Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Toronto to Chicago from £116

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 12/12. 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

Deals available from 900+ travel sites.

'This year, momondo is the #1 place for airfares on the internet.'
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.

Find the cheapest flights from Toronto to Chicago

Cheap return flights

These are some of the best return flight deals from Toronto to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Toronto to Chicago.

Cheap last-minute flights

Planning a quick getaway from Toronto to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without stopovers.

Cheap bus & train deals from Toronto to Chicago

Find recent round-trip train or bus tickets from Toronto to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
11:00 - 11:59YYZ-ORD
1h 59mdirect
07:19 - 09:58ORD-YYZ
1h 39mdirect
£193United Airlines
Find Deal
Wed, 11 Dec - Thu, 12 Dec
14:45 - 23:20YYZ-ORD
9h 35m1 stop
07:19 - 09:58ORD-YYZ
1h 39mdirect
£205United Airlines
Find Deal
Thu, 12 Dec - Sun, 15 Dec
18:35 - 19:32YYZ-ORD
1h 57mdirect
18:06 - 08:05ORD-YYZ
12h 59m1 stop
Mon, 16 Dec - Thu, 26 Dec
12:20 - 13:11YYZ-ORD
1h 51mdirect
21:13 - 23:59ORD-YYZ
1h 46mdirect
Thu, 12 Dec - Wed, 25 Dec
08:25 - 14:45YTZ-ORD
7h 20m1 stop
13:55 - 20:43ORD-YTZ
5h 48m1 stop
£224Air Canada
Find Deal
Wed, 22 Jan - Thu, 23 Jan
06:30 - 14:38YYZ-ORD
9h 08m1 stop
10:30 - 19:09ORD-YYZ
7h 39m1 stop
£225Delta
Find Deal
Tue, 31 Dec - Wed, 22 Jan
06:30 - 14:38YYZ-ORD
9h 08m1 stop
10:05 - 17:14ORD-YYZ
6h 09m1 stop
£231Delta
Find Deal
Tue, 31 Dec - Sun, 19 Jan
07:35 - 12:15YYZ-ORD
5h 40m1 stop
07:22 - 13:00ORD-YYZ
4h 38m1 stop
£234American Airlines
Find Deal
Wed, 1 Jan - Fri, 17 Jan
06:15 - 07:30YYZ-ORD
2h 15mdirect
11:53 - 17:24ORD-YYZ
4h 31m1 stop
£242American Airlines
Find Deal
Tue, 31 Dec - Fri, 17 Jan
10:20 - 18:55YTZ-ORD
9h 35m2 stops
07:20 - 14:50ORD-YTZ
6h 30m1 stop
£244Air Canada
Find Deal
Wed, 22 Jan - Thu, 23 Jan
12:20 - 13:11YYZ-ORD
1h 51mdirect
£116United Airlines
Find Deal
Thu, 12 Dec
12:20 - 18:36YYZ-ORD
7h 16m1 stop
£120United Airlines
Find Deal
Fri, 13 Dec
08:00 - 08:57YYZ-ORD
1h 57mdirect
£125United Airlines
Find Deal
Fri, 17 Jan
09:00 - 10:05YYZ-ORD
2h 05mdirect
£126Air Canada
Find Deal
Sat, 14 Dec
10:00 - 16:43YYZ-ORD
7h 43m1 stop
£128United Airlines
Find Deal
Wed, 11 Dec
14:55 - 22:25YYZ-ORD
8h 30m1 stop
£130Delta
Find Deal
Sat, 14 Dec
10:05 - 18:41YYZ-ORD
9h 36m1 stop
£137Delta
Find Deal
Fri, 17 Jan
08:25 - 16:58YTZ-ORD
9h 33m2 stops
