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Cheap flights from Toronto to Chicago from C$ 176

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 26/4. Fares are subject to change and may not be available on all flights or dates of travel.
YTO — CHI
26 Mar — 2 Apr1
1 adult

Cheapflights Tip: The best prices from Toronto to Chicago are usually found in April or September, booked 81 days in advance, depart on a Friday or Thursday and return on a Tuesday

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 21 March 2025.

Round-trip from

C$ 277

One-way from

C$ 176

Popular in

December

Cheapest in

April

Average price

C$ 399

Good round-trip deal

C$ 279 or less

Good one-way deal

C$ 170 or less
Air Canada
  • Air Canada
  • 10/4-12/4
  • 1 total stop
  • 7h 32m total
  • Toronto to Chicago
Air Canada
  • Air Canada
  • 26/4
  • 1 total stop
  • 5h 30m total
  • Toronto to Chicago
Highest demand for flights based on searches. 4% potential increase in price (C$ 23 potential increase over avg. RT price).
Cheapest flight prices on average. 0% potential price decrease (C$ 6 potential savings vs. average RT price).
Average for round-trip flights in March 2025
Price to beat on a round-trip flight from Toronto (YTO) to Chicago (CHI).
Price to beat on a one-way flight from Toronto (YTO) to Chicago (CHI).

Find flight deals from Toronto to Chicago

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 21 March 2025.

Thu 10/42:05 p.m.YYZ - ORD
1 stop5h 49mAir Canada
Sat 12/46:01 p.m.ORD - YYZ
Nonstop1h 43mAir Canada
Deal found 21/3C$ 277
Sun 27/43:50 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 6/59:40 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 20/3C$ 277
Fri 2/57:55 a.m.YTZ - MDW
Nonstop1h 50mAir Transat
Sat 3/59:40 a.m.MDW - YTZ
Nonstop1h 42mAir Transat
Deal found 20/3C$ 283
Sun 25/51:00 p.m.YYZ - ORD
Nonstop2h 01mMultiple Airlines
Fri 30/59:35 a.m.ORD - YYZ
Nonstop1h 40mMultiple Airlines
Deal found 20/3C$ 285
Sat 26/412:25 p.m.YTZ - ORD
1 stop6h 57mAir Canada
Wed 30/47:00 a.m.ORD - YTZ
1 stop6h 50mAir Canada
Deal found 20/3C$ 291
Thu 1/53:35 p.m.YTZ - MDW
Nonstop1h 49mMultiple Airlines
Sat 10/59:40 a.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 21/3C$ 294
Fri 25/47:20 a.m.YYZ - ORD
1 stop5h 24mUnited Airlines
Tue 29/45:59 p.m.ORD - YYZ
1 stop4h 55mUnited Airlines
Deal found 20/3C$ 321
Wed 16/43:59 p.m.YYZ - MDW
1 stop3h 21mDelta
Wed 23/49:20 a.m.MDW - YYZ
1 stop6h 58mDelta
Deal found 20/3C$ 326
Sun 20/49:00 a.m.YYZ - ORD
Nonstop2h 01mSWISS
Sat 26/44:15 p.m.ORD - YYZ
1 stop6h 39mSWISS
Deal found 20/3C$ 327
Wed 9/41:15 p.m.YYZ - ORD
Nonstop1h 55mAmerican Airlines
Sat 12/45:10 a.m.ORD - YYZ
1 stop4h 55mAmerican Airlines
Deal found 19/3C$ 328
Wed 9/46:00 a.m.YYZ - ORD
1 stop4h 12mDelta
Sat 12/46:15 a.m.ORD - YYZ
1 stop6h 20mDelta
Deal found 19/3C$ 340
Mon 7/41:05 p.m.YKF - ORD
1 stop28h 22mMultiple Airlines
Tue 15/45:36 a.m.ORD - YKF
3 stops36h 49mMultiple Airlines
Deal found 20/3C$ 413

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 21 March 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

Thu 10/4

2:05 p.m.-6:54 p.m.

