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 3 September 2026.

Thu 24/98:05 a.m. -

Nonstop1h 55m

Sun 27/99:55 a.m. -

Nonstop1h 45m

Deal found 31/8C$ 286

Fri 23/1012:15 p.m. -

Nonstop2h 10m

Fri 30/107:25 a.m. -

Nonstop1h 41m

Deal found 2/9C$ 286

Fri 16/1012:15 p.m. -

Nonstop2h 10m

Fri 23/102:00 p.m. -

Nonstop1h 48m

Deal found 1/9C$ 287

Mon 21/99:00 p.m. -

Nonstop2h 05m

Wed 30/98:40 p.m. -

Nonstop1h 46m

Deal found 31/8C$ 294

Fri 25/912:15 p.m. -

Nonstop2h 06m

Sun 27/92:00 p.m. -

Nonstop1h 42m

Deal found 2/9C$ 294

Fri 2/107:35 p.m. -

Nonstop2h 10m

Sun 4/107:25 a.m. -

Nonstop1h 48m

Deal found 2/9C$ 296

Thu 24/91:00 p.m. -

Nonstop2h 05m

Sun 27/99:20 p.m. -

Nonstop1h 39m

Deal found 31/8C$ 297

Fri 25/912:15 p.m. -

Nonstop2h 06m

Mon 28/97:25 a.m. -

Nonstop1h 42m

Deal found 31/8C$ 297

Sun 27/910:10 a.m. -

Nonstop1h 50m

Wed 30/911:45 a.m. -

Nonstop1h 40m

Deal found 30/8C$ 299

Sat 17/101:45 p.m. -

Nonstop1h 50m

Sun 18/103:20 p.m. -

Nonstop1h 40m

Deal found 2/9C$ 301

Sat 17/108:05 a.m. -

Nonstop1h 55m

Sat 24/109:55 a.m. -

Nonstop1h 45m

Deal found 1/9C$ 303

Thu 24/910:10 a.m. -

Nonstop1h 50m

Sun 27/911:45 a.m. -

Nonstop1h 40m

Deal found 31/8C$ 303

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

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Sat 26/9

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$ 185

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Tue 13/10

7:35 p.m.-8:45 p.m.

Nonstop2h 10m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 185

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Thu 29/10

7:20 p.m.-8:21 p.m.

Nonstop2h 01m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 185

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Tue 6/10

7:35 p.m.-8:45 p.m.

Nonstop2h 10m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 186

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Mon 5/10

7:35 p.m.-8:45 p.m.

Nonstop2h 10m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 186

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Fri 16/10

2:45 p.m.-3:51 p.m.

Nonstop2h 06m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 192

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Thu 24/9

11:00 a.m.-12:00 p.m.

Nonstop2h 00m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 192

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Thu 1/10

6:50 p.m.-7:48 p.m.

Nonstop1h 58m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 192

Quickest round-trip

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Thu 24/9

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$ 194

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Tue 29/9

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$ 196

Flights are sorted by cheapest round-trip flights first.

Deals found on 29/8

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

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$ 443. If you're looking for a direct round-trip flight to Chicago, you can expect to pay around C$ 1,148.
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, November 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$ 1,707.

See more FAQs

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