Cheap Flights from Toronto, ON to Chicago, IL from $55

One way Round trip

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On Cheapflightsplus.com you will find 39 direct and 687 connecting flights from Toronto to Chicago. You can compare airfare deals from 11 airlines and multiple travel sites from $55, 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: $55 (one-way), $94 (round-trip).

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Best Flights from Toronto to Chicago Today

Take a look at the list of non stop flights and flights with layovers from Toronto to Chicago with the lowest price of $55. The fastest direct flight takes 1h 49m and the fastest connecting – 3h 11m.

Price	Departure	Arrival	Flight Duration	Airline	Flight
from $55 Find flight	07:30 Toronto Toronto Island	08:19 Chicago Midway	1h 49m	Porter Airlines	PD2387
from $61 Find flight	15:35 Toronto Toronto Island	16:24 Chicago Midway	1h 49m	Porter Airlines	PD2393
from $72 Find flight	08:15 Toronto Pearson International	09:08 Chicago O'Hare International	1h 53m	United Airlines	UA8533
from $72 Find flight	10:00 Toronto Pearson International	10:53 Chicago O'Hare International	1h 53m	United Airlines	UA8278
from $72 Find flight	14:10 Toronto Pearson International	15:04 Chicago O'Hare International	1h 54m	United Airlines	UA8307
from $87 Find flight	07:30 Toronto Toronto Island	08:19 Chicago Midway	1h 49m	Air Transat	TS7060
from $88 Find flight	17:15 Toronto Pearson International	18:15 Chicago O'Hare International	2h 0m	United Airlines	UA1371
from $108 Find flight	14:10 Toronto Pearson International	15:04 Chicago O'Hare International	1h 54m	Air Canada	AC507
from $147 Find flight	14:45 Toronto Pearson International	15:50 Chicago O'Hare International	2h 5m	United Airlines	UA3404
from $153 Find flight	08:15 Toronto Pearson International	09:09 Chicago O'Hare International	1h 54m	Air Canada	AC503
from $171 Find flight	16:30 Toronto Pearson International	17:24 Chicago O'Hare International	1h 54m	Air Canada	AC8909
from $177 Find flight	11:00 Toronto Pearson International	12:01 Chicago O'Hare International	2h 1m	United Airlines	UA5650
from $231 Find flight	11:00 Toronto Pearson International	12:01 Chicago O'Hare International	2h 1m	United Airlines	UA5563
from $84 Find flight	19:47 Toronto Pearson International	23:15 Chicago O'Hare International	4h 28m layover 0h 45m - Washington D.C.	United Airlines	UA3466 UA1738
from $100 Find flight	07:20 Toronto Pearson International	13:15 Chicago O'Hare International	6h 55m layover 3h 8m - Washington D.C.	United Airlines	UA8552 UA1577
from $101 Find flight	07:25 Toronto Toronto Island	11:24 Chicago O'Hare International	4h 59m layover 1h 2m - Montreal	Air Canada	AC7952 AC3098

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*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on June 02, 2025

Flight Schedule Toronto (Ontario) to Chicago (Illinois)

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	Flight Details	Flight Duration	Price
07:00 — 07:56	07:00 — 07:56 UA490 United Airlines Toronto — Chicago	1h 56m	Find flight from$93
07:00 — 07:59	07:00 — 07:59 AC5141 Air Canada Toronto — Chicago	1h 59m	Find flight from$108
07:30 — 08:19	07:30 — 08:19 PD2387 Porter Airlines Toronto — Chicago	1h 49m	Find flight from$55
07:30 — 08:19	07:30 — 08:19 TS7060 Air Transat Toronto — Chicago	1h 49m	Find flight from$87
08:15 — 09:08	08:15 — 09:08 UA8533 United Airlines Toronto — Chicago	1h 53m	Find flight from$72
08:15 — 09:09	08:15 — 09:09 AC503 Air Canada Toronto — Chicago	1h 54m	Find flight from$153
08:15 — 09:08	08:15 — 09:08 AC8901 Air Canada Toronto — Chicago	1h 53m	Find flight from$161
09:00 — 09:55	09:00 — 09:55 UA1538 United Airlines Toronto — Chicago	1h 55m	Find flight from$72
09:00 — 09:59	09:00 — 09:59 AC5143 Air Canada Toronto — Chicago	1h 59m	Find flight from$108
10:00 — 10:53	10:00 — 10:53 UA8278 United Airlines Toronto — Chicago	1h 53m	Find flight from$72
11:00 — 12:03	11:00 — 12:03 UA5676 United Airlines Toronto — Chicago	2h 3m	Find flight from$150
11:00 — 12:01	11:00 — 12:01 AC4408 Air Canada Toronto — Chicago	2h 1m	Find flight from$161
11:00 — 12:01	11:00 — 12:01 UA5650 United Airlines Toronto — Chicago	2h 1m	Find flight from$177
12:00 — 12:53	12:00 — 12:53 UA8694 United Airlines Toronto — Chicago	1h 53m	Find flight from$93
12:10 — 13:04	12:10 — 13:04 AC505 Air Canada Toronto — Chicago	1h 54m	Find flight from$153
13:00 — 14:01	13:00 — 14:01 UA3605 United Airlines Toronto — Chicago	2h 1m	Find flight from$72
13:00 — 14:01	13:00 — 14:01 AC5588 Air Canada Toronto — Chicago	2h 1m	Find flight from$108
13:00 — 14:01	13:00 — 14:01 UA3499 United Airlines Toronto — Chicago	2h 1m	Find flight from$149
14:10 — 15:04	14:10 — 15:04 UA8307 United Airlines Toronto — Chicago	1h 54m	Find flight from$72
14:10 — 15:04	14:10 — 15:04 AC507 Air Canada Toronto — Chicago	1h 54m	Find flight from$108
14:45 — 15:48	14:45 — 15:48 UA3616 United Airlines Toronto — Chicago	2h 3m	Find flight from$93
14:45 — 15:50	14:45 — 15:50 UA3404 United Airlines Toronto — Chicago	2h 5m	Find flight from$147
14:45 — 15:48	14:45 — 15:48 UA5258 United Airlines Toronto — Chicago	2h 3m	Find flight from$153
14:45 — 15:50	14:45 — 15:50 AC5137 Air Canada Toronto — Chicago	2h 5m	Find flight from$153
15:35 — 16:24	15:35 — 16:24 PD2393 Porter Airlines Toronto — Chicago	1h 49m	Find flight from$61
15:35 — 16:24	15:35 — 16:24 TS7314 Air Transat Toronto — Chicago	1h 49m	Find flight from$92
16:30 — 17:23	16:30 — 17:23 UA8287 United Airlines Toronto — Chicago	1h 53m	Find flight from$153
16:30 — 17:24	16:30 — 17:24 AC8909 Air Canada Toronto — Chicago	1h 54m	Find flight from$171
17:14 — 18:21	17:14 — 18:21 UA5536 United Airlines Toronto — Chicago	2h 7m	Find flight from$153
17:15 — 18:15	17:15 — 18:15 UA1371 United Airlines Toronto — Chicago	2h	Find flight from$88
17:15 — 18:12	17:15 — 18:12 UA2121 United Airlines Toronto — Chicago	1h 57m	Find flight from$93
17:15 — 18:15	17:15 — 18:15 AC4990 Air Canada Toronto — Chicago	2h	Find flight from$108
18:35 — 19:29	18:35 — 19:29 UA8293 United Airlines Toronto — Chicago	1h 54m	Find flight from$72
18:35 — 19:29	18:35 — 19:29 AC511 Air Canada Toronto — Chicago	1h 54m	Find flight from$161
21:00 — 22:07	21:00 — 22:07 UA5928 United Airlines Toronto — Chicago	2h 7m	Find flight from$72
21:00 — 22:05	21:00 — 22:05 UA4808 United Airlines Toronto — Chicago	2h 5m	Find flight from$88
21:00 — 22:05	21:00 — 22:05 UA3640 United Airlines Toronto — Chicago	2h 5m	Find flight from$93
21:00 — 22:05	21:00 — 22:05 AC4961 Air Canada Toronto — Chicago	2h 5m	Find flight from$108
06:30 — 11:49	06:30 — 08:12 UA8714 United Airlines Toronto — Newark 1h 58m stop 10:10 — 11:49 UA1525 United Airlines Newark — Chicago	6h 19m including layover	Find flight from$86
06:30 — 13:07	06:30 — 08:07 UA8714 United Airlines Toronto — Newark 3h 20m stop 11:37 — 13:14 UA1875 United Airlines Newark — Chicago	7h 37m including layover	Find flight from$90
07:20 — 13:13	07:20 — 08:54 UA8552 United Airlines Toronto — Washington D.C. 3h 6m stop 12:00 — 13:13 UA374 United Airlines Washington D.C. — Chicago	6h 53m including layover	Find flight from$84
10:32 — 14:55	10:32 — 12:15 UA3648 United Airlines Toronto — Newark 1h 5m stop 13:20 — 14:55 UA2053 United Airlines Newark — Chicago	5h 23m including layover	Find flight from$84
12:10 — 19:55	12:10 — 13:38 UA8670 United Airlines Toronto — Washington D.C. 5h 9m stop 18:47 — 19:55 UA2304 United Airlines Washington D.C. — Chicago	8h 45m including layover	Find flight from$84
12:45 — 20:11	12:45 — 14:28 UA3649 United Airlines Toronto — Newark 4h 2m stop 18:30 — 20:11 UA254 United Airlines Newark — Chicago	8h 26m including layover	Find flight from$84
13:55 — 21:26	13:55 — 15:34 UA8660 United Airlines Toronto — Newark 4h 9m stop 20:30 — 22:12 UA546 United Airlines Newark — Chicago	8h 31m including layover	Find flight from$85
16:00 — 21:26	16:00 — 17:39 UA8621 United Airlines Toronto — Newark 2h 4m stop 20:30 — 22:12 UA546 United Airlines Newark — Chicago	6h 26m including layover	Find flight from$84
16:30 — 20:15	16:30 — 18:03 UA8548 United Airlines Toronto — Washington D.C. 56m stop 19:11 — 20:27 UA1193 United Airlines Washington D.C. — Chicago	4h 45m including layover	Find flight from$84
18:00 — 23:30	18:00 — 19:48 UA3460 United Airlines Toronto — Newark 1h 54m stop 21:55 — 23:37 UA1308 United Airlines Newark — Chicago	6h 30m including layover	Find flight from$84
19:47 — 23:15	19:47 — 21:25 UA3466 United Airlines Toronto — Washington D.C. 45m stop 22:18 — 23:30 UA1738 United Airlines Washington D.C. — Chicago	4h 28m including layover	Find flight from$84
21:10 — 07:38 +1 day	21:10 — 22:47 UA8266 United Airlines Toronto — Newark 7h 11m stop 06:00 — 07:38 UA2164 United Airlines Newark — Chicago	11h 28m including layover	Find flight from$84

