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 19/7. Fares are subject to change and may not be available on all flights or dates of travel.
YTO — CHI
23 Jul — 30 Jul1
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 September or November, booked 88 days in advance, depart on a Friday or Thursday and return on a Thursday
Cheap flight deals from Toronto to Chicago
Enter your travel dates to find the best prices.
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Best
Direct
Last-minute
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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 23 June 2026.
Fri 10/78:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 13/73:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 22/6C$ 288
Thu 9/71:45 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 13/73:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 22/6C$ 289
Sat 5/91:00 p.m.
YYZ
-
ORD
Nonstop2h 05m
Multiple Airlines
Mon 7/99:50 a.m.
ORD
-
YYZ
Nonstop1h 45m
Multiple Airlines
Deal found 22/6C$ 290
Mon 6/78:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Thu 9/73:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 22/6C$ 290
Sat 10/101:40 p.m.
YTZ
-
ORD
Nonstop1h 55m
Porter Airlines
Thu 15/1011:45 a.m.
ORD
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 22/6C$ 290
Thu 2/712:25 p.m.
YYZ
-
ORD
Nonstop1h 57m
Air Canada
Sun 5/79:50 a.m.
ORD
-
YYZ
Nonstop1h 45m
Air Canada
Deal found 18/6C$ 292
Mon 6/71:45 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Wed 8/710:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 19/6C$ 292
Sat 10/101:40 p.m.
YTZ
-
ORD
Nonstop1h 55m
Porter Airlines
Wed 14/107:00 a.m.
ORD
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 22/6C$ 292
Wed 5/88:05 a.m.
YYZ
-
ORD
Nonstop1h 55m
Air Canada
Wed 12/82:15 p.m.
ORD
-
YYZ
Nonstop1h 46m
Air Canada
Deal found 21/6C$ 293
Sat 4/78:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sun 5/710:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 20/6C$ 293
Fri 14/87:25 p.m.
YTZ
-
ORD
Nonstop2h 04m
Air Canada
Tue 18/88:40 a.m.
ORD
-
YTZ
1 stop6h 11m
Air Canada
Deal found 20/6C$ 293
Thu 9/72:00 p.m.
YYZ
-
ORD
Nonstop1h 55m
Air Canada
Sun 12/72:15 p.m.
ORD
-
YYZ
Nonstop1h 46m
Air Canada
Deal found 21/6C$ 295
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 23 June 2026.
Sat 18/78:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sun 19/73:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 22/6C$ 288
Sun 12/78:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Air Transat
Tue 14/73:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Air Transat
Deal found 20/6C$ 302
Sat 18/77:00 a.m.
YYZ
-
ORD
Nonstop2h 00m
United Airlines
Mon 17/85:53 p.m.
ORD
-
YYZ
Nonstop1h 51m
United Airlines
Deal found 22/6C$ 307
Sat 18/77:00 a.m.
YYZ
-
ORD
Nonstop2h 00m
Multiple Airlines
Sat 25/73:40 p.m.
ORD
-
YYZ
1 stop6h 40m
Multiple Airlines
Deal found 18/6C$ 322
Sat 5/912:09 p.m.
YYZ
-
MDW
1 stop5h 50m
Delta
Tue 8/95:45 p.m.
MDW
-
YYZ
1 stop4h 14m
Delta
Deal found 22/6C$ 336
Mon 6/78:20 a.m.
YTZ
-
ORD
1 stop4h 51m
Air Canada
Wed 8/710:41 a.m.
ORD
-
YTZ
1 stop6h 39m
Air Canada
Deal found 22/6C$ 358
Thu 16/78:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sat 18/710:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 20/6C$ 299
Sat 4/711:00 a.m.
YYZ
-
ORD
Nonstop2h 00m
United Airlines
Sun 5/77:09 a.m.
ORD
-
YYZ
Nonstop1h 45m
United Airlines
Deal found 20/6C$ 307
Thu 20/88:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 24/83:15 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 20/6C$ 299
Sat 10/102:15 p.m.
YYZ
-
ORD
1 stop7h 09m
Delta
Fri 16/107:05 a.m.
ORD
-
YYZ
1 stop7h 14m
Delta
Deal found 22/6C$ 337
Fri 14/88:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Air Transat
Mon 17/83:15 p.m.
MDW
-
YTZ
Nonstop1h 40m
Air Transat
Deal found 19/6C$ 337
Wed 29/78:45 a.m.
YYZ
-
ORD
Nonstop2h 00m
Multiple Airlines
Mon 3/88:40 p.m.
ORD
-
YYZ
Nonstop1h 46m
Multiple Airlines
Deal found 22/6C$ 346
Thu 10/92:45 p.m.
YYZ
-
ORD
Nonstop2h 06m
United Airlines
Mon 14/95:53 p.m.
ORD
-
YYZ
Nonstop1h 51m
United Airlines
Deal found 19/6C$ 329
Wed 29/78:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Thu 6/83:15 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 22/6C$ 306
Sat 10/1012:15 p.m.
YYZ
-
MDW
1 stop7h 22m
Delta
Sun 18/109:30 a.m.
MDW
-
YYZ
1 stop6h 52m
Delta
Deal found 22/6C$ 337
Tue 4/812:15 p.m.
YTZ
-
ORD
Nonstop2h 04m
Air Canada
Thu 6/87:25 a.m.
ORD
-
YTZ
Nonstop1h 42m
Air Canada
Deal found 22/6C$ 378
Sun 19/78:45 a.m.
YYZ
-
ORD
Nonstop2h 00m
Multiple Airlines
Tue 21/75:35 p.m.
ORD
-
YYZ
Nonstop1h 45m
Multiple Airlines
Deal found 22/6C$ 346
Fri 17/71:45 p.m.
YTZ
-
MDW
Nonstop1h 50m
Air Transat
Sun 19/73:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Air Transat
Deal found 22/6C$ 353
Wed 29/78:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sun 2/810:20 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 22/6C$ 306
Sun 11/1012:15 p.m.
YYZ
-
MDW
1 stop7h 22m
Delta
Wed 14/101:00 p.m.
MDW
-
YYZ
1 stop3h 22m
Delta
Deal found 22/6C$ 337
Sun 19/78:45 a.m.
YYZ
-
ORD
Nonstop2h 00m
United Airlines
Tue 21/78:40 a.m.
ORD
-
YYZ
1 stop4h 39m
United Airlines
Deal found 22/6C$ 346
Fri 11/99:45 a.m.
YYZ
-
MDW
1 stop8h 12m
Delta
Mon 14/99:30 a.m.
MDW
-
YYZ
1 stop4h 45m
Delta
Deal found 18/6C$ 339
Sat 18/78:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sat 25/710:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 18/6C$ 309
Fri 3/79:00 p.m.
YYZ
-
ORD
Nonstop2h 05m
United Airlines
Mon 6/79:20 p.m.
ORD
-
YYZ
Nonstop1h 39m
United Airlines
Deal found 19/6C$ 346
Fri 7/87:25 p.m.
YTZ
-
ORD
Nonstop2h 04m
Multiple Airlines
Sun 9/810:41 a.m.
ORD
-
YTZ
1 stop6h 39m
Multiple Airlines
Deal found 22/6C$ 394
Sun 26/78:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Tue 28/710:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 21/6C$ 313
Sun 5/77:00 a.m.
YYZ
-
ORD
Nonstop2h 00m
United Airlines
Tue 7/77:10 a.m.
ORD
-
YYZ
1 stop5h 37m
United Airlines
Deal found 18/6C$ 347
Sat 18/76:10 a.m.
YYZ
-
MDW
1 stop7h 28m
Delta
Sat 25/76:35 p.m.
MDW
-
YYZ
1 stop3h 27m
Delta
Deal found 20/6C$ 354
Sat 18/77:25 p.m.
YTZ
-
ORD
Nonstop2h 04m
Multiple Airlines
Sat 25/710:41 a.m.
ORD
-
YTZ
1 stop6h 39m
Multiple Airlines
Deal found 18/6C$ 395
Mon 6/78:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Thu 9/73:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 22/6C$ 315
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 23 June 2026.
Fri 10/78:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 13/73:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 22/6C$ 288
Thu 9/71:45 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 13/73:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 22/6C$ 289
Sat 5/91:00 p.m.
YYZ
-
ORD
Nonstop2h 05m
Multiple Airlines
Mon 7/99:50 a.m.
ORD
-
YYZ
Nonstop1h 45m
Multiple Airlines
Deal found 22/6C$ 290
Mon 6/78:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Thu 9/73:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 22/6C$ 290
Sat 10/101:40 p.m.
YTZ
-
ORD
Nonstop1h 55m
Porter Airlines
Thu 15/1011:45 a.m.
ORD
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 22/6C$ 290
Thu 2/712:25 p.m.
YYZ
-
ORD
Nonstop1h 57m
Air Canada
Sun 5/79:50 a.m.
ORD
-
YYZ
Nonstop1h 45m
Air Canada
Deal found 18/6C$ 292
Mon 6/71:45 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Wed 8/710:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 19/6C$ 292
Sat 10/101:40 p.m.
YTZ
-
ORD
Nonstop1h 55m
Porter Airlines
Wed 14/107:00 a.m.
ORD
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 22/6C$ 292
Wed 5/88:05 a.m.
YYZ
-
ORD
Nonstop1h 55m
Air Canada
Wed 12/82:15 p.m.
ORD
-
YYZ
Nonstop1h 46m
Air Canada
Deal found 21/6C$ 293
Sat 4/78:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sun 5/710:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 20/6C$ 293
Thu 9/77:25 p.m.
YTZ
-
ORD
Nonstop2h 04m
Air Canada
Thu 16/72:00 p.m.
ORD
-
YTZ
Nonstop1h 42m
Air Canada
Deal found 21/6C$ 293
Thu 9/72:00 p.m.
YYZ
-
ORD
Nonstop1h 55m
Air Canada
Sun 12/72:15 p.m.
ORD
-
YYZ
Nonstop1h 46m
Air Canada
Deal found 21/6C$ 295
Last-minute flights from Toronto to Chicago
Discover last-minute flight deals from Toronto to Chicago. Data last updated 23 June 2026 and is based on user searches.
Thu 2/712:25 p.m.
YYZ
-
ORD
Nonstop1h 57m
Air Canada
Sun 5/79:50 a.m.
ORD
-
YYZ
Nonstop1h 45m
Air Canada
Deal found 18/6C$ 292
Sat 4/78:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sun 5/710:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 20/6C$ 293
Sun 5/78:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Wed 8/710:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 21/6C$ 295
Mon 6/78:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Thu 9/73:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 22/6C$ 290
Mon 6/71:45 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Wed 8/710:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 19/6C$ 292
Wed 8/71:45 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sat 11/710:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 19/6C$ 296
Thu 9/71:45 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 13/73:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 22/6C$ 289
Thu 9/77:25 p.m.
YTZ
-
ORD
Nonstop2h 04m
Air Canada
Thu 16/72:00 p.m.
ORD
-
YTZ
Nonstop1h 42m
Air Canada
Deal found 21/6C$ 293
Thu 9/72:00 p.m.
YYZ
-
ORD
Nonstop1h 55m
Air Canada
Sun 12/72:15 p.m.
ORD
-
YYZ
Nonstop1h 46m
Air Canada
Deal found 21/6C$ 295
Thu 9/74:00 p.m.
YYZ
-
ORD
1 stop5h 05m
Air Canada
Mon 13/78:40 p.m.
ORD
-
YYZ
Nonstop1h 45m
Air Canada
Deal found 20/6C$ 298
Fri 10/78:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 13/73:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 22/6C$ 288
Tue 21/77:25 p.m.
YTZ
-
ORD
Nonstop2h 04m
Air Canada
Thu 30/77:25 a.m.
ORD
-
YTZ
Nonstop1h 42m
Air Canada
Deal found 21/6C$ 295
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 23 June 2026.
Sun 19/78:05 a.m.
YYZ
-
ORD
Nonstop1h 55m
Air Canada
Deal found 21/6C$ 191
Fri 17/71:45 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 23/6C$ 191
Wed 22/71:00 p.m.
YYZ
-
ORD
Nonstop2h 06m
United Airlines
Deal found 19/6C$ 193
Mon 14/94:00 p.m.
YYZ
-
ORD
1 stop5h 12m
Air Canada
Deal found 21/6C$ 194
Fri 18/98:30 a.m.
YTZ
-
ORD
1 stop7h 22m
Air Canada
Deal found 22/6C$ 194
Thu 17/96:15 a.m.
YYZ
-
ORD
1 stop5h 02m
Air Canada
Deal found 19/6C$ 196
Thu 20/87:25 p.m.
YTZ
-
ORD
Nonstop2h 04m
Air Canada
Deal found 19/6C$ 196
Wed 12/83:00 p.m.
YYZ
-
ORD
1 stop6h 05m
Air Canada
Deal found 22/6C$ 197
Mon 24/88:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 20/6C$ 197
Tue 14/712:15 p.m.
YTZ
-
ORD
Nonstop2h 04m
Air Canada
Deal found 19/6C$ 197
Tue 11/82:00 p.m.
YYZ
-
ORD
Nonstop1h 55m
Air Canada
Deal found 23/6C$ 198
Fri 17/77:25 p.m.
YTZ
-
ORD
Nonstop2h 04m
Air Canada
Deal found 21/6C$ 198
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 23 June 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 23 June 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
Quickest round-trip
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Sat 18/7
8:50 a.m.-9:40 a.m.
Nonstop1h 50m
Chicago Midway
Sun 19/7
3:20 p.m.-6:00 p.m.
Nonstop1h 40m
C$ 288
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Thu 16/7
8:50 a.m.-9:40 a.m.
Nonstop1h 50m
Chicago Midway
Sat 18/7
10:25 a.m.-1:05 p.m.
Nonstop1h 40m
C$ 299
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Thu 20/8
8:50 a.m.-9:40 a.m.
Nonstop1h 50m
Chicago Midway
Mon 24/8
3:15 p.m.-5:55 p.m.
Nonstop1h 40m
C$ 299
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Sun 12/7
8:50 a.m.-9:40 a.m.
Nonstop1h 50m
Chicago Midway
Tue 14/7
3:20 p.m.-6:00 p.m.
Nonstop1h 40m
C$ 302
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Wed 29/7
8:50 a.m.-9:40 a.m.
Nonstop1h 50m
Chicago Midway
Thu 6/8
3:15 p.m.-5:55 p.m.
Nonstop1h 40m
C$ 306
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Wed 29/7
8:50 a.m.-9:40 a.m.
Nonstop1h 50m
Chicago Midway
Sun 2/8
10:20 a.m.-1:00 p.m.
Nonstop1h 40m
C$ 306
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Sat 18/7
7:00 a.m.-8:00 a.m.
Nonstop2h 00m
Chicago O'Hare Intl
Mon 17/8
5:53 p.m.-8:44 p.m.
Nonstop1h 51m
C$ 307
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Sat 4/7
11:00 a.m.-12:00 p.m.
Nonstop2h 00m
Chicago O'Hare Intl
Sun 5/7
7:09 a.m.-9:54 a.m.
Nonstop1h 45m
C$ 307
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Sat 18/7
8:50 a.m.-9:40 a.m.
Nonstop1h 50m
Chicago Midway
Sat 25/7
10:25 a.m.-1:05 p.m.
Nonstop1h 40m
C$ 309
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Sun 26/7
8:50 a.m.-9:40 a.m.
Nonstop1h 50m
Chicago Midway
Tue 28/7
10:25 a.m.-1:05 p.m.
Nonstop1h 40m
C$ 313
Flights are sorted by cheapest round-trip flights first.
Deals found on 18/6
Showing 1-10 of 60 resultsSorted by cheapest first
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2
3
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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
YTZ-MDW
YYZ-ORD
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
YTZ-MDW
YYZ-ORD
YTZ-ORD
YYZ-MDW
What is the cheapest month to book a flight from Toronto to Chicago?
Currently, August is the cheapest month in which you can book a flight from Toronto to Chicago (average of C$ 360). Flying from Toronto to Chicago in January is currently the most expensive (average of C$ 1,183). 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 23 June 2026.
Unlike in the afternoon, when flights are generally more expensive, you can save up to 25% on flights from Toronto to Chicago by exploring options for tickets in the morning.
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 23 June 2026.
The most flights from YTO to CHI are scheduled on a Monday (78 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (61 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 136 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 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 8% of flights being delayed.
How far ahead should I book a flight from Toronto to Chicago?
To ensure you get the cheapest price possible for a flight from Toronto to Chicago, you should look to book at least 87 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 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 20 June 2026.
Travelers seeking maximum savings on their Toronto to Chicago flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Monday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
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 23 June 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.
Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.
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.
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.
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 long is the flight from Toronto to Chicago?
Airlines like Porter Airlines, Air Transat, and United Airlines 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$ 116 on this airline. Additional options worth looking into are Air Canada and American Airlines, starting at C$ 137 and C$ 256 round-trip. Users have found that Porter Airlines is 69% 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$ 158), United Airlines (C$ 160), and American Airlines (C$ 169).
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 Island - Chicago O'Hare Intl or Toronto Pearson Intl - 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 (100%), EVA Air (100%), Qatar Airways (90%).
What are the cheapest flights from Toronto to Chicago?
On average you can expect to pay C$ 1,344 for a flight from Toronto to Chicago. The cheapest flight overall is C$ 220 while the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl) is currently priced at C$ 290.
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, August is the cheapest month in which you can book a flight from Toronto to Chicago (average of C$ 360). Flying from Toronto to Chicago in January is currently the most expensive (average of C$ 1,183). 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 23 June 2026.
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on 23 June 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 23 June 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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