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 21/7. Fares are subject to change and may not be available on all flights or dates of travel.
YTO — CHI
21 Apr — 28 Apr1
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.
Cheapest
Best
Direct
Last-minute
One-way
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 22 March 2026.
Tue 21/49:25 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Tue 28/411:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 18/3C$ 263
Sat 2/58:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sat 9/510:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 17/3C$ 265
Mon 8/61:45 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Wed 10/63:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 18/3C$ 268
Sat 2/58:55 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 4/510:30 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 22/3C$ 269
Sat 11/411:20 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sat 18/412:55 p.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 18/3C$ 270
Thu 18/67:20 p.m.
YTZ
-
ORD
Nonstop1h 56m
Air Canada
Sun 21/67:25 a.m.
ORD
-
YTZ
Nonstop1h 41m
Air Canada
Deal found 19/3C$ 270
Sat 25/76:15 a.m.
YYZ
-
ORD
1 stop5h 01m
Air Canada
Wed 29/75:35 p.m.
ORD
-
YYZ
Nonstop1h 45m
Air Canada
Deal found 20/3C$ 272
Thu 9/76:15 a.m.
YYZ
-
ORD
1 stop5h 01m
Air Canada
Sun 12/79:50 a.m.
ORD
-
YYZ
Nonstop1h 45m
Air Canada
Deal found 22/3C$ 273
Thu 23/49:25 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 27/411:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 17/3C$ 273
Fri 17/42:30 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 20/411:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 17/3C$ 274
Wed 22/49:25 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sat 25/412:55 p.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 18/3C$ 276
Thu 10/91:40 p.m.
YTZ
-
ORD
Nonstop1h 55m
Porter Airlines
Sun 13/911:45 a.m.
ORD
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 22/3C$ 276
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 22 March 2026.
Thu 23/49:25 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 27/411:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 17/3C$ 273
Thu 16/712:45 p.m.
YYZ
-
ORD
1 stop11h 41m
United Airlines
Mon 20/79:40 p.m.
ORD
-
YYZ
1 stop11h 24m
United Airlines
Deal found 21/3C$ 294
Fri 10/72:15 p.m.
YYZ
-
ORD
1 stop7h 09m
Delta
Mon 13/77:10 a.m.
ORD
-
YYZ
1 stop7h 08m
Delta
Deal found 20/3C$ 307
Thu 30/49:25 a.m.
YTZ
-
MDW
Nonstop1h 50m
Multiple Airlines
Mon 4/57:30 a.m.
MDW
-
YTZ
1 stop6h 40m
Multiple Airlines
Deal found 18/3C$ 368
Mon 8/68:20 a.m.
YTZ
-
ORD
1 stop4h 51m
Air Canada
Wed 10/62:00 p.m.
ORD
-
YTZ
Nonstop1h 41m
Air Canada
Deal found 21/3C$ 508
Sat 2/58:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 4/53:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 19/3C$ 274
Fri 10/78:50 a.m.
YYZ
-
ORD
Nonstop2h 00m
United Airlines
Tue 14/77:09 a.m.
ORD
-
YYZ
Nonstop1h 45m
United Airlines
Deal found 20/3C$ 300
Sun 3/52:15 p.m.
YYZ
-
ORD
1 stop7h 25m
Delta
Sun 10/58:42 a.m.
ORD
-
YYZ
1 stop8h 49m
Delta
Deal found 19/3C$ 309
Mon 15/61:45 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Thu 18/63:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 17/3C$ 291
Sat 18/72:24 p.m.
YYZ
-
ORD
1 stop7h 07m
Delta
Mon 27/72:07 p.m.
ORD
-
YYZ
1 stop7h 55m
Delta
Deal found 22/3C$ 309
Tue 28/49:25 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Wed 29/411:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 18/3C$ 309
Tue 5/52:15 p.m.
YYZ
-
MDW
1 stop4h 43m
Delta
Sat 9/59:22 a.m.
MDW
-
YYZ
1 stop3h 08m
Delta
Deal found 18/3C$ 309
Mon 13/43:00 p.m.
YTZ
-
ORD
1 stop10h 22m
Multiple Airlines
Mon 20/412:47 p.m.
