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Cheap flights from Toronto to Chicago from $104

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 11/10. 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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Cheap round-trip flights

United Airlines Logo
6:52 am - 7:58 amYYZ-ORD
2h 06mnonstop
United Airlines Logo
6:28 pm - 9:21 pmORD-YYZ
1h 53mnonstop
$146United Airlines
Find Deal
Sat, Nov 1 - Sat, Nov 8
Porter Airlines Logo
7:50 am - 8:39 amYTZ-MDW
1h 49mnonstop
Porter Airlines Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
$146Porter Airlines
Find Deal
Thu, Oct 2 - Thu, Oct 9
Air Canada Logo
6:35 pm - 7:29 pmYYZ-ORD
1h 54mnonstop
Air Canada Logo
9:55 am - 12:38 pmORD-YYZ
1h 43mnonstop
$159Air Canada
Find Deal
Thu, Oct 2 - Sun, Oct 5
Air Canada Logo
12:20 pm - 1:14 pmYYZ-ORD
1h 54mnonstop
Air Canada Logo
9:55 am - 12:38 pmORD-YYZ
1h 43mnonstop
$160Air Canada
Find Deal
Thu, Oct 2 - Sun, Oct 5
American Airlines Logo
6:15 am - 7:30 amYYZ-ORD
2h 15mnonstop
American Airlines Logo
5:30 pm - 8:15 pmORD-YYZ
1h 45mnonstop
$174American Airlines
Find Deal
Fri, Jan 16 - Fri, Jan 23
American Airlines Logo
3:10 pm - 4:05 pmYYZ-ORD
1h 55mnonstop
American Airlines Logo
7:00 am - 2:44 pmORD-YYZ
6h 44m1 stop
$180American Airlines
Find Deal
Wed, Oct 8 - Tue, Oct 14
Logo
9:00 am - 9:55 amYYZ-ORD
1h 55mnonstop
Logo
8:25 pm - 11:08 pmORD-YYZ
1h 43mnonstop
$187
Find Deal
Thu, Sep 18 - Thu, Oct 2
Logo
9:00 am - 9:55 amYYZ-ORD
1h 55mnonstop
Logo
2:00 pm - 4:43 pmORD-YYZ
1h 43mnonstop
$188
Find Deal
Thu, Sep 18 - Wed, Sep 24
Air Transat Logo
9:15 am - 10:05 amYTZ-MDW
1h 50mnonstop
Air Transat Logo
11:00 am - 1:42 pmMDW-YTZ
1h 42mnonstop
$203Air Transat
Find Deal
Sat, Nov 29 - Thu, Dec 4
Air Transat Logo
7:50 am - 8:39 amYTZ-MDW
1h 49mnonstop
Air Transat Logo
5:20 pm - 8:02 pmMDW-YTZ
1h 42mnonstop
$214Air Transat
Find Deal
Fri, Oct 3 - Mon, Oct 6

United Airlines flights from Toronto to Chicago

Our best United Airlines deals on Toronto to Chicago flight tickets
United Airlines
Nov 1
YYZ6:52 amToronto Pearson Intl
2h 06m
ORD7:58 amChicago O'Hare Intl
Nov 8
ORD6:28 pmChicago O'Hare Intl
1h 53m
YYZ9:21 pmToronto Pearson Intl
$146
Find similar
United Airlines
Nov 1
YYZ8:55 amToronto Pearson Intl
2h 05m
ORD10:00 amChicago O'Hare Intl
Nov 8
ORD6:20 pmChicago O'Hare Intl
4h 26m
1 stop
YYZ11:46 pmToronto Pearson Intl
$156
Find similar
United Airlines
Nov 1
YYZ8:55 amToronto Pearson Intl
2h 05m
ORD10:00 amChicago O'Hare Intl
Nov 1
ORD6:20 pmChicago O'Hare Intl
4h 26m
1 stop
YYZ11:46 pmToronto Pearson Intl
$177
Find similar

Air Canada flights from Toronto to Chicago

Our best Air Canada deals on Toronto to Chicago flight tickets
Air Canada
Oct 2
YYZ6:35 pmToronto Pearson Intl
1h 54m
ORD7:29 pmChicago O'Hare Intl
Oct 5
ORD9:55 amChicago O'Hare Intl
1h 43m
YYZ12:38 pmToronto Pearson Intl
$159
Find similar
Air Canada
Oct 2
YYZ12:20 pmToronto Pearson Intl
1h 54m
ORD1:14 pmChicago O'Hare Intl
Oct 5
ORD9:55 amChicago O'Hare Intl
1h 43m
YYZ12:38 pmToronto Pearson Intl
$160
Find similar
Air Canada
Oct 2
YYZ2:10 pmToronto Pearson Intl
1h 54m
ORD3:04 pmChicago O'Hare Intl
Oct 5
ORD9:55 amChicago O'Hare Intl
1h 43m
YYZ12:38 pmToronto Pearson Intl
$161
Find similar

momondo 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, momondo users made 832,500 searches. Data last updated August 25, 2025.
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

