Cheap Flights from Toronto, ON to Chicago, IL from $151

Return flight: Chicago – Toronto

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

To find the cheapest one way airline ticket select the date with the lowest price on the calendar below and click «Find Flights». To search for round-trip flight deals click on the link «Check prices for return flights» and select the date of the return flight. Cheapest flights in November: $151 (one-way), $259 (round-trip).
Direct flights
  • Check to choose departure date Check to choose departure date
Check prices for return flight
Find flights
Full flight schedule will help you in detecting at what time planes fly from Toronto to Chicago. You can also specify the concrete flights and airlines on the route and how long the flight actually is. Use the calendar for today, tomorrow or other specific date as some flights are available only on certain days of the week.
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
*Departure and arrival times - local. Updated on February 8, 2025

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.

Economy class
$151
Find
Business class
?
Find
First class
?
Find

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.

See more direct flights

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.

See more connecting flights

Airports

You can fly from Toronto to Chicago from 3 airports (Buttonville Municipal, Toronto Island, Pearson International).

Toronto airports

  • Buttonville Municipal-YKZ
    Find
  • Toronto Island-YTZ
    from $151
    Find
  • Pearson International-YYZ
    from $155
    Find

Chicago airports

  • O'Hare International-ORD
    Find
  • Midway-MDW
    Find
  • Dupage County-DPA
    Find
  • Chicago FSS-CHI
    Find
  • Merrill C Meigs (closed)-CGX
    Find
  • Pal-Waukee-PWK
    Find
  • Chicago NAS-NOH
    Find

How to book a plane ticket yourself?

How to book an air 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.

Back