ORD
-
YTZ
1 stop5h 08m
Multiple Airlines
Deal found 21/3C$ 406
Sun 3/56:10 a.m.
YYZ
-
MDW
1 stop3h 37m
Delta
Sun 10/59:22 a.m.
MDW
-
YYZ
1 stop3h 08m
Delta
Deal found 19/3C$ 309
Thu 18/67:20 p.m.
YTZ
-
ORD
Nonstop1h 56m
United Airlines
Sun 21/67:25 a.m.
ORD
-
YTZ
Nonstop1h 41m
United Airlines
Deal found 18/3C$ 383
Sat 2/52:15 p.m.
YYZ
-
MDW
1 stop4h 43m
Delta
Mon 4/56:38 p.m.
MDW
-
YYZ
1 stop3h 18m
Delta
Deal found 19/3C$ 309
Fri 19/67:20 p.m.
YTZ
-
ORD
Nonstop1h 56m
United Airlines
Sun 21/67:25 a.m.
ORD
-
YTZ
Nonstop1h 41m
United Airlines
Deal found 19/3C$ 383
Tue 7/49:25 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Fri 10/44:05 p.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 19/3C$ 353
Tue 7/46:15 p.m.
YTZ
-
ORD
1 stop7h 07m
Multiple Airlines
Fri 10/46:01 p.m.
ORD
-
YTZ
1 stop18h 19m
Multiple Airlines
Deal found 22/3C$ 443
Tue 9/612:15 p.m.
YTZ
-
ORD
Nonstop1h 55m
United Airlines
Tue 16/62:00 p.m.
ORD
-
YTZ
Nonstop1h 41m
United Airlines
Deal found 18/3C$ 383
Fri 24/42:30 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Tue 28/411:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 19/3C$ 353
Fri 19/67:20 p.m.
YTZ
-
ORD
Nonstop1h 56m
Air Canada
Mon 22/67:25 a.m.
ORD
-
YTZ
Nonstop1h 41m
Air Canada
Deal found 17/3C$ 521
Thu 18/62:15 p.m.
YYZ
-
ORD
1 stop7h 09m
Delta
Sun 21/68:55 a.m.
ORD
-
YYZ
1 stop7h 28m
Delta
Deal found 19/3C$ 328
Mon 6/43:00 p.m.
YTZ
-
ORD
1 stop10h 22m
Multiple Airlines
Wed 8/46:01 p.m.
ORD
-
YTZ
1 stop15h 24m
Multiple Airlines
Deal found 19/3C$ 482
Thu 4/62:20 p.m.
YYZ
-
MDW
1 stop5h 13m
Delta
Sun 7/69:17 a.m.
MDW
-
YYZ
1 stop7h 07m
Delta
Deal found 21/3C$ 329
Mon 1/68:40 p.m.
YKF
-
ORD
1 stop21h 00m
WestJet
Fri 5/65:30 p.m.
ORD
-
YKF
1 stop25h 20m
WestJet
Deal found 19/3C$ 1,207
Wed 13/51:45 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 18/53:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 18/3C$ 399
Fri 31/712:15 p.m.
YYZ
-
ORD
1 stop7h 26m
Delta
Sun 2/87:10 a.m.
ORD
-
YYZ
1 stop7h 08m
Delta
Deal found 20/3C$ 377
Thu 18/66:00 a.m.
YYZ
-
MDW
1 stop7h 30m
Delta
Sun 21/69:30 a.m.
MDW
-
YYZ
1 stop6h 53m
Delta
Deal found 19/3C$ 387
Mon 15/612:15 p.m.
YTZ
-
ORD
Nonstop1h 55m
United Airlines
Thu 18/62:00 p.m.
ORD
-
YTZ
Nonstop1h 41m
United Airlines
Deal found 17/3C$ 595
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 22 March 2026.
Tue 21/49:25 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Tue 28/411:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 18/3C$ 263
Sat 2/58:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sat 9/510:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 17/3C$ 265
Mon 8/61:45 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Wed 10/63:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 18/3C$ 268
Sat 2/58:55 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 4/510:30 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 22/3C$ 269
Sat 11/411:20 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sat 18/412:55 p.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 18/3C$ 270
Thu 18/67:20 p.m.
