Cheap Flights from Toronto, ON to Chicago, IL from $84

Return flight: Chicago – Toronto

On Cheapflightsplus.com you will find 9 direct and 56 connecting flights from Toronto to Chicago. You can compare airfare deals from 9 airlines and multiple travel sites from $84, 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: $84 (one-way), $144 (round-trip).
Direct flights
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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
11:00 — 12:01
11:00 — 12:01 UA3499 United Airlines
Toronto — Chicago
2h 1m
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from$209
12:20 — 13:13
12:20 — 13:13 UA8694 United Airlines
Toronto — Chicago
1h 53m
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from$127
13:00 — 14:01
13:00 — 14:01 UA3605 United Airlines
Toronto — Chicago
2h 1m
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from$98
14:10 — 15:04
14:10 — 15:04 UA8307 United Airlines
Toronto — Chicago
1h 54m
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from$98
15:35 — 16:24
15:35 — 16:24 PD2393 Porter Airlines
Toronto — Chicago
1h 49m
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from$84
15:35 — 16:24
15:35 — 16:24 TS7314 Air Transat
Toronto — Chicago
1h 49m
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from$126
17:15 — 18:15
17:15 — 18:15 UA1371 United Airlines
Toronto — Chicago
2h
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from$127
18:35 — 19:29
18:35 — 19:29 UA8293 United Airlines
Toronto — Chicago
1h 54m
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from$98
21:00 — 22:05
21:00 — 22:05 UA3640 United Airlines
Toronto — Chicago
2h 5m
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from$203
06:15 — 14:19
06:15 — 08:37 WS8135 WestJet
Toronto — Atlanta
4h 34m stop
13:11 — 14:19 WS7273 WestJet
Atlanta — Chicago
9h 4m
including layover
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from$259
06:30 — 12:02
06:30 — 07:45 WS6353 WestJet
Toronto — Minneapolis
2h 50m stop
10:35 — 12:02 WS7997 WestJet
Minneapolis — Chicago
6h 32m
including layover
Find flight
from$288
07:15 — 20:00
07:15 — 08:55 PD603 Porter Airlines
Toronto — New York
9h 35m stop
18:30 — 20:00 NK1179 Spirit Airlines
New York — Chicago
13h 45m
including layover
Find flight
from$213
08:10 — 14:33
08:10 — 09:39 UA8271 United Airlines
Toronto — Washington D.C.
3h 43m stop
13:20 — 14:33 UA2331 United Airlines
Washington D.C. — Chicago
7h 23m
including layover
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from$137
09:45 — 20:00
09:45 — 11:15 PD2127 Porter Airlines
Toronto — New York
7h 15m stop
18:30 — 20:00 NK1179 Spirit Airlines
New York — Chicago
11h 15m
including layover
Find flight
from$209
12:15 — 16:52
12:10 — 13:41 UA8670 United Airlines
Toronto — Washington D.C.
1h 57m stop
15:35 — 16:48 UA1057 United Airlines
Washington D.C. — Chicago
5h 37m
including layover
Find flight
from$226
13:20 — 18:49
13:20 — 15:44 WS7106 WestJet
Toronto — Atlanta
1h 45m stop
17:29 — 18:49 WS6651 WestJet
Atlanta — Chicago
6h 29m
including layover
Find flight
from$239
14:50 — 20:00
14:50 — 16:30 PD605 Porter Airlines
Toronto — New York
2h stop
18:30 — 20:00 NK1179 Spirit Airlines
New York — Chicago
6h 10m
including layover
Find flight
from$213
16:00 — 15:06
+1 day
16:00 — 18:54 WS1224 WestJet
Toronto — Orlando
18h 15m stop
18:20 — 20:17 F93853 Frontier Airlines
Orlando — Chicago
24h 6m
including layover
Find flight
from$428
18:05 — 13:50
+1 day
18:05 — 06:15 AY5992 Finnair
Toronto — London
4h 50m stop
11:05 — 13:50 AY5535 Finnair
London — Chicago
20h 45m
including layover
Find flight
from$3463
20:05 — 06:03
+1 day
20:05 — 21:55 PD655 Porter Airlines
Toronto — Las Vegas
2h 39m stop
00:34 — 06:03 NK1053 Spirit Airlines
Las Vegas — Chicago
10h 58m
including layover
Find flight
from$259
20:05 — 06:03
+1 day
20:05 — 21:58 TS7230 Air Transat
Toronto — Las Vegas
2h 39m stop
00:34 — 06:03 NK1053 Spirit Airlines
Las Vegas — Chicago
10h 58m
including layover
Find flight
from$282
21:10 — 07:38
+1 day
21:10 — 22:47 UA8266 United Airlines
Toronto — Newark
7h 12m stop
06:00 — 07:38 UA2164 United Airlines
Newark — Chicago
11h 28m
including layover
Find flight
from$114
07:00 — 20:00
07:00 — 07:58 PD2205 Porter Airlines
Toronto — Ottawa
2h 57m stop
11:00 — 12:30 PD2335 Porter Airlines
Ottawa — New York
6h stop
18:30 — 20:00 NK1179 Spirit Airlines
New York — Chicago
14h
including layover
Find flight
from$219
08:30 — 23:53
08:30 — 10:00 PD2123 Porter Airlines
Toronto — Newark
7h 23m stop
17:23 — 20:35 NK1218 Spirit Airlines
Newark — Miami
55m stop
21:30 — 23:53 NK1219 Spirit Airlines
Miami — Chicago
16h 23m
including layover
Find flight
from$566
09:30 — 15:31
+1 day
09:30 — 10:28 PD2219 Porter Airlines
Toronto — Ottawa
5h 57m stop
16:25 — 19:44 PD505 Porter Airlines
Ottawa — Orlando
17h 39m stop
13:23 — 15:31 NK1369 Spirit Airlines
Orlando — Chicago
31h 1m
including layover
Find flight
from$401
11:40 — 09:41
+1 day
11:40 — 12:53 SY1918 Sun Country Airlines
Toronto — Minneapolis
6h 57m stop
19:50 — 23:08 G4246 Allegiant Air
Minneapolis — Fletcher
9h 52m stop
09:00 — 09:41 G41848 Allegiant Air
Fletcher — Chicago
23h 1m
including layover
Find flight
from$355
16:00 — 11:41
+1 day
16:00 — 18:55 WS1224 WestJet
Toronto — Orlando
2h 4m stop
20:59 — 23:11 F93311 Frontier Airlines
Orlando — Denver
9h 4m stop
08:15 — 11:41 F92210 Frontier Airlines
Denver — Chicago
20h 41m
including layover
Find flight
from$750
17:15 — 07:04
+1 day
17:15 — 18:45 PD2141 Porter Airlines
Toronto — Newark
3h 15m stop
22:00 — 00:32 NK1212 Spirit Airlines
Newark — Atlanta
5h 28m stop
06:00 — 07:04 NK1116 Spirit Airlines
Atlanta — Chicago
14h 49m
including layover
Find flight
from$566
22:25 — 17:39
+1 day
22:25 — 00:44 WS679 WestJet
Toronto — Calgary
9h 46m stop
10:30 — 14:07 WS1610 WestJet
Calgary — Minneapolis
1h 58m stop
16:05 — 17:39 WS8011 WestJet
Minneapolis — Chicago
20h 14m
including layover
Find flight
from$960
22:30 — 13:06
+1 day
22:30 — 00:13 WS535 WestJet
Toronto — Winnipeg
8h 22m stop
08:35 — 10:05 WS5407 WestJet
Winnipeg — Minneapolis
1h 22m stop
11:27 — 13:06 WS8687 WestJet
Minneapolis — Chicago
15h 36m
including layover
Find flight
from$972
23:05 — 21:16
+1 day
23:05 — 00:27 WS598 WestJet
Toronto — Montreal
9h 33m stop
10:00 — 14:23 WS2902 WestJet
Montreal — Punta Cana
2h 45m stop
17:08 — 21:16 F981 Frontier Airlines
Punta Cana — Chicago
23h 11m
including layover
Find flight
from$521
23:15 — 08:07
+2 days
23:15 — 00:22 WS374 WestJet
Toronto — Ottawa
16h 3m stop
16:25 — 19:44 PD505 Porter Airlines
Ottawa — Orlando
10h 21m stop
06:05 — 08:07 F93043 Frontier Airlines
Orlando — Chicago
33h 52m
including layover
Find flight
from$673
*Departure and arrival times - local. Updated on July 26, 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 06:04 to 23:50 from 3 Toronto airports and arrive 06:04 to 23:50 to 7 Chicago airports. Average flight time is 1h 54m.

