Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Toronto to Chicago from $128

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 10/20. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Toronto to Chicago

Cheap round-trip flights

Logo
4:00 pm - 11:44 pmYYZ-ORD
8h 44m1 stop
Logo
12:53 pm - 9:07 pmORD-YYZ
7h 14m1 stop
$196
Find Deal
Mon, Oct 20 - Thu, Oct 23
Logo
4:00 pm - 11:44 pmYYZ-ORD
8h 44m1 stop
Logo
12:53 pm - 9:07 pmORD-YYZ
7h 14m1 stop
$197
Find Deal
Mon, Oct 20 - Thu, Oct 23
WestJet Logo
6:30 am - 4:43 pmYYZ-ORD
11h 13m1 stop
WestJet Logo
2:20 pm - 12:26 amORD-YYZ
9h 06m1 stop
$235WestJet
Find Deal
Thu, Oct 16 - Thu, Oct 30
WestJet Logo
6:15 am - 9:12 amYYZ-ORD
3h 57m1 stop
WestJet Logo
10:30 am - 5:19 pmORD-YYZ
5h 49m1 stop
$236WestJet
Find Deal
Sat, Oct 18 - Sat, Oct 25
Porter Airlines Logo
7:50 am - 8:39 amYTZ-MDW
1h 49mnonstop
Porter Airlines Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
$240Porter Airlines
Find Deal
Sat, Oct 18 - Sat, Oct 25
Porter Airlines Logo
3:35 pm - 4:24 pmYTZ-MDW
1h 49mnonstop
Porter Airlines Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
$241Porter Airlines
Find Deal
Thu, Oct 16 - Sun, Oct 19
Air Canada Logo
3:25 pm - 8:17 pmYTZ-ORD
5h 52m1 stop
Air Canada Logo
8:40 am - 2:45 pmORD-YTZ
5h 05m1 stop
$251Air Canada
Find Deal
Sat, Oct 18 - Sat, Oct 25
Air Canada Logo
3:25 pm - 8:06 pmYTZ-ORD
5h 41m1 stop
Air Canada Logo
8:40 am - 4:45 pmORD-YTZ
7h 05m1 stop
$265Air Canada
Find Deal
Sat, Oct 4 - Mon, Oct 6
Air Transat Logo
7:50 am - 8:39 amYTZ-MDW
1h 49mnonstop
Air Transat Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
$272Air Transat
Find Deal
Mon, Oct 13 - Mon, Oct 20
Air Transat Logo
7:50 am - 8:39 amYTZ-MDW
1h 49mnonstop
Air Transat Logo
5:20 pm - 8:02 pmMDW-YTZ
1h 42mnonstop
$281Air Transat
Find Deal
Sun, Oct 5 - Tue, Oct 7

Air Canada flights from Toronto to Chicago

Our best Air Canada deals on Toronto to Chicago flight tickets
Air Canada
Oct 18
YTZ3:25 pmToronto Island
5h 52m
1 stop
ORD8:17 pmChicago O'Hare Intl
Oct 25
ORD8:40 amChicago O'Hare Intl
5h 05m
1 stop
YTZ2:45 pmToronto Island
$251
Find similar
Air Canada
Oct 4
YTZ3:25 pmToronto Island
5h 41m
1 stop
ORD8:06 pmChicago O'Hare Intl
Oct 6
ORD8:40 amChicago O'Hare Intl
7h 05m
1 stop
YTZ4:45 pmToronto Island
$265
Find similar
Air Canada
Oct 4
YTZ3:25 pmToronto Island
5h 41m
1 stop
ORD8:06 pmChicago O'Hare Intl
Oct 6
ORD8:40 amChicago O'Hare Intl
7h 05m
1 stop
YTZ4:45 pmToronto Island
$267
Find similar