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 11/1

6:52 am-7:58 am

Nonstop2h 06m

Chicago O'Hare Intl

Sat 11/8

6:28 pm-9:21 pm

Nonstop1h 53m

$146

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 10/2

7:50 am-8:39 am

Nonstop1h 49m

Chicago Midway

Thu 10/9

9:35 am-12:17 pm

Nonstop1h 42m

$146

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 10/2

6:35 pm-7:29 pm

Nonstop1h 54m

Chicago O'Hare Intl

Sun 10/5

9:55 am-12:38 pm

Nonstop1h 43m

$159

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 10/2

12:20 pm-1:14 pm

Nonstop1h 54m

Chicago O'Hare Intl

Sun 10/5

9:55 am-12:38 pm

Nonstop1h 43m

$160

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 1/16

6:15 am-7:30 am

Nonstop2h 15m

Chicago O'Hare Intl

Fri 1/23

5:30 pm-8:15 pm

Nonstop1h 45m

$174

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 10/8

3:10 pm-4:05 pm

Nonstop1h 55m

Chicago O'Hare Intl

Tue 10/14

7:00 am-2:44 pm

1 stop6h 44m

$180

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 9/18

9:00 am-9:55 am

Nonstop1h 55m

Chicago O'Hare Intl

Thu 10/2

8:25 pm-11:08 pm

Nonstop1h 43m

$187

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 9/18

9:00 am-9:55 am

Nonstop1h 55m

Chicago O'Hare Intl

Wed 9/24

2:00 pm-4:43 pm

Nonstop1h 43m

$188

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 11/29

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Thu 12/4

11:00 am-1:42 pm

Nonstop1h 42m

$203

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 10/3

7:50 am-8:39 am

Nonstop1h 49m

Chicago Midway

Mon 10/6

5:20 pm-8:02 pm

Nonstop1h 42m

$214

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 to Chicago?

The month of July is, on average, the cheapest month to fly to Chicago from Toronto, with most prices found around $217. If you’re not able to fly to Chicago in July, then June is your next best option. Flight prices from Toronto to Chicago during June average around $224.

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 Friday when prices can be found for as low as $387. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Toronto to Chicago for around $636.

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

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Toronto to Chicago during this time can be as low as $388. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $571.

What is the cheapest Toronto to Chicago flight route?

Fly from Toronto Pearson Intl to Chicago O'Hare Intl for the best Toronto - Chicago flight prices

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

You are more likely to see cheaper flights to Chicago from Toronto when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $295 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Toronto for as low as $239 on momondo.

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 15% 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 August 2025, prices for Toronto to Chicago flights are approximately 29% cheaper 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

$162

Fastest flight time

1h 49m

Direct flights

Every day

Airports in Chicago

1 airport
The best one-way flight to Chicago from Toronto in the past 72 hours is $162. The best round-trip flight deal from Toronto to Chicago found on momondo in the last 72 hours is $188.
The fastest flight from Toronto to Chicago takes 1h 49m
Direct flights go from Toronto to Chicago every day.
There is 1 airport near Chicago: Chicago Midway (MDW)
Search flight deals

  • How far is Toronto to Chicago by plane?

    There are 435.3 mi between Toronto and Chicago. Flights usually cover this in 1h 49m, 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 $145Free CancellationRating
7.1
10,000 reviews
Search Air Canada flights
Porter AirlinesPriceFrom $158Free CancellationRating
7.9
344 reviews
Search Porter Airlines flights
United AirlinesPriceFrom $165Free CancellationRating
7.4
8,940 reviews
Search United Airlines flights
American AirlinesPriceFrom $196Free 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 13 times per week, with 344 momondo users rating the airline 7.9/10. The cheapest Porter Airlines deal from Toronto to Chicago in the last 72 hours was $158 (round-trip), much lower than the average airfare cost of $253 for Porter Airlines flights on this route.

  • United Airlines Flights From Toronto to Chicago

    United Airlines (7.4/10 from 8,940 reviews) operates around 82 flights from Toronto to Chicago in any given week. The average United Airlines airfare for this route is around $284, with deals from around $165 rare but found on momondo. Referenced prices are for round-trip Toronto to Chicago flight searches in the last 72 hours.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

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.

An easier way to manage your Chicago trip

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport