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 19/10. Fares are subject to change and may not be available on all flights or dates of travel.
YTO — CHI
19 Oct — 26 Oct1
Round-trip
1 adult
Economy
Round-trip
1 adult, Economy
Cheapflights Tip: The best prices from Toronto to Chicago are usually found in July or June, booked 68 days in advance, depart on a Friday or Saturday and return on a Thursday
Cheap 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 19 September 2025.
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 19 September 2025.
Wed 15/106:30 a.m.YYZ - ORD
1 stop13h 08mMultiple Airlines
Wed 22/107:43 p.m.ORD - YYZ
1 stop17h 22mMultiple Airlines
Deal found 17/9C$ 296
Mon 20/104:00 p.m.YYZ - ORD
1 stop8h 44mMultiple Airlines
Thu 23/101:26 p.m.ORD - YYZ
1 stop6h 41mMultiple Airlines
Deal found 16/9C$ 299
Tue 21/106:30 a.m.YYZ - ORD
1 stop13h 08mMultiple Airlines
Thu 30/105:05 a.m.ORD - YYZ
1 stop8h 35mMultiple Airlines
Deal found 16/9C$ 312
Sun 19/104:00 p.m.YYZ - ORD
1 stop24h 49mMultiple Airlines
Fri 31/105:05 a.m.ORD - YYZ
1 stop8h 35mMultiple Airlines
Deal found 16/9C$ 313
Mon 20/104:00 p.m.YYZ - ORD
1 stop8h 44mMultiple Airlines
Fri 31/107:51 p.m.ORD - YYZ
1 stop17h 29mMultiple Airlines
Deal found 16/9C$ 318
Mon 20/104:00 p.m.YYZ - ORD
1 stop8h 44mMultiple Airlines
Fri 24/105:05 a.m.ORD - YYZ
1 stop8h 00mMultiple Airlines
Deal found 18/9C$ 321
Sun 19/104:00 p.m.YYZ - ORD
1 stop24h 49mMultiple Airlines
Thu 30/102:20 p.m.ORD - YYZ
1 stop9h 06mMultiple Airlines
Deal found 16/9C$ 324
Thu 2/106:30 a.m.YYZ - ORD
1 stop12h 09mMultiple Airlines
Tue 7/105:05 a.m.ORD - YYZ
1 stop8h 00mMultiple Airlines
Deal found 18/9C$ 331
Sat 1/1112:25 p.m.YYZ - ORD
1 stop7h 24mWestJet
Sat 8/117:10 a.m.ORD - YYZ
1 stop3h 10mWestJet
Deal found 17/9C$ 332
Sat 1/116:20 a.m.YYZ - MDW
1 stop5h 10mWestJet
Sat 8/113:00 p.m.MDW - YYZ
1 stop7h 18mWestJet
Deal found 17/9C$ 332
Fri 31/107:15 a.m.YYZ - ORD
1 stop12h 31mMultiple Airlines
Thu 6/114:01 p.m.ORD - YYZ
1 stop28h 06mMultiple Airlines
Deal found 16/9C$ 334
Fri 24/106:00 a.m.YKF - ORD
1 stop11h 43mWestJet
Sun 26/102:20 p.m.ORD - YKF
1 stop14h 08mWestJet
Deal found 16/9C$ 338
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 19 September 2025.
Fri 24/106:00 a.m.YKF - ORD
1 stop11h 43mWestJet
Sun 26/102:20 p.m.ORD - YKF
1 stop14h 08mWestJet
Deal found 16/9C$ 338
Thu 9/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Sun 12/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 17/9C$ 343
Sat 1/113:30 p.m.YTZ - ORD
1 stop5h 30mAir Canada
Sat 8/1112:50 p.m.ORD - YTZ
1 stop6h 05mAir Canada
Deal found 17/9C$ 375
Thu 27/113:30 p.m.YYZ - ORD
Nonstop2h 22mUnited Airlines
Sun 30/119:20 p.m.ORD - YYZ
Nonstop1h 39mUnited Airlines
Deal found 16/9C$ 390
Thu 6/116:50 a.m.YYZ - ORD
Nonstop2h 06mMultiple Airlines
Wed 12/1110:00 a.m.ORD - YYZ
Nonstop1h 40mMultiple Airlines
Deal found 17/9C$ 392
Thu 6/119:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 11/1111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 17/9C$ 343
Thu 23/109:45 a.m.YYZ - ORD
1 stop7h 26mWestJet
Sat 25/107:00 a.m.ORD - YYZ
1 stop5h 40mWestJet
Deal found 18/9C$ 360
Thu 16/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Thu 23/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 17/9C$ 345
Wed 12/117:00 a.m.YYZ - ORD
1 stop5h 18mAir Canada
Fri 14/118:15 p.m.ORD - YYZ
Nonstop1h 39mAir Canada
Deal found 18/9C$ 389
Sun 2/115:50 a.m.YYZ - ORD
Nonstop2h 05mUnited Airlines
Tue 11/1111:15 a.m.ORD - YYZ
Nonstop1h 46mUnited Airlines
Deal found 16/9C$ 390
Thu 27/116:05 a.m.YYZ - ORD
1 stop3h 52mWestJet
Sat 29/116:45 a.m.ORD - YYZ
1 stop3h 39mWestJet
Deal found 18/9C$ 361
Wed 12/119:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Fri 14/114:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 18/9C$ 345
Wed 15/107:45 a.m.YTZ - ORD
1 stop10h 28mMultiple Airlines
Fri 17/106:40 a.m.ORD - YTZ
1 stop11h 15mMultiple Airlines
Deal found 16/9C$ 419
Sat 1/116:50 a.m.YYZ - ORD
Nonstop2h 06mUnited Airlines
Tue 11/1111:15 a.m.ORD - YYZ
Nonstop1h 46mUnited Airlines
Deal found 17/9C$ 392
Sun 26/103:30 p.m.YTZ - ORD
1 stop5h 30mAir Canada
Tue 11/117:15 a.m.ORD - YTZ
1 stop6h 40mAir Canada
Deal found 17/9C$ 397
Thu 16/107:24 p.m.YYZ - MDW
1 stop23h 19mWestJet
Thu 23/109:20 a.m.MDW - YYZ
2 stops14h 11mWestJet
Deal found 18/9C$ 372
Sat 25/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Mon 27/104:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 17/9C$ 349
Thu 23/109:00 a.m.YYZ - ORD
Nonstop1h 55mUnited Airlines
Sat 25/107:10 a.m.ORD - YYZ
Nonstop1h 48mUnited Airlines
Deal found 18/9C$ 392
Fri 31/107:00 a.m.YTZ - ORD
2 stops15h 33mMultiple Airlines
Tue 11/115:05 a.m.ORD - YTZ
2 stops16h 18mMultiple Airlines
Deal found 16/9C$ 440
Sat 11/103:25 p.m.YTZ - ORD
1 stop5h 52mAir Canada
Wed 15/108:40 a.m.ORD - YTZ
1 stop7h 05mAir Canada
Deal found 18/9C$ 412
Thu 25/126:00 a.m.YYZ - MDW
1 stop12h 19mWestJet
Sat 31/12:00 p.m.MDW - YYZ
1 stop8h 04mWestJet
Deal found 17/9C$ 375
Fri 7/119:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 11/1111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 18/9C$ 350
Tue 28/109:00 a.m.YYZ - ORD
Nonstop2h 05mUnited Airlines
Mon 10/111:19 p.m.ORD - YYZ
Nonstop1h 43mUnited Airlines
Deal found 17/9C$ 392
Sun 26/102:05 p.m.YTZ - ORD
2 stops11h 58mMultiple Airlines
Wed 29/105:05 a.m.ORD - YTZ
2 stops16h 18mMultiple Airlines
Deal found 17/9C$ 441
Fri 17/106:20 a.m.YYZ - MDW
1 stop12h 23mWestJet
Tue 21/101:48 p.m.MDW - YYZ
1 stop8h 30mWestJet
Deal found 17/9C$ 375
Fri 17/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Fri 24/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 18/9C$ 352
Sat 4/1010:25 a.m.YTZ - ORD
1 stop5h 23mAir Canada
Wed 15/108:40 a.m.ORD - YTZ
1 stop5h 05mAir Canada
Deal found 17/9C$ 443
Thu 23/106:00 a.m.YHM - ORD
1 stop11h 43mMultiple Airlines
Sat 25/105:30 p.m.ORD - YHM
2 stops27h 48mMultiple Airlines
Deal found 17/9C$ 451
Fri 24/106:00 p.m.YYZ - MDW
1 stop5h 14mWestJet
Sun 26/1010:35 a.m.MDW - YYZ
1 stop5h 15mWestJet
Deal found 16/9C$ 375
Mon 17/119:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Wed 26/1111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 19/9C$ 353
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 19 September 2025.
Tue 14/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Thu 16/105:20 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 16/9C$ 341
Mon 20/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Thu 23/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 16/9C$ 342
Thu 9/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Sun 12/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 17/9C$ 343
Thu 9/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Sat 11/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 18/9C$ 347
Thu 16/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Sat 18/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 17/9C$ 349
Thu 16/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Thu 23/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 18/9C$ 350
Fri 17/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Fri 24/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 18/9C$ 352
Wed 15/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Wed 22/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 17/9C$ 353
Thu 23/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Sat 25/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 18/9C$ 354
Wed 22/103:35 p.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Sat 25/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 18/9C$ 356
Sun 2/116:30 p.m.YYZ - ORD
Nonstop2h 00mAir Canada
Sun 9/118:00 a.m.ORD - YYZ
Nonstop1h 40mAir Canada
Deal found 18/9C$ 357
Wed 15/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Mon 20/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 17/9C$ 357
Last-minute flights from Toronto to Chicago
Discover last-minute flight deals from Toronto to Chicago. Data last updated 19 September 2025 and is based on user searches.
Thu 9/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Sun 12/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 17/9C$ 343
Thu 9/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Sat 11/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 18/9C$ 347
Tue 14/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Thu 16/105:20 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 16/9C$ 341
Wed 15/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Wed 22/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 17/9C$ 353
Wed 15/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Mon 20/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 17/9C$ 357
Thu 16/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Sat 18/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 17/9C$ 349
Thu 16/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Thu 23/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 18/9C$ 350
Fri 17/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Fri 24/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 18/9C$ 352
Mon 20/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Thu 23/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 16/9C$ 342
Wed 22/103:35 p.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Fri 24/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 18/9C$ 356
Thu 23/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Sat 25/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 18/9C$ 354
Fri 24/106:00 a.m.YKF - ORD
1 stop11h 43mWestJet
Sun 26/102:20 p.m.ORD - YKF
1 stop14h 08mWestJet
Deal found 16/9C$ 338
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 19 September 2025.
Sun 19/104:00 p.m.YYZ - ORD
1 stop24h 49mMultiple Airlines
Deal found 16/9C$ 185
Fri 14/114:00 p.m.YYZ - ORD
1 stop5h 31mMultiple Airlines
Deal found 17/9C$ 188
Mon 20/104:00 p.m.YYZ - ORD
1 stop8h 44mMultiple Airlines
Deal found 16/9C$ 192
Mon 3/119:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 17/9C$ 193
Fri 17/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 18/9C$ 194
Wed 15/106:30 a.m.YYZ - ORD
1 stop13h 08mMultiple Airlines
Deal found 16/9C$ 196
Thu 9/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 17/9C$ 200
Mon 10/114:00 p.m.YYZ - ORD
1 stop5h 31mMultiple Airlines
Deal found 18/9C$ 201
Mon 20/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 16/9C$ 201
Sat 11/103:25 p.m.YTZ - ORD
1 stop5h 52mAir Canada
Deal found 18/9C$ 201
Tue 16/127:15 a.m.YYZ - ORD
1 stop15h 08mMultiple Airlines
Deal found 18/9C$ 203
Thu 13/119:30 p.m.YYZ - ORD
1 stop17h 05mMultiple Airlines
Deal found 17/9C$ 204
Cheapflights Fare Finder
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 19 September 2025.
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
YKF - ORD
YKFORD
Toronto Region of Waterloo Intl
Fri 24/10
6:00 a.m.-4:43 p.m.
1 stop11h 43m
Chicago O'Hare Intl
Sun 26/10
2:20 p.m.-5:28 a.m.