YTZ
-
ORD
Nonstop1h 56m
Air Canada
Sun 21/67:25 a.m.
ORD
-
YTZ
Nonstop1h 41m
Air Canada
Deal found 19/3C$ 270
Wed 24/67:20 a.m.
YYZ
-
ORD
Nonstop2h 12m
American Airlines
Wed 8/78:37 p.m.
ORD
-
YYZ
Nonstop1h 52m
American Airlines
Deal found 22/3C$ 272
Thu 23/49:25 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 27/411:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 17/3C$ 273
Fri 17/42:30 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 20/411:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 17/3C$ 274
Wed 22/49:25 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sat 25/412:55 p.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 18/3C$ 276
Thu 10/91:40 p.m.
YTZ
-
ORD
Nonstop1h 55m
Porter Airlines
Sun 13/911:45 a.m.
ORD
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 22/3C$ 276
Wed 9/98:40 p.m.
YTZ
-
ORD
Nonstop1h 55m
Porter Airlines
Wed 16/97:00 a.m.
ORD
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 22/3C$ 278
Last-minute flights from Toronto to Chicago
Discover last-minute flight deals from Toronto to Chicago. Data last updated 22 March 2026 and is based on user searches.
Wed 8/49:25 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Fri 10/44:05 p.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 17/3C$ 280
Sat 11/411:20 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sat 18/412:55 p.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 18/3C$ 270
Thu 16/49:25 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 20/411:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 17/3C$ 276
Fri 17/42:30 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 20/411:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 17/3C$ 274
Sat 18/411:20 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Tue 28/411:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 20/3C$ 284
Sat 18/411:20 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sat 25/412:55 p.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 19/3C$ 287
Sun 19/42:30 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Tue 28/411:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 18/3C$ 291
Tue 21/49:25 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Tue 28/411:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 18/3C$ 263
Wed 22/49:25 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Thu 23/411:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 21/3C$ 289
Thu 23/49:25 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 27/411:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 17/3C$ 273
Thu 23/49:25 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Fri 24/44:05 p.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 18/3C$ 277
Thu 30/46:10 a.m.
YYZ
-
MDW
1 stop3h 37m
Delta
Mon 4/56:38 p.m.
MDW
-
YYZ
1 stop3h 18m
Delta
Deal found 18/3C$ 351
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 22 March 2026.
Tue 21/78:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 20/3C$ 174
Fri 17/77:20 p.m.
YTZ
-
ORD
Nonstop1h 56m
Air Canada
Deal found 20/3C$ 174
Sat 2/58:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Air Transat
Deal found 18/3C$ 176
Thu 17/98:40 p.m.
YTZ
-
ORD
Nonstop1h 55m
Porter Airlines
Deal found 18/3C$ 176
Tue 21/710:50 a.m.
YTZ
-
ORD
1 stop5h 05m
Air Canada
Deal found 22/3C$ 177
Thu 4/65:15 p.m.
YYZ
-
ORD
Nonstop2h 03m
United Airlines
Deal found 18/3C$ 178
Tue 21/49:25 a.m.
YTZ
-
MDW
Nonstop1h 50m
Air Transat
Deal found 17/3C$ 178
Wed 22/76:15 a.m.
YYZ
-
ORD
1 stop5h 01m
Air Canada
Deal found 20/3C$ 180
Sat 11/411:20 a.m.
YTZ
-
MDW
Nonstop1h 50m
Air Transat
Deal found 18/3C$ 180
Thu 9/710:50 a.m.
YTZ
-
ORD
1 stop5h 05m
Air Canada
Deal found 21/3C$ 180
Fri 24/710:15 a.m.
YYZ
-
ORD
Nonstop2h 06m
Air Canada
Deal found 21/3C$ 181
Thu 16/49:25 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 20/3C$ 181
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 22 March 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 22 March 2026.
Use the filters below to find and compare flights from Toronto to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
Cheapest round-trip
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Thu 23/4
9:25 a.m.-10:15 a.m.
Nonstop1h 50m
Chicago Midway
Mon 27/4
11:00 a.m.-1:42 p.m.
