Direct flights to Chicago | Cheapflights

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Last-minute

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Cheapest flights to Chicago
Explore the most affordable flight options available to Chicago. Find the lowest fares based on data from user searches, with prices last updated on 29 July 2026.

Thu 10/96:50 p.m.

YYZ

-

ORD

Nonstop1h 58m

Air Canada

Sun 13/95:35 p.m.

ORD

-

YYZ

Nonstop1h 43m

Air Canada

Deal found 27/7C$ 291

Mon 31/88:55 a.m.

YTZ

-

MDW

Nonstop1h 50m

Porter Airlines

Mon 21/93:20 p.m.

MDW

-

YTZ

Nonstop1h 40m

Porter Airlines

Deal found 26/7C$ 291

Wed 23/912:15 p.m.

YTZ

-

ORD

Nonstop2h 06m

Air Canada

Sun 27/92:00 p.m.

ORD

-

YTZ

Nonstop1h 42m

Air Canada

Deal found 24/7C$ 291

Tue 25/88:55 a.m.

YTZ

-

MDW

Nonstop1h 50m

Porter Airlines

Wed 9/911:45 a.m.

MDW

-

YTZ

Nonstop1h 40m

Porter Airlines

Deal found 25/7C$ 292

Fri 18/912:25 p.m.

YYZ

-

ORD

Nonstop1h 58m

Air Canada

Mon 21/98:40 p.m.

ORD

-

YYZ

Nonstop1h 43m

Air Canada

Deal found 25/7C$ 293

Fri 4/95:27 p.m.

YYZ

-

ORD

Nonstop2h 03m

United Airlines

Tue 15/99:18 p.m.

ORD

-

YYZ

Nonstop1h 41m

United Airlines

Deal found 28/7C$ 295

Wed 2/96:55 p.m.

YYZ

-

ORD

Nonstop1h 57m

Air Canada

Wed 9/99:55 a.m.

ORD

-

YYZ

Nonstop1h 45m

Air Canada

Deal found 28/7C$ 296

Thu 10/912:15 p.m.

YTZ

-

ORD

Nonstop2h 06m

Air Canada

Thu 17/97:25 a.m.

ORD

-

YTZ

Nonstop1h 42m

Air Canada

Deal found 27/7C$ 296

Fri 21/81:45 p.m.

YTZ

-

MDW

Nonstop1h 50m

Porter Airlines

Sun 23/83:15 p.m.

MDW

-

YTZ

Nonstop1h 40m

Porter Airlines

Deal found 26/7C$ 298

Fri 11/97:35 p.m.

YTZ

-

ORD

Nonstop2h 06m

Air Canada

Sat 12/97:25 a.m.

ORD

-

YTZ

Nonstop1h 42m

Air Canada

Deal found 26/7C$ 298

Wed 9/96:50 p.m.

YYZ

-

ORD

Nonstop1h 58m

Air Canada

Wed 16/92:15 p.m.

ORD

-

YYZ

Nonstop1h 46m

Air Canada

Deal found 26/7C$ 299

Thu 27/88:55 a.m.

YTZ

-

MDW

Nonstop1h 50m

Porter Airlines

Mon 31/810:25 a.m.

MDW

-

YTZ

Nonstop1h 40m

Porter Airlines

Deal found 25/7C$ 299

Best time to book a flight to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago with our price prediction graph.

YTO-CHI

YTZ-ORD

YYZ-ORD

YTZ-MDW

Estimated round-trip price

Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Fly from

Route

Depart

Return

Price

Cheapest round-trip

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Wed 23/9

12:15 p.m.-1:21 p.m.

Nonstop2h 06m

Chicago O'Hare Intl

Sun 27/9

2:00 p.m.-4:42 p.m.

Nonstop1h 42m

C$ 291

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 4/9

8:50 a.m.-9:53 a.m.

Nonstop2h 03m

Chicago O'Hare Intl

Tue 8/9

9:18 p.m.-11:59 p.m.

Nonstop1h 41m

C$ 295

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 1/9

10:15 a.m.-11:21 a.m.

Nonstop2h 06m

Chicago O'Hare Intl

Wed 16/9

5:35 p.m.-8:18 p.m.

Nonstop1h 43m

C$ 295

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 24/9

5:15 p.m.-6:30 p.m.

Nonstop2h 15m

Chicago O'Hare Intl

Sun 27/9

8:50 a.m.-11:49 a.m.

Nonstop1h 59m

C$ 295

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 11/9

5:15 p.m.-6:18 p.m.

Nonstop2h 03m

Chicago O'Hare Intl

Mon 14/9

9:55 a.m.-12:40 p.m.

Nonstop1h 45m

C$ 295

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 4/9

5:27 p.m.-6:30 p.m.

Nonstop2h 03m

Chicago O'Hare Intl

Tue 15/9

9:18 p.m.-11:59 p.m.

Nonstop1h 41m

C$ 295

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 14/9

9:00 p.m.-10:05 p.m.

Nonstop2h 05m

Chicago O'Hare Intl

Sun 27/9

9:55 a.m.-12:40 p.m.

Nonstop1h 45m

C$ 295

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 7/9

7:00 a.m.-8:00 a.m.

Nonstop2h 00m

Chicago O'Hare Intl

Sat 12/9

9:55 a.m.-12:40 p.m.

Nonstop1h 45m

C$ 295

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Thu 3/9

7:35 p.m.-8:41 p.m.

Nonstop2h 06m

Chicago O'Hare Intl

Sun 6/9

7:25 a.m.-10:07 a.m.

Nonstop1h 42m

C$ 298

Quickest round-trip

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 6/9

10:10 a.m.-11:00 a.m.

Nonstop1h 50m

Chicago Midway

Sat 12/9

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

C$ 308

Flights are sorted by cheapest round-trip flights first.

Deals found on 29/7

Showing 1-10 of 58 resultsSorted by cheapest first

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6

Reviews of airlines flying non-stop to Chicago

Read through reviews of airlines serving the United States, such as Porter Airlines,Air Transat, andUnited Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Porter Airlines

8.0

Very good

Reviews

1 / 20

6.0

Good

Shannon,Jul 2026

YQT - YOW

Seats need to be a bit bigger & I'm not impressed that you have to pay to change seats

Porter Airlines

8.0

Very good

Porter Airlines

8.0

Very good

Reviews

1 / 20

6.0

Good

Shannon,Jul 2026

YQT - YOW

Seats need to be a bit bigger & I'm not impressed that you have to pay to change seats

7.8

Good

Porter Airlines

8.0

Very good

Reviews

1 / 20

6.0

Good

Shannon,Jul 2026

YQT - YOW

Seats need to be a bit bigger & I'm not impressed that you have to pay to change seats

United Airlines

7.4

Good

Porter Airlines

8.0

Very good

Reviews

1 / 20

6.0

Good

Shannon,Jul 2026

YQT - YOW

Seats need to be a bit bigger & I'm not impressed that you have to pay to change seats

American Airlines

7.1

Good

Porter Airlines

8.0

Very good

Reviews

1 / 20

6.0

Good

Shannon,Jul 2026

YQT - YOW

Seats need to be a bit bigger & I'm not impressed that you have to pay to change seats

7.1

Good

Porter Airlines

8.0

Very good

Reviews

1 / 20

6.0

Good

Shannon,Jul 2026

YQT - YOW

Seats need to be a bit bigger & I'm not impressed that you have to pay to change seats

FAQ about direct flights to Chicago

How much are direct flights to Chicago?
On average, a one-way direct flight to Chicago will cost users approximately C$ 851. If you're looking for a direct round-trip flight to Chicago, you can expect to pay around C$ 2,021.
Which airlines fly direct to Chicago?
At the moment, Air Canada, United Airlines, Porter Airlines, American Airlines, WestJet, Delta offer direct flights to Chicago. Air Canada is currently the most popular airline that flies direct to Chicago.
What is the best time of year to fly direct to Chicago?
If you're seeking the lowest price on a direct flight to Chicago, January is worth consideration, as prices are usually at their lowest, on average. February may be most appealing to users looking for the quietest time to visit Chicago, when demand is typically at its lowest.
What is the most popular direct flight origin to Chicago?
Currently, the most popular direct flight origin to Chicago is Toronto Pearson Intl Airport. A round-trip direct flight from Toronto Pearson Intl Airport to Chicago typically costs around C$ 2,654.

See more FAQs

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