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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 23 August 2026.

Wed 9/910:10 a.m. -

Nonstop1h 50m

Thu 10/93:20 p.m. -

Nonstop1h 40m

Deal found 18/8C$ 278

Thu 10/92:00 p.m. -

Nonstop1h 55m

Sun 13/98:40 p.m. -

Nonstop1h 46m

Deal found 19/8C$ 279

Thu 17/910:10 a.m. -

Nonstop1h 50m

Sat 19/93:20 p.m. -

Nonstop1h 40m

Deal found 21/8C$ 279

Fri 25/912:15 p.m. -

Nonstop2h 06m

Mon 28/97:25 a.m. -

Nonstop1h 42m

Deal found 18/8C$ 279

Fri 11/92:00 p.m. -

Nonstop1h 55m

Sun 27/99:55 a.m. -

Nonstop1h 45m

Deal found 19/8C$ 281

Sat 19/910:10 a.m. -

Nonstop1h 50m

Wed 23/93:20 p.m. -

Nonstop1h 40m

Deal found 22/8C$ 281

Mon 21/97:35 p.m. -

Nonstop2h 06m

Wed 23/97:25 a.m. -

Nonstop1h 42m

Deal found 22/8C$ 281

Thu 17/912:25 p.m. -

Nonstop1h 58m

Sun 20/98:40 p.m. -

Nonstop1h 46m

Deal found 23/8C$ 282

Sat 12/910:10 a.m. -

Nonstop1h 50m

Wed 23/911:45 a.m. -

Nonstop1h 40m

Deal found 22/8C$ 282

Tue 15/912:15 p.m. -

Nonstop2h 06m

Wed 23/92:00 p.m. -

Nonstop1h 42m

Deal found 22/8C$ 282

Fri 11/96:50 p.m. -

Nonstop1h 58m

Sun 13/98:40 p.m. -

Nonstop1h 46m

Deal found 21/8C$ 284

Thu 10/91:45 p.m. -

Nonstop1h 50m

Sun 13/911:45 a.m. -

Nonstop1h 40m

Deal found 19/8C$ 284

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-MDW

YYZ-ORD

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

Wed 9/9

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

Nonstop1h 50m

Chicago Midway

Fri 11/9

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

Nonstop1h 40m

C$ 278

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Mon 14/9

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

Nonstop2h 05m

Chicago O'Hare Intl

Mon 21/9

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

Nonstop1h 41m

C$ 292

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Mon 14/9

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

Nonstop2h 05m

Chicago O'Hare Intl

Sat 26/9

5:53 p.m.-8:44 p.m.

Nonstop1h 51m

C$ 295

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Sun 20/9

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

Nonstop2h 06m

Chicago O'Hare Intl

Thu 24/9

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

Nonstop1h 42m

C$ 301

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Thu 17/9

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

Nonstop1h 50m

Chicago Midway

Mon 21/9

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

Nonstop1h 40m

C$ 318

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Fri 25/9

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

Nonstop2h 06m

Chicago O'Hare Intl

Tue 29/9

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

Nonstop1h 42m

C$ 318

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Wed 9/9

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

Nonstop2h 06m

Chicago O'Hare Intl

Sat 12/9

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

Nonstop1h 42m

C$ 318

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Thu 10/9

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

Nonstop2h 06m

Chicago O'Hare Intl

Sun 13/9

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

Nonstop1h 42m

C$ 318

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Tue 8/9

1:00 p.m.-2:05 p.m.

Nonstop2h 05m

Chicago O'Hare Intl

Sat 12/9

7:09 a.m.-9:54 a.m.

Nonstop1h 45m

C$ 330

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Wed 9/9

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

Nonstop2h 00m

Chicago O'Hare Intl

Fri 11/9

2:52 p.m.-5:56 p.m.

Nonstop2h 04m

C$ 330

Flights are sorted by cheapest round-trip flights first.

Deals found on 19/8

Showing 1-10 of 57 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

10.0

Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.

Porter Airlines

8.0

Very good

Porter Airlines

8.0

Very good

Reviews

1 / 20

10.0

Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.

7.8

Good

Porter Airlines

8.0

Very good

Reviews

1 / 20

10.0

Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.

United Airlines

7.4

Good

Porter Airlines

8.0

Very good

Reviews

1 / 20

10.0

Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.

American Airlines

7.1

Good

Porter Airlines

8.0

Very good

Reviews

1 / 20

10.0

Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.

7.1

Good

Porter Airlines

8.0

Very good

Reviews

1 / 20

10.0

Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.

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$ 461. If you're looking for a direct round-trip flight to Chicago, you can expect to pay around C$ 1,217.
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, December is worth consideration, as prices are usually at their lowest, on average. January 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$ 1,359.

See more FAQs

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