This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/6. Fares are subject to change and may not be available on all flights or dates of travel.
YTO — CHI
5 Mar — 12 Mar1
Round-trip
1 adult
Economy
Round-trip
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Toronto to Chicago are usually found in July or June, booked 78 days in advance, depart on a Friday or Saturday and return on a Friday
Cheap flight deals from Toronto to Chicago
Enter your travel dates to find the best prices.
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Best
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Cheapest flights from Toronto to Chicago
Explore the most affordable flight options available from Toronto to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 3 February 2026.
Thu 16/49:15 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Wed 22/411:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 1/2C$ 264
Thu 19/32:30 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Thu 26/311:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 2/2C$ 265
Thu 26/22:15 p.m.
YYZ
-
ORD
Nonstop1h 55m
Air Canada
Sun 1/38:00 a.m.
ORD
-
YYZ
Nonstop1h 40m
Air Canada
Deal found 1/2C$ 266
Thu 19/32:30 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sun 22/34:15 p.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 3/2C$ 266
Thu 26/29:20 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Thu 5/311:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 2/2C$ 268
Tue 24/26:40 p.m.
YYZ
-
ORD
Nonstop2h 05m
Air Canada
Mon 9/38:00 a.m.
ORD
-
YYZ
Nonstop1h 40m
Air Canada
Deal found 2/2C$ 269
Mon 2/39:15 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Thu 5/311:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 2/2C$ 269
Thu 19/39:15 a.m.
YTZ
-
MDW
Nonstop1h 50m
Air Transat
Thu 26/311:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Air Transat
Deal found 31/1C$ 270
Thu 5/39:15 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Thu 12/311:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 3/2C$ 274
Thu 12/39:00 p.m.
YYZ
-
ORD
Nonstop2h 04m
United Airlines
Mon 16/36:25 p.m.
ORD
-
YYZ
Nonstop1h 53m
United Airlines
Deal found 2/2C$ 276
Thu 26/28:45 a.m.
YYZ
-
ORD
Nonstop2h 05m
Lufthansa
Sun 1/36:28 p.m.
ORD
-
YYZ
Nonstop1h 53m
Lufthansa
Deal found 1/2C$ 279
Thu 12/39:15 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 16/311:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 2/2C$ 279
Best flights from Toronto to Chicago
Discover carefully curated flight deals from Toronto to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 3 February 2026.
Thu 21/54:00 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 25/510:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 31/1C$ 264
Thu 19/39:15 a.m.
YTZ
-
MDW
Nonstop1h 50m
Air Transat
Thu 26/311:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Air Transat
Deal found 31/1C$ 270
Wed 1/48:50 a.m.
YYZ
-
ORD
Nonstop2h 00m
United Airlines
Sun 5/47:04 a.m.
ORD
-
YYZ
Nonstop1h 50m
United Airlines
Deal found 1/2C$ 276
Thu 19/39:15 a.m.
YTZ
-
MDW
Nonstop1h 50m
Multiple Airlines
Thu 26/311:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Multiple Airlines
Deal found 2/2C$ 285
Tue 3/38:15 a.m.
YYZ
-
ORD
Nonstop1h 58m
Air Canada
Tue 10/31:55 p.m.
ORD
-
YYZ
Nonstop1h 39m
Air Canada
Deal found 2/2C$ 311
Thu 26/26:10 a.m.
YYZ
-
MDW
1 stop3h 44m
Delta
Sun 1/31:28 p.m.
MDW
-
YYZ
1 stop8h 12m
Delta
Deal found 1/2C$ 320
Thu 16/49:15 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Wed 22/411:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 1/2C$ 264
Sat 28/38:45 a.m.
YYZ
-
ORD
Nonstop2h 05m
United Airlines
Sat 4/49:15 p.m.
ORD
-
YYZ
Nonstop1h 44m
United Airlines
Deal found 2/2C$ 276
Sat 30/58:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 1/610:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 2/2C$ 264
Thu 12/36:20 a.m.
YYZ
-
MDW
1 stop3h 33m
Delta
Tue 17/39:30 a.m.
MDW
-
YYZ
1 stop5h 29m
Delta
Deal found 2/2C$ 320
Thu 19/32:30 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Thu 26/311:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 2/2C$ 265
Sat 4/48:50 a.m.
YYZ
-
ORD
Nonstop2h 00m
United Airlines
Sun 5/49:15 p.m.
ORD
-
YYZ
Nonstop1h 44m
United Airlines
Deal found 2/2C$ 313
Thu 23/412:16 p.m.
YYZ
-
MDW
1 stop6h 42m
Delta
Mon 4/59:27 a.m.
MDW
-
YYZ
1 stop6h 54m
Delta
Deal found 1/2C$ 320
Thu 19/32:30 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sun 22/34:15 p.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 2/2C$ 270
Thu 18/612:15 p.m.
YTZ
-
ORD
Nonstop1h 55m
Air Canada
Sun 21/611:05 a.m.
ORD
-
YTZ
1 stop5h 46m
Air Canada
Deal found 2/2C$ 378
Thu 12/39:00 p.m.
YYZ
-
ORD
Nonstop2h 04m
United Airlines
Sun 15/311:11 a.m.
ORD
-
YYZ
Nonstop1h 50m
United Airlines
Deal found 1/2C$ 313
Sun 1/36:10 a.m.
YYZ
-
MDW
1 stop3h 44m
Delta
Thu 5/39:34 a.m.
MDW
-
YYZ
1 stop5h 36m
Delta
Deal found 2/2C$ 320
Mon 16/39:15 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Wed 18/311:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 2/2C$ 272
Sun 5/48:50 a.m.
YYZ
-
ORD
Nonstop2h 00m
United Airlines
Wed 8/45:57 p.m.
ORD
-
YYZ
Nonstop1h 47m
United Airlines
Deal found 2/2C$ 313
Thu 12/312:15 p.m.
YYZ
-
MDW
1 stop6h 39m
Delta
Mon 16/39:35 a.m.
MDW
-
YYZ
1 stop6h 42m
Delta
Deal found 1/2C$ 320
Tue 3/36:15 p.m.
YTZ
-
ORD
1 stop7h 25m
Multiple Airlines
Tue 10/36:51 p.m.
ORD
-
YTZ
1 stop14h 44m
Multiple Airlines
Deal found 2/2C$ 430
Mon 30/39:15 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Fri 3/44:15 p.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 2/2C$ 272
Mon 30/311:00 a.m.
YYZ
-
ORD
Nonstop2h 03m
United Airlines
Fri 3/47:04 a.m.
ORD
-
YYZ
Nonstop1h 50m
United Airlines
Deal found 2/2C$ 313
Thu 5/36:10 a.m.
YYZ
-
MDW
1 stop7h 36m
Delta
Mon 9/36:34 p.m.
MDW
-
YYZ
1 stop3h 05m
Delta
Deal found 31/1C$ 320
Thu 26/29:25 a.m.
YTZ
-
ORD
1 stop10h 04m
Multiple Airlines
Sun 1/36:40 a.m.
ORD
-
YTZ
2 stops12h 23m
Multiple Airlines
Deal found 1/2C$ 436
Thu 5/39:15 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Thu 12/311:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 3/2C$ 274
Fri 12/68:40 p.m.
YKF
-
ORD
1 stop21h 00m
WestJet
Mon 15/65:30 p.m.
ORD
-
YKF
1 stop25h 20m
WestJet
Deal found 2/2C$ 990
Thu 12/38:30 a.m.
YTZ
-
ORD
1 stop7h 25m
Air Canada
Sun 15/37:15 a.m.
ORD
-
YTZ
1 stop6h 10m
Air Canada
Deal found 3/2C$ 455
Fri 22/511:00 a.m.
YYZ
-
ORD
Nonstop2h 00m
United Airlines
Tue 26/57:08 a.m.
ORD
-
YYZ
Nonstop1h 45m
United Airlines
Deal found 1/2C$ 313
Thu 26/26:10 a.m.
YYZ
-
MDW
1 stop3h 44m
Delta
Thu 5/39:34 a.m.
MDW
-
YYZ
1 stop5h 36m
Delta
Deal found 1/2C$ 320
Direct flights from Toronto to Chicago
Explore direct flight options from Toronto to Chicago based on user searches, and compare prices and availability for your desired travel dates. Data last updated 3 February 2026.
Thu 16/49:15 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Wed 22/411:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 1/2C$ 264
Thu 19/39:15 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Thu 26/311:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 2/2C$ 265
Thu 26/22:15 p.m.
YYZ
-
ORD
Nonstop1h 55m
Air Canada
Sun 1/38:00 a.m.
ORD
-
YYZ
Nonstop1h 40m
Air Canada
Deal found 1/2C$ 266
Thu 19/32:30 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sun 22/34:15 p.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 3/2C$ 266
Thu 26/29:20 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Thu 5/311:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 2/2C$ 268
Tue 24/24:50 p.m.
YYZ
-
ORD
Nonstop1h 58m
Air Canada
Fri 27/38:40 p.m.
ORD
-
YYZ
Nonstop1h 39m
Air Canada
Deal found 2/2C$ 269
Mon 2/39:15 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Thu 5/311:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 2/2C$ 269
Thu 19/39:15 a.m.
YTZ
-
MDW
Nonstop1h 50m
Air Transat
Thu 26/311:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Air Transat
Deal found 31/1C$ 270
Thu 5/39:15 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Thu 12/311:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 3/2C$ 274
Thu 12/39:00 p.m.
YYZ
-
ORD
Nonstop2h 04m
United Airlines
Mon 16/36:25 p.m.
ORD
-
YYZ
Nonstop1h 53m
United Airlines
Deal found 2/2C$ 276
Thu 26/28:45 a.m.
YYZ
-
ORD
Nonstop2h 05m
Lufthansa
Sun 1/36:28 p.m.
ORD
-
YYZ
Nonstop1h 53m
Lufthansa
Deal found 2/2C$ 279
Thu 12/39:15 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 16/311:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 2/2C$ 279
Last-minute flights from Toronto to Chicago
Discover last-minute flight deals from Toronto to Chicago. Data last updated 3 February 2026 and is based on user searches.
Tue 24/26:40 p.m.
YYZ
-
ORD
Nonstop2h 05m
Air Canada
Mon 9/38:00 a.m.
ORD
-
YYZ
Nonstop1h 40m
Air Canada
Deal found 2/2C$ 269
Thu 26/26:40 p.m.
YYZ
-
ORD
Nonstop2h 05m
Air Canada
Sun 1/38:40 p.m.
ORD
-
YYZ
Nonstop1h 40m
Air Canada
Deal found 3/2C$ 264
Thu 26/29:20 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Thu 5/311:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 2/2C$ 268
Thu 26/28:45 a.m.
YYZ
-
ORD
Nonstop2h 05m
Lufthansa
Sun 1/36:28 p.m.
ORD
-
YYZ
Nonstop1h 53m
Lufthansa
Deal found 1/2C$ 279
Mon 2/39:15 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Thu 5/311:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 2/2C$ 269
Thu 5/39:15 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Thu 12/311:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 3/2C$ 274
Wed 11/39:15 a.m.
YTZ
-
MDW
Nonstop1h 50m
Multiple Airlines
Sat 14/312:45 p.m.
MDW
-
YTZ
Nonstop1h 42m
Multiple Airlines
Deal found 2/2C$ 284
Thu 12/39:00 p.m.
YYZ
-
ORD
Nonstop2h 04m
United Airlines
Mon 16/36:25 p.m.
ORD
-
YYZ
Nonstop1h 53m
United Airlines
Deal found 2/2C$ 276
Thu 12/39:15 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 16/311:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 2/2C$ 279
Thu 19/32:30 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Thu 26/311:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 2/2C$ 265
Thu 19/32:30 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sun 22/34:15 p.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 3/2C$ 266
Thu 19/39:15 a.m.
YTZ
-
MDW
Nonstop1h 50m
Air Transat
Thu 26/311:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Air Transat
Deal found 31/1C$ 270
One-way flights from Toronto to Chicago
Search for one-way flight options from Toronto to Chicago. Find affordable one-way fares based on user searches. Data last updated 3 February 2026.
Mon 1/64:00 p.m.
YYZ
-
ORD
Nonstop1h 59m
Air Canada
Deal found 2/2C$ 171
Sun 15/312:05 p.m.
YYZ
-
ORD
Nonstop1h 56m
Air Canada
Deal found 3/2C$ 173
Tue 3/39:00 p.m.
YYZ
-
ORD
Nonstop2h 04m
United Airlines
Deal found 2/2C$ 175
Fri 27/29:20 a.m.
YTZ
-
MDW
Nonstop1h 50m
Air Transat
Deal found 2/2C$ 175
Sat 30/54:00 p.m.
