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Cheap flights from Toronto to Chicago from £84

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 1/9. 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

United Airlines Logo
09:00 - 09:55YYZ-ORD
1h 55mdirect
United Airlines Logo
18:01 - 20:44ORD-YYZ
1h 43mdirect
£130United Airlines
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週三, 1 10月 - 週六, 4 10月
United Airlines Logo
07:00 - 07:59YYZ-ORD
1h 59mdirect
United Airlines Logo
07:10 - 09:58ORD-YYZ
1h 48mdirect
£134United Airlines
Find Deal
週日, 14 9月 - 週日, 21 9月
Air Canada Logo
06:15 - 09:51YYZ-ORD
4h 36m1 stop
Air Canada Logo
20:25 - 23:08ORD-YYZ
1h 43mdirect
£142Air Canada
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週五, 12 9月 - 週五, 19 9月
Air Canada Logo
06:15 - 09:51YYZ-ORD
4h 36m1 stop
Air Canada Logo
20:25 - 23:08ORD-YYZ
1h 43mdirect
£147Air Canada
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週日, 14 9月 - 週日, 21 9月
Delta Logo
06:30 - 10:20YYZ-ORD
4h 50m1 stop
Delta Logo
07:10 - 11:20ORD-YYZ
3h 10m1 stop
£160Delta
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週一, 1 9月 - 週三, 24 9月
Delta Logo
10:20 - 16:34YYZ-ORD
7h 14m1 stop
Delta Logo
07:10 - 14:45ORD-YYZ
6h 35m1 stop
£161Delta
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週二, 7 10月 - 週二, 14 10月
American Airlines Logo
17:17 - 23:48YYZ-ORD
7h 31m1 stop
American Airlines Logo
08:10 - 16:33ORD-YYZ
7h 23m1 stop
£172American Airlines
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週日, 21 9月 - 週二, 23 9月
American Airlines Logo
06:30 - 07:25YYZ-ORD
1h 55mdirect
American Airlines Logo
11:48 - 14:31ORD-YYZ
1h 43mdirect
£192American Airlines
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週日, 21 9月 - 週二, 23 9月
Logo
14:45 - 15:48YYZ-ORD
2h 03mdirect
Logo
14:00 - 16:43ORD-YYZ
1h 43mdirect
£204
Find Deal
週四, 4 9月 - 週日, 7 9月
Logo
20:40 - 17:39YTZ-ORD
21h 59m2 stops
Logo
18:44 - 20:50ORD-YTZ
25h 06m3 stops
£289
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週日, 14 9月 - 週日, 21 9月

Delta flights from Toronto to Chicago

Our best Delta deals on Toronto to Chicago flight tickets
Delta
1 Sept
YYZ06:30Toronto Pearson Intl
4h 50m
1 stop
ORD10:20Chicago O'Hare Intl
24 Sept
ORD07:10Chicago O'Hare Intl
3h 10m
1 stop
YYZ11:20Toronto Pearson Intl
£160
Find similar
Delta
7 Oct
YYZ10:20Toronto Pearson Intl
7h 14m
1 stop
ORD16:34Chicago O'Hare Intl
14 Oct
ORD07:10Chicago O'Hare Intl
6h 35m
1 stop
YYZ14:45Toronto Pearson Intl
£161
Find similar
Delta
20 Aug
YYZ16:11Toronto Pearson Intl
5h 12m
1 stop
ORD20:23Chicago O'Hare Intl
4 Sept
ORD09:10Chicago O'Hare Intl
7h 13m
1 stop
YYZ17:23Toronto Pearson Intl
£164
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United Airlines flights from Toronto to Chicago

Our best United Airlines deals on Toronto to Chicago flight tickets
United Airlines
1 Oct
YYZ09:00Toronto Pearson Intl
1h 55m
ORD09:55Chicago O'Hare Intl
4 Oct
ORD18:01Chicago O'Hare Intl
1h 43m
YYZ20:44Toronto Pearson Intl
£130
Find similar
United Airlines
14 Sept
YYZ07:00Toronto Pearson Intl
1h 59m
ORD07:59Chicago O'Hare Intl
21 Sept
ORD07:10Chicago O'Hare Intl
1h 48m
YYZ09:58Toronto Pearson Intl
£134
Find similar
United Airlines
7 Nov
YYZ08:55Toronto Pearson Intl
2h 05m
ORD10:00Chicago O'Hare Intl
9 Nov
ORD07:10Chicago O'Hare Intl
1h 48m
YYZ09:58Toronto Pearson Intl
£135
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 1 8月 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

週三 1/10

09:00-09:55

Nonstop1h 55m

Chicago O'Hare Intl

週六 4/10

18:01-20:44

Nonstop1h 43m

£130

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

週日 14/9

07:00-07:59

Nonstop1h 59m

Chicago O'Hare Intl

週日 21/9

07:10-09:58

Nonstop1h 48m

£134

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

週五 12/9

06:15-09:51

1 stop4h 36m

Chicago O'Hare Intl

週五 19/9

20:25-23:08

Nonstop1h 43m

£142

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

週日 14/9

06:15-09:51

1 stop4h 36m

Chicago O'Hare Intl

週日 21/9

20:25-23:08

Nonstop1h 43m

£147

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

週一 1/9

06:30-10:20

1 stop4h 50m

Chicago O'Hare Intl

週三 24/9

07:10-11:20

1 stop3h 10m

£160

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

週二 7/10

10:20-16:34

1 stop7h 14m

Chicago O'Hare Intl

週二 14/10

07:10-14:45

1 stop6h 35m

£161

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

週日 21/9

17:17-23:48

1 stop7h 31m

Chicago O'Hare Intl

週二 23/9

08:10-16:33

1 stop7h 23m

£172

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

週日 21/9

06:30-07:25

Nonstop1h 55m

Chicago O'Hare Intl

週二 23/9

11:48-14:31

Nonstop1h 43m

£192

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

週四 4/9

14:45-15:48

Nonstop2h 03m

Chicago O'Hare Intl

週日 7/9

14:00-16:43

Nonstop1h 43m

£204

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

週日 14/9

20:40-17:39

2 stops21h 59m

Chicago O'Hare Intl

週日 21/9

18:44-20:50

3 stops25h 06m

£289

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 cheapest month to fly to Chicago?

The cheapest month to fly to Chicago from Toronto is in June. Flight prices, which tend to average around £169, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of June, then book flights to Chicago from Toronto during April instead. Flights to Chicago in April, while not as cheap as those in June, still average around £178.

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 Monday when prices can be found for as low as £247. 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 £897.

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 £309 when looking at flights departing in the morning. Flights at midday are often more expensive, with an average ticket price of £859.

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 £223 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 £181 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 August 2025, prices for Toronto to Chicago flights are approximately 31% 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

£84

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 £84. The best return flight deal from Toronto to Chicago found on momondo in the last 72 hours is £130.
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 53m 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 £140Free CancellationRating
7.1
9,851 reviews
Search Air Canada flights

  • Air Canada Flights From Toronto to Chicago

    Air Canada flies from Toronto to Chicago around 64 times per week, with 9,851 momondo users rating the airline 7.1/10. The cheapest Air Canada deal from Toronto to Chicago in the last 72 hours was £185 (round-trip), much lower than the average airfare cost of £266 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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1 adult
週三 6/8
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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