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Cheap flights from Toronto to Chicago from £130

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 20/1. 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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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.
11:31 - 12:31YYZ-ORD
2h 00mdirect
08:11 - 10:51ORD-YYZ
1h 40mdirect
£221American Airlines
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Thu, 13 Feb - Sun, 16 Feb
11:31 - 12:31YYZ-ORD
2h 00mdirect
09:45 - 15:30ORD-YYZ
4h 45m1 stop
£224American Airlines
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Thu, 13 Feb - Sun, 16 Feb
10:10 - 12:55YYZ-ORD
3h 45m1 stop
16:15 - 23:07ORD-YYZ
5h 52m1 stop
£226Delta
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Wed, 12 Feb - Tue, 18 Feb
13:20 - 20:53YYZ-ORD
8h 33m1 stop
06:59 - 16:09ORD-YYZ
8h 10m1 stop
£227Delta
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Thu, 13 Feb - Sun, 16 Feb
17:29 - 21:54YYZ-ORD
5h 25m1 stop
09:45 - 15:30ORD-YYZ
4h 45m1 stop
£232American Airlines
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Thu, 13 Feb - Sun, 16 Feb
09:00 - 10:10YYZ-ORD
2h 10mdirect
16:51 - 19:45ORD-YYZ
1h 54mdirect
£235United Airlines
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Tue, 7 Jan - Wed, 8 Jan
14:00 - 14:51YYZ-ORD
1h 51mdirect
16:00 - 18:41ORD-YYZ
1h 41mdirect
£239United Airlines
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Sun, 19 Jan - Wed, 22 Jan
08:25 - 14:45YTZ-ORD
7h 20m1 stop
15:35 - 21:50ORD-YTZ
5h 15m1 stop
£250Air Canada
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Thu, 13 Feb - Sun, 16 Feb
07:20 - 20:25YYZ-ORD
14h 05m1 stop
07:20 - 14:41ORD-YYZ
6h 21m1 stop
Fri, 3 Jan - Fri, 10 Jan
21:00 - 11:58YYZ-ORD
15h 58m1 stop
18:06 - 08:05ORD-YYZ
12h 59m1 stop
Thu, 2 Jan - Fri, 3 Jan
21:00 - 22:13YYZ-ORD
2h 13mdirect
£130United Airlines
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Mon, 20 Jan
10:10 - 16:13YYZ-ORD
7h 03m1 stop
£133Delta
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Mon, 20 Jan
14:45 - 21:58YYZ-ORD
8h 13m1 stop
£134Delta
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Wed, 12 Feb
07:25 - 11:32YTZ-ORD
5h 07m1 stop
£151Air Canada
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Thu, 10 Apr
09:00 - 14:50YYZ-ORD
6h 50m1 stop
£154Air Canada
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Thu, 10 Apr
08:00 - 19:43YYZ-ORD
12h 43m2 stops
£169WestJet
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Thu, 19 Jun
06:15 - 20:34YYZ-ORD
15h 19m1 stop
£171WestJet
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Sun, 4 May
00:30 - 07:57YYZ-ORD
8h 27m1 stop
Sat, 22 Mar
00:40 - 18:00YYZ-ORD
18h 20m1 stop
£2,837Austrian Airlines
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Mon, 24 Mar
00:40 - 18:00YYZ-ORD
18h 20m1 stop
£2,864Austrian Airlines
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Wed, 12 Mar
18:35 - 19:32YYZ-ORD
1h 57mdirect
21:05 - 08:34ORD-YYZ
10h 29m1 stop
£335United Airlines
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Fri, 27 Dec - Mon, 30 Dec
19:40 - 23:25YYZ-ORD
4h 45m1 stop
20:30 - 23:11ORD-YYZ
1h 41mdirect
£340United Airlines
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Fri, 27 Dec - Sat, 4 Jan
18:35 - 19:32YYZ-ORD
1h 57mdirect
21:05 - 09:58ORD-YYZ
11h 53m1 stop
£341United Airlines
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Mon, 23 Dec - Mon, 6 Jan
08:10 - 18:42YYZ-ORD
11h 32m1 stop
16:00 - 08:34ORD-YYZ
15h 34m1 stop
£345United Airlines
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Mon, 23 Dec - Mon, 6 Jan
15:30 - 16:41YYZ-ORD
2h 11mdirect
18:28 - 21:25ORD-YYZ
1h 57mdirect
£352United Airlines
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Mon, 23 Dec - Mon, 6 Jan
06:00 - 16:40YYZ-ORD
11h 40m1 stop
17:30 - 09:09ORD-YYZ
14h 39m1 stop
£370WestJet
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Wed, 25 Dec - Thu, 2 Jan
17:00 - 13:51YYZ-ORD
21h 51m1 stop
17:30 - 09:09ORD-YYZ
14h 39m1 stop
£377WestJet
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Mon, 23 Dec - Sat, 28 Dec
15:30 - 16:41YYZ-ORD
2h 11mdirect
21:13 - 23:59ORD-YYZ
1h 46mdirect
Mon, 23 Dec - Tue, 24 Dec
14:15 - 16:40YYZ-ORD
3h 25m1 stop
15:18 - 23:08ORD-YYZ
6h 50m1 stop
£445Delta
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Mon, 23 Dec - Wed, 25 Dec
17:15 - 20:59YYZ-ORD
4h 44m1 stop
07:00 - 16:14ORD-YYZ
8h 14m1 stop
£460Delta
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Mon, 23 Dec - Fri, 27 Dec
11:31 - 12:31YYZ-ORD
2h 00mdirect
08:11 - 10:51ORD-YYZ
1h 40mdirect
£221American Airlines
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Thu, 13 Feb - Sun, 16 Feb
09:00 - 10:10YYZ-ORD
2h 10mdirect
16:51 - 19:45ORD-YYZ
1h 54mdirect
£235United Airlines
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Tue, 7 Jan - Wed, 8 Jan
14:00 - 14:51YYZ-ORD
1h 51mdirect
16:00 - 18:41ORD-YYZ
1h 41mdirect
£239United Airlines
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Sun, 19 Jan - Wed, 22 Jan
17:30 - 18:43YYZ-ORD
2h 13mdirect
18:28 - 21:25ORD-YYZ
1h 57mdirect
£239United Airlines
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Sat, 25 Jan - Mon, 27 Jan
09:00 - 10:10YYZ-ORD
2h 10mdirect
16:00 - 18:41ORD-YYZ
1h 41mdirect
£251United Airlines
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Tue, 7 Jan - Wed, 8 Jan
21:00 - 22:06YYZ-ORD
2h 06mdirect
14:05 - 16:46ORD-YYZ
1h 41mdirect
£256United Airlines
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Fri, 14 Feb - Mon, 24 Feb
14:00 - 14:51YYZ-ORD
1h 51mdirect
09:50 - 12:25ORD-YYZ
1h 35mdirect
£257United Airlines
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Thu, 13 Feb - Sun, 16 Feb
18:40 - 19:37YYZ-ORD
1h 57mdirect
20:30 - 23:11ORD-YYZ
1h 41mdirect
£274United Airlines
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Thu, 13 Feb - Sat, 22 Mar
17:30 - 18:39YYZ-ORD
2h 09mdirect
17:01 - 19:45ORD-YYZ
1h 44mdirect
£277United Airlines
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Sat, 1 Mar - Wed, 5 Mar
12:20 - 13:11YYZ-ORD
1h 51mdirect
09:50 - 12:25ORD-YYZ
1h 35mdirect
£278United Airlines
Find Deal
Fri, 21 Mar - Tue, 25 Mar