YYZ
-
ORD
Nonstop1h 59m
Air Canada
Deal found 2/2C$ 179
Mon 1/67:20 p.m.
YTZ
-
ORD
Nonstop1h 56m
Air Canada
Deal found 2/2C$ 179
Sun 31/51:55 p.m.
YYZ
-
ORD
Nonstop2h 00m
Air Canada
Deal found 2/2C$ 180
Wed 15/49:15 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 2/2C$ 180
Tue 28/46:30 a.m.
YYZ
-
ORD
1 stop15h 47m
Multiple Airlines
Deal found 2/2C$ 182
Tue 3/33:40 p.m.
YYZ
-
ORD
1 stop9h 07m
Multiple Airlines
Deal found 3/2C$ 183
Tue 21/42:30 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 1/2C$ 184
Sat 18/411:00 a.m.
YTZ
-
MDW
Nonstop1h 50m
Air Transat
Deal found 2/2C$ 186
Find flight deals from Toronto to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Toronto (YTO) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 3 February 2026.
Customize your flight search to find flights from Toronto to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 3 February 2026.
Use the filters below to find and compare flights from Toronto to Chicago that are best for you.
Fly from
Toronto
Fly to
Chicago
Route
Depart
Return
Price
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Thu 21/5
4:00 p.m.-4:50 p.m.
Nonstop1h 50m
Chicago Midway
Mon 25/5
10:25 a.m.-1:05 p.m.
Nonstop1h 40m
C$ 264
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Thu 16/4
9:15 a.m.-10:05 a.m.
Nonstop1h 50m
Chicago Midway
Wed 22/4
11:00 a.m.-1:42 p.m.
Nonstop1h 42m
C$ 264
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Sat 30/5
8:50 a.m.-9:40 a.m.
Nonstop1h 50m
Chicago Midway
Mon 1/6
10:25 a.m.-1:05 p.m.
Nonstop1h 40m
C$ 264
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Thu 19/3
2:30 p.m.-3:20 p.m.
Nonstop1h 50m
Chicago Midway
Thu 26/3
11:00 a.m.-1:42 p.m.
Nonstop1h 42m
C$ 265
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Thu 19/3
9:15 a.m.-10:05 a.m.
Nonstop1h 50m
Chicago Midway
Thu 26/3
11:00 a.m.-1:42 p.m.
Nonstop1h 42m
C$ 270
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Thu 19/3
2:30 p.m.-3:20 p.m.
Nonstop1h 50m
Chicago Midway
Sun 22/3
4:15 p.m.-6:57 p.m.
Nonstop1h 42m
C$ 270
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Mon 16/3
9:15 a.m.-10:05 a.m.
Nonstop1h 50m
Chicago Midway
Wed 18/3
11:00 a.m.-1:42 p.m.
Nonstop1h 42m
C$ 272
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Mon 30/3
9:15 a.m.-10:05 a.m.
Nonstop1h 50m
Chicago Midway
Fri 3/4
4:15 p.m.-6:57 p.m.
Nonstop1h 42m
C$ 272
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Thu 5/3
9:15 a.m.-10:05 a.m.
Nonstop1h 50m
Chicago Midway
Thu 12/3
11:00 a.m.-1:42 p.m.
Nonstop1h 42m
C$ 274
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Wed 1/4
8:50 a.m.-9:50 a.m.
Nonstop2h 00m
Chicago O'Hare Intl
Sun 5/4
7:04 a.m.-9:54 a.m.
Nonstop1h 50m
C$ 276
Flights are sorted by cheapest round-trip flights first.
Deals found on 1/2
Showing 1-10 of 60 results
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Best time to book a flight from Toronto to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Toronto with our price prediction graph.
YTO-CHI
YYZ-ORD
YTZ-MDW
YTZ-ORD
YYZ-MDW
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Toronto to Chicago
YTO-CHI
YYZ-ORD
YTZ-MDW
YTZ-ORD
YYZ-MDW
How far ahead should I book a flight from Toronto to Chicago?
Use this chart to determine the optimal time to book a round-trip flight from Toronto to Chicago. Price data was last updated on 30 January 2026.
To ensure you get the cheapest price possible for a flight from Toronto to Chicago, you should look to book at least 78 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest month to book a flight from Toronto to Chicago?
