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Cheap flights from Toronto to Chicago from £99

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 13/10. 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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0 bags

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Cheap return flights

Logo
07:00 - 16:53YYZ-ORD
10h 53m1 stop
Logo
18:06 - 21:07ORD-YYZ
26h 01m1 stop
£169
Find Deal
Thu, 30 Oct - Thu, 6 Nov
Logo
07:15 - 18:46YYZ-ORD
12h 31m1 stop
Logo
18:06 - 21:07ORD-YYZ
26h 01m1 stop
£184
Find Deal
Fri, 31 Oct - Sun, 2 Nov
WestJet Logo
15:35 - 20:23YYZ-ORD
5h 48m1 stop
WestJet Logo
11:23 - 21:55ORD-YYZ
9h 32m1 stop
£186WestJet
Find Deal
Wed, 29 Oct - Wed, 5 Nov
Logo
16:00 - 23:44YYZ-ORD
8h 44m1 stop
Logo
19:43 - 14:05ORD-YYZ
17h 22m1 stop
£189
Find Deal
Mon, 13 Oct - Mon, 20 Oct
Air Canada Logo
07:00 - 11:18YYZ-ORD
5h 18m1 stop
Air Canada Logo
14:00 - 16:39ORD-YYZ
1h 39mdirect
£196Air Canada
Find Deal
Wed, 29 Oct - Wed, 5 Nov
Air Canada Logo
08:15 - 09:15YYZ-ORD
2h 00mdirect
Air Canada Logo
10:00 - 12:40ORD-YYZ
1h 40mdirect
£197Air Canada
Find Deal
Wed, 29 Oct - Wed, 5 Nov
WestJet Logo
12:15 - 16:11YYZ-ORD
4h 56m1 stop
WestJet Logo
18:59 - 08:55ORD-YYZ
12h 56m1 stop
£198WestJet
Find Deal
Fri, 24 Oct - Fri, 24 Oct
United Airlines Logo
13:00 - 14:01YYZ-ORD
2h 01mdirect
United Airlines Logo
18:01 - 20:44ORD-YYZ
1h 43mdirect
£202United Airlines
Find Deal
Fri, 17 Oct - Tue, 21 Oct
United Airlines Logo
07:00 - 07:58YYZ-ORD
1h 58mdirect
United Airlines Logo
21:12 - 23:58ORD-YYZ
1h 46mdirect
£203United Airlines
Find Deal
Sun, 12 Oct - Sat, 18 Oct
United Airlines Logo
09:00 - 09:55YYZ-ORD
1h 55mdirect
United Airlines Logo
21:12 - 23:58ORD-YYZ
1h 46mdirect
£204United Airlines
Find Deal
Sun, 12 Oct - Sat, 18 Oct

United Airlines flights from Toronto to Chicago

Our best United Airlines deals on Toronto to Chicago flight tickets
United Airlines
17 Oct
YYZ13:00Toronto Pearson Intl
2h 01m
ORD14:01Chicago O'Hare Intl
21 Oct
ORD18:01Chicago O'Hare Intl
1h 43m
YYZ20:44Toronto Pearson Intl
£202
Find similar
United Airlines
12 Oct
YYZ07:00Toronto Pearson Intl
1h 58m
ORD07:58Chicago O'Hare Intl
18 Oct
ORD21:12Chicago O'Hare Intl
1h 46m
YYZ23:58Toronto Pearson Intl
£203
Find similar
United Airlines
12 Oct
YYZ09:00Toronto Pearson Intl
1h 55m
ORD09:55Chicago O'Hare Intl
18 Oct
ORD21:12Chicago O'Hare Intl
1h 46m
YYZ23:58Toronto Pearson Intl
£204
Find similar

Delta flights from Toronto to Chicago

Our best Delta deals on Toronto to Chicago flight tickets
Delta
27 Sept
YYZ12:30Toronto Pearson Intl
5h 31m
1 stop
ORD17:01Chicago O'Hare Intl
3 Oct
ORD07:00Chicago O'Hare Intl
8h 08m
1 stop
YYZ16:08Toronto Pearson Intl
£319
Find similar
Delta
19 Sept
YYZ10:20Toronto Pearson Intl
8h 27m
1 stop
ORD17:47Chicago O'Hare Intl
29 Sept
ORD17:55Chicago O'Hare Intl
4h 41m
1 stop
YYZ23:36Toronto Pearson Intl
£400
Find similar
Delta
18 Sept
YYZ12:15Toronto Pearson Intl
5h 05m
1 stop
ORD16:20Chicago O'Hare Intl
28 Sept
ORD09:10Chicago O'Hare Intl
5h 12m
1 stop
YYZ15:22Toronto Pearson Intl
£429
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 15 September 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

Thu 30/10

07:00-16:53

1 stop10h 53m

Chicago O'Hare Intl

Thu 6/11

18:06-21:07

1 stop26h 01m

£169

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 31/10

07:15-18:46

1 stop12h 31m

Chicago O'Hare Intl

Sun 2/11

18:06-21:07

1 stop26h 01m

£184

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 29/10

15:35-20:23

1 stop5h 48m

Chicago O'Hare Intl

Wed 5/11

11:23-21:55

1 stop9h 32m

£186

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 13/10

16:00-23:44

1 stop8h 44m

Chicago O'Hare Intl

Mon 20/10

19:43-14:05

1 stop17h 22m

£189

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 29/10

07:00-11:18

1 stop5h 18m

Chicago O'Hare Intl

Wed 5/11

14:00-16:39

Nonstop1h 39m

£196

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 29/10

08:15-09:15

Nonstop2h 00m

Chicago O'Hare Intl

Wed 5/11

10:00-12:40

Nonstop1h 40m

£197

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 24/10

12:15-16:11

1 stop4h 56m

Chicago O'Hare Intl

Fri 24/10

18:59-08:55

1 stop12h 56m

£198

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 17/10

13:00-14:01

Nonstop2h 01m

Chicago O'Hare Intl

Tue 21/10

18:01-20:44

Nonstop1h 43m

£202

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sun 12/10

07:00-07:58

Nonstop1h 58m

Chicago O'Hare Intl

Sat 18/10

21:12-23:58

Nonstop1h 46m

£203

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sun 12/10

09:00-09:55

Nonstop1h 55m

Chicago O'Hare Intl

Sat 18/10

21:12-23:58

Nonstop1h 46m

£204

Flights are sorted by cheapest return 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 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 £160, 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 £166.

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 Thursday when prices can be found for as low as £366. 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 Saturday, with ticket prices averaging around £820.

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 £296 when looking at flights departing in the morning. Flights in the evening are often more expensive, with an average ticket price of £693.

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 £215 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 £159 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 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 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

£341

Fastest flight time

1h 53m

Direct flights

Every day

Airports in Chicago

1 airport
The best one-way flight to Chicago from Toronto in the past 72 hours is £341. The best return flight deal from Toronto to Chicago found on momondo in the last 72 hours is £450.
The fastest flight from Toronto to Chicago takes 1h 53m
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 54m 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?

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 £135Free CancellationRating
7.1
10,000 reviews
Search Air Canada flights

  • Air Canada Flights From Toronto to Chicago

    Air Canada flies from Toronto to Chicago around 89 times per week, with 10,000 momondo users rating the airline 7.1/10. The cheapest Air Canada deal from Toronto to Chicago in the last 72 hours was £184 (round-trip), much lower than the average airfare cost of £253 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.

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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