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 23 October 2026.

Thu 12/1110:30 a.m. -

Nonstop2h 05m

Sun 15/1112:15 p.m. -

Nonstop1h 45m

Deal found 20/10C$ 302

Thu 24/1210:30 a.m. -

Nonstop2h 05m

Tue 5/16:20 p.m. -

Nonstop1h 46m

Deal found 20/10C$ 304

Fri 20/114:35 p.m. -

Nonstop2h 05m

Mon 23/116:20 p.m. -

Nonstop1h 45m

Deal found 21/10C$ 306

Thu 19/1110:30 a.m. -

Nonstop2h 05m

Thu 26/1112:15 p.m. -

Nonstop1h 45m

Deal found 20/10C$ 307

Thu 19/114:35 p.m. -

Nonstop2h 05m

Mon 23/116:20 p.m. -

Nonstop1h 45m

Deal found 20/10C$ 309

Thu 12/118:20 a.m. -

Nonstop2h 03m

Sun 15/118:45 a.m. -

Nonstop1h 42m

Deal found 21/10C$ 310

Wed 2/1210:30 a.m. -

Nonstop2h 05m

Wed 9/126:20 p.m. -

Nonstop1h 45m

Deal found 21/10C$ 311

Thu 31/1210:30 a.m. -

Nonstop2h 05m

Mon 4/112:15 p.m. -

Nonstop1h 45m

Deal found 21/10C$ 313

Fri 11/128:05 a.m. -

Nonstop2h 03m

Sun 13/128:50 p.m. -

Nonstop1h 42m

Deal found 21/10C$ 314

Sat 5/124:35 p.m. -

Nonstop2h 05m

Sat 12/126:20 p.m. -

Nonstop1h 45m

Deal found 21/10C$ 314

Fri 20/1111:45 a.m. -

Nonstop2h 25m

Mon 23/119:42 a.m. -

Nonstop1h 49m

Deal found 19/10C$ 317

Fri 25/1210:30 a.m. -

Nonstop2h 05m

Tue 5/112:20 p.m. -

Nonstop1h 46m

Deal found 20/10C$ 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

YYZ-ORD

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

Quickest round-trip

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Sat 5/12

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$ 194

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Sun 27/12

6:45 a.m.-7:57 a.m.

Nonstop2h 12m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 196

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Sat 20/3

7:09 a.m.-8:39 a.m.

Nonstop2h 30m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 196

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Mon 30/11

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$ 196

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Sat 28/11

7:09 a.m.-8:39 a.m.

Nonstop2h 30m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 196

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Sun 22/11

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$ 196

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Thu 26/11

1:16 p.m.-2:36 p.m.

Nonstop2h 20m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 196

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Sun 15/11

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$ 196

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Thu 3/12

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

Mon 1/2

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$ 203

Flights are sorted by cheapest round-trip flights first.

Deals found on 21/10

Showing 1-10 of 44 resultsSorted by cheapest first

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2

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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$ 766. If you're looking for a direct round-trip flight to Chicago, you can expect to pay around C$ 819.
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$ 765.

See more FAQs

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