Currently, April is the cheapest month in which you can book a flight from Toronto to Chicago (average of C$ 112). Flying from Toronto to Chicago in February is currently the most expensive (average of C$ 251). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from YTO to CHI?
Find hourly flight availability from Toronto to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 3 February 2026.
Unlike in the evening, when flights are generally more expensive, you can save up to 21% on flights from Toronto to Chicago by exploring options for tickets in the afternoon.
What is the cheapest day to fly from Toronto to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Toronto to Chicago. Price data was last updated on 31 January 2026.
Travelers seeking maximum savings on their Toronto to Chicago flight should consider departing on Monday mornings when fares are most often at their lowest. Saturday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Toronto to Chicago
Explore weekly flight availability from Toronto to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated 3 February 2026.
The most flights from YTO to CHI are scheduled on a Monday (64 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (37 on average).
How often are flights from Toronto to Chicago delayed?
About 12% of weekly flights between Toronto and Chicago have experienced delays in the past year, with the average delay time being 138 minutes.
What is the most punctual flight time for Toronto to Chicago flights?
Historically, flights departing at night are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Tuesday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Toronto to Chicago flights?
Over the past year, United Airlines has had the lowest number of delays on this route, with just 7% of flights being delayed.
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated 3 February 2026.
Get a feel of what it's like to fly with Porter Airlines,Air Transat, andUnited Airlines from Toronto to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
It's good. Planes are new and fresh. WiFi is best and stands out
Toronto to Chicago Travel Guide
O’Hare International Airport is on the northwest side of the city in Chicago. It’s about 14 miles away from the city centre. The airport was built to take over for Midway originally. It’s a busy airport that is a hub for major airlines like United and American Airlines.
Midway International Airport used to be the main airport in Chicago until O’Hare came along. This airport is still the second busiest one in the state of Illinois though. This is a major hub for Southwest Airlines.
Related info for your journey
Find useful and relevant information for your journey from Toronto to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
What airports serve Toronto to Chicago flights?
Flying out of Toronto to go to Chicago, you’ll show up to board your flight at Pearson International Airport in Toronto. Your flight will be heading for either Chicago O’Hare or Chicago Midway International Airport. You’ll find a variety of options for this route. You can fly direct, with one-stop, or more. There is a large range of prices for these flights.
Which airlines fly directly from Toronto to Chicago?
You can find a lot of direct flights from Toronto to Chicago. American Airlines has a few from Pearson to O’Hare. They’re about two hours long. Air Canada flies the same route. United also flies non-stop between Pearson and O’Hare.
What are the stopover options between Toronto to Chicago?
American Airlines has one-stop flights that land in Charlotte on the way to Chicago. This stopover varies in the time it adds to your travel day. You could be looking at six and a half hours, but also up to eleven hours. Delta makes a stopover in Detroit on the way to either Midway or O’Hare. These flights are only a few hours longer than the direct flights. Air Canada has a route that goes through Montreal before landing at O’Hare.
Do I need a passport or visa to fly from Toronto to Chicago?
While you do need your passport because you’re passing over the border into the US, you do not need a visa if you’re only going for a leisure trip. If you will be working or going to school, or investing on your trip, then you will need some kind of visa.
How can passengers contribute to sustainability when flying from Toronto to Chicago?
Pack a little if you want to minimize your carbon footprint when traveling from Toronto to Chicago. It is one of the easiest strategies for travelers to boost sustainable development. This is accurate since flying efficiently reduces the weight of the airplane, which in turn reduces fuel consumption. Before you even get to the runway, flying out of a green airport will reduce your carbon impact. These airports reduce their emissions through the use of alternative energy, the purchase of biofuels, or the application of green design principles during additions and upgrades.
What sustainability practices does Toronto Pearson International Airport offer?
By 2030, Toronto Pearson International Airport (YYZ) wants to have net-zero carbon emissions. It includes "Scope 1" emissions from the fleet of vehicles and natural gas consumption of the airport, as well as "Scope 2" emissions from the production of the airport's electrical needs. The airport's Scope 2 emissions, which make up 93% of emission levels within its operational procedures, will be totally eradicated by cutting power use and transitioning to 100% green sources. Toronto Pearson Airport will continue to prioritize operational management while concentrating on indirect "Scope 3" emissions.