Nonstop1h 42m
C$ 273
Quickest round-trip
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Sat 2/5
8:50 a.m.-9:40 a.m.
Nonstop1h 50m
Chicago Midway
Mon 4/5
3:20 p.m.-6:00 p.m.
Nonstop1h 40m
C$ 274
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Mon 15/6
1:45 p.m.-2:35 p.m.
Nonstop1h 50m
Chicago Midway
Thu 18/6
3:20 p.m.-6:00 p.m.
Nonstop1h 40m
C$ 291
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Thu 16/7
12:45 p.m.-11:26 p.m.
1 stop11h 41m
Chicago O'Hare Intl
Mon 20/7
9:40 p.m.-10:04 a.m.
1 stop11h 24m
C$ 294
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Fri 10/7
8:50 a.m.-9:50 a.m.
Nonstop2h 00m
Chicago O'Hare Intl
Tue 14/7
7:09 a.m.-9:54 a.m.
Nonstop1h 45m
C$ 300
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Fri 10/7
2:15 p.m.-8:24 p.m.
1 stop7h 09m
Chicago O'Hare Intl
Mon 13/7
7:10 a.m.-3:18 p.m.
1 stop7h 08m
C$ 307
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Sun 3/5
2:15 p.m.-8:40 p.m.
1 stop7h 25m
Chicago O'Hare Intl
Sun 10/5
8:42 a.m.-6:31 p.m.
1 stop8h 49m
C$ 309
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Sat 18/7
2:24 p.m.-8:31 p.m.
1 stop7h 07m
Chicago O'Hare Intl
Mon 27/7
2:07 p.m.-11:02 p.m.
1 stop7h 55m
C$ 309
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Tue 28/4
9:25 a.m.-10:15 a.m.
Nonstop1h 50m
Chicago Midway
Wed 29/4
11:00 a.m.-1:42 p.m.
Nonstop1h 42m
C$ 309
TorontoChicago
YYZ - MDW
YYZMDW
Toronto Pearson Intl
Tue 5/5
2:15 p.m.-5:58 p.m.
1 stop4h 43m
Chicago Midway
Sat 9/5
9:22 a.m.-1:30 p.m.
1 stop3h 08m
C$ 309
Flights are sorted by cheapest round-trip flights first.
Deals found on 20/3
Showing 1-10 of 60 resultsSorted by cheapest first
1
2
3
...
6
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
YTZ-MDW
YYZ-MDW
YYZ-ORD
YTZ-ORD
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
YTZ-MDW
YYZ-MDW
YYZ-ORD
YTZ-ORD
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 13 March 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, June is the cheapest month in which you can book a flight from Toronto to Chicago (average of C$ 114). Flying from Toronto to Chicago in February is currently the most expensive (average of C$ 243). 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 22 March 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 14 March 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 22 March 2026.
The most flights from YTO to CHI are scheduled on a Friday (65 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (53 on average).
How much does it cost to fly round-trip from Toronto to Chicago?
How often are flights from Toronto to Chicago delayed?
About 13% of weekly flights between Toronto and Chicago have experienced delays in the past year, with the average delay time being 139 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?
Thursday tends to have the lowest number of delays on this route, whereas Saturday 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 8% 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 22 March 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.
I'm 6ft 4in. The seats don't have enough room. But was a good flight.
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 Delta fly from Toronto to Chicago in about 1h 50m. The time it takes to get you to your destination can typically vary by up to 9h 51m. Airlines will cover a distance of 711 km. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.
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$ 223 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 Air Canada (C$ 148), United Airlines (C$ 155), and American Airlines (C$ 163).
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: Emirates (100%), Copa Airlines (85%), Republic Airways (75%).
What are the cheapest flights from Toronto to Chicago?
On average you can expect to pay C$ 1,255 for a flight from Toronto to Chicago. The cheapest flight overall is C$ 223 while the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl) is currently priced at C$ 259.
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, June is the cheapest month in which you can book a flight from Toronto to Chicago (average of C$ 114). Flying from Toronto to Chicago in February is currently the most expensive (average of C$ 243). 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 22 March 2026.
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on 22 March 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 22 March 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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