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 19/3. Fares are subject to change and may not be available on all flights or dates of travel.
YTO — CHI
22 Jan — 29 Jan1
Round-trip
1 adult
Economy
The best prices from Toronto to Chicago are usually found in April or February, booked 87 days in advance, depart on a Saturday or Wednesday and return on a Saturday
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 17 January 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 17 January 2025.
Fri 14/211:20 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 16/21:05 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 15/1C$ 339
Thu 6/27:15 a.m.YYZ - ORD
1 stop8h 37mMultiple Airlines
Sun 9/26:15 p.m.ORD - YYZ
1 stop16h 10mMultiple Airlines
Deal found 16/1C$ 344
Thu 6/29:00 a.m.YYZ - ORD
Nonstop2h 10mUnited Airlines
Mon 10/22:05 p.m.ORD - YYZ
Nonstop1h 41mUnited Airlines
Deal found 15/1C$ 356
Fri 7/23:25 p.m.YTZ - ORD
1 stop5h 30mAir Canada
Sun 9/27:20 a.m.ORD - YTZ
1 stop6h 30mAir Canada
Deal found 15/1C$ 362
Fri 7/22:05 p.m.YYZ - ORD
1 stop5h 33mAir Canada
Mon 10/210:53 a.m.ORD - YYZ
Nonstop1h 49mAir Canada
Deal found 16/1C$ 365
Thu 20/211:20 a.m.YTZ - MDW
Nonstop1h 50mAir Transat
Sun 23/21:05 p.m.MDW - YTZ
Nonstop1h 42mAir Transat
Deal found 16/1C$ 366
Fri 7/26:20 p.m.YYZ - ORD
Nonstop2h 00mBritish Airways
Sun 9/28:11 a.m.ORD - YYZ
Nonstop1h 40mBritish Airways
Deal found 16/1C$ 369
Thu 10/41:15 p.m.YYZ - ORD
Nonstop1h 55mAmerican Airlines
Sat 12/46:45 a.m.ORD - YYZ
1 stop7h 34mAmerican Airlines
Deal found 16/1C$ 377
Wed 19/210:10 a.m.YYZ - ORD
1 stop3h 45mDelta
Mon 24/22:35 p.m.ORD - YYZ
1 stop8h 04mDelta
Deal found 16/1C$ 385
Fri 7/26:00 a.m.YYZ - MDW
1 stop3h 51mDelta
Sun 9/25:05 p.m.MDW - YYZ
1 stop4h 44mDelta
Deal found 14/1C$ 391
Thu 6/212:20 p.m.YYZ - ORD
1 stop7h 18mLufthansa
Sun 9/24:00 p.m.ORD - YYZ
1 stop5h 15mLufthansa
Deal found 16/1C$ 397
Thu 6/21:05 p.m.YTZ - ORD
2 stops21h 34mMultiple Airlines
Sun 9/25:35 a.m.ORD - YTZ
2 stops13h 30mMultiple Airlines
Deal found 15/1C$ 410
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 17 January 2025.
Wed 19/211:20 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 25/21:05 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 16/1C$ 339
Thu 6/27:15 a.m.YYZ - ORD
1 stop8h 37mMultiple Airlines
Sun 9/26:15 p.m.ORD - YYZ
1 stop16h 10mMultiple Airlines
Deal found 16/1C$ 344
Fri 7/211:20 a.m.YTZ - MDW
Nonstop1h 50mAir Transat
Sun 9/21:05 p.m.MDW - YTZ
Nonstop1h 42mAir Transat
Deal found 16/1C$ 349
Thu 6/29:00 a.m.YYZ - ORD
Nonstop2h 10mUnited Airlines
Mon 10/22:05 p.m.ORD - YYZ
Nonstop1h 41mUnited Airlines
Deal found 15/1C$ 356
Thu 6/210:25 a.m.YTZ - ORD
1 stop5h 20mAir Canada
Mon 10/23:35 p.m.ORD - YTZ
1 stop5h 15mAir Canada
Deal found 15/1C$ 364
Fri 7/26:20 p.m.YYZ - ORD
Nonstop2h 00mBritish Airways
Sun 9/28:11 a.m.ORD - YYZ
Nonstop1h 40mBritish Airways
Deal found 16/1C$ 369
Thu 10/41:15 p.m.YYZ - ORD
Nonstop1h 55mAmerican Airlines
Sat 12/46:45 a.m.ORD - YYZ
1 stop7h 34mAmerican Airlines
Deal found 16/1C$ 377
Wed 19/210:10 a.m.YYZ - ORD
1 stop3h 45mDelta
Mon 24/22:35 p.m.ORD - YYZ
1 stop8h 04mDelta
Deal found 16/1C$ 385
Thu 6/212:20 p.m.YYZ - ORD
1 stop7h 18mLufthansa
Sun 9/24:00 p.m.ORD - YYZ
1 stop5h 15mLufthansa
Deal found 16/1C$ 397
Fri 14/22:45 p.m.YYZ - ORD
1 stop8h 13mKLM
Tue 18/27:30 a.m.ORD - YYZ
1 stop4h 56mKLM
Deal found 16/1C$ 415
Thu 13/27:45 a.m.YYZ - ORD
1 stop6h 10mWestJet
Mon 17/26:59 a.m.ORD - YYZ
1 stop3h 57mWestJet
Deal found 16/1C$ 438
Fri 7/22:05 p.m.YYZ - ORD
1 stop5h 33mAir Canada
Mon 10/210:53 a.m.ORD - YYZ
Nonstop1h 49mAir Canada
Deal found 16/1C$ 365
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 17 January 2025.
Fri 14/211:20 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 16/21:05 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 15/1C$ 339
Thu 6/29:00 a.m.YYZ - ORD
Nonstop2h 10mUnited Airlines
Mon 10/22:05 p.m.ORD - YYZ
Nonstop1h 41mUnited Airlines
Deal found 15/1C$ 356
Thu 10/41:15 p.m.YYZ - ORD
Nonstop1h 55mAmerican Airlines
Sat 12/411:55 a.m.ORD - YYZ
Nonstop1h 35mAmerican Airlines
Deal found 16/1C$ 362
Thu 20/211:20 a.m.YTZ - MDW
Nonstop1h 50mAir Transat
Sun 23/21:05 p.m.MDW - YTZ
Nonstop1h 42mAir Transat
Deal found 16/1C$ 366
Fri 7/26:20 p.m.YYZ - ORD
Nonstop2h 00mBritish Airways
Sun 9/28:11 a.m.ORD - YYZ
Nonstop1h 40mBritish Airways
Deal found 16/1C$ 369
Fri 7/29:00 a.m.YYZ - ORD
Nonstop2h 10mMultiple Airlines
Sun 23/28:30 p.m.ORD - YYZ
Nonstop1h 41mMultiple Airlines
Deal found 16/1C$ 375
Fri 21/22:00 p.m.YYZ - ORD
Nonstop1h 51mAir Canada
Sun 23/28:30 p.m.ORD - YYZ
Nonstop1h 41mAir Canada
Deal found 16/1C$ 392
Thu 20/22:00 p.m.YYZ - ORD
Nonstop1h 51mLufthansa
Sun 23/28:30 p.m.ORD - YYZ
Nonstop1h 41mLufthansa
Deal found 16/1C$ 420
Tue 18/211:20 a.m.YTZ - MDW
Nonstop1h 50mMultiple Airlines
Fri 21/21:05 p.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 14/1C$ 451
Last-minute flights from Toronto to Chicago
Discover last-minute flight deals from Toronto to Chicago. Data last updated 17 January 2025 and is based on user searches.
Tue 21/16:30 a.m.YYZ - MDW
1 stop7h 16mWestJet
Tue 28/11:26 p.m.MDW - YYZ
1 stop8h 45mWestJet
Deal found 14/1C$ 556
Wed 22/112:20 p.m.YKF - ORD
1 stop22h 07mMultiple Airlines
Sat 25/112:25 p.m.ORD - YKF
2 stops46h 55mMultiple Airlines
Deal found 15/1C$ 539
Thu 23/110:10 a.m.YYZ - MDW
1 stop3h 58mDelta
Thu 30/19:34 a.m.MDW - YYZ
1 stop5h 38mDelta
Deal found 15/1C$ 516
Thu 23/112:20 p.m.YYZ - ORD
Nonstop1h 51mUnited Airlines
Thu 30/16:00 a.m.ORD - YYZ
1 stop4h 46mUnited Airlines
Deal found 15/1C$ 552
Thu 23/111:15 p.m.YYZ - MDW
2 stops16h 27mMultiple Airlines
Thu 30/17:25 a.m.MDW - YYZ
1 stop9h 05mMultiple Airlines
Deal found 15/1C$ 681
Sat 25/17:00 a.m.YYZ - ORD
1 stop8h 23mMultiple Airlines
Mon 27/17:26 a.m.ORD - YYZ
1 stop15h 27mMultiple Airlines
Deal found 15/1C$ 346
Sat 25/111:20 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Fri 31/11:05 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 14/1C$ 401
Sat 25/15:30 p.m.YYZ - ORD
Nonstop2h 13mAir Canada
Fri 31/18:25 p.m.ORD - YYZ
Nonstop1h 41mAir Canada
Deal found 14/1C$ 474
Sat 25/112:25 p.m.YTZ - ORD
1 stop7h 25mAir Canada
Mon 27/11:55 p.m.ORD - YTZ
1 stop5h 48mAir Canada
Deal found 15/1C$ 519
Sun 26/111:31 a.m.YYZ - ORD
Nonstop2h 00mAmerican Airlines
Wed 29/19:49 a.m.ORD - YYZ
Nonstop1h 41mAmerican Airlines
Deal found 15/1C$ 490
Sun 26/110:10 a.m.YYZ - ORD
1 stop3h 45mDelta
Wed 29/110:05 a.m.ORD - YYZ
1 stop6h 09mDelta
Deal found 15/1C$ 499
Sun 26/11:20 p.m.YYZ - ORD
1 stop3h 53mWestJet
Wed 29/111:50 a.m.ORD - YYZ
2 stops10h 45mWestJet
Deal found 15/1C$ 562
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 17 January 2025.
Mon 24/39:30 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 16/1C$ 208
Tue 11/28:00 p.m.YYZ - ORD
1 stop11h 07mMultiple Airlines
Deal found 16/1C$ 213
Thu 6/210:25 a.m.YTZ - ORD
1 stop5h 20mAir Canada
Deal found 16/1C$ 213
Thu 6/29:00 a.m.YYZ - ORD
1 stop6h 45mAir Canada
Deal found 16/1C$ 221
Wed 19/210:55 a.m.YYZ - ORD
1 stop6h 56mAmerican Airlines
Deal found 16/1C$ 227
Fri 24/11:05 p.m.YKF - ORD
1 stop11h 27mMultiple Airlines
Deal found 15/1C$ 229
Wed 12/29:00 p.m.YYZ - ORD
Nonstop2h 13mUnited Airlines
Deal found 15/1C$ 231
Sun 9/27:40 a.m.YYZ - MDW
1 stop8h 41mMultiple Airlines
Deal found 15/1C$ 233
Thu 13/26:30 a.m.YYZ - ORD
1 stop10h 00mDelta
Deal found 16/1C$ 236
Thu 6/27:45 a.m.YYZ - MDW
1 stop6h 20mDelta
Deal found 16/1C$ 240
Wed 12/23:30 p.m.YTZ - ORD
2 stops20h 10mMultiple Airlines
Deal found 15/1C$ 246
Wed 26/26:15 p.m.YHM - ORD
1 stop22h 41mWestJet
Deal found 16/1C$ 256
Find flights from Toronto to Chicago within your budget
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 17 January 2025.
Fly from
Any airport
Fly to
Any airport
Route
Depart
Return
Price
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Fri 14/2
11:20 a.m.-12:10 p.m.
Nonstop1h 50m
Chicago Midway
Sun 16/2
1:05 p.m.-3:47 p.m.
Nonstop1h 42m
C$ 339
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Thu 6/2
7:15 a.m.-2:52 p.m.
1 stop8h 37m
Chicago O'Hare Intl
Sun 9/2
6:15 p.m.-11:25 a.m.
1 stop16h 10m
C$ 344
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Wed 5/2
6:20 p.m.-7:20 p.m.
Nonstop2h 00m
Chicago O'Hare Intl
Wed 12/2
8:11 a.m.-10:51 a.m.
Nonstop1h 40m
C$ 346
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Fri 7/2
8:00 a.m.-2:45 p.m.
1 stop7h 45m
Chicago O'Hare Intl
Mon 10/2
10:53 a.m.-1:42 p.m.
Nonstop1h 49m
C$ 352
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Thu 6/2
9:00 a.m.-10:10 a.m.
Nonstop2h 10m
Chicago O'Hare Intl
Mon 10/2
2:05 p.m.-4:46 p.m.
Nonstop1h 41m
C$ 356
TorontoChicago
YTZ - ORD
YTZORD
Toronto Island
Fri 7/2
3:25 p.m.-7:55 p.m.
1 stop5h 30m
Chicago O'Hare Intl
Sun 9/2
7:20 a.m.-2:50 p.m.
1 stop6h 30m
C$ 362
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Thu 20/2
11:20 a.m.-12:10 p.m.
Nonstop1h 50m
Chicago Midway
Sun 23/2
1:05 p.m.-3:47 p.m.
Nonstop1h 42m
C$ 366
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Thu 13/2
7:45 a.m.-12:55 p.m.
1 stop6h 10m
Chicago O'Hare Intl
Mon 17/2
6:59 a.m.-4:09 p.m.
1 stop8h 10m
C$ 391
TorontoChicago
YYZ - MDW
YYZMDW
Toronto Pearson Intl
Fri 7/2
6:00 a.m.-8:51 a.m.
1 stop3h 51m
Chicago Midway
Sun 9/2
5:05 p.m.-10:49 p.m.
1 stop4h 44m
C$ 391
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Thu 6/2
12:20 p.m.-6:38 p.m.
1 stop7h 18m
Chicago O'Hare Intl
Sun 9/2
4:00 p.m.-10:15 p.m.
1 stop5h 15m
C$ 397
Flights are sorted by cheapest round-trip flights first.
Deals found on 15/1
Showing 1-10 of 39 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.
Travel insights for flights from Toronto to Chicago
Get recent, data-driven insights about flights from Toronto to Chicago including ideal travel times, pricing trends, and more.
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 10 January 2025.
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 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$ 355). 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 17 January 2025.
Unlike at noon, when flights are generally more expensive, you can save up to 13% on flights from Toronto to Chicago by exploring options for tickets in the afternoon.
What is the cheapest day to fly from Toronto to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Toronto to Chicago. Price data was last updated on 30 June 2024.
Travelers seeking maximum savings on their Toronto to Chicago flight should consider departing on Tuesday evenings 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 17 January 2025.
The most flights from YTO to CHI are scheduled on a Monday (54 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (32 on average).
Rainfall in Chicago by month
Plan your trip to Chicago by taking into account the average rainfall totals by month.
In terms of precipitation, rainfall in Chicago ranges from 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago when rainfall is around 43.0 mm.
Temperature in Chicago by month
Plan your trip to Chicago by taking into account the average temperature totals by month.
If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).
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 17 January 2025.
Get a feel of what it's like to fly with Air Canada, United Airlines and American Airlines from Toronto to Chicago by reading reviews from past customers. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta has consistently been the best U.S. airline for my travels and this flight was no exception
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.
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$ 339 on this airline. Additional options worth looking into are Air Transat and United Airlines, starting at C$ 349 and C$ 356 round-trip. Users have found that Porter Airlines is 13% 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$ 208), Air Canada (C$ 213), and American Airlines (C$ 227).
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: Emirates (92%), Japan Airlines (92%), Republic Airways (90%).
What are the cheapest flights from Toronto to Chicago?
On average you can expect to pay C$ 1,477 for a flight from Toronto to Chicago. The cheapest flight overall is C$ 219 while the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl) is currently priced at C$ 356.
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$ 355). 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.
Browse thousands of different options on Cheapflights for your next trip
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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 17 January 2025.
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on 17 January 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 17 January 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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