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Cheap flights from Toronto to Chicago from C$ 159

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 17/10. 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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Find the cheapest flights from Toronto to Chicago

Cheap round-trip flights

Logo
4:00 p.m. - 11:44 p.m.YYZ-ORD
8h 44m1 stop
Logo
12:53 p.m. - 9:07 p.m.ORD-YYZ
7h 14m1 stop
C$ 271
Find Deal
Mon, 20 Oct - Thu, 23 Oct
Logo
4:00 p.m. - 11:44 p.m.YYZ-ORD
8h 44m1 stop
Logo
12:53 p.m. - 9:07 p.m.ORD-YYZ
7h 14m1 stop
C$ 273
Find Deal
Mon, 20 Oct - Thu, 23 Oct
Logo
4:00 p.m. - 11:44 p.m.YYZ-ORD
8h 44m1 stop
Logo
7:43 p.m. - 2:05 p.m.ORD-YYZ
17h 22m1 stop
C$ 275
Find Deal
Mon, 20 Oct - Wed, 22 Oct
WestJet Logo
6:00 a.m. - 4:43 p.m.YKF-ORD
11h 43m1 stop
WestJet Logo
2:20 p.m. - 5:28 a.m.ORD-YKF
14h 08m1 stop
C$ 287WestJet
Find Deal
Thu, 23 Oct - Mon, 27 Oct
WestJet Logo
6:00 a.m. - 4:43 p.m.YKF-ORD
11h 43m1 stop
WestJet Logo
2:20 p.m. - 5:28 a.m.ORD-YKF
14h 08m1 stop
C$ 309WestJet
Find Deal
Thu, 23 Oct - Mon, 27 Oct
WestJet Logo
6:00 a.m. - 4:43 p.m.YKF-ORD
11h 43m1 stop
WestJet Logo
2:20 p.m. - 5:28 a.m.ORD-YKF
14h 08m1 stop
C$ 310WestJet
Find Deal
Fri, 24 Oct - Sun, 26 Oct
Air Canada Logo
3:25 p.m. - 8:17 p.m.YTZ-ORD
5h 52m1 stop
Air Canada Logo
8:40 a.m. - 2:45 p.m.ORD-YTZ
5h 05m1 stop
C$ 347Air Canada
Find Deal
Sat, 18 Oct - Sat, 25 Oct
Air Canada Logo
3:25 p.m. - 8:06 p.m.YTZ-ORD
5h 41m1 stop
Air Canada Logo
8:40 a.m. - 4:45 p.m.ORD-YTZ
7h 05m1 stop
C$ 367Air Canada
Find Deal
Sat, 4 Oct - Mon, 6 Oct
Air Canada Logo
3:25 p.m. - 8:06 p.m.YTZ-ORD
5h 41m1 stop
Air Canada Logo
8:40 a.m. - 4:45 p.m.ORD-YTZ
7h 05m1 stop
C$ 370Air Canada
Find Deal
Sat, 4 Oct - Mon, 6 Oct
Air Canada Logo
3:25 p.m. - 8:17 p.m.YTZ-ORD
5h 52m1 stop
Air Canada Logo
8:40 a.m. - 4:45 p.m.ORD-YTZ
7h 05m1 stop
C$ 386Air Canada
Find Deal
Sat, 18 Oct - Mon, 20 Oct

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
18 Oct
YTZ3:25 p.m.Toronto Island
5h 52m
1 stop
ORD8:17 p.m.Chicago O'Hare Intl
25 Oct
ORD8:40 a.m.Chicago O'Hare Intl
5h 05m
1 stop
YTZ2:45 p.m.Toronto Island
C$ 347
Find similar
Air Canada
4 Oct
YTZ3:25 p.m.Toronto Island
5h 41m
1 stop
ORD8:06 p.m.Chicago O'Hare Intl
6 Oct
ORD8:40 a.m.Chicago O'Hare Intl
7h 05m
1 stop
YTZ4:45 p.m.Toronto Island
C$ 367
Find similar
Air Canada
4 Oct
YTZ3:25 p.m.Toronto Island
5h 41m
1 stop
ORD8:06 p.m.Chicago O'Hare Intl
6 Oct
ORD8:40 a.m.Chicago O'Hare Intl
7h 05m
1 stop
YTZ4:45 p.m.Toronto Island
C$ 370
Find similar

WestJet flights from Toronto to Chicago O'Hare Intl Airport

Our best WestJet deals on Toronto to Chicago O'Hare Intl Airport flight tickets
WestJet
23 Oct
YKF6:00 a.m.Toronto Region of Waterloo Intl
11h 43m
1 stop
ORD4:43 p.m.Chicago O'Hare Intl
27 Oct
ORD2:20 p.m.Chicago O'Hare Intl
14h 08m
1 stop
YKF5:28 a.m.Toronto Region of Waterloo Intl
C$ 287
Find similar
WestJet
23 Oct
YKF6:00 a.m.Toronto Region of Waterloo Intl
11h 43m
1 stop
ORD4:43 p.m.Chicago O'Hare Intl
27 Oct
ORD2:20 p.m.Chicago O'Hare Intl
14h 08m
1 stop
YKF5:28 a.m.Toronto Region of Waterloo Intl
C$ 309
Find similar
WestJet
24 Oct
YKF6:00 a.m.Toronto Region of Waterloo Intl
11h 43m
1 stop
ORD4:43 p.m.Chicago O'Hare Intl
26 Oct
ORD2:20 p.m.Chicago O'Hare Intl
14h 08m
1 stop
YKF5:28 a.m.Toronto Region of Waterloo Intl
C$ 310
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 15 September 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

Mon 20/10

4:00 p.m.-11:44 p.m.

1 stop8h 44m

Chicago O'Hare Intl

Thu 23/10

12:53 p.m.-9:07 p.m.

1 stop7h 14m

C$ 271

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 20/10

4:00 p.m.-11:44 p.m.

1 stop8h 44m

Chicago O'Hare Intl

Thu 23/10

12:53 p.m.-9:07 p.m.

1 stop7h 14m

C$ 273

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 20/10

4:00 p.m.-11:44 p.m.

1 stop8h 44m

Chicago O'Hare Intl

Wed 22/10

7:43 p.m.-2:05 p.m.

1 stop17h 22m

C$ 275

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Thu 23/10

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

1 stop11h 43m

Chicago O'Hare Intl

Mon 27/10

2:20 p.m.-5:28 a.m.

1 stop14h 08m

C$ 287

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Thu 23/10

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

1 stop11h 43m

Chicago O'Hare Intl

Mon 27/10

2:20 p.m.-5:28 a.m.

1 stop14h 08m

C$ 309

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Fri 24/10

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

1 stop11h 43m

Chicago O'Hare Intl

Sun 26/10

2:20 p.m.-5:28 a.m.

1 stop14h 08m

C$ 310

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sat 18/10

3:25 p.m.-8:17 p.m.

1 stop5h 52m

Chicago O'Hare Intl

Sat 25/10

8:40 a.m.-2:45 p.m.

1 stop5h 05m

C$ 347

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sat 4/10

3:25 p.m.-8:06 p.m.

1 stop5h 41m

Chicago O'Hare Intl

Mon 6/10

8:40 a.m.-4:45 p.m.

1 stop7h 05m

C$ 367

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sat 4/10

3:25 p.m.-8:06 p.m.

1 stop5h 41m

Chicago O'Hare Intl

Mon 6/10

8:40 a.m.-4:45 p.m.

1 stop7h 05m

C$ 370

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sat 18/10

3:25 p.m.-8:17 p.m.

1 stop5h 52m

Chicago O'Hare Intl

Mon 20/10

8:40 a.m.-4:45 p.m.

1 stop7h 05m

C$ 386

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 typical price of a round-trip flight between Toronto and Chicago O'Hare Intl Airport?

What is the cheapest month to fly to Chicago O'Hare Intl Airport?

In general, May 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$ 364. The month of November is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Toronto averaging around C$ 379.

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$ 740. 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$ 1,182.

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$ 628. 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 in the afternoon when prices are C$ 1,283 on average. Flights to Chicago O'Hare Intl Airport from Toronto in the afternoon 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$ 404 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$ 299 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?

You could potentially save up to 10% on your flight if you consider stops on a Toronto to Chicago O'Hare Intl Airport flight.

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

As of September 2025, prices for Toronto to Chicago O'Hare Intl Airport flights are approximately 31% 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$ 491

Fastest flight time

1h 53m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Toronto in the past 72 hours is C$ 491. The best round-trip flight deal from Toronto to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is C$ 543.
The fastest flight from Toronto to Chicago O'Hare Intl Airport takes 1h 53m
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 3h 57m.

  • 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$ 196Free CancellationRating
7.9
363 reviews
Search Porter Airlines flights
Air CanadaPriceFrom C$ 264Free CancellationRating
7.1
10,000 reviews
Search Air Canada flights
American AirlinesPriceFrom C$ 268Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom C$ 279Free CancellationRating
7.4
8,929 reviews
Search United Airlines flights
WestJetPriceFrom C$ 383Free CancellationRating
7.2
3,091 reviews
Search WestJet flights

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

    United Airlines is one of the most popular airlines flying from Toronto to Chicago O'Hare Intl Airport, operating 89 flights/week on average for this route. A good United Airlines flight deal for Toronto to Chicago O'Hare Intl Airport starts from C$ 202 round-trip, up to an average price of C$ 302. Our users have rated United Airlines at 7.4/10.

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

    American Airlines is also a popular choice for this route. American Airlines flight deals for Toronto to Chicago O'Hare Intl Airport start from as low as C$ 193 round-trip, depending on your selected dates, with average American Airlines deals seen on momondo around C$ 359. American Airlines operates 32 flights to Chicago O'Hare Intl Airport from Toronto in an average week. Users have rated it 7.2/10 across 10,000 reviews.

Travelling to a place near Chicago?

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

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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