Direct flights to Chicago | Cheapflights

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Last-minute

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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 10 November 2026.

Sat 26/1210:29 a.m. -

Nonstop2h 05m

Sun 3/16:20 p.m. -

Nonstop1h 45m

Deal found 9/11C$ 358

Fri 18/1210:29 a.m. -

Nonstop2h 05m

Fri 18/126:20 p.m. -

Nonstop1h 45m

Deal found 9/11C$ 363

Wed 9/1210:29 a.m. -

Nonstop2h 05m

Fri 18/1212:15 p.m. -

Nonstop1h 45m

Deal found 9/11C$ 375

Wed 2/124:35 p.m. -

Nonstop2h 05m

Sun 6/1212:15 p.m. -

Nonstop1h 45m

Deal found 9/11C$ 380

Wed 25/114:35 p.m. -

Nonstop2h 05m

Mon 30/1112:15 p.m. -

Nonstop1h 45m

Deal found 9/11C$ 381

Tue 1/124:35 p.m. -

Nonstop2h 05m

Fri 4/1212:15 p.m. -

Nonstop1h 45m

Deal found 8/11C$ 387

Wed 23/1210:29 a.m. -

Nonstop2h 05m

Wed 30/1212:15 p.m. -

Nonstop1h 45m

Deal found 8/11C$ 389

Sat 5/124:35 p.m. -

Nonstop2h 05m

Sat 12/126:20 p.m. -

Nonstop1h 45m

Deal found 5/11C$ 391

Mon 7/1210:29 a.m. -

Nonstop2h 05m

Mon 14/126:20 p.m. -

Nonstop1h 45m

Deal found 8/11C$ 396

Thu 26/112:35 p.m. -

Nonstop2h 03m

Sun 29/1110:15 a.m. -

Nonstop1h 37m

Deal found 9/11C$ 398

Thu 3/124:35 p.m. -

Nonstop2h 05m

Sun 6/126:20 p.m. -

Nonstop1h 45m

Deal found 7/11C$ 398

Fri 4/124:35 p.m. -

Nonstop2h 05m

Sun 6/1212:15 p.m. -

Nonstop1h 45m

Deal found 6/11C$ 399

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

Tue 1/12

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$ 209

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Wed 2/12

10:29 a.m.-11:34 a.m.

Nonstop2h 05m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 216

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Wed 2/12

3:22 p.m.-4:42 p.m.

Nonstop2h 20m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 219

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Wed 25/11

2:35 p.m.-3:38 p.m.

Nonstop2h 03m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 234

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Tue 1/12

6:21 p.m.-7:41 p.m.

Nonstop2h 20m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 234

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Tue 8/12

6:23 p.m.-7:43 p.m.

Nonstop2h 20m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 234

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Sat 28/11

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$ 237

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Tue 29/12

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$ 237

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Thu 26/11

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$ 244

Quickest round-trip

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Tue 12/1

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

Nonstop1h 55m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 246

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

Showing 1-10 of 45 resultsSorted by cheapest first

1

2

3

...

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$ 499. If you're looking for a direct round-trip flight to Chicago, you can expect to pay around C$ 1,502.
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, May 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$ 629.

See more FAQs

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