Cheap Flights from Toronto, ON to Chicago, IL from $151
On Cheapflightsplus.com you will find 9 direct and 47 connecting flights from Toronto to Chicago. You can compare airfare deals from 5 airlines and multiple travel sites from $151, book and save on cheap plane tickets and last minute offers. Also check out YTO-CHI flight schedule to find best flight time, convenient departure and arrival airports.
Find One-Way and Round-Trip Toronto to Chicago Flight Deals
Best Flights from Toronto to Chicago Today
Price | Departure | Arrival | Flight Duration | Airline | Flight |
---|---|---|---|---|---|
from $151 | 11:20 Toronto Toronto Island | 12:10 Chicago Midway | 1h 50m | Porter Airlines | PD2387 |
from $174 | 11:10 Toronto Toronto Island | 12:00 Chicago Midway | 1h 50m | Air Transat | TS7060 |
from $181 | 11:00 Toronto Pearson International | 12:09 Chicago O'Hare International | 2h 9m | United Airlines | UA3556 |
from $276 | 06:52 Toronto Pearson International | 08:01 Chicago O'Hare International | 2h 9m | United Airlines | UA5345 |
from $339 | 12:20 Toronto Pearson International | 13:11 Chicago O'Hare International | 1h 51m | United Airlines | UA8694 |
from $155 | 07:15 Toronto Pearson International | 15:33 Chicago O'Hare International | 9h 18m layover 2h 45m - Fort Myers | Porter Airlines | PD535 NK528 |
from $186 | 08:35 Toronto Pearson International | 17:02 Chicago O'Hare International | 9h 27m layover 3h 4m - Fort Myers | WestJet | WS1236 NK2930 |
from $189 | 16:55 Toronto Pearson International | 15:33+1 день Chicago O'Hare International | 23h 38m layover 17h 8m - Fort Myers | WestJet | WS1172 NK528 |
from $197 | 16:30 Toronto Pearson International | 20:24 Chicago O'Hare International | 4h 54m layover 0h 53m - Washington D.C. | United Airlines | UA8548 UA1748 |
from $197 | 09:30 Toronto Pearson International | 14:40 Chicago O'Hare International | 6h 10m layover 1h 45m - Newark | United Airlines | UA3701 UA1946 |
from $197 | 07:45 Toronto Pearson International | 13:11 Chicago O'Hare International | 6h 26m layover 2h 0m - Newark | United Airlines | UA3435 UA1875 |
from $197 | 07:15 Toronto Pearson International | 13:11 Chicago O'Hare International | 6h 56m layover 2h 31m - Newark | United Airlines | UA3607 UA1875 |
from $197 | 21:00 Toronto Pearson International | 07:40+1 день Chicago O'Hare International | 11h 40m layover 7h 43m - Washington D.C. | United Airlines | UA8556 UA1793 |
from $203 | 07:15 Toronto Pearson International | 15:33 Chicago O'Hare International | 9h 18m layover 2h 45m - Fort Myers | Air Transat | TS7462 NK528 |
from $208 | 19:55 Toronto Pearson International | 09:55+1 день Chicago O'Hare International | 15h 0m layover 6h 29m - Tampa 1h 7m - Miami | Porter Airlines | PD527 NK1955 NK2 |
from $253 | 20:00 Toronto Pearson International | 11:52+2 дня Chicago Midway | 40h 52m layover 15h 19m - Las Vegas 15h 48m - Denver | WestJet | WS1118 F92430 F92210 |
Flight Schedule Toronto (Ontario) to Chicago (Illinois)
Departure | Arrival | Flight Details | Flight Duration | Price |
---|---|---|---|---|
06:52 — 08:01
|
06:52 — 08:01
