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 October 2026.

Thu 19/114:35 p.m. -

Nonstop2h 05m

Mon 23/116:20 p.m. -

Nonstop1h 45m

Deal found 27/10C$ 299

Thu 19/114:35 p.m. -

Nonstop2h 05m

Sun 22/116:20 p.m. -

Nonstop1h 45m

Deal found 27/10C$ 300

Fri 20/114:35 p.m. -

Nonstop2h 05m

Mon 23/116:20 p.m. -

Nonstop1h 45m

Deal found 26/10C$ 303

Tue 1/124:35 p.m. -

Nonstop2h 05m

Fri 1/16:20 p.m. -

Nonstop1h 45m

Deal found 25/10C$ 304

Mon 16/114:35 p.m. -

Nonstop2h 05m

Sun 22/116:20 p.m. -

Nonstop1h 45m

Deal found 26/10C$ 306

Fri 20/114:35 p.m. -

Nonstop2h 05m

Sun 22/116:20 p.m. -

Nonstop1h 45m

Deal found 26/10C$ 309

Fri 13/118:20 a.m. -

Nonstop2h 03m

Sun 15/1110:15 a.m. -

Nonstop1h 37m

Deal found 23/10C$ 313

Fri 20/114:35 p.m. -

Nonstop2h 05m

Tue 24/116:20 p.m. -

Nonstop1h 45m

Deal found 26/10C$ 313

Sun 22/1112:05 p.m. -

Nonstop2h 15m

Tue 24/111:55 p.m. -

Nonstop1h 47m

Deal found 27/10C$ 314

Fri 27/1110:30 a.m. -

Nonstop2h 05m

Wed 16/1212:15 p.m. -

Nonstop1h 45m

Deal found 25/10C$ 316

Sat 14/118:20 a.m. -

Nonstop2h 03m

Sun 15/1110:15 a.m. -

Nonstop1h 37m

Deal found 23/10C$ 317

Fri 13/1110:30 a.m. -

Nonstop2h 05m

Sun 15/1112:15 p.m. -

Nonstop1h 45m

Deal found 23/10C$ 317

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

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 9/12

4:35 p.m.-5:40 p.m.

Nonstop2h 05m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 191

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Mon 23/11

10:30 a.m.-11:35 a.m.

Nonstop2h 05m

Chicago O'Hare Intl

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

Sun 22/11

10:30 a.m.-11:35 a.m.

Nonstop2h 05m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 195

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Tue 1/12

6:55 p.m.-7:58 p.m.

Nonstop2h 03m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 198

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Fri 18/12

10:30 a.m.-11:35 a.m.

Nonstop2h 05m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 202

Quickest round-trip

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Sun 10/1

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

Nonstop1h 55m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 202

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Tue 1/12

10:30 a.m.-11:35 a.m.

Nonstop2h 05m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 203

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Wed 9/12

4:35 p.m.-5:40 p.m.

Nonstop2h 05m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 205

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Thu 10/12

4:35 p.m.-5:40 p.m.

Nonstop2h 05m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 205

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Fri 27/11

4:30 p.m.-5:43 p.m.

Nonstop2h 13m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 206

Flights are sorted by cheapest round-trip flights first.

Deals found on 25/10

Showing 1-10 of 42 resultsSorted by cheapest first

1

2

3

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5

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

8.0

Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.

Porter Airlines

8.0

Very good

Porter Airlines

8.0

Very good

Reviews

1 / 20

8.0

Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.

7.7

Good

Porter Airlines

8.0

Very good

Reviews

1 / 20

8.0

Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.

United Airlines

7.3

Good

Porter Airlines

8.0

Very good

Reviews

1 / 20

8.0

Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.

7.1

Good

Porter Airlines

8.0

Very good

Reviews

1 / 20

8.0

Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.

American Airlines

7.0

Good

Porter Airlines

8.0

Very good

Reviews

1 / 20

8.0

Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.

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$ 687. If you're looking for a direct round-trip flight to Chicago, you can expect to pay around C$ 841.
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 Calgary. A round-trip direct flight from Calgary to Chicago typically costs around C$ 651.

See more FAQs

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