WestJet flights from Toronto to Chicago

Our best WestJet deals on Toronto to Chicago flight tickets
WestJet
Oct 16
YYZ6:30 amToronto Pearson Intl
11h 13m
1 stop
ORD4:43 pmChicago O'Hare Intl
Oct 30
ORD2:20 pmChicago O'Hare Intl
9h 06m
1 stop
YYZ12:26 amToronto Pearson Intl
$235
Find similar
WestJet
Oct 18
YYZ6:15 amToronto Pearson Intl
3h 57m
1 stop
ORD9:12 amChicago O'Hare Intl
Oct 25
ORD10:30 amChicago O'Hare Intl
5h 49m
1 stop
YYZ5:19 pmToronto Pearson Intl
$236
Find similar
WestJet
Oct 16
YYZ8:00 amToronto Pearson Intl
9h 43m
1 stop
ORD4:43 pmChicago O'Hare Intl
Oct 30
ORD2:20 pmChicago O'Hare Intl
9h 06m
1 stop
YYZ12:26 amToronto Pearson Intl
$237
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 September 15, 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

Mon 10/20

4:00 pm-11:44 pm

1 stop8h 44m

Chicago O'Hare Intl

Thu 10/23

12:53 pm-9:07 pm

1 stop7h 14m

$196

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 10/20

4:00 pm-11:44 pm

1 stop8h 44m

Chicago O'Hare Intl

Thu 10/23

12:53 pm-9:07 pm

1 stop7h 14m

$197

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 10/16

6:30 am-4:43 pm

1 stop11h 13m

Chicago O'Hare Intl

Thu 10/30

2:20 pm-12:26 am

1 stop9h 06m

$235

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 10/18

6:15 am-9:12 am

1 stop3h 57m

Chicago O'Hare Intl

Sat 10/25

10:30 am-5:19 pm

1 stop5h 49m

$236

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 10/18

7:50 am-8:39 am

Nonstop1h 49m

Chicago Midway

Sat 10/25

9:35 am-12:17 pm

Nonstop1h 42m

$240

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 10/16

3:35 pm-4:24 pm

Nonstop1h 49m

Chicago Midway

Sun 10/19

9:35 am-12:17 pm

Nonstop1h 42m

$241

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sat 10/18

3:25 pm-8:17 pm

1 stop5h 52m

Chicago O'Hare Intl

Sat 10/25

8:40 am-2:45 pm

1 stop5h 05m

$251

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sat 10/4

3:25 pm-8:06 pm

1 stop5h 41m

Chicago O'Hare Intl

Mon 10/6

8:40 am-4:45 pm

1 stop7h 05m

$265

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 10/13

7:50 am-8:39 am

Nonstop1h 49m

Chicago Midway

Mon 10/20

9:35 am-12:17 pm

Nonstop1h 42m

$272

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 10/5

7:50 am-8:39 am

Nonstop1h 49m

Chicago Midway

Tue 10/7

5:20 pm-8:02 pm

Nonstop1h 42m

$281

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 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 $225.

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 $395. 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 $639.

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 $391. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $575.

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?

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 $292 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 $216 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 12% 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 September 2025, prices for Toronto to Chicago flights are approximately 28% 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

$179

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 $179. The best round-trip flight deal from Toronto to Chicago found on momondo in the last 72 hours is $181.
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 $146Free CancellationRating
7.1
10,000 reviews
Search Air Canada flights
Porter AirlinesPriceFrom $158Free CancellationRating
7.9
363 reviews
Search Porter Airlines flights
United AirlinesPriceFrom $165Free CancellationRating
7.4
8,929 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 11 times per week, with 363 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 $258 for Porter Airlines flights on this route.

  • United Airlines Flights From Toronto to Chicago

    United Airlines (7.4/10 from 8,929 reviews) operates around 89 flights from Toronto to Chicago in any given week. The average United Airlines airfare for this route is around $286, 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

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Wed 10/15
Wed 10/22
By creating a price alert you accept our terms of use and privacy policy.

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