  • The fastest flight 1h 49m
  • Average flight time 1h 54m
  • The earliest flight 06:04
  • The latest flight 23:50
  • Distance 436 ml

The cheapest months to travel to Chicago are october (from 84 $), september (from 99 $), july (from 103 $).

The most expensive months are february (from 224 $), january (from 208 $), november (from 183 $).

What is the lowest airfare Toronto to Chicago?

The cheapest plane ticket found by our users is $84. This airfare is for economy class on one-way PD2393 flight by Porter Airlines for October 7, 2025 which leaves Toronto Island in Toronto at 15:35 am and arrives at Chicago Midway at 16:24.

Economy class
$84
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Business class
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First class
?
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Popular Airlines on the Route

The flight Toronto — Chicago is served by 9 regular airlines and 4 low-cost airlines. Most of the flights on this route are operated by Air Canada - 1 departures per week at the price of from $ 1029 . And the most expensive tickets are offered by Finnair airline - from $ 3496.

Direct flights

There are 9 nonstop flights on the route. The fastest direct flight is PD2393 by Porter Airlines takes 1h 49m and the cheapest is PD2393 by Porter Airlines for $84.

See more direct flights

Connecting Flights

There are 56 flights with layovers on the route. The fastest connecting flight is UA3633 by United Airlines takes 5h 7m and the cheapest is PD2393 by Porter Airlines for $114.

  • from $1029
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  • from $209
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  • from $114
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  • F8 - Freedom Airlines
    from $257
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  • AV - Avianca
    from $1131
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  • SY - Sun Country Airlines
    from $355
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  • AY - Finnair
    from $3463
    Find
  • WS - WestJet
    from $239
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  • TS - Air Transat
    from $251
    Find
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
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  • Toronto Island-YTZ
    from $84
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  • Pearson International-YYZ
    from $98
    Find

Chicago airports

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

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