Cheap flights from Toronto to Chicago from C$ 182

YTO — CHI
19 Oct — 26 Oct1
1 adult
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Toronto to Chicago are usually found in February or January, booked 88 days in advance, depart on a Friday or Thursday and return on a Tuesday

Cheap flight deals from Toronto to Chicago

Enter your travel dates to find the best prices.

Cheapest flights from Toronto to Chicago

Fri 23/107:00 a.m. -
Nonstop2h 00m
Sun 25/109:21 p.m. -
Nonstop1h 38m
Deal found 14/9C$ 287
Thu 1/1010:45 a.m. -
1 stop5h 07m
Sun 4/108:45 a.m. -
1 stop6h 05m
Deal found 14/9C$ 287
Fri 2/101:45 p.m. -
Nonstop1h 50m
Sun 4/1011:45 a.m. -
Nonstop1h 40m
Deal found 18/9C$ 290
Mon 2/118:20 a.m. -
2 stops7h 40m
Mon 9/111:55 p.m. -
Nonstop1h 47m
Deal found 18/9C$ 290
Fri 2/104:00 p.m. -
1 stop5h 12m
Sun 4/108:40 p.m. -
Nonstop1h 46m
Deal found 18/9C$ 291
Wed 7/101:45 p.m. -
Nonstop1h 50m
Sun 11/1011:45 a.m. -
Nonstop1h 40m
Deal found 16/9C$ 294
Mon 5/101:45 p.m. -
Nonstop1h 50m
Wed 7/1011:45 a.m. -
Nonstop1h 40m
Deal found 18/9C$ 295
Fri 23/104:00 p.m. -
1 stop5h 12m
Sun 25/1010:15 a.m. -
Nonstop1h 37m
Deal found 16/9C$ 297
Fri 2/101:45 p.m. -
Nonstop1h 50m
Sat 3/1011:45 a.m. -
Nonstop1h 40m
Deal found 18/9C$ 297
Fri 2/107:35 p.m. -
Nonstop2h 10m
Mon 5/102:00 p.m. -
Nonstop1h 48m
Deal found 18/9C$ 297
Fri 30/106:45 a.m. -
Nonstop2h 09m
Tue 3/111:55 p.m. -
1 stop6h 40m
Deal found 15/9C$ 298
Wed 7/1012:15 p.m. -
Nonstop2h 10m
Wed 14/102:00 p.m. -
Nonstop1h 48m
Deal found 16/9C$ 298

Find flight deals from Toronto to Chicago

Round-trip from

C$ 287

One-way from

C$ 182

Popular in

October

Cheapest in

February

Average price

C$ 392

Good round-trip deal

C$ 330 or less

Good one-way deal

C$ 192 or less
Air Canada
  • Air Canada
  • 1/10-4/10
  • 2 total stops
  • 11h 12m total
  • Toronto to Chicago
United Airlines
  • United Airlines
  • 29/9-31/12
  • Nonstop
  • 2h 00m total
  • Toronto to Chicago
Highest demand for flights based on searches. 3% potential increase in price (C$ 17 potential increase over avg. RT price).
Cheapest flight prices on average. 0% potential price decrease (C$ 5 potential savings vs. average RT price).
Average for round-trip flights in September 2026
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).

Cheapflights Fare Finder

 
Use the filters below to find and compare flights from Toronto to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Sat 14/11

6:45 a.m.-7:54 a.m.

Nonstop2h 09m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 182

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Tue 17/11

10:53 a.m.-11:57 a.m.

Nonstop2h 04m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 182
Quickest round-trip

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Thu 1/10

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 183

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Mon 23/11

4:35 p.m.-5:40 p.m.

Nonstop2h 05m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 183

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Thu 22/10

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 185

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Tue 6/10

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 190

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Sat 28/11

6:45 a.m.-7:54 a.m.

Nonstop2h 09m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 199

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Mon 19/10

9:00 p.m.-10:06 p.m.

Nonstop2h 06m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 200

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Sun 11/10

10:15 a.m.-11:21 a.m.

Nonstop2h 06m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 200

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Sat 3/10

6:00 a.m.-9:07 a.m.

1 stop4h 07m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 202

Flights are sorted by cheapest round-trip flights first.

Deals found on 14/9

Showing 1-10 of 60 resultsSorted by cheapest first
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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

Cheapflights Insights

Everything you need to know about your flight from Toronto to Chicago

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$ 347). Flying from Toronto to Chicago in October is currently the most expensive (average of C$ 458). 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?

Unlike in the evening, when flights are generally more expensive, you can save up to 18% on flights from Toronto to Chicago by exploring options for tickets in the morning.

Weekly flight availability from Toronto to Chicago

The most flights from YTO to CHI are scheduled on a Thursday (79 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (47 on average).

How much does it cost to fly round-trip from Toronto to Chicago?

Airfare is below average for this route at the moment.
Toronto to Chicago flights typically cost between C$ 320 and C$ 532 in October.
The cheapest round-trip price found within the last 5 days was C$ 287 on Air Canada (1 Oct-4 Oct).

How often are flights from Toronto to Chicago delayed?

About 14% of weekly flights between Toronto and Chicago have experienced delays in the past year, with the average delay time being 135 minutes.

What is the most punctual flight time for Toronto to Chicago flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Thursday tends to have the lowest number of delays on this route, whereas Saturday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Toronto to Chicago flights?

Over the past year, United Airlines has had the lowest number of delays on this route, with just 9% of flights being delayed.

How far ahead should I book a flight from Toronto to Chicago?

To ensure you get the cheapest price possible for a flight from Toronto to Chicago, you should look to book at least 87 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest day to fly from Toronto to Chicago?

Travelers seeking maximum savings on their Toronto to Chicago flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Monday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Chicago

Get 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.

Comfort

8.0

Crew

8.6

Entertainment

6.9

Food

7.6

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.

Comfort

8.0

Crew

8.6

Entertainment

6.9

Food

7.6

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.

Comfort

8.0

Crew

8.6

Entertainment

6.9

Food

7.6

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.

Comfort

8.0

Crew

8.6

Entertainment

6.9

Food

7.6

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.

Comfort

8.0

Crew

8.6

Entertainment

6.9

Food

7.6

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.

Comfort

8.0

Crew

8.6

Entertainment

6.9

Food

7.6

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.

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

  • 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.

  • How long is the flight from Toronto to Chicago?

    Airlines like Porter Airlines, Air Canada, 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 5h 35m. 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 Air Canada. Our recent data shows that you can find tickets from as low as C$ 135 on this airline. Additional options worth looking into are Porter Airlines and American Airlines, starting at C$ 222 and C$ 263 round-trip. Users have found that Air Canada is 65% 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 United Airlines (C$ 158), Air Canada (C$ 165), and American Airlines (C$ 167).

  • 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: Sun Country Air (100%), Copa Airlines (84%), Egyptair (81%).

  • What are the cheapest flights from Toronto to Chicago?

    On average you can expect to pay C$ 1,636 for a flight from Toronto to Chicago. The cheapest flight overall is C$ 207 while the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl) is currently priced at C$ 281.

  • 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$ 347). Flying from Toronto to Chicago in October is currently the most expensive (average of C$ 458). 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

Fly from Toronto to Chicago on these airlines

Top 5 airlines flying from Toronto to Chicago

AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 135AverageC$ 428FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Porter AirlinesCheapestC$ 222AverageC$ 429FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
American AirlinesCheapestC$ 263AverageC$ 433FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
United AirlinesCheapestC$ 297AverageC$ 422FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 355AverageC$ 441FlexibilityNo cancel feeOn-time60%
Search WestJet flights

Helpful tips for your next trip to Chicago

  • 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

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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