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Cheap flights from Toronto to Chicago from C$ 159

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Toronto to Chicago departing on 12/2. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Toronto to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Toronto to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Toronto to Chicago.

Cheap last-minute flights

Planning a quick getaway from Toronto to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Toronto to Chicago

Find recent round-trip train or bus tickets from Toronto to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
12:20 p.m. - 1:11 p.m.YYZ-ORD
1h 51mdirect
4:00 p.m. - 6:41 p.m.ORD-YYZ
1h 41mdirect
C$ 249Air Canada
Find Deal
Fri, 10 Jan - Mon, 13 Jan
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 306Porter Airlines
Find Deal
Thu, 12 Dec - Sun, 15 Dec
10:20 a.m. - 11:10 a.m.YTZ-MDW
1h 50mdirect
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 311Porter Airlines
Find Deal
Fri, 13 Dec - Tue, 17 Dec
2:00 p.m. - 2:51 p.m.YYZ-ORD
1h 51mdirect
8:25 p.m. - 11:06 p.m.ORD-YYZ
1h 41mdirect
C$ 342United Airlines
Find Deal
Thu, 12 Dec - Mon, 16 Dec
5:30 p.m. - 6:37 p.m.YYZ-ORD
2h 07mdirect
7:19 a.m. - 9:58 a.m.ORD-YYZ
1h 39mdirect
C$ 344Air Canada
Find Deal
Fri, 13 Dec - Sun, 15 Dec
9:40 a.m. - 10:30 a.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 356Air Transat
Find Deal
Thu, 12 Dec - Sun, 15 Dec
2:45 p.m. - 11:20 p.m.YYZ-ORD
9h 35m1 stop
7:19 a.m. - 9:58 a.m.ORD-YYZ
1h 39mdirect
C$ 363United Airlines
Find Deal
Thu, 12 Dec - Sun, 15 Dec
9:40 a.m. - 10:30 a.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 364Air Transat
Find Deal
Thu, 12 Dec - Sun, 15 Dec
6:00 a.m. - 12:30 p.m.YYZ-ORD
7h 30m1 stop
5:10 a.m. - 3:45 p.m.ORD-YYZ
9h 35m1 stop
C$ 383American Airlines
Find Deal
Thu, 12 Dec - Sun, 15 Dec
6:00 a.m. - 12:30 p.m.YYZ-ORD
7h 30m1 stop
6:00 a.m. - 11:56 a.m.ORD-YYZ
4h 56m1 stop
C$ 405American Airlines
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Sun, 8 Dec - Wed, 11 Dec
2:00 p.m. - 2:51 p.m.YYZ-ORD
1h 51mdirect
C$ 159Air Canada
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Wed, 12 Feb
11:10 a.m. - 12:00 p.m.YTZ-MDW
1h 50mdirect
C$ 186Porter Airlines
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Sat, 14 Dec
11:10 a.m. - 12:00 p.m.YTZ-MDW
1h 50mdirect
C$ 190Porter Airlines
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Sat, 14 Dec
6:35 p.m. - 7:32 p.m.YYZ-ORD
1h 57mdirect
C$ 205United Airlines
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Tue, 17 Dec
8:25 a.m. - 2:45 p.m.YTZ-ORD
7h 20m1 stop
C$ 205Air Canada
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Sat, 14 Dec
12:20 p.m. - 6:36 p.m.YYZ-ORD
7h 16m1 stop
C$ 212United Airlines
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Wed, 18 Dec
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
C$ 237Air Transat
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Mon, 6 Jan
6:15 a.m. - 7:30 a.m.YYZ-ORD
2h 15mdirect
C$ 247American Airlines
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Thu, 5 Dec
11:31 a.m. - 12:31 p.m.YYZ-ORD
2h 00mdirect
C$ 253American Airlines
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Wed, 12 Feb
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
C$ 283Air Transat
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Sat, 21 Dec
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
12:05 p.m. - 2:47 p.m.MDW-YTZ
1h 42mdirect
C$ 524Porter Airlines
Find Deal
Mon, 25 Nov - Mon, 9 Dec
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
1:05 p.m. - 3:47 p.m.MDW-YTZ
1h 42mdirect
C$ 529Air Transat
Find Deal
Tue, 26 Nov - Sat, 18 Jan
6:20 p.m. - 7:20 p.m.YYZ-ORD
2h 00mdirect
6:01 a.m. - 11:59 a.m.ORD-YYZ
4h 58m1 stop
C$ 566American Airlines
Find Deal
Tue, 26 Nov - Wed, 4 Dec
2:55 p.m. - 6:32 p.m.YYZ-MDW
4h 37m1 stop
9:30 a.m. - 11:41 p.m.MDW-YYZ
13h 11m1 stop
C$ 566WestJet
Find Deal
Tue, 26 Nov - Tue, 3 Dec
6:15 a.m. - 7:30 a.m.YYZ-ORD
2h 15mdirect
6:30 p.m. - 9:20 p.m.ORD-YYZ
1h 50mdirect
C$ 568American Airlines
Find Deal
Mon, 25 Nov - Mon, 9 Dec
12:20 p.m. - 1:11 p.m.YYZ-ORD
1h 51mdirect
2:05 p.m. - 4:46 p.m.ORD-YYZ
1h 41mdirect
C$ 580Air Canada
Find Deal
Tue, 26 Nov - Tue, 21 Jan
3:25 p.m. - 7:55 p.m.YTZ-ORD
5h 30m1 stop
2:00 p.m. - 8:43 p.m.ORD-YTZ
5h 43m1 stop
C$ 585Air Canada
Find Deal
Tue, 26 Nov - Wed, 4 Dec
12:15 p.m. - 8:25 p.m.YYZ-ORD
9h 10m1 stop
6:17 a.m. - 1:41 p.m.ORD-YYZ
6h 24m1 stop
C$ 585WestJet
Find Deal
Tue, 26 Nov - Thu, 28 Nov
6:35 p.m. - 7:32 p.m.YYZ-ORD
1h 57mdirect
7:19 a.m. - 9:58 a.m.ORD-YYZ
1h 39mdirect
C$ 661United Airlines
Find Deal
Sat, 23 Nov - Thu, 28 Nov
9:00 p.m. - 10:07 p.m.YYZ-ORD
2h 07mdirect
9:14 p.m. - 11:59 p.m.ORD-YYZ
1h 45mdirect
C$ 704United Airlines
Find Deal
Fri, 22 Nov - Mon, 25 Nov
12:20 p.m. - 1:11 p.m.YYZ-ORD
1h 51mdirect
4:00 p.m. - 6:41 p.m.ORD-YYZ
1h 41mdirect
C$ 249Air Canada
Find Deal
Fri, 10 Jan - Mon, 13 Jan
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 306Porter Airlines
Find Deal
Thu, 12 Dec - Sun, 15 Dec
10:20 a.m. - 11:10 a.m.YTZ-MDW
1h 50mdirect
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 311Porter Airlines
Find Deal
Fri, 13 Dec - Tue, 17 Dec
2:00 p.m. - 2:51 p.m.YYZ-ORD
1h 51mdirect
8:25 p.m. - 11:06 p.m.ORD-YYZ
1h 41mdirect
C$ 342United Airlines
Find Deal
Thu, 12 Dec - Mon, 16 Dec
5:30 p.m. - 6:37 p.m.YYZ-ORD
2h 07mdirect
7:19 a.m. - 9:58 a.m.ORD-YYZ
1h 39mdirect
C$ 344Air Canada
Find Deal
Fri, 13 Dec - Sun, 15 Dec
9:40 a.m. - 10:30 a.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 356Air Transat
Find Deal
Thu, 12 Dec - Sun, 15 Dec
9:40 a.m. - 10:30 a.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 364Air Transat
Find Deal
Thu, 12 Dec - Sun, 15 Dec
9:00 p.m. - 10:07 p.m.YYZ-ORD
2h 07mdirect
7:19 a.m. - 9:58 a.m.ORD-YYZ
1h 39mdirect
C$ 374United Airlines
Find Deal
Thu, 12 Dec - Sun, 15 Dec
4:44 p.m. - 5:44 p.m.YYZ-ORD
2h 00mdirect
1:25 p.m. - 4:00 p.m.ORD-YYZ
1h 35mdirect
C$ 487American Airlines
Find Deal
Tue, 3 Dec - Wed, 4 Dec
6:15 a.m. - 7:30 a.m.YYZ-ORD
2h 15mdirect
1:25 p.m. - 4:00 p.m.ORD-YYZ
1h 35mdirect
C$ 635American Airlines
Find Deal
Sun, 1 Dec - Wed, 4 Dec

Lufthansa flights from Toronto to Chicago

Our best Lufthansa deals on Toronto to Chicago flight tickets
Lufthansa
12 Dec
YYZ6:52 a.m.Toronto Pearson Intl
2h 13m
ORD8:05 a.m.Chicago O'Hare Intl
15 Dec
ORD7:19 a.m.Chicago O'Hare Intl
1h 39m
YYZ9:58 a.m.Toronto Pearson Intl
Lufthansa
12 Dec
YYZ6:52 a.m.Toronto Pearson Intl
2h 13m
ORD8:05 a.m.Chicago O'Hare Intl
15 Dec
ORD7:19 a.m.Chicago O'Hare Intl
1h 39m
YYZ9:58 a.m.Toronto Pearson Intl

Air Canada flights from Toronto to Chicago

Our best Air Canada deals on Toronto to Chicago flight tickets
Air Canada
10 Jan
YYZ12:20 p.m.Toronto Pearson Intl
1h 51m
ORD1:11 p.m.Chicago O'Hare Intl
13 Jan
ORD4:00 p.m.Chicago O'Hare Intl
1h 41m
YYZ6:41 p.m.Toronto Pearson Intl
Air Canada
13 Dec
YYZ5:30 p.m.Toronto Pearson Intl
2h 07m
ORD6:37 p.m.Chicago O'Hare Intl
15 Dec
ORD7:19 a.m.Chicago O'Hare Intl
1h 39m
YYZ9:58 a.m.Toronto Pearson Intl
Air Canada
12 Dec
YYZ6:25 a.m.Toronto Pearson Intl
5h 29m
1 stop
ORD10:54 a.m.Chicago O'Hare Intl
16 Dec
ORD9:50 a.m.Chicago O'Hare Intl
1h 41m
YYZ12:31 p.m.Toronto Pearson Intl

See travel insights to Chicago from

How to get the cheapest flight ticket from Toronto to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between Toronto and Chicago?

What is the cheapest month to fly to Chicago?

The month of February is another great option to travel to Chicago, with average flight prices from Toronto averaging around C$ 339.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Saturday when prices can be found for as low as C$ 371. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around C$ 393. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago.

What is the cheapest time of day to depart on your flight to Chicago?

In the afternoon is the cheapest time of day to fly from Toronto to Chicago when you can find flight prices for as low as C$ 367. Flying to Chicago in the afternoon is an ideal time because this is during off-peak travel hours. At noon is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 418 per ticket.

What is the cheapest Toronto to Chicago flight route?

Fly from Toronto Island to Chicago Midway for the best Toronto - Chicago flight prices

How far in advance should I book a flight to Chicago?

The best time to book a flight to Chicago from Toronto is 34 days out, which is when prices tend to be around C$ 370. Don’t hesitate to check prices now though, because momondo users recently found tickets for as low as C$ 427.

What cabin class options are available on Toronto to Chicago flights?

There are 4 cabin classes available to choose from on Toronto to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Toronto to Chicago flights?

You could potentially save up to 8% on your flight if you consider stops on a Toronto to Chicago flight.

How have Toronto to Chicago flight prices changed over time?

As of November 2024, prices for Toronto to Chicago flights are approximately 8% more expensive when compared to flights at the same time last year.

When to book flights from Toronto to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Toronto to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Toronto to Chicago (YTO to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Toronto to Chicago

Best price found

C$ 159

Fastest flight time

1h 50m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Toronto in the past 72 hours is C$ 159. The best round-trip flight deal from Toronto to Chicago found on momondo in the last 72 hours is C$ 249.
The fastest flight from Toronto to Chicago takes 1h 50m
Direct flights go from Toronto to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

  • How far is Toronto to Chicago by plane?

    Chicago is 700.6 km away from Toronto. Flights usually cover this in 1h 50m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Toronto to Chicago?

    Prices for flights from Toronto to Chicago are updated daily.

  • How many operators does momondo search for flights from Toronto to Chicago?

  • How old do you have to be to fly from Toronto to Chicago?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Toronto to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Toronto to Chicago?

  • What is the most popular airline from Toronto to Chicago?


Best airlines flying from Toronto to Chicago

Compare and see reviews for airlines that fly from Toronto to Chicago with momondo
Airline
Rating
Free Cancellation
Price
Porter AirlinesPriceFrom C$ 271Free CancellationRating
7.8
288 reviews
Search Porter Airlines flights
Air CanadaPriceFrom C$ 303Free CancellationRating
7.0
8,246 reviews
Search Air Canada flights
United AirlinesPriceFrom C$ 348Free CancellationRating
7.4
9,172 reviews
Search United Airlines flights
American AirlinesPriceFrom C$ 349Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
WestJetPriceFrom C$ 433Free CancellationRating
7.3
2,811 reviews
Search WestJet flights
  • Porter Airlines Flights From Toronto to Chicago

    Across 10 Porter Airlines flights from Toronto to Chicago this week, the average price was C$ 255, with the best Porter Airlines deals starting from C$ 194 round-trip. 288 users have rated Porter Airlines on momondo, with an average score of 7.8/10.

  • United Airlines Flights From Toronto to Chicago

    United Airlines is also a popular choice for this route. United Airlines flight deals for Toronto to Chicago start from as low as C$ 249 round-trip, depending on your selected dates, with average United Airlines deals seen on momondo around C$ 314. United Airlines operates 64 flights to Chicago from Toronto in an average week. Users have rated it 7.4/10 across 9,172 reviews.


Why use momondo?

Why should I use momondo to find a flight deal from Toronto to Chicago?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Toronto.

Can I find flights from Toronto to Chicago with flexible booking policies on momondo?

Yes. All flights to Chicago from Toronto on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Toronto to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Toronto.

I’m not ready to book a flight from Toronto to Chicago right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Toronto to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.


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Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 25.6 km from Chicago