Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Toronto to Chicago from £101

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 28/11. 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.

Voted winner of Europe's Best Travel App 2023

Save money when you book flights with momondo

Big names, great deals

Big names, great deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customise 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 return flights

Enter your travel dates to find the best prices.
United Airlines Logo
08:55 - 10:02YYZ-ORD
2h 07mdirect
United Airlines Logo
18:28 - 21:21ORD-YYZ
1h 53mdirect
£139United Airlines
Find Deal
Tue, 24 Feb - Sat, 28 Feb
American Airlines Logo
06:00 - 07:15YYZ-ORD
2h 15mdirect
American Airlines Logo
07:11 - 15:57ORD-YYZ
7h 46m1 stop
£145American Airlines
Find Deal
Wed, 26 Nov - Fri, 28 Nov
United Airlines Logo
19:40 - 23:44YYZ-ORD
5h 04m1 stop
United Airlines Logo
11:15 - 14:01ORD-YYZ
1h 46mdirect
£146United Airlines
Find Deal
Fri, 12 Dec - Fri, 9 Jan
Air Canada Logo
16:50 - 17:48YYZ-ORD
1h 58mdirect
Air Canada Logo
20:15 - 22:54ORD-YYZ
1h 39mdirect
£147Air Canada
Find Deal
Wed, 26 Nov - Fri, 28 Nov
Air Canada Logo
06:20 - 11:18YYZ-ORD
5h 58m1 stop
Air Canada Logo
15:35 - 21:44ORD-YYZ
5h 09m1 stop
£148Air Canada
Find Deal
Wed, 26 Nov - Fri, 28 Nov
Delta Logo
15:38 - 18:26YYZ-ORD
3h 48m1 stop
Delta Logo
12:29 - 20:29ORD-YYZ
7h 00m1 stop
£152Delta
Find Deal
Mon, 17 Nov - Wed, 19 Nov
United Airlines Logo
17:30 - 18:39YYZ-ORD
2h 09mdirect
United Airlines Logo
07:10 - 09:58ORD-YYZ
1h 48mdirect
£153United Airlines
Find Deal
Fri, 14 Nov - Sun, 16 Nov
Multiple Airlines Logo
18:30 - 19:30YYZ-ORD
2h 00mdirect
Multiple Airlines Logo
07:10 - 09:58ORD-YYZ
1h 48mdirect
£158Multiple Airlines
Find Deal
Thu, 1 Jan - Wed, 7 Jan
Delta Logo
06:05 - 08:57YYZ-ORD
3h 52m1 stop
Delta Logo
10:45 - 17:15ORD-YYZ
5h 30m1 stop
£160Delta
Find Deal
Thu, 27 Nov - Tue, 2 Dec
Multiple Airlines Logo
21:00 - 22:05YYZ-ORD
2h 05mdirect
Multiple Airlines Logo
20:15 - 22:54ORD-YYZ
1h 39mdirect
£186Multiple Airlines
Find Deal
Tue, 30 Dec - Sat, 3 Jan

United Airlines flights from Toronto to Chicago

Our best United Airlines deals on Toronto to Chicago flight tickets
United Airlines
24 Feb
YYZ08:55Toronto Pearson Intl
2h 07m
ORD10:02Chicago O'Hare Intl
28 Feb
ORD18:28Chicago O'Hare Intl
1h 53m
YYZ21:21Toronto Pearson Intl
£139
Find similar
United Airlines
12 Dec
YYZ19:40Toronto Pearson Intl
5h 04m
1 stop
ORD23:44Chicago O'Hare Intl
9 Jan
ORD11:15Chicago O'Hare Intl
1h 46m
YYZ14:01Toronto Pearson Intl
£146
Find similar
United Airlines
14 Nov
YYZ17:30Toronto Pearson Intl
2h 09m
ORD18:39Chicago O'Hare Intl
16 Nov
ORD07:10Chicago O'Hare Intl
1h 48m
YYZ09:58Toronto Pearson Intl
£153
Find similar