1 stop5h 49m

Chicago O'Hare Intl

Sat 12/4

6:01 p.m.-8:44 p.m.

Nonstop1h 43m

C$ 277

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 27/4

3:50 p.m.-4:40 p.m.

Nonstop1h 50m

Chicago Midway

Tue 6/5

9:40 a.m.-12:22 p.m.

Nonstop1h 42m

C$ 277

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 2/5

7:55 a.m.-8:45 a.m.

Nonstop1h 50m

Chicago Midway

Sat 3/5

9:40 a.m.-12:22 p.m.

Nonstop1h 42m

C$ 283

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sun 25/5

1:00 p.m.-2:01 p.m.

Nonstop2h 01m

Chicago O'Hare Intl

Fri 30/5

9:35 a.m.-12:15 p.m.

Nonstop1h 40m

C$ 285

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sat 26/4

12:25 p.m.-6:22 p.m.

1 stop6h 57m

Chicago O'Hare Intl

Wed 30/4

7:00 a.m.-2:50 p.m.

1 stop6h 50m

C$ 291

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 1/5

3:35 p.m.-4:24 p.m.

Nonstop1h 49m

Chicago Midway

Sat 10/5

9:40 a.m.-12:22 p.m.

Nonstop1h 42m

C$ 294

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 25/4

7:20 a.m.-11:44 a.m.

1 stop5h 24m

Chicago O'Hare Intl

Tue 29/4

5:59 p.m.-11:54 p.m.

1 stop4h 55m

C$ 321

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 16/4

3:59 p.m.-6:20 p.m.

1 stop3h 21m

Chicago Midway

Wed 23/4

9:20 a.m.-5:18 p.m.

1 stop6h 58m

C$ 326

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sun 20/4

9:00 a.m.-10:01 a.m.

Nonstop2h 01m

Chicago O'Hare Intl

Sat 26/4

4:15 p.m.-11:54 p.m.

1 stop6h 39m

C$ 327

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 9/4

1:15 p.m.-2:10 p.m.

Nonstop1h 55m

Chicago O'Hare Intl

Sat 12/4

5:10 a.m.-11:05 a.m.

1 stop4h 55m

C$ 328

Flights are sorted by cheapest round-trip flights first.

Deals found on 20/3

Showing 1-10 of 37 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 14 March 2025.

To ensure you get the cheapest price possible for a flight from Toronto to Chicago, you should look to book at least 81 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 21 March 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 65% 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 30 June 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. Wednesday 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 21 March 2025.

The most flights from YTO to CHI are scheduled on a Friday (58 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (41 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 21 March 2025.
Get a feel of what it's like to fly with Delta, Porter Airlines and Air Transat 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.

Food

7.3

Boarding

8.2

Entertainment

7.9

Crew

8.5

Comfort

8.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
8.0
Very good

Food

7.3

Boarding

8.2

Entertainment

7.9

Crew

8.5

Comfort

8.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Food

7.3

Boarding

8.2

Entertainment

7.9

Crew

8.5

Comfort

8.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Food

7.3

Boarding

8.2

Entertainment

7.9

Crew

8.5

Comfort

8.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Food

7.3

Boarding

8.2

Entertainment

7.9

Crew

8.5

Comfort

8.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Food

7.3

Boarding

8.2

Entertainment

7.9

Crew

8.5

Comfort

8.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

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.
  • What airports serve Toronto to Chicago flights?

    Flying out of Toronto to go to Chicago, you’ll show up to board your flight at Pearson International Airport in Toronto. Your flight will be heading for either Chicago O’Hare or Chicago Midway International Airport. You’ll find a variety of options for this route. You can fly direct, with one-stop, or more. There is a large range of prices for these flights.

  • Which airlines fly directly from Toronto to Chicago?

    You can find a lot of direct flights from Toronto to Chicago. American Airlines has a few from Pearson to O’Hare. They’re about two hours long. Air Canada flies the same route. United also flies non-stop between Pearson and O’Hare.

  • What are the stopover options between Toronto to Chicago?

    American Airlines has one-stop flights that land in Charlotte on the way to Chicago. This stopover varies in the time it adds to your travel day. You could be looking at six and a half hours, but also up to eleven hours. Delta makes a stopover in Detroit on the way to either Midway or O’Hare. These flights are only a few hours longer than the direct flights. Air Canada has a route that goes through Montreal before landing at O’Hare.

  • Do I need a passport or visa to fly from Toronto to Chicago?

    While you do need your passport because you’re passing over the border into the US, you do not need a visa if you’re only going for a leisure trip. If you will be working or going to school, or investing on your trip, then you will need some kind of visa.

  • How can passengers contribute to sustainability when flying from Toronto to Chicago?

    Pack a little if you want to minimize your carbon footprint when traveling from Toronto to Chicago. It is one of the easiest strategies for travelers to boost sustainable development. This is accurate since flying efficiently reduces the weight of the airplane, which in turn reduces fuel consumption. Before you even get to the runway, flying out of a green airport will reduce your carbon impact. These airports reduce their emissions through the use of alternative energy, the purchase of biofuels, or the application of green design principles during additions and upgrades.

  • What sustainability practices does Toronto Pearson International Airport offer?

    By 2030, Toronto Pearson International Airport (YYZ) wants to have net-zero carbon emissions. It includes "Scope 1" emissions from the fleet of vehicles and natural gas consumption of the airport, as well as "Scope 2" emissions from the production of the airport's electrical needs. The airport's Scope 2 emissions, which make up 93% of emission levels within its operational procedures, will be totally eradicated by cutting power use and transitioning to 100% green sources. Toronto Pearson  Airport will continue to prioritize operational management while concentrating on indirect "Scope 3" emissions.

  • Which alternative means of transportation is available along this route?

    If you intend to travel from Toronto to Chicago without adding to global warming emissions, a flight is your best bet. Flying is the most environmentally beneficial form of transportation since it allows for the most efficient long-distance transportation of people. However, you should opt for nonstop flights, as they consume less fuel per passenger as compared to connecting flights. Alternatively, you can opt for Amtrak trains which are more sustainable compared to trains as they produce at least 50% fewer carbon emissions. The best part is some of these trains adopt green energy; hence are sustainable.

  • What are the cheapest airlines flying from Toronto to Chicago round-trip?

    Our cheapest airline available from Toronto to Chicago is Air Canada. Our recent data shows that you can find tickets from as low as C$ 277 on this airline. Additional options worth looking into are Porter Airlines and Air Transat, starting at C$ 277 and C$ 283 round-trip. Users have found that Air Canada is 30% 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$ 176), Porter Airlines (C$ 178), and United Airlines (C$ 185).

  • What are the most popular routes from Toronto to Chicago?

  • 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 (88%), Emirates (87%), ANA (86%).

  • What are the cheapest flights from Toronto to Chicago?

    On average you can expect to pay C$ 2,919 for a flight from Toronto to Chicago. The cheapest flight overall is C$ 209 while the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl) is currently priced at C$ 285.

  • Can I find deals for flights from Toronto to Chicago that include hotel bookings?

    Yes. In addition to deals on Toronto to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Toronto to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Toronto to Chicago.

  • 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.

See more FAQs

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 21 March 2025.

Top 5 airlines flying from Toronto to Chicago

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 21 March 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 270AverageC$ 378FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 315AverageC$ 435FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
American AirlinesCheapestC$ 334AverageC$ 546FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
United AirlinesCheapestC$ 344AverageC$ 472FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 461AverageC$ 641FlexibilityNo cancel feeOn-time60%
Search WestJet flights

Helpful tips for your next trip to Chicago

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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