UA5345
United Airlines
Toronto — Chicago
|
2h 9m |
Find flight
from$276 |
|
09:00 — 10:04
|
09:00 — 10:04
UA1538
United Airlines
Toronto — Chicago
|
2h 4m |
Find flight
from$339 |
|
11:00 — 12:09
|
11:00 — 12:09
UA3556
United Airlines
Toronto — Chicago
|
2h 9m |
Find flight
from$181 |
|
11:10 — 12:00
|
11:10 — 12:00
TS7060
Air Transat
Toronto — Chicago
|
1h 50m |
Find flight
from$174 |
|
11:20 — 12:10
|
11:20 — 12:10
PD2387
Porter Airlines
Toronto — Chicago
|
1h 50m |
Find flight
from$151 |
|
12:20 — 13:11
|
12:20 — 13:11
UA8694
United Airlines
Toronto — Chicago
|
1h 51m |
Find flight
from$339 |
|
14:00 — 14:51
|
14:00 — 14:51
UA8307
United Airlines
Toronto — Chicago
|
1h 51m |
Find flight
from$339 |
|
18:40 — 19:37
|
18:40 — 19:37
UA8293
United Airlines
Toronto — Chicago
|
1h 57m |
Find flight
from$339 |
|
21:00 — 22:06
|
21:00 — 22:06
UA5728
United Airlines
Toronto — Chicago
|
2h 6m |
Find flight
from$339 |
|
06:15 — 09:00
|
06:00 — 07:41
WS6342
WestJet
Toronto — Detroit
30m stop
08:40 — 09:16
WS7062
WestJet
Detroit — Chicago
|
3h 45m including layover |
Find flight
from$227 |
|
07:15 — 15:33
|
07:15 — 10:35
PD535
Porter Airlines
Toronto — Fort Myers
2h 45m stop
13:20 — 15:33
NK528
Spirit Airlines
Fort Myers — Chicago
|
9h 18m including layover |
Find flight
from$155 |
|
07:15 — 17:02
|
07:15 — 10:35
PD535
Porter Airlines
Toronto — Fort Myers
4h 25m stop
15:00 — 17:02
NK2930
Spirit Airlines
Fort Myers — Chicago
|
10h 47m including layover |
Find flight
from$155 |
|
08:00 — 12:05
|
08:00 — 09:14
UA8697
United Airlines
Toronto — Nashville
51m stop
10:05 — 12:05
UA5338
United Airlines
Nashville — Chicago
|
5h 5m including layover |
Find flight
from$573 |
|
08:35 — 17:02
|
08:35 — 11:56
WS1236
WestJet
Toronto — Fort Myers
3h 4m stop
15:00 — 17:02
NK2930
Spirit Airlines
Fort Myers — Chicago
|
9h 27m including layover |
Find flight
from$186 |
|
09:30 — 14:40
|
09:30 — 11:13
UA3701
United Airlines
Toronto — Newark
1h 45m stop
12:58 — 14:40
UA1946
United Airlines
Newark — Chicago
|
6h 10m including layover |
Find flight
from$197 |
|
10:00 — 14:03
|
10:00 — 11:39
UA3636
United Airlines
Toronto — Washington D.C.
1h 6m stop
12:45 — 14:03
UA1709
United Airlines
Washington D.C. — Chicago
|
5h 3m including layover |
Find flight
from$293 |
|
12:25 — 20:40
|
12:25 — 15:50
PD515
Porter Airlines
Toronto — Miami
2h 30m stop
18:20 — 20:40
NK3
Spirit Airlines
Miami — Chicago
|
9h 15m including layover |
Find flight
from$302 |
|
12:45 — 18:55
|
12:45 — 14:29
UA3649
United Airlines
Toronto — Newark
2h 41m stop
17:10 — 18:55
UA661
United Airlines
Newark — Chicago
|
7h 10m including layover |
Find flight
from$293 |
|
15:00 — 22:52
|
15:00 — 16:30
PD2137
Porter Airlines
Toronto — Newark
4h 45m stop
22:55 — 00:34
NK329
Spirit Airlines
Newark — Chicago
|
8h 52m including layover |
Find flight
from$227 |
|
15:00 — 22:52
|
15:00 — 16:30
TS7363
Air Transat
Toronto — Newark
4h 45m stop
22:55 — 00:34
NK329
Spirit Airlines
Newark — Chicago
|
8h 52m including layover |
Find flight
from$254 |
|
16:30 — 20:24
|
16:30 — 18:07
UA8548
United Airlines
Toronto — Washington D.C.
53m stop
19:00 — 20:24
UA1748
United Airlines
Washington D.C. — Chicago
|
4h 54m including layover |
Find flight
from$197 |
|
16:55 — 15:33
+1 day
|
16:55 — 20:12
WS1172
WestJet
Toronto — Fort Myers
17h 8m stop
13:20 — 15:33
NK528
Spirit Airlines
Fort Myers — Chicago
|
23h 38m including layover |
Find flight
from$189 |
|
19:55 — 14:02
+1 day
|
19:55 — 23:01
TS7481
Air Transat
Toronto — Tampa
13h 18m stop
12:19 — 14:02
F91185
Frontier Airlines
Tampa — Chicago
|
19h 7m including layover |
Find flight
from$209 |
|
20:00 — 06:33
+1 day
|
20:00 — 22:09
WS1118
WestJet
Toronto — Las Vegas
2h 46m stop
06:11 — 11:48
F92330
Frontier Airlines
Las Vegas — Chicago
|
11h 33m including layover |
Find flight
from$236 |
|
21:00 — 07:40
+1 day
|
21:00 — 22:37
UA8556
United Airlines
Toronto — Washington D.C.
7h 43m stop
06:30 — 07:42
UA1793
United Airlines
Washington D.C. — Chicago
|
11h 40m including layover |
Find flight
from$197 |
|
10:20 — 23:42
|
10:20 — 13:05
PD681
Porter Airlines
Toronto — San Diego
2h 5m stop
15:10 — 16:33
NK3792
Spirit Airlines
San Diego — Las Vegas
1h 22m stop
17:55 — 23:42
NK184
Spirit Airlines
Las Vegas — Chicago
|
14h 22m including layover |
Find flight
from$318 |
|
14:00 — 22:52
|
14:00 — 15:12
PD163
Porter Airlines
Toronto — Ottawa
2h 10m stop
17:20 — 18:50
PD2339
Porter Airlines
Ottawa — Newark
2h 25m stop
22:55 — 00:34
NK329
Spirit Airlines
Newark — Chicago
|
9h 52m including layover |
Find flight
from$238 |
|
19:55 — 09:55
+1 day
|
19:55 — 23:01
PD527
Porter Airlines
Toronto — Tampa
6h 29m stop
05:30 — 06:33
NK1955
Spirit Airlines
Tampa — Miami
1h 7m stop
07:40 — 09:55
NK2
Spirit Airlines
Miami — Chicago
|
15h including layover |
Find flight
from$208 |
|
20:00 — 11:52
+2 days
|
20:00 — 22:13
WS1118
WestJet
Toronto — Las Vegas
15h 19m stop
13:32 — 16:42
F92430
Frontier Airlines
Las Vegas — Denver
15h 48m stop
08:30 — 11:52
F92210
Frontier Airlines
Denver — Chicago
|
40h 52m including layover |
Find flight
from$253 |
|
22:35 — 14:55
+1 day
|
22:35 — 01:02
WS679
WestJet
Toronto — Calgary
6h 43m stop
07:45 — 11:41
WS6392
WestJet
Calgary — Minneapolis
1h 42m stop
13:23 — 14:55
WS7775
WestJet
Minneapolis — Chicago
|
17h 20m including layover |
Find flight
from$256 |
|
22:40 — 04:47
+2 days
|
22:40 — 01:08
WS731
WestJet
Toronto — Vancouver
16h 28m stop
17:30 — 20:15
WS1790
WestJet
Vancouver — Las Vegas
2h 43m stop
11:37 — 17:28
F92146
Frontier Airlines
Las Vegas — Chicago
|
31h 7m including layover |
Find flight
from$259 |
|
23:00 — 22:52
+1 day
|
23:00 — 00:09
WS374
WestJet
Toronto — Ottawa
9h 51m stop
10:00 — 11:30
PD2323
Porter Airlines
Ottawa — Newark
9h 45m stop
21:15 — 22:52
NK329
Spirit Airlines
Newark — Chicago
|
24h 52m including layover |
Find flight
from$272 |
|
23:15 — 13:14
+1 day
|
23:15 — 00:39
WS598
WestJet
Toronto — Montreal
6h 21m stop
07:00 — 09:22
WS6331
WestJet
Montreal — Detroit
3h 18m stop
12:40 — 13:14
WS7701
WestJet
Detroit — Chicago
|
14h 59m including layover |
Find flight
from$284 |
Flight Information
Below we will explain in detail what the flights cost on the destination from Toronto to Chicago depends on and how to choose the most interesting flight option for you.
Distance between Toronto and Chicago is 701 miles. Time difference between the cities is 1h. Airplanes depart 06:15 to 23:15 from 3 Toronto airports and arrive 06:15 to 23:15 to 7 Chicago airports. Average flight time is 1h 57m.
- The fastest flight 1h 50m
- Average flight time 1h 57m
- The earliest flight 06:15
- The latest flight 23:15
- Distance 436 ml
The cheapest months to travel to Chicago are february (from 76 $), january (from 120 $), december (from 127 $).
The most expensive months are november (from 146 $), december (from 127 $), january (from 120 $).
What is the lowest airfare Toronto to Chicago?
The cheapest plane ticket found by our users is $151. This airfare is for economy class on one-way PD2387 flight by Porter Airlines for February 21, 2025 which leaves Toronto Island in Toronto at 11:20 am and arrives at Chicago Midway at 12:10.
Popular Airlines on the Route
The flight Toronto — Chicago is served by 5 regular airlines and 3 low-cost airlines. Most of the flights on this route are operated by Air Canada - 1 departures per week at the price of from $ 420 . And the most expensive tickets are offered by WestJet airline - from $ 642.
Direct flights
There are 9 nonstop flights on the route. The fastest direct flight is PD2387 by Porter Airlines takes 1h 50m and the cheapest is PD2387 by Porter Airlines for $151.
- from $151Find
- from $181Find
- TS - Air Transatfrom $174Find
Connecting Flights
There are 47 flights with layovers on the route. The fastest connecting flight is WS6342 by WestJet takes 3h 45m and the cheapest is PD2387 by Porter Airlines for $155.
- from $420Find
- from $155Find
- from $186Find
- from $197Find
- TS - Air Transatfrom $203Find
Airports
You can fly from Toronto to Chicago from 3 airports (Buttonville Municipal, Toronto Island, Pearson International).
Toronto airports
- Buttonville Municipal-YKZFind
- Toronto Island-YTZfrom $151Find
- Pearson International-YYZfrom $155Find
Chicago airports
- O'Hare International-ORDFind
- Midway-MDWFind
- Dupage County-DPAFind
- Chicago FSS-CHIFind
- Merrill C Meigs (closed)-CGXFind
- Pal-Waukee-PWKFind
- Chicago NAS-NOHFind
Airplanes
There are flights to Chicago from Toronto by 5 airlines that use 1 aircraft brands. They range from huge modern airplanes to small-sized.
- Embraer 175from $339Find
Top International Destinations from Toronto
Our state-of-the art metasearch will definitely provide you with the best airfare on international flights. We’re proud to partner with many reliable travel suppliers located outside the US what gives us an opportunity to offer the most competitive prices on far destinations.
- from $73Find
- from $72Find
- from $54Find
- from $78Find
- from $62Find
- from $66Find
- from $73Find
- from $65Find
- from $64Find
- from $77Find
How to book a plane ticket yourself?

- Fill in the search parameters — cities of departure and destination, departure and return dates and click «Find flights»
- Select the best flight that you like. Please, check the airports of departure and arrival. Select the best fare, but pay attention to the following flight details - airports of departure and arrival, flight duration and layovers. Please use filters and sort to find the best flight.
- Click «Buy» when you are ready — our system will redirect you to the site that sells the selected flight ticket.
- Fill in all passenger and payment information — passport and contact information, please double check all passengers’ names and make a payment for your itinerary.
- That's it — you will receive an email with your e-ticket usually within 10 minutes after your flight is confirmed. Please, print the e-ticket and have it with you at the airport. You would need to have only a passport and/or a required form of ID to travel. Please, check your Visa requirements if you travel outside of the United States or Canada.
To find a plane ticket, please select dates.