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Cheap flights from Toronto to Chicago from C$ 168

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 2/2. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
Air Canada Logo
6:40 p.m. - 7:40 p.m.
YYZ
-
ORD
2h 00mdirect
Air Canada Logo
8:00 a.m. - 10:40 a.m.
ORD
-
YYZ
1h 40mdirect
C$ 259Air Canada
Sat, 31 Jan - Wed, 4 Feb
American Airlines Logo
4:30 p.m. - 11:27 p.m.
YYZ
-
ORD
7h 57m1 stop
American Airlines Logo
7:20 a.m. - 1:03 p.m.
ORD
-
YYZ
4h 43m1 stop
C$ 261American Airlines
Tue, 3 Feb - Tue, 10 Feb
American Airlines Logo
1:12 p.m. - 2:12 p.m.
YYZ
-
ORD
2h 00mdirect
American Airlines Logo
1:21 p.m. - 4:02 p.m.
ORD
-
YYZ
1h 41mdirect
C$ 266American Airlines
Tue, 24 Feb - Fri, 27 Feb
American Airlines Logo
6:00 a.m. - 7:15 a.m.
YYZ
-
ORD
2h 15mdirect
American Airlines Logo
9:41 a.m. - 12:34 p.m.
ORD
-
YYZ
1h 53mdirect
C$ 267American Airlines
Thu, 5 Feb - Sun, 8 Feb
American Airlines Logo
7:04 p.m. - 8:04 p.m.
YYZ
-
ORD
2h 00mdirect
American Airlines Logo
8:07 a.m. - 10:53 a.m.
ORD
-
YYZ
1h 46mdirect
C$ 269American Airlines
Thu, 5 Feb - Sun, 8 Feb
Air Canada Logo
4:00 p.m. - 8:10 p.m.
YYZ
-
ORD
5h 10m1 stop
Air Canada Logo
8:40 p.m. - 11:19 p.m.
ORD
-
YYZ
1h 39mdirect
C$ 270Air Canada
Sat, 31 Jan - Wed, 4 Feb
Multiple Airlines Logo
7:35 a.m. - 10:04 p.m.
YYZ
-
ORD
15h 29m1 stop
Multiple Airlines Logo
5:32 p.m. - 11:20 p.m.
ORD
-
YYZ
28h 48m1 stop
C$ 273Multiple Airlines
Wed, 21 Jan - Wed, 28 Jan
Multiple Airlines Logo
7:35 a.m. - 9:43 a.m.
YYZ
-
ORD
27h 08m1 stop
Multiple Airlines Logo
5:32 p.m. - 11:20 p.m.
ORD
-
YYZ
28h 48m1 stop
C$ 274Multiple Airlines
Mon, 19 Jan - Wed, 28 Jan
WestJet Logo
6:00 a.m. - 4:43 p.m.
YKF
-
ORD
11h 43m1 stop
WestJet Logo
6:00 a.m. - 12:45 a.m.
ORD
-
YKF
17h 45m2 stops
C$ 864WestJet
Tue, 2 Jun - Mon, 8 Jun
WestJet Logo
6:00 a.m. - 4:48 p.m.
YKF
-
ORD
11h 48m2 stops
WestJet Logo
6:00 a.m. - 12:45 a.m.
ORD
-
YKF
17h 45m2 stops
C$ 1,107WestJet
Wed, 3 Jun - Sun, 7 Jun

Air Canada flights from Toronto to Chicago O'Hare Intl Airport

Our best Air Canada deals on Toronto to Chicago O'Hare Intl Airport flight tickets
Air Canada
31 Jan
YYZ6:40 p.m.Toronto Pearson Intl
2h 00m
ORD7:40 p.m.Chicago O'Hare Intl
4 Feb
ORD8:00 a.m.Chicago O'Hare Intl
1h 40m
YYZ10:40 a.m.Toronto Pearson Intl
C$ 259
Find similar
Air Canada
24 Feb
YYZ6:45 p.m.Toronto Pearson Intl
2h 00m
ORD7:45 p.m.Chicago O'Hare Intl
27 Feb
ORD8:40 p.m.Chicago O'Hare Intl
1h 39m
YYZ11:19 p.m.Toronto Pearson Intl
C$ 266
Find similar
Air Canada
31 Jan
YYZ4:00 p.m.Toronto Pearson Intl
5h 10m
1 stop
ORD8:10 p.m.Chicago O'Hare Intl
4 Feb
ORD8:40 p.m.Chicago O'Hare Intl
1h 39m
YYZ11:19 p.m.Toronto Pearson Intl
C$ 270
Find similar

American Airlines flights from Toronto to Chicago O'Hare Intl Airport

Our best American Airlines deals on Toronto to Chicago O'Hare Intl Airport flight tickets
American Airlines
3 Feb
YYZ4:30 p.m.Toronto Pearson Intl
7h 57m
1 stop
ORD11:27 p.m.Chicago O'Hare Intl
10 Feb
ORD7:20 a.m.Chicago O'Hare Intl
4h 43m
1 stop
YYZ1:03 p.m.Toronto Pearson Intl
C$ 261
Find similar
American Airlines
5 Feb
YYZ6:00 a.m.Toronto Pearson Intl
2h 15m
ORD7:15 a.m.Chicago O'Hare Intl
8 Feb
ORD9:41 a.m.Chicago O'Hare Intl
1h 53m
YYZ12:34 p.m.Toronto Pearson Intl
C$ 267
Find similar
American Airlines
5 Feb
YYZ7:04 p.m.Toronto Pearson Intl
2h 00m
ORD8:04 p.m.Chicago O'Hare Intl
8 Feb
ORD8:07 a.m.Chicago O'Hare Intl
1h 46m
YYZ10:53 a.m.Toronto Pearson Intl
C$ 269
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Toronto to Chicago O'Hare Intl Airport 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 96,600 searches. Data last updated 20 December 2025.
Use the filters below to find and compare flights from Toronto to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 31/1

6:40 p.m.-7:40 p.m.

Nonstop2h 00m

Chicago O'Hare Intl

Wed 4/2

8:00 a.m.-10:40 a.m.

Nonstop1h 40m

C$ 259

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 3/2

4:30 p.m.-11:27 p.m.

1 stop7h 57m

Chicago O'Hare Intl

Tue 10/2

7:20 a.m.-1:03 p.m.

1 stop4h 43m

C$ 261

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 24/2

1:12 p.m.-2:12 p.m.

Nonstop2h 00m

Chicago O'Hare Intl

Fri 27/2

1:21 p.m.-4:02 p.m.

Nonstop1h 41m

C$ 266

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 5/2

6:00 a.m.-7:15 a.m.

Nonstop2h 15m

Chicago O'Hare Intl

Sun 8/2

9:41 a.m.-12:34 p.m.

Nonstop1h 53m

C$ 267

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 5/2

7:04 p.m.-8:04 p.m.

Nonstop2h 00m

Chicago O'Hare Intl

Sun 8/2

8:07 a.m.-10:53 a.m.

Nonstop1h 46m

C$ 269

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 31/1

4:00 p.m.-8:10 p.m.

1 stop5h 10m

Chicago O'Hare Intl

Wed 4/2

8:40 p.m.-11:19 p.m.

Nonstop1h 39m

C$ 270

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 21/1

7:35 a.m.-10:04 p.m.

1 stop15h 29m

Chicago O'Hare Intl

Wed 28/1

5:32 p.m.-11:20 p.m.

1 stop28h 48m

C$ 273

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 19/1

7:35 a.m.-9:43 a.m.

1 stop27h 08m

Chicago O'Hare Intl

Wed 28/1

5:32 p.m.-11:20 p.m.

1 stop28h 48m

C$ 274

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Tue 2/6

6:00 a.m.-4:43 p.m.

1 stop11h 43m

Chicago O'Hare Intl

Mon 8/6

6:00 a.m.-12:45 a.m.

2 stops17h 45m

C$ 864

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Wed 3/6

6:00 a.m.-4:48 p.m.

2 stops11h 48m

Chicago O'Hare Intl

Sun 7/6

6:00 a.m.-12:45 a.m.

2 stops17h 45m

C$ 1,107

Flights are sorted by cheapest round-trip 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 O'Hare Intl Airport

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 O'Hare Intl Airport?

In general, November is the cheapest month to fly from Toronto to Chicago O'Hare Intl Airport. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 298. The month of May is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Toronto averaging around C$ 363.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Friday when prices can be found for as low as C$ 670. This is often the case because there is less demand to fly during this day of the week. When flying out on a Tuesday, the most expensive travel day of the week, you can expect to see flight prices from Toronto to Chicago O'Hare Intl Airport for around C$ 1,088.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

In the evening is the cheapest time of day to fly from Toronto to Chicago O'Hare Intl Airport when you can find flight prices for as low as C$ 626. Flying to Chicago O'Hare Intl Airport in the evening is an ideal time because this is during off-peak travel hours. If you have a flexible travel schedule, then try to avoid flying at noon when prices are C$ 1,115 on average. Flights to Chicago O'Hare Intl Airport from Toronto at noon are generally more expensive because this time of day is more convenient for travellers’ schedules.

What is the cheapest Toronto to Chicago O'Hare Intl flight route?

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

How far in advance should I book a flight to Chicago O'Hare Intl Airport?

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Toronto when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around C$ 401 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Toronto for as low as C$ 269 on momondo.

What cabin class options are available on Toronto to Chicago O'Hare Intl flights?

There are 4 cabin classes available to choose from on Toronto to Chicago O'Hare Intl 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 O'Hare Intl Airport flights?

No. A direct flight is the cheapest option for a flight between Toronto to Chicago O'Hare Intl Airport.

How have Toronto to Chicago O'Hare Intl Airport flight prices changed over time?

As of December 2025, prices for Toronto to Chicago O'Hare Intl Airport flights are approximately 6% cheaper when compared to flights at the same time last year.

When to book flights from Toronto to Chicago O'Hare Intl Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Toronto to Chicago O'Hare Intl Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Toronto to Chicago O'Hare Intl Airport (YTO to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Toronto to Chicago O'Hare Intl Airport

Best price found

C$ 294

Fastest flight time

1h 55m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Toronto in the past 72 hours is C$ 294. The best round-trip flight deal from Toronto to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is C$ 627.
The fastest flight from Toronto to Chicago O'Hare Intl Airport takes 1h 55m
Direct flights go from Toronto to Chicago O'Hare Intl Airport every day.
Search flight deals

  • How far is Toronto to Chicago O'Hare Intl by plane?

    There are 718.7 km between Toronto and Chicago O'Hare Intl. By plane, this route typically takes 1h 55m.

  • When did momondo last update prices for flights from Toronto to Chicago O'Hare Intl Airport?

    Prices for flights from Toronto to Chicago O'Hare Intl Airport are refreshed on a daily basis.

  • How many operators does momondo search for flights from Toronto to Chicago O'Hare Intl Airport?

  • How old do you have to be to fly from Toronto to Chicago O'Hare Intl Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Toronto to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The travel and health documents you'll need for your trip to Chicago O'Hare Intl Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago O'Hare Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Toronto to Chicago O'Hare Intl Airport?

  • What is the most popular airline from Toronto to Chicago O'Hare Intl Airport?

Best airlines flying from Toronto to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Toronto to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
Porter AirlinesPriceFrom C$ 222Free CancellationRating
8.0
399 reviews
Search Porter Airlines flights
Air CanadaPriceFrom C$ 257Free CancellationRating
7.1
10,550 reviews
Search Air Canada flights
American AirlinesPriceFrom C$ 259Free CancellationRating
7.2
11,050 reviews
Search American Airlines flights
United AirlinesPriceFrom C$ 263Free CancellationRating
7.4
9,097 reviews
Search United Airlines flights
WestJetPriceFrom C$ 368Free CancellationRating
7.2
3,207 reviews
Search WestJet flights

  • Porter Airlines Flights From Toronto to Chicago O'Hare Intl Airport

    Porter Airlines is one of the most popular airlines flying from Toronto to Chicago O'Hare Intl Airport, operating 28 flights/week on average for this route. A good Porter Airlines flight deal for Toronto to Chicago O'Hare Intl Airport starts from C$ 222 round-trip, up to an average price of C$ 274. Our users have rated Porter Airlines at 8.0/10.

  • United Airlines Flights From Toronto to Chicago O'Hare Intl Airport

    United Airlines is also a popular choice for this route. United Airlines flight deals for Toronto to Chicago O'Hare Intl Airport start from as low as C$ 263 round-trip, depending on your selected dates, with average United Airlines deals seen on momondo around C$ 407. United Airlines operates 66 flights to Chicago O'Hare Intl Airport from Toronto in an average week. Users have rated it 7.4/10 across 9,097 reviews.

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Schaumburg
Rosemont
Hoffman Estates
Northbrook
Tinley Park
Munster
Skokie
Hammond
Harvey
Naperville
Glenview
Great Lakes
Wheeling
Elmhurst
Harvard
Merrillville
Elk Grove Village
Oak Brook
Kenosha

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?

Yes. All flights to Chicago from Toronto on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

momondo provides multiple filters to help you find the best flight to Chicago from Toronto. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

If you are not ready to book a flight from Toronto to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.

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