Departure	Arrival	Flight Details	Flight Time	Price
		stop stop	including layover	Find flight from$

*Departure and arrival times - local. Updated on June 2, 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 00:30 to 23:50 from 3 Toronto airports and arrive 00:30 to 23:50 to 7 Chicago airports. Average flight time is 1h 59m.

The fastest flight 1h 49m
Average flight time 1h 59m
The earliest flight 00:30
The latest flight 23:50
Distance 436 ml

The cheapest months to travel to Chicago are september (from 74 $), october (from 82 $), august (from 98 $).

The most expensive months are november (from 179 $), december (from 156 $), february (from 148 $).

What is the lowest airfare Toronto to Chicago?

The cheapest plane ticket found by our users is $55. This airfare is for economy class on one-way PD2387 flight by Porter Airlines for September 27, 2025 which leaves Toronto Island in Toronto at 07:30 am and arrives at Chicago Midway at 08:19.

Economy class

$55

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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 11 regular airlines and 4 low-cost airlines. Most of the flights on this route are operated by Air Canada - 97 departures per week at the price of from $ 101 . And the most expensive tickets are offered by SWISS International Air Lines airline - from $ 3158.

Direct flights

There are 39 nonstop flights on the route. The fastest direct flight is PD2387 by Porter Airlines takes 1h 49m and the cheapest is PD2387 by Porter Airlines for $55.

AC - Air Canada

from $108

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PD - Porter Airlines

from $55

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UA - United Airlines

from $72

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TS - Air Transat

from $87

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Connecting Flights

There are 687 flights with layovers on the route. The fastest connecting flight is UA8112 by United Airlines takes 3h 11m and the cheapest is PD2387 by Porter Airlines for $84.

AC - Air Canada

from $101

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PD - Porter Airlines

from $129

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UA - United Airlines

from $84

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F8 - Freedom Airlines

from $120

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AS - Alaska Airlines

from $218

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AV - Avianca

from $408

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SY - Sun Country Airlines

from $162

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WS - WestJet

from $132

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AM - Aeromexico

from $498

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LX - SWISS International Air Lines

from $3152

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TS - Air Transat

from $146

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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 $55
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Pearson International-YYZ

from $72
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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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Airplanes

There are flights to Chicago from Toronto by 11 airlines that use 2 aircraft brands. They range from huge modern airplanes to small-sized.

Boeing 737

from $108

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Embraer 175

from $108

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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.

Toronto — Ontario

from $75

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Toronto — Miami

from $55

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Toronto — Orlando

from $64

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Toronto — New York

from $54

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Toronto — Las Vegas

from $72

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Toronto — Boston

from $78

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Toronto — Chicago

from $73

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Toronto — Los Angeles

from $65

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Toronto — Nashville

from $56

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Toronto — Tampa

from $66

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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.