Which alternative means of transportation is available along this route?
If you intend to travel from Toronto to Chicago without adding to global warming emissions, a flight is your best bet. Flying is the most environmentally beneficial form of transportation since it allows for the most efficient long-distance transportation of people. However, you should opt for nonstop flights, as they consume less fuel per passenger as compared to connecting flights. Alternatively, you can opt for Amtrak trains which are more sustainable compared to trains as they produce at least 50% fewer carbon emissions. The best part is some of these trains adopt green energy; hence are sustainable.
How long is the flight from Toronto to Chicago?
Airlines like Porter Airlines, United Airlines, and Air Canada fly from Toronto to Chicago in about 1h 50m. The time it takes to get you to your destination is usually consistent. Airlines will cover a distance of 711 km. Most flights are nonstop.
What are the cheapest airlines flying from Toronto to Chicago round-trip?
Our cheapest airline available from Toronto to Chicago is Porter Airlines. Our recent data shows that you can find tickets from as low as C$ 112 on this airline. Additional options worth looking into are American Airlines and Air Canada, starting at C$ 222 and C$ 244 round-trip. Users have found that Porter Airlines is 67% cheaper than the other options available to this destination.
What are the cheapest airlines to fly from Toronto to Chicago one-way?
The cheapest airlines for a one-way flight from Toronto to Chicago are Porter Airlines (C$ 127), United Airlines (C$ 159), and Air Canada (C$ 161).
What are the most popular routes from Toronto to Chicago?
When deciding which route to take from Toronto to Chicago consider Toronto Pearson Intl - Chicago O'Hare Intl, Toronto Pearson Intl - Chicago Midway or Toronto Island - Chicago Midway as they are the most popular.
What are the most reliable airlines from Toronto to Chicago?
Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Toronto to Chicago on time: Copa Airlines (79%), Egyptair (72%), Japan Airlines (70%).
What are the cheapest flights from Toronto to Chicago?
On average you can expect to pay C$ 1,636 for a flight from Toronto to Chicago. The cheapest flight overall is C$ 225 while the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl) is currently priced at C$ 258.
Can I find deals for business class flights from Toronto to Chicago?
Yes. Cheapflights offers flight deals from Toronto to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.
What is the cheapest month to book a flight from Toronto to Chicago?
Currently, April is the cheapest month in which you can book a flight from Toronto to Chicago (average of C$ 112). Flying from Toronto to Chicago in February is currently the most expensive (average of C$ 251). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
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Fly from Toronto to Chicago on these airlines
Choose from the following airlines for your flight from Toronto to Chicago. Flights are based on user searches made on Cheapflights and were last updated on 3 February 2026.
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on 3 February 2026.
Discover the top 5 airlines that operate flights from Toronto to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 3 February 2026.
Get useful tips and recommendations to enhance your travel experience on your next trip to Chicago. Learn about must-visit attractions, local customs, transportation options, weather conditions, and other valuable tips to make your trip more enjoyable and hassle-free.
Flights from Toronto to Chicago depart from Toronto Pearson International Airport (YYZ). The airport demonstrates its dedication to sustainability by using solar power to run its everyday activities.
United Airlines flying along this route endorses sustainability practices. The airline is adopting the use of Sustainable Aviation fuel (SAF) in its fleet and doing away with old planes while adopting modern ones which are fuel efficient.
Before booking your flight ticket, look for a green airport to reduce your carbon footprint. If you need information about sustainable airports like Chicago O’Hare (ORD), explore the carbon Airport Accreditation list.
Fly with Cheapflights
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How does Cheapflights help users find flights from Toronto to Chicago?
Deals for Toronto to Chicago flights are sourced from 900+ travel sites when you use Cheapflights. When all flight results come back, Cheapflights lets you sort and filter flights using different criteria to choose better, like price, airport, cabin class, and plenty of other options.
Why should you use Cheapflights to find cheap flight tickets from Toronto to Chicago?
By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Chicago from Toronto.
Can Cheapflights find flights from Toronto to Chicago with no change fees?
Cheapflights does show flights with no change fees to all users. To see these options for flights from Toronto to Chicago, users can toggle the no change fees filter when performing a flight search.
Can Cheapflights notify me if prices for flights from Toronto to Chicago become cheaper?
Yes, Cheapflights offers price alerts on Toronto to Chicago flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.
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