1 stop14h 08m
C$ 338
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Thu 9/10
7:50 a.m.-8:39 a.m.
Nonstop1h 49m
Chicago Midway
Sun 12/10
9:35 a.m.-12:17 p.m.
Nonstop1h 42m
C$ 343
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Thu 6/11
9:15 a.m.-10:05 a.m.
Nonstop1h 50m
Chicago Midway
Tue 11/11
11:00 a.m.-1:42 p.m.
Nonstop1h 42m
C$ 343
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Thu 16/10
7:50 a.m.-8:39 a.m.
Nonstop1h 49m
Chicago Midway
Thu 23/10
9:35 a.m.-12:17 p.m.
Nonstop1h 42m
C$ 345
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Wed 12/11
9:15 a.m.-10:05 a.m.
Nonstop1h 50m
Chicago Midway
Fri 14/11
4:15 p.m.-6:57 p.m.
Nonstop1h 42m
C$ 345
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Sat 25/10
7:50 a.m.-8:39 a.m.
Nonstop1h 49m
Chicago Midway
Mon 27/10
4:15 p.m.-6:57 p.m.
Nonstop1h 42m
C$ 349
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Fri 7/11
9:15 a.m.-10:05 a.m.
Nonstop1h 50m
Chicago Midway
Tue 11/11
11:00 a.m.-1:42 p.m.
Nonstop1h 42m
C$ 350
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Fri 17/10
7:50 a.m.-8:39 a.m.
Nonstop1h 49m
Chicago Midway
Fri 24/10
9:35 a.m.-12:17 p.m.
Nonstop1h 42m
C$ 352
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Mon 17/11
9:15 a.m.-10:05 a.m.
Nonstop1h 50m
Chicago Midway
Wed 26/11
11:00 a.m.-1:42 p.m.
Nonstop1h 42m
C$ 353
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Thu 23/10
9:45 a.m.-4:11 p.m.
1 stop7h 26m
Chicago O'Hare Intl
Sat 25/10
7:00 a.m.-1:40 p.m.
1 stop5h 40m
C$ 360
Flights are sorted by cheapest round-trip flights first.
Deals found on 17/9
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.
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
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 12 September 2025.
To ensure you get the cheapest price possible for a flight from Toronto to Chicago, you should look to book at least 68 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, January is the cheapest month in which you can book a flight from Toronto to Chicago (average of C$ 261). Flying from Toronto to Chicago in March is currently the most expensive (average of C$ 348). 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 19 September 2025.
Unlike in the afternoon, when flights are generally more expensive, you can save up to 47% on flights from Toronto to Chicago by exploring options for tickets in the evening.
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 October 2024.
Travelers seeking maximum savings on their Toronto to Chicago flight should consider departing on Friday evenings when fares are most often at their lowest. Tuesday afternoons 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 19 September 2025.
The most flights from YTO to CHI are scheduled on a Thursday (65 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (43 on average).
How much does it cost to fly round-trip from Toronto to Chicago?
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 19 September 2025.
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.
Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
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 WestJet, Porter Airlines, and Air Canada fly from Toronto to Chicago in about 1h 49m. The time it takes to get you to your destination can typically vary by up to 9h 54m. 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$ 196 on this airline. Additional options worth looking into are Air Canada and American Airlines, starting at C$ 263 and C$ 267 round-trip. Users have found that Porter Airlines is 44% 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$ 201), Air Canada (C$ 201), and WestJet (C$ 212).
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: EVA Air (88%), Egyptair (85%), Copa Airlines (85%).
What are the cheapest flights from Toronto to Chicago?
On average you can expect to pay C$ 1,699 for a flight from Toronto to Chicago. The cheapest flight overall is C$ 239 while the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl) is currently priced at C$ 339.
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, January is the cheapest month in which you can book a flight from Toronto to Chicago (average of C$ 261). Flying from Toronto to Chicago in March is currently the most expensive (average of C$ 348). 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 19 September 2025.
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on 19 September 2025.
Browse through other flights departing from Toronto. Flights are based on user searches made on Cheapflights and were last updated on 19 September 2025.
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 19 September 2025.
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.
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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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