrive at 11:59pm in Chicago (ORD)
US$607

7:10pm - 4:51pm
Mon Sep 15th 2025

24h 11m
St. John s (YYT) → Chicago (ORD)

3 Stops

Mon Sep 15th 2025 PAL Airlines · PB 927 Depart at 7:10pm from St. John s (YYT) Fly for 1h 15m Arrive at 8:25pm in Deer Lake (YDF)

Layover in Deer Lake for 9h 0m

Tue Sep 16th 2025 Air Canada · AC 1547 Depart at 5:25am from Deer Lake (YDF) Fly for 3h 10m Arrive at 7:05am in Toronto (YYZ)

Layover in Toronto for 2h 10m

Tue Sep 16th 2025 Air Canada · AC 704 Depart at 9:15am from Toronto (YYZ) Fly for 1h 34m Arrive at 10:49am in New York (LGA)

Layover in New York for 4h 24m

Tue Sep 16th 2025 Spirit Airlines · NK 494 Depart at 3:13pm from New York (LGA) Fly for 2h 38m Arrive at 4:51pm in Chicago (ORD)
US$645

1:15pm - 9:08am
Mon Sep 15th 2025

22h 23m
St. John s (YYT) → Chicago (ORD)

3 Stops

Mon Sep 15th 2025 Porter Airlines · PD 296 Depart at 1:15pm from St. John s (YYT) Fly for 3h 1m Arrive at 2:46pm in Ottawa (YOW)

Layover in Ottawa for 3h 44m

Mon Sep 15th 2025 Porter Airlines · PD 285 Depart at 6:30pm from Ottawa (YOW) Fly for 4h 25m Arrive at 8:55pm in Edmonton (YEG)

Layover in Edmonton for 3h 50m

Tue Sep 16th 2025 Air Canada · AC 178 Depart at 12:45am from Edmonton (YEG) Fly for 3h 46m Arrive at 6:31am in Toronto (YYZ)

Layover in Toronto for 1h 44m

Tue Sep 16th 2025 Air Canada · AC 8901 Depart at 8:15am from Toronto (YYZ) Fly for 1h 53m Arrive at 9:08am in Chicago (ORD)
US$747

1:15pm - 10:07pm
Mon Sep 15th 2025

11h 22m
St. John s (YYT) → Chicago (ORD)

2 Stops

Mon Sep 15th 2025 Porter Airlines · PD 296 Depart at 1:15pm from St. John s (YYT) Fly for 3h 1m Arrive at 2:46pm in Ottawa (YOW)

Layover in Ottawa for 3h 9m

Mon Sep 15th 2025 Air Canada · AC 465 Depart at 5:55pm from Ottawa (YOW) Fly for 1h 8m Arrive at 7:03pm in Toronto (YYZ)

Layover in Toronto for 1h 57m

Mon Sep 15th 2025 Air Canada · AC 4961 Depart at 9:00pm from Toronto (YYZ) Fly for 2h 7m Arrive at 10:07pm in Chicago (ORD)

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

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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 St. John s to Chicago (YYT to ORD)

Sarah Belizaire

John Ford

Roaming Sonaa

Andy Travels

Travel With Bender

Wesley Mergard

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