£146Air Canada
Find Deal
Sat, 14 Dec
18:30 - 14:55YYZ-ORD
21h 25m2 stops
£190WestJet
Find Deal
Thu, 13 Mar
17:00 - 18:05YYZ-ORD
26h 05m1 stop
£199WestJet
Find Deal
Sat, 21 Dec
08:00 - 08:57YYZ-ORD
1h 57mdirect
07:19 - 09:58ORD-YYZ
1h 39mdirect
£373United Airlines
Find Deal
Sat, 23 Nov - Sun, 1 Dec
21:00 - 22:07YYZ-ORD
2h 07mdirect
21:14 - 23:59ORD-YYZ
1h 45mdirect
£398United Airlines
Find Deal
Fri, 22 Nov - Mon, 25 Nov
06:30 - 16:52YYZ-ORD
11h 22m1 stop
09:45 - 23:35ORD-YYZ
12h 50m2 stops
£410WestJet
Find Deal
Thu, 21 Nov - Thu, 28 Nov
09:00 - 10:05YYZ-ORD
2h 05mdirect
21:05 - 11:15ORD-YYZ
13h 10m1 stop
£436United Airlines
Find Deal
Thu, 21 Nov - Sat, 23 Nov
06:15 - 14:19YYZ-ORD
9h 04m1 stop
11:15 - 22:15ORD-YYZ
10h 00m1 stop
£440United Airlines
Find Deal
Fri, 22 Nov - Sun, 24 Nov
12:20 - 13:11YYZ-ORD
1h 51mdirect
21:14 - 23:59ORD-YYZ
1h 45mdirect
£472United Airlines
Find Deal
Fri, 22 Nov - Sat, 23 Nov
20:00 - 18:46YYZ-ORD
23h 46m2 stops
09:45 - 23:35ORD-YYZ
12h 50m2 stops
£508WestJet
Find Deal
Thu, 21 Nov - Thu, 28 Nov
11:00 - 11:59YYZ-ORD
1h 59mdirect
20:25 - 23:06ORD-YYZ
1h 41mdirect
£526United Airlines
Find Deal
Thu, 21 Nov - Sat, 23 Nov
06:52 - 08:05YYZ-ORD
2h 13mdirect
16:00 - 22:15ORD-YYZ
5h 15m1 stop
£539United Airlines
Find Deal
Sat, 23 Nov - Wed, 27 Nov
21:00 - 22:07YYZ-ORD
2h 07mdirect
21:14 - 23:59ORD-YYZ
1h 45mdirect
£660United Airlines
Find Deal
Sun, 24 Nov - Mon, 2 Dec
11:00 - 11:59YYZ-ORD
1h 59mdirect
07:19 - 09:58ORD-YYZ
1h 39mdirect
£193United Airlines
Find Deal
Wed, 11 Dec - Thu, 12 Dec
21:00 - 22:07YYZ-ORD
2h 07mdirect
07:19 - 09:58ORD-YYZ
1h 39mdirect
£209United Airlines
Find Deal
Mon, 9 Dec - Wed, 11 Dec
12:20 - 13:11YYZ-ORD
1h 51mdirect
18:38 - 21:25ORD-YYZ
1h 47mdirect
£212United Airlines
Find Deal
Thu, 12 Dec - Mon, 16 Dec
12:20 - 13:11YYZ-ORD
1h 51mdirect
21:13 - 23:59ORD-YYZ
1h 46mdirect
Thu, 12 Dec - Wed, 25 Dec
09:00 - 10:05YYZ-ORD
2h 05mdirect
07:19 - 09:58ORD-YYZ
1h 39mdirect
£224United Airlines
Find Deal
Thu, 5 Dec - Sun, 8 Dec
15:30 - 16:30YYZ-ORD
2h 00mdirect
07:19 - 09:58ORD-YYZ
1h 39mdirect
£227United Airlines
Find Deal
Sat, 7 Dec - Wed, 11 Dec
12:20 - 13:11YYZ-ORD
1h 51mdirect
14:05 - 16:46ORD-YYZ
1h 41mdirect
£248Air Canada
Find Deal
Tue, 31 Dec - Thu, 16 Jan
08:00 - 08:57YYZ-ORD
1h 57mdirect
09:50 - 12:31ORD-YYZ
1h 41mdirect
Wed, 18 Dec - Wed, 25 Dec
14:00 - 14:51YYZ-ORD
1h 51mdirect
09:50 - 12:31ORD-YYZ
1h 41mdirect
£268Air Canada
Find Deal
Wed, 1 Jan - Sat, 18 Jan
13:10 - 14:10YYZ-ORD
2h 00mdirect
15:00 - 17:35ORD-YYZ
1h 35mdirect
£432American Airlines
Find Deal
Sun, 1 Dec - Tue, 21 Jan

United Airlines flights from Toronto to Chicago

Our best United Airlines deals on Toronto to Chicago flight tickets
United Airlines
11 Dec
YYZ11:00Toronto Pearson Intl
1h 59m
ORD11:59Chicago O'Hare Intl
12 Dec
ORD07:19Chicago O'Hare Intl
1h 39m
YYZ09:58Toronto Pearson Intl
United Airlines
12 Dec
YYZ14:45Toronto Pearson Intl
9h 35m
1 stop
ORD23:20Chicago O'Hare Intl
15 Dec
ORD07:19Chicago O'Hare Intl
1h 39m
YYZ09:58Toronto Pearson Intl
United Airlines
9 Dec
YYZ21:00Toronto Pearson Intl
2h 07m
ORD22:07Chicago O'Hare Intl
11 Dec
ORD07:19Chicago O'Hare Intl
1h 39m
YYZ09:58Toronto Pearson Intl

Air Canada flights from Toronto to Chicago

Our best Air Canada deals on Toronto to Chicago flight tickets
Air Canada
22 Jan
YTZ08:25Toronto Island
7h 20m
1 stop
ORD14:45Chicago O'Hare Intl
23 Jan
ORD13:55Chicago O'Hare Intl
5h 48m
1 stop
YTZ20:43Toronto Island
Air Canada
22 Jan
YTZ10:20Toronto Island
9h 35m
2 stops
ORD18:55Chicago O'Hare Intl
23 Jan
ORD07:20Chicago O'Hare Intl
6h 30m
1 stop
YTZ14:50Toronto Island
Air Canada
31 Dec
YYZ12:20Toronto Pearson Intl
1h 51m
ORD13:11Chicago O'Hare Intl
16 Jan
ORD14:05Chicago O'Hare Intl
1h 41m
YYZ16:46Toronto Pearson Intl

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 from Toronto to Chicago?

April. The cheapest time of year to fly to Chicago from Toronto is April. The most expensive is November.

What is the cheapest day to depart Toronto for Chicago?

Friday. The cheapest day of the week is usually Friday. The most expensive is usually Tuesday.

When is the cheapest time to fly from Toronto to Chicago?

In the evening. Toronto to Chicago flights are approximately 2% more expensive in the morning than in the evening

What is the cheapest Toronto to Chicago flight route?

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

How far in advance should you book Toronto to Chicago flights?

34 days before. The cheapest time to buy a flight from Toronto to Chicago is approximately 34 days to departure

What cabin class options are available on Toronto to Chicago flights?

There are 2 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 November 2024, prices for Toronto to Chicago flights are approximately 8% more expensive 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

£116

Fastest flight time

1h 51m

Direct flights

Every day

Airports in Chicago

1 airport
The best one-way flight to Chicago from Toronto in the past 72 hours is £116. The best return flight deal from Toronto to Chicago found on momondo in the last 72 hours is £193.
The fastest flight from Toronto to Chicago takes 1h 51m
Direct flights go from Toronto to Chicago every day.
There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)

  • How far is Toronto to Chicago by plane?

    Toronto and Chicago are 435.3 mi apart from one another. 1h 51m 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 £191Free CancellationRating
7.0
8,237 reviews
Search Air Canada flights
  • Air Canada Flights From Toronto to Chicago

    Air Canada flies from Toronto to Chicago around 66 times per week, with 8,237 momondo users rating the airline 7.0/10. The cheapest Air Canada deal from Toronto to Chicago in the last 72 hours was £242 (round-trip), much lower than the average airfare cost of £346 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.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
From?
To?
Tue 26/11
Tue 3/12
Email me momondo's favourite deals

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