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 23/11. Fares are subject to change and may not be available on all flights or dates of travel.
YTO — CHI
4 Dec — 11 Dec1
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 77 days in advance, depart on a Friday or Thursday 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 4 November 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 4 November 2025.
Sun 23/117:14 p.m.YYZ - ORD
1 stop5h 26mAmerican Airlines
Mon 1/125:00 a.m.ORD - YYZ
1 stop5h 03mAmerican Airlines
Deal found 2/11C$ 258
Thu 11/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 14/124:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 2/11C$ 258
Thu 4/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Fri 12/124:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 2/11C$ 263
Thu 11/126:00 a.m.YYZ - ORD
Nonstop2h 15mAmerican Airlines
Sun 14/128:10 a.m.ORD - YYZ
Nonstop1h 46mAmerican Airlines
Deal found 3/11C$ 264
Wed 19/1111:32 a.m.YYZ - ORD
Nonstop1h 55mAmerican Airlines
Tue 25/116:06 a.m.ORD - YYZ
1 stop4h 48mAmerican Airlines
Deal found 3/11C$ 267
Fri 12/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 14/124:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 1/11C$ 267
Thu 20/119:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 23/1111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 2/11C$ 268
Fri 5/126:00 a.m.YYZ - ORD
Nonstop2h 15mAmerican Airlines
Sun 7/128:00 a.m.ORD - YYZ
1 stop7h 35mAmerican Airlines
Deal found 4/11C$ 271
Thu 11/127:00 a.m.YYZ - ORD
1 stop5h 18mAir Canada
Mon 15/128:15 p.m.ORD - YYZ
Nonstop1h 39mAir Canada
Deal found 4/11C$ 272
Thu 11/127:00 a.m.YYZ - ORD
1 stop5h 18mAir Canada
Sun 14/128:15 p.m.ORD - YYZ
Nonstop1h 39mAir Canada
Deal found 2/11C$ 274
Fri 21/112:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 23/1111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 3/11C$ 274
Sun 16/119:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 24/114:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 2/11C$ 275
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 4 November 2025.
Fri 16/111:00 a.m.YYZ - ORD
Nonstop2h 08mUnited Airlines
Mon 16/26:28 p.m.ORD - YYZ
Nonstop1h 53mUnited Airlines
Deal found 2/11C$ 258
Thu 11/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 14/124:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 2/11C$ 258
Thu 26/210:05 a.m.YYZ - ORD
1 stop4h 16mDelta
Tue 3/32:03 p.m.ORD - YYZ
1 stop4h 05mDelta
Deal found 4/11C$ 282
Thu 20/119:00 a.m.YYZ - ORD
Nonstop2h 05mMultiple Airlines
Mon 24/118:15 p.m.ORD - YYZ
Nonstop1h 39mMultiple Airlines
Deal found 2/11C$ 284
Sat 17/110:30 a.m.YTZ - ORD
1 stop5h 25mAir Canada
Mon 16/23:35 p.m.ORD - YTZ
1 stop5h 00mAir Canada
Deal found 3/11C$ 312
Sat 17/18:55 a.m.YYZ - ORD
Nonstop2h 06mUnited Airlines
Mon 16/24:47 p.m.ORD - YYZ
Nonstop1h 58mUnited Airlines
Deal found 2/11C$ 258
Thu 4/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Fri 12/124:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 2/11C$ 263
Wed 25/27:45 a.m.YYZ - ORD
1 stop6h 36mDelta
Tue 3/32:03 p.m.ORD - YYZ
1 stop4h 05mDelta
Deal found 4/11C$ 282
Thu 4/129:00 p.m.YYZ - ORD
Nonstop2h 05mMultiple Airlines
Sun 7/128:00 a.m.ORD - YYZ
Nonstop1h 40mMultiple Airlines
Deal found 2/11C$ 284
Fri 12/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 14/124:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 1/11C$ 267
Mon 5/16:40 p.m.YYZ - ORD
1 stop5h 55mUnited Airlines
Sun 11/111:15 a.m.ORD - YYZ
Nonstop1h 46mUnited Airlines
Deal found 4/11C$ 271
Mon 5/17:45 a.m.YYZ - ORD
1 stop6h 22mDelta
Mon 12/16:08 p.m.ORD - YYZ
1 stop3h 33mDelta
Deal found 4/11C$ 282
Sat 6/123:30 p.m.YTZ - ORD
1 stop5h 40mAir Canada
Tue 9/127:05 a.m.ORD - YTZ
1 stop6h 50mAir Canada
Deal found 2/11C$ 313
Thu 20/119:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 24/1111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 3/11C$ 274
Mon 5/17:45 a.m.YYZ - MDW
1 stop6h 03mDelta
Fri 9/16:30 p.m.MDW - YYZ
1 stop3h 11mDelta
Deal found 4/11C$ 282
Tue 6/13:30 p.m.YYZ - ORD
Nonstop2h 10mUnited Airlines
Sun 11/16:05 a.m.ORD - YYZ
1 stop4h 43mUnited Airlines
Deal found 4/11C$ 289
Sat 15/1111:00 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sat 22/1112:45 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 1/11C$ 278
Sun 11/16:00 a.m.YYZ - MDW
1 stop3h 54mDelta
Mon 12/16:14 p.m.MDW - YYZ
1 stop3h 27mDelta
Deal found 4/11C$ 282
Wed 7/15:30 p.m.YYZ - ORD
Nonstop2h 20mUnited Airlines
Sun 11/16:05 a.m.ORD - YYZ
1 stop4h 43mUnited Airlines
Deal found 4/11C$ 289
Thu 11/128:50 a.m.YTZ - ORD
1 stop5h 01mAir Canada
Sun 14/127:10 a.m.ORD - YTZ
2 stops10h 03mAir Canada
Deal found 3/11C$ 358
Sun 16/119:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Wed 19/1111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 2/11C$ 278
Sun 11/16:00 a.m.YYZ - MDW
1 stop3h 54mDelta
Thu 15/19:50 a.m.MDW - YYZ
1 stop5h 09mDelta
Deal found 4/11C$ 282
Fri 26/129:00 a.m.YYZ - ORD
Nonstop2h 05mUnited Airlines
Wed 7/19:15 p.m.ORD - YYZ
Nonstop1h 44mUnited Airlines
Deal found 3/11C$ 289
Sat 6/128:30 a.m.YTZ - ORD
1 stop7h 25mAir Canada
Mon 8/1212:50 p.m.ORD - YTZ
1 stop7h 45mAir Canada
Deal found 2/11C$ 358
Tue 25/119:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 2/1211:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 3/11C$ 281
Sun 11/16:00 a.m.YYZ - MDW
1 stop3h 54mDelta
Tue 13/16:14 p.m.MDW - YYZ
1 stop3h 27mDelta
Deal found 4/11C$ 282
Tue 23/129:00 p.m.YYZ - ORD
Nonstop2h 05mUnited Airlines
Tue 6/16:28 p.m.ORD - YYZ
Nonstop1h 53mUnited Airlines
Deal found 3/11C$ 289
Fri 12/127:00 a.m.YHM - ORD
1 stop8h 21mMultiple Airlines
Wed 17/125:00 a.m.ORD - YHM
1 stop9h 00mMultiple Airlines
Deal found 2/11C$ 424
Thu 11/128:50 a.m.YTZ - ORD
1 stop5h 01mAir Canada
Mon 15/1210:38 a.m.ORD - YTZ
1 stop6h 17mAir Canada
Deal found 4/11C$ 364
Fri 28/112:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 1/1211:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 3/11C$ 281
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 4 November 2025.
Thu 23/48:15 a.m.YYZ - ORD
Nonstop1h 55mAir Canada
Tue 5/510:00 a.m.ORD - YYZ
Nonstop1h 45mAir Canada
Deal found 3/11C$ 258
Thu 11/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 14/124:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 2/11C$ 258
Sun 15/39:00 a.m.YYZ - ORD
Nonstop2h 09mMultiple Airlines
Wed 18/33:55 p.m.ORD - YYZ
Nonstop1h 39mMultiple Airlines
Deal found 3/11C$ 260
Thu 4/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Fri 12/124:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 2/11C$ 263
Thu 11/126:00 a.m.YYZ - ORD
Nonstop2h 15mAmerican Airlines
Sun 14/128:10 a.m.ORD - YYZ
Nonstop1h 46mAmerican Airlines
Deal found 3/11C$ 264
Fri 12/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 14/124:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 1/11C$ 267
Thu 20/112:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 24/114:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 2/11C$ 268
Mon 9/29:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sat 28/212:45 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 2/11C$ 270
Thu 11/124:50 p.m.YYZ - ORD
Nonstop1h 58mAir Canada
Mon 15/122:00 p.m.ORD - YYZ
Nonstop1h 39mAir Canada
Deal found 4/11C$ 272
Fri 21/112:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 23/1111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 3/11C$ 274
Sun 16/119:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 24/114:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 2/11C$ 275
Sat 15/1111:00 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sat 22/1112:45 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 1/11C$ 278
Last-minute flights from Toronto to Chicago
Discover last-minute flight deals from Toronto to Chicago. Data last updated 4 November 2025 and is based on user searches.
Sun 16/119:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 24/114:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 2/11C$ 275
Thu 20/119:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 23/1111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 2/11C$ 268
Fri 21/112:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 23/1111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 3/11C$ 274
Sat 22/116:20 p.m.YYZ - ORD
Nonstop2h 00mAmerican Airlines
Fri 28/115:00 a.m.ORD - YYZ
1 stop5h 03mAmerican Airlines
Deal found 4/11C$ 267
Tue 2/127:30 a.m.YYZ - ORD
1 stop7h 29mAmerican Airlines
Sat 6/128:00 a.m.ORD - YYZ
1 stop7h 35mAmerican Airlines
Deal found 4/11C$ 258
Thu 4/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Fri 12/124:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 2/11C$ 263
Fri 5/126:00 a.m.YYZ - ORD
Nonstop2h 15mAmerican Airlines
Sun 7/128:00 a.m.ORD - YYZ
1 stop7h 35mAmerican Airlines
Deal found 4/11C$ 271
Thu 11/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 14/124:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 2/11C$ 258
Thu 11/126:00 a.m.YYZ - ORD
Nonstop2h 15mAmerican Airlines
Sun 14/128:10 a.m.ORD - YYZ
Nonstop1h 46mAmerican Airlines
Deal found 3/11C$ 264
Thu 11/127:00 a.m.YYZ - ORD
1 stop5h 18mAir Canada
Mon 15/128:15 p.m.ORD - YYZ
Nonstop1h 39mAir Canada
Deal found 4/11C$ 272
Thu 11/127:00 a.m.YYZ - ORD
1 stop5h 18mAir Canada
Sun 14/128:00 a.m.ORD - YYZ
Nonstop1h 40mAir Canada
Deal found 3/11C$ 277
Fri 12/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 14/124:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 1/11C$ 267
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 4 November 2025.
Sun 23/116:05 a.m.YYZ - MDW
1 stop7h 29mDelta
Deal found 2/11C$ 181
Wed 26/111:00 p.m.YYZ - ORD
1 stop8h 00mAir Canada
Deal found 2/11C$ 182
Thu 27/118:30 a.m.YTZ - ORD
1 stop7h 25mAir Canada
Deal found 2/11C$ 182
Wed 3/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 2/11C$ 184
Sun 23/118:50 a.m.YTZ - ORD
2 stops7h 05mAir Canada
Deal found 3/11C$ 184
Sun 23/1110:00 a.m.YYZ - ORD
1 stop5h 55mAir Canada
Deal found 3/11C$ 185
Fri 28/116:05 a.m.YYZ - ORD
1 stop7h 39mDelta
Deal found 3/11C$ 187
Mon 17/112:30 p.m.YTZ - MDW
Nonstop1h 50mAir Transat
Deal found 3/11C$ 187
Wed 19/1110:30 a.m.YTZ - ORD
1 stop5h 25mAir Canada
Deal found 2/11C$ 187
Wed 26/116:05 a.m.YYZ - MDW
1 stop3h 49mDelta
Deal found 3/11C$ 187
Sun 23/119:15 a.m.YTZ - MDW
Nonstop1h 50mAir Transat
Deal found 3/11C$ 188
Tue 25/1110:30 a.m.YTZ - ORD
1 stop5h 25mAir Canada
Deal found 2/11C$ 188
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 4 November 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
YYZ - ORD
YYZORD
Toronto Pearson Intl
Fri 16/1
11:00 a.m.-12:08 p.m.
Nonstop2h 08m
Chicago O'Hare Intl
Mon 16/2
6:28 p.m.-9:21 p.m.
Nonstop1h 53m
C$ 258
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Thu 11/12
2:30 p.m.-3:20 p.m.
Nonstop1h 50m
Chicago Midway
Sun 14/12
4:15 p.m.-6:57 p.m.
Nonstop1h 42m
C$ 258
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Sat 17/1
8:55 a.m.-10:01 a.m.
Nonstop2h 06m
Chicago O'Hare Intl
Mon 16/2
4:47 p.m.-7:45 p.m.
Nonstop1h 58m
C$ 258
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Thu 4/12
2:30 p.m.-3:20 p.m.
Nonstop1h 50m
Chicago Midway
Fri 12/12
4:15 p.m.-6:57 p.m.
Nonstop1h 42m
C$ 263
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Fri 12/12
2:30 p.m.-3:20 p.m.
Nonstop1h 50m
Chicago Midway
Sun 14/12
4:15 p.m.-6:57 p.m.
Nonstop1h 42m
C$ 267
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Mon 5/1
6:40 p.m.-11:35 p.m.
1 stop5h 55m
Chicago O'Hare Intl
Sun 11/1
11:15 a.m.-2:01 p.m.
Nonstop1h 46m
C$ 271
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Thu 20/11
9:15 a.m.-10:05 a.m.
Nonstop1h 50m
Chicago Midway
Mon 24/11
11:00 a.m.-1:42 p.m.
Nonstop1h 42m
C$ 274
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Sat 15/11
11:00 a.m.-11:50 a.m.
Nonstop1h 50m
Chicago Midway
Sat 22/11
12:45 p.m.-3:27 p.m.
Nonstop1h 42m
C$ 278
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Sun 16/11
9:15 a.m.-10:05 a.m.
Nonstop1h 50m
Chicago Midway
Wed 19/11
11:00 a.m.-1:42 p.m.
Nonstop1h 42m
C$ 278
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Tue 25/11
9:15 a.m.-10:05 a.m.
Nonstop1h 50m
Chicago Midway
Tue 2/12
11:00 a.m.-1:42 p.m.
Nonstop1h 42m
C$ 281
Flights are sorted by cheapest round-trip flights first.
Deals found on 2/11
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 31 October 2025.
To ensure you get the cheapest price possible for a flight from Toronto to Chicago, you should look to book at least 77 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$ 117). Flying from Toronto to Chicago in February is currently the most expensive (average of C$ 267). 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 4 November 2025.
Unlike at noon, when flights are generally more expensive, you can save up to 29% on flights from Toronto to Chicago by exploring options for tickets in the morning.
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 16 December 2024.
Travelers seeking maximum savings on their Toronto to Chicago flight should consider departing on Sunday mornings when fares are most often at their lowest. Sunday at noon 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 4 November 2025.
The most flights from YTO to CHI are scheduled on a Monday (65 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (41 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 4 November 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.
I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.
I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.
I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.
I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.
I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.
I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.
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 United Airlines, Porter 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 2h 26m. 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$ 199 on this airline. Additional options worth looking into are American Airlines and Air Canada, starting at C$ 264 and C$ 265 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 Delta (C$ 181), Porter Airlines (C$ 184), and Air Canada (C$ 184).
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 Midway 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: EVA Air (94%), Egyptair (92%), ANA (88%).
What are the cheapest flights from Toronto to Chicago?
On average you can expect to pay C$ 2,094 for a flight from Toronto to Chicago. The cheapest flight overall is C$ 221 while the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl) is currently priced at C$ 215.
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$ 117). Flying from Toronto to Chicago in February is currently the most expensive (average of C$ 267). 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 4 November 2025.
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on 4 November 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 4 November 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.
Fly with Cheapflights
Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.
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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