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 28 August 2026.

Fri 2/1010:10 a.m. -

Nonstop1h 50m

Mon 5/103:20 p.m. -

Nonstop1h 40m

Deal found 24/8C$ 280

Sat 19/91:45 p.m. -

Nonstop1h 50m

Mon 21/911:45 a.m. -

Nonstop1h 40m

Deal found 26/8C$ 283

Wed 16/97:35 p.m. -

Nonstop2h 06m

Wed 23/92:00 p.m. -

Nonstop1h 42m

Deal found 23/8C$ 283

Thu 17/912:25 p.m. -

Nonstop1h 58m

Sun 20/98:40 p.m. -

Nonstop1h 46m

Deal found 26/8C$ 284

Thu 17/91:45 p.m. -

Nonstop1h 50m

Wed 30/93:20 p.m. -

Nonstop1h 40m

Deal found 24/8C$ 284

Sat 26/97:35 p.m. -

Nonstop2h 06m

Sat 3/102:00 p.m. -

Nonstop1h 42m

Deal found 27/8C$ 284

Fri 2/106:50 p.m. -

Nonstop1h 58m

Mon 5/103:45 p.m. -

Nonstop1h 46m

Deal found 27/8C$ 286

Fri 25/910:10 a.m. -

Nonstop1h 50m

Fri 25/93:20 p.m. -

Nonstop1h 40m

Deal found 28/8C$ 286

Tue 13/1012:15 p.m. -

Nonstop2h 06m

Fri 16/107:25 a.m. -

Nonstop1h 53m

Deal found 26/8C$ 286

Tue 6/101:45 p.m. -

Nonstop1h 50m

Fri 9/103:20 p.m. -

Nonstop1h 40m

Deal found 27/8C$ 287

Sun 11/108:05 a.m. -

Nonstop1h 55m

Sun 18/103:45 p.m. -

Nonstop1h 46m

Deal found 27/8C$ 291

Fri 18/91:45 p.m. -

Nonstop1h 50m

Sun 20/911:45 a.m. -

Nonstop1h 40m

Deal found 24/8C$ 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-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

Quickest round-trip

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Tue 6/10

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

Nonstop1h 50m

Chicago Midway

Fri 9/10

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

Nonstop1h 40m

C$ 287

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Thu 24/9

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

Nonstop2h 05m

Chicago O'Hare Intl

Sun 27/9

4:33 p.m.-7:37 p.m.

Nonstop2h 04m

C$ 294

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Mon 21/9

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

Nonstop2h 05m

Chicago O'Hare Intl

Sat 3/10

9:20 p.m.-11:59 p.m.

Nonstop1h 39m

C$ 305

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$ 320

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Fri 18/9

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

Nonstop2h 00m

Chicago O'Hare Intl

Sun 20/9

12:59 p.m.-3:46 p.m.

Nonstop1h 47m

C$ 333

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Mon 21/9

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

Nonstop2h 05m

Chicago O'Hare Intl

Wed 23/9

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

Nonstop1h 51m

C$ 333

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Thu 17/9

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

Nonstop2h 06m

Chicago O'Hare Intl

Sun 20/9

8:40 p.m.-11:26 p.m.

Nonstop1h 46m

C$ 334

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Thu 17/9

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

Nonstop2h 06m

Chicago O'Hare Intl

Sun 20/9

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

Nonstop1h 41m

C$ 336

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Wed 7/10

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

Nonstop2h 00m

Chicago O'Hare Intl

Thu 15/10

9:20 p.m.-11:59 p.m.

Nonstop1h 39m

C$ 352

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Thu 8/10

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

Nonstop2h 06m

Chicago O'Hare Intl

Thu 15/10

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

Nonstop1h 59m

C$ 352

Flights are sorted by cheapest round-trip flights first.

Deals found on 23/8

Showing 1-10 of 53 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$ 464. If you're looking for a direct round-trip flight to Chicago, you can expect to pay around C$ 1,226.
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. 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$ 1,369.

See more FAQs

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