Direct flights to Chicago | Cheapflights

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Cheapest

Best

Last-minute

One-way

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 6 August 2026.

Thu 10/94:00 p.m. -

Nonstop1h 58m

Sun 13/95:35 p.m. -

Nonstop1h 43m

Deal found 6/8C$ 281

Tue 1/91:45 p.m. -

Nonstop1h 50m

Sun 20/911:45 a.m. -

Nonstop1h 40m

Deal found 5/8C$ 281

Sat 5/97:00 a.m. -

Nonstop2h 00m

Sun 13/95:35 p.m. -

Nonstop1h 43m

Deal found 3/8C$ 282

Tue 8/912:15 p.m. -

Nonstop2h 06m

Fri 11/92:00 p.m. -

Nonstop1h 42m

Deal found 5/8C$ 282

Wed 16/96:50 p.m. -

Nonstop1h 58m

Sun 20/92:15 p.m. -

Nonstop1h 46m

Deal found 5/8C$ 284

Fri 11/91:45 p.m. -

Nonstop1h 50m

Tue 15/911:45 a.m. -

Nonstop1h 40m

Deal found 4/8C$ 284

Sat 12/97:35 p.m. -

Nonstop2h 06m

Fri 18/97:25 a.m. -

Nonstop1h 42m

Deal found 4/8C$ 284

Thu 17/98:05 a.m. -

Nonstop1h 55m

Thu 24/99:55 a.m. -

Nonstop1h 45m

Deal found 5/8C$ 285

Sat 12/92:00 p.m. -

Nonstop1h 55m

Sun 13/92:15 p.m. -

Nonstop1h 46m

Deal found 4/8C$ 286

Fri 6/114:35 p.m. -

Nonstop1h 55m

Mon 9/116:10 p.m. -

Nonstop1h 40m

Deal found 4/8C$ 286

Mon 31/81:45 p.m. -

Nonstop1h 50m

Tue 1/93:20 p.m. -

Nonstop1h 40m

Deal found 4/8C$ 289

Fri 28/88:55 a.m. -

Nonstop1h 50m

Wed 2/93:20 p.m. -

Nonstop1h 40m

Deal found 4/8C$ 291

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

YYZ-ORD

YTZ-MDW

YTZ-ORD

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

Quickest round-trip

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Sun 13/9

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

Nonstop1h 50m

Chicago Midway

Sat 19/9

11:45 a.m.-2:25 p.m.

Nonstop1h 40m

C$ 284

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Wed 19/8

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

Chicago Midway

Mon 24/8

10:25 a.m.-1:05 p.m.

Nonstop1h 40m

C$ 296

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Sat 29/8

8:50 a.m.-9:40 a.m.

Nonstop1h 50m

Chicago Midway

Sat 5/9

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

Nonstop1h 40m

C$ 296

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Sat 22/8

8:50 a.m.-9:40 a.m.

Nonstop1h 50m

Chicago Midway

Thu 27/8

10:25 a.m.-1:05 p.m.

Nonstop1h 40m

C$ 298

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Tue 18/8

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

Chicago Midway

Tue 25/8

10:25 a.m.-1:05 p.m.

Nonstop1h 40m

C$ 298

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Fri 28/8

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

Nonstop2h 06m

Chicago O'Hare Intl

Mon 31/8

7:25 a.m.-10:18 a.m.

Nonstop1h 53m

C$ 309

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Thu 15/10

7:25 p.m.-8:29 p.m.

Nonstop2h 04m

Chicago O'Hare Intl

Fri 16/10

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

Nonstop1h 42m

C$ 309

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Wed 9/9

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

Chicago Midway

Thu 10/9

11:45 a.m.-2:25 p.m.

Nonstop1h 40m

C$ 309

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Fri 6/11

4:35 p.m.-5:30 p.m.

Nonstop1h 55m

Chicago O'Hare Intl

Tue 10/11

6:10 p.m.-8:50 p.m.

Nonstop1h 40m

C$ 309

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Mon 14/9

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

Nonstop2h 06m

Chicago O'Hare Intl

Wed 16/9

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

Nonstop1h 42m

C$ 310

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/8

Showing 1-10 of 59 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$ 540. If you're looking for a direct round-trip flight to Chicago, you can expect to pay around C$ 1,520.
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$ 2,113.

See more FAQs

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