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Cheap flights from Toronto to Chicago from $135

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 12/16. 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 pm - 1:11 pmYYZ-ORD
1h 51mnonstop
4:00 pm - 6:41 pmORD-YYZ
1h 41mnonstop
$178Air Canada
Find Deal
Fri, Jan 10 - Mon, Jan 13
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$219Porter Airlines
Find Deal
Thu, Dec 12 - Sun, Dec 15
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$223Porter Airlines
Find Deal
Thu, Dec 12 - Sun, Dec 15
12:00 pm - 6:41 pmYYZ-ORD
7h 41m1 stop
7:19 am - 9:58 amORD-YYZ
1h 39mnonstop
$237Air Canada
Find Deal
Wed, Dec 11 - Thu, Dec 12
11:00 am - 11:59 amYYZ-ORD
1h 59mnonstop
7:19 am - 9:58 amORD-YYZ
1h 39mnonstop
$245United Airlines
Find Deal
Wed, Dec 11 - Thu, Dec 12
2:45 pm - 11:20 pmYYZ-ORD
9h 35m1 stop
7:19 am - 9:58 amORD-YYZ
1h 39mnonstop
$260United Airlines
Find Deal
Thu, Dec 12 - Sun, Dec 15
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$260Air Transat
Find Deal
Thu, Dec 12 - Sun, Dec 15
9:40 am - 10:30 amYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$261Air Transat
Find Deal
Thu, Dec 12 - Sun, Dec 15
7:35 am - 12:15 pmYYZ-ORD
5h 40m1 stop
7:22 am - 1:00 pmORD-YYZ
4h 38m1 stop
$297American Airlines
Find Deal
Wed, Jan 1 - Fri, Jan 17
7:35 am - 3:11 pmYYZ-ORD
8h 36m1 stop
8:02 am - 4:40 pmORD-YYZ
7h 38m1 stop
$298American Airlines
Find Deal
Wed, Dec 11 - Thu, Dec 12
10:20 am - 11:10 amYTZ-MDW
1h 50mnonstop
$135Porter Airlines
Find Deal
Mon, Dec 16
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
$136Porter Airlines
Find Deal
Thu, Dec 19
10:25 am - 2:45 pmYTZ-ORD
5h 20m1 stop
$138Air Canada
Find Deal
Mon, Dec 16
6:35 pm - 7:32 pmYYZ-ORD
1h 57mnonstop
$142Air Canada
Find Deal
Tue, Dec 17
12:20 pm - 1:11 pmYYZ-ORD
1h 51mnonstop
$147United Airlines
Find Deal
Sat, Dec 14
9:30 am - 10:20 amYTZ-MDW
1h 50mnonstop
$155Air Transat
Find Deal
Tue, Dec 17
6:15 am - 7:30 amYYZ-ORD
2h 15mnonstop
$158American Airlines
Find Deal
Sat, Jan 18
6:15 am - 7:30 amYYZ-ORD
2h 15mnonstop
$159American Airlines
Find Deal
Wed, Jan 8
12:20 pm - 6:38 pmYYZ-ORD
7h 18m1 stop
$163United Airlines
Find Deal
Sat, Jan 18
10:20 am - 11:10 amYTZ-MDW
1h 50mnonstop
$163Air Transat
Find Deal
Wed, Dec 18
3:25 pm - 7:55 pmYTZ-ORD
5h 30m1 stop
11:35 am - 5:50 pmORD-YTZ
5h 15m1 stop
$349Air Canada
Find Deal
Mon, Nov 25 - Fri, Nov 29
7:30 am - 7:16 pmYYZ-ORD