Delta flights from Toronto to Chicago

Our best Delta deals on Toronto to Chicago flight tickets
Delta
12 Feb
YYZ10:10Toronto Pearson Intl
3h 45m
1 stop
ORD12:55Chicago O'Hare Intl
18 Feb
ORD16:15Chicago O'Hare Intl
5h 52m
1 stop
YYZ23:07Toronto Pearson Intl
Delta
13 Feb
YYZ10:10Toronto Pearson Intl
3h 45m
1 stop
ORD12:55Chicago O'Hare Intl
16 Feb
ORD06:59Chicago O'Hare Intl
8h 10m
1 stop
YYZ16:09Toronto Pearson Intl
Delta
8 Jan
YYZ06:00Toronto Pearson Intl
4h 16m
1 stop
ORD09:16Chicago O'Hare Intl
29 Jan
ORD10:05Chicago O'Hare Intl
6h 09m
1 stop
YYZ17:14Toronto Pearson Intl

United Airlines flights from Toronto to Chicago

Our best United Airlines deals on Toronto to Chicago flight tickets
United Airlines
7 Jan
YYZ09:00Toronto Pearson Intl
2h 10m
ORD10:10Chicago O'Hare Intl
8 Jan
ORD16:51Chicago O'Hare Intl
1h 54m
YYZ19:45Toronto Pearson Intl
United Airlines
19 Jan
YYZ14:00Toronto Pearson Intl
1h 51m
ORD14:51Chicago O'Hare Intl
22 Jan
ORD16:00Chicago O'Hare Intl
1h 41m
YYZ18:41Toronto Pearson Intl
United Airlines
24 Jan
YYZ21:00Toronto Pearson Intl
2h 13m
ORD22:13Chicago O'Hare Intl
31 Jan
ORD12:51Chicago O'Hare Intl
5h 29m
1 stop
YYZ19:20Toronto 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 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 April. Flight prices, which tend to average around £190, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of April, then book flights to Chicago from Toronto during February instead. Flights to Chicago in February, while not as cheap as those in April, still average around £193.

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 Wednesday when prices can be found for as low as £0. 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 Tuesday, with ticket prices averaging around £278.

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

Flying to Chicago from Toronto at midday is the least expensive time of day to depart. momondo users have found prices as low as £0 when looking at flights departing at midday. Flights in the afternoon are often more expensive, with an average ticket price of £290.

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?

The ideal time to book your flight to Chicago is 48 days in advance, when prices tend to average £235. However, in the past 72 hours, people saw flights from Toronto for as low as £152.

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 1% 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 December 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

£130

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 £130. The best return flight deal from Toronto to Chicago found on momondo in the last 72 hours is £221.
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 £192Free CancellationRating
7.0
8,413 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 8,413 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.


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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