American Airlines flights from Toronto to Chicago

Our best American Airlines deals on Toronto to Chicago flight tickets
American Airlines
26 Nov
YYZ06:00Toronto Pearson Intl
2h 15m
ORD07:15Chicago O'Hare Intl
28 Nov
ORD07:11Chicago O'Hare Intl
7h 46m
1 stop
YYZ15:57Toronto Pearson Intl
£145
Find similar
American Airlines
18 Nov
YYZ06:00Toronto Pearson Intl
2h 15m
ORD07:15Chicago O'Hare Intl
20 Nov
ORD07:35Chicago O'Hare Intl
4h 27m
1 stop
YYZ13:02Toronto Pearson Intl
£175
Find similar
American Airlines
17 Nov
YYZ10:57Toronto Pearson Intl
6h 56m
1 stop
ORD16:53Chicago O'Hare Intl
19 Nov
ORD05:00Chicago O'Hare Intl
5h 14m
1 stop
YYZ11:14Toronto Pearson Intl
£194
Find similar

momondo Fare Finder

 
Customise 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 279,928 searches. Data last updated 30 October 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

Tue 24/2

08:55-10:02

Nonstop2h 07m

Chicago O'Hare Intl

Sat 28/2

18:28-21:21

Nonstop1h 53m

£139

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 26/11

06:00-07:15

Nonstop2h 15m

Chicago O'Hare Intl

Fri 28/11

07:11-15:57

1 stop7h 46m

£145

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 12/12

19:40-23:44

1 stop5h 04m

Chicago O'Hare Intl

Fri 9/1

11:15-14:01

Nonstop1h 46m

£146

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 26/11

16:50-17:48

Nonstop1h 58m

Chicago O'Hare Intl

Fri 28/11

20:15-22:54

Nonstop1h 39m

£147

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 26/11

06:20-11:18

1 stop5h 58m

Chicago O'Hare Intl

Fri 28/11

15:35-21:44

1 stop5h 09m

£148

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 17/11

15:38-18:26

1 stop3h 48m

Chicago O'Hare Intl

Wed 19/11

12:29-20:29

1 stop7h 00m

£152

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 14/11

17:30-18:39

Nonstop2h 09m

Chicago O'Hare Intl

Sun 16/11

07:10-09:58

Nonstop1h 48m

£153

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 1/1

18:30-19:30

Nonstop2h 00m

Chicago O'Hare Intl

Wed 7/1

07:10-09:58

Nonstop1h 48m

£158

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 27/11

06:05-08:57

1 stop3h 52m

Chicago O'Hare Intl

Tue 2/12

10:45-17:15

1 stop5h 30m

£160

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 30/12

21:00-22:05

Nonstop2h 05m

Chicago O'Hare Intl

Sat 3/1

20:15-22:54

Nonstop1h 39m

£186

Flights are sorted by cheapest return 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 cheapest month to fly to Chicago from Toronto is in July. Flight prices, which tend to average around £164, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of July, then book flights to Chicago from Toronto during June instead. Flights to Chicago in June, while not as cheap as those in July, still average around £170.

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 £233. This is often the case because there is less demand to fly during this day of the week. The most expensive day to fly to Chicago is Sunday, with ticket prices averaging around £795.

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

Flying to Chicago from Toronto in the morning is the least expensive time of day to depart. momondo users have found prices as low as £301 when looking at flights departing in the morning. Flights at midday are often more expensive, with an average ticket price of £595.

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 £221 when searching weeks before you fly. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Toronto for as low as £147 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?

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 October 2025, prices for Toronto to Chicago flights are approximately 33% 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 return 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

£151

Fastest flight time

1h 55m

Direct flights

Every day

Airports in Chicago

1 airport
The best one-way flight to Chicago from Toronto in the past 72 hours is £151. The best return flight deal from Toronto to Chicago found on momondo in the last 72 hours is £497.
The fastest flight from Toronto to Chicago takes 1h 55m
Direct flights go from Toronto to Chicago every day.
There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)
Search flight deals

  • How far is Toronto to Chicago by plane?

    Toronto and Chicago are 435.3 mi apart from one another. 1h 55m is a normal flight duration for this route.

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

    Prices for flights from Toronto to Chicago were last updated today.

  • 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 a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to 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 £139Free CancellationRating
7.1
10,372 reviews
Search Air Canada flights

  • Air Canada Flights From Toronto to Chicago

    Air Canada flies from Toronto to Chicago around 60 times per week, with 10,372 momondo users rating the airline 7.1/10. The cheapest Air Canada deal from Toronto to Chicago in the last 72 hours was £139 (round-trip), much lower than the average airfare cost of £173 for Air Canada flights on this route.

Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Toronto to Chicago. momondo saves you time and could save you money on your trip.

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

Flights from Toronto to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

momondo helps you find the best flight between Toronto and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

Price alerts on flights to Chicago from Toronto are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Chicago trip

We make it super easy to schedule, organise 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
Sat 29/11
Sat 6/12
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