12h 46m1 stop
1:20 pm - 9:21 pmORD-YYZ
7h 01m1 stop
Mon, Nov 25 - Fri, Nov 29
9:30 am - 10:20 amYTZ-MDW
1h 50mnonstop
11:15 am - 1:57 pmMDW-YTZ
1h 42mnonstop
$384Porter Airlines
Find Deal
Fri, Nov 22 - Tue, Dec 3
1:10 pm - 2:10 pmYYZ-ORD
2h 00mnonstop
1:25 pm - 4:00 pmORD-YYZ
1h 35mnonstop
$389American Airlines
Find Deal
Fri, Nov 22 - Tue, Dec 3
9:30 am - 10:20 amYTZ-MDW
1h 50mnonstop
11:15 am - 1:57 pmMDW-YTZ
1h 42mnonstop
$393Porter Airlines
Find Deal
Sun, Nov 24 - Tue, Dec 3
6:20 pm - 7:20 pmYYZ-ORD
2h 00mnonstop
5:00 am - 11:00 amORD-YYZ
5h 00m1 stop
$398American Airlines
Find Deal
Fri, Nov 22 - Tue, Dec 3
9:00 am - 10:05 amYYZ-ORD
2h 05mnonstop
4:52 pm - 7:45 pmORD-YYZ
1h 53mnonstop
$409United Airlines
Find Deal
Sat, Nov 23 - Tue, Dec 3
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
11:15 am - 1:57 pmMDW-YTZ
1h 42mnonstop
$411Air Transat
Find Deal
Mon, Nov 25 - Tue, Dec 3
9:30 am - 10:20 amYTZ-MDW
1h 50mnonstop
11:15 am - 1:57 pmMDW-YTZ
1h 42mnonstop
$429Air Transat
Find Deal
Sun, Nov 24 - Tue, Dec 3
6:35 pm - 7:32 pmYYZ-ORD
1h 57mnonstop
7:19 am - 9:58 amORD-YYZ
1h 39mnonstop
$473United Airlines
Find Deal
Sat, Nov 23 - Thu, Nov 28
12:20 pm - 1:11 pmYYZ-ORD
1h 51mnonstop
4:00 pm - 6:41 pmORD-YYZ
1h 41mnonstop
$178Air Canada
Find Deal
Fri, Jan 10 - Mon, Jan 13
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$219Porter Airlines
Find Deal
Thu, Dec 12 - Sun, Dec 15
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$223Porter Airlines
Find Deal
Thu, Dec 12 - Sun, Dec 15
9:00 pm - 10:07 pmYYZ-ORD
2h 07mnonstop
7:19 am - 9:58 amORD-YYZ
1h 39mnonstop
$237Air Canada
Find Deal
Mon, Dec 9 - Thu, Dec 12
11:00 am - 11:59 amYYZ-ORD
1h 59mnonstop
7:19 am - 9:58 amORD-YYZ
1h 39mnonstop
$245United Airlines
Find Deal
Wed, Dec 11 - Thu, Dec 12
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$260Air Transat
Find Deal
Thu, Dec 12 - Sun, Dec 15
9:40 am - 10:30 amYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$261Air Transat
Find Deal
Thu, Dec 12 - Sun, Dec 15
12:20 pm - 1:11 pmYYZ-ORD
1h 51mnonstop
7:19 am - 9:58 amORD-YYZ
1h 39mnonstop
$268United Airlines
Find Deal
Wed, Dec 11 - Thu, Dec 12
6:15 am - 7:30 amYYZ-ORD
2h 15mnonstop
6:30 pm - 9:20 pmORD-YYZ
1h 50mnonstop
$415American Airlines
Find Deal
Sat, Nov 30 - Sat, Dec 7
6:15 am - 7:30 amYYZ-ORD
2h 15mnonstop
6:34 pm - 9:29 pmORD-YYZ
1h 55mnonstop
$474American Airlines
Find Deal
Sat, Nov 30 - Mon, Dec 2

Delta flights from Toronto to Chicago

Our best Delta deals on Toronto to Chicago flight tickets
Delta
Dec 12
YYZ6:30 amToronto Pearson Intl
9h 13m
1 stop
ORD2:43 pmChicago O'Hare Intl
Dec 19
ORD7:00 amChicago O'Hare Intl
8h 14m
1 stop
YYZ4:14 pmToronto Pearson Intl
Delta
Dec 31
YYZ6:30 amToronto Pearson Intl
9h 08m
1 stop
ORD2:38 pmChicago O'Hare Intl
Jan 16
ORD12:35 pmChicago O'Hare Intl
6h 56m
1 stop
YYZ8:31 pmToronto Pearson Intl
Delta
Dec 31
YYZ6:30 amToronto Pearson Intl
9h 08m
1 stop
ORD2:38 pmChicago O'Hare Intl
Jan 19
ORD10:05 amChicago O'Hare Intl
6h 09m
1 stop
YYZ5:14 pmToronto Pearson Intl

Air Canada flights from Toronto to Chicago

Our best Air Canada deals on Toronto to Chicago flight tickets
Air Canada
Jan 10
YYZ12:20 pmToronto Pearson Intl
1h 51m
ORD1:11 pmChicago O'Hare Intl
Jan 13
ORD4:00 pmChicago O'Hare Intl
1h 41m
YYZ6:41 pmToronto Pearson Intl
Air Canada
Dec 11
YYZ12:00 pmToronto Pearson Intl
7h 41m
1 stop
ORD6:41 pmChicago O'Hare Intl
Dec 12
ORD7:19 amChicago O'Hare Intl
1h 39m
YYZ9:58 amToronto Pearson Intl
Air Canada
Dec 14
YTZ8:25 amToronto Island
7h 20m
1 stop
ORD2:45 pmChicago O'Hare Intl
Jan 10
ORD11:35 amChicago O'Hare Intl
5h 15m
1 stop
YTZ5:50 pmToronto Island

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 cheapest month to fly from Toronto to Chicago?

April. The cheapest time of year to fly to Chicago from Toronto is April. Most expensive is November

What is the cheapest day to depart Toronto for Chicago?

Wednesday. The cheapest day of the week is typically Wednesday. The most expensive is typically Sunday

When is the cheapest time to fly from Toronto to Chicago?

In the evening. Toronto to Chicago flights are approximately 10% more expensive at noon than in the evening

What is the cheapest Toronto to Chicago flight route?

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

How far in advance should you book Toronto to Chicago flights?

34 days before. The cheapest time to buy a flight from Toronto to Chicago is approximately 34 days to departure

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?

No. A direct flight is the cheapest option for a flight between Toronto to Chicago.

How have Toronto to Chicago flight prices changed over time?

As of November 2024, prices for Toronto to Chicago flights are approximately 9% 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

$135

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 $135. The best round-trip flight deal from Toronto to Chicago found on momondo in the last 72 hours is $178.
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?

    There are 435.3 mi between Toronto and Chicago. 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?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check 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 necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted 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
Air CanadaPriceFrom $157Free CancellationRating
7.0
8,237 reviews
Search Air Canada flights
Porter AirlinesPriceFrom $205Free CancellationRating
7.8
288 reviews
Search Porter Airlines flights
United AirlinesPriceFrom $219Free CancellationRating
7.4
9,171 reviews
Search United Airlines flights
American AirlinesPriceFrom $236Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
  • Porter Airlines Flights From Toronto to Chicago

    Porter Airlines flies from Toronto to Chicago around 9 times per week, with 288 momondo users rating the airline 7.8/10. The cheapest Porter Airlines deal from Toronto to Chicago in the last 72 hours was $205 (round-trip), much lower than the average airfare cost of $255 for Porter Airlines flights on this route.

  • United Airlines Flights From Toronto to Chicago

    United Airlines (7.4/10 from 9,171 reviews) operates around 65 flights from Toronto to Chicago in any given week. The average United Airlines airfare for this route is around $288, with deals from around $219 rare but found on momondo. Referenced prices are for round-trip Toronto to Chicago flight searches in the last 72 hours.


Why use momondo?

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

It is quick and easy to find Toronto to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

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

Yes. momondo enables you to select and highlight flights to Chicago from Toronto with this policy.

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?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Toronto and alert you when they change.


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Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago