Direct flights to Chicago | Cheapflights

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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 8 September 2026.

Sat 26/911:00 a.m. -

Nonstop2h 00m

Sun 27/912:59 p.m. -

Nonstop1h 47m

Deal found 5/9C$ 285

Wed 21/1012:15 p.m. -

Nonstop2h 10m

Wed 28/101:55 p.m. -

Nonstop1h 47m

Deal found 6/9C$ 285

Fri 25/98:50 a.m. -

Nonstop1h 58m

Tue 29/99:55 a.m. -

Nonstop1h 45m

Deal found 4/9C$ 286

Fri 25/91:45 p.m. -

Nonstop1h 50m

Thu 1/103:20 p.m. -

Nonstop1h 40m

Deal found 8/9C$ 286

Thu 1/1012:15 p.m. -

Nonstop2h 10m

Sun 4/102:00 p.m. -

Nonstop1h 48m

Deal found 8/9C$ 286

Tue 6/101:45 p.m. -

Nonstop1h 50m

Thu 15/103:20 p.m. -

Nonstop1h 40m

Deal found 8/9C$ 287

Thu 29/1010:35 a.m. -

Nonstop2h 05m

Mon 2/1112:20 p.m. -

Nonstop1h 46m

Deal found 8/9C$ 287

Sun 18/101:45 p.m. -

Nonstop1h 50m

Mon 19/103:20 p.m. -

Nonstop1h 40m

Deal found 5/9C$ 289

Thu 24/97:35 p.m. -

Nonstop2h 06m

Sun 27/97:25 a.m. -

Nonstop1h 42m

Deal found 8/9C$ 289

Sat 26/98:05 a.m. -

Nonstop1h 55m

Sun 27/99:55 a.m. -

Nonstop1h 45m

Deal found 4/9C$ 290

Sat 24/1012:15 p.m. -

Nonstop2h 10m

Sun 25/106:20 p.m. -

Nonstop1h 46m

Deal found 7/9C$ 290

Sat 3/1012:25 p.m. -

Nonstop1h 58m

Mon 5/108:40 p.m. -

Nonstop1h 46m

Deal found 5/9C$ 292

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 Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Wed 30/9

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

Nonstop2h 06m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 182

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Sun 4/10

12:15 p.m.-1:25 p.m.

Nonstop2h 10m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 184

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Tue 13/10

12:15 p.m.-1:25 p.m.

Nonstop2h 10m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 184

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Sat 28/11

5:55 p.m.-7:05 p.m.

Nonstop2h 10m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 198

Quickest round-trip

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Thu 1/10

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

Nonstop1h 50m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 198

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Sun 29/11

6:45 a.m.-7:54 a.m.

Nonstop2h 09m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 198

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Mon 28/9

9:00 p.m.-10:06 p.m.

Nonstop2h 06m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 198

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Wed 30/9

8:50 a.m.-9:48 a.m.

Nonstop1h 58m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 198

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Mon 30/11

6:45 a.m.-7:54 a.m.

Nonstop2h 09m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 198

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Sun 4/10

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

Nonstop1h 50m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 199

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/9

Showing 1-10 of 60 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$ 416. If you're looking for a direct round-trip flight to Chicago, you can expect to pay around C$ 1,177.
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$ 1,561.

See more FAQs

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