Direct flights to Chicago | Cheapflights

Find flight deals to Chicago

Enter your travel dates to find the best prices.

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 30 October 2026.

Thu 19/114:35 p.m. -

Nonstop2h 05m

Mon 23/116:20 p.m. -

Nonstop1h 45m

Deal found 27/10C$ 298

Thu 19/114:35 p.m. -

Nonstop2h 05m

Sun 22/116:20 p.m. -

Nonstop1h 45m

Deal found 27/10C$ 299

Fri 20/114:35 p.m. -

Nonstop2h 05m

Mon 23/116:20 p.m. -

Nonstop1h 45m

Deal found 26/10C$ 302

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$ 305

Fri 20/114:35 p.m. -

Nonstop2h 05m

Sun 22/116:20 p.m. -

Nonstop1h 45m

Deal found 26/10C$ 308

Fri 11/122:35 p.m. -

Nonstop2h 03m

Mon 14/1210:05 a.m. -

Nonstop1h 37m

Deal found 26/10C$ 312

Fri 20/114:35 p.m. -

Nonstop2h 05m

Tue 24/116:20 p.m. -

Nonstop1h 45m

Deal found 26/10C$ 312

Sun 22/1112:05 p.m. -

Nonstop2h 15m

Tue 24/111:55 p.m. -

Nonstop1h 47m

Deal found 27/10C$ 313

Fri 27/1110:30 a.m. -

Nonstop2h 05m

Wed 16/1212:15 p.m. -

Nonstop1h 45m

Deal found 25/10C$ 315

Mon 16/114:30 p.m. -

Nonstop2h 13m

Mon 16/118:40 p.m. -

Nonstop1h 43m

Deal found 26/10C$ 319

Fri 11/1210:29 a.m. -

Nonstop2h 05m

Fri 18/1212:15 p.m. -

Nonstop1h 45m

Deal found 27/10C$ 319

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

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$ 190

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$ 190

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

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Fri 4/12

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$ 215

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Fri 11/12

8:05 a.m.-9:08 a.m.

Nonstop2h 03m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 215

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Fri 4/12

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$ 217

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$ 222

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Thu 19/11

12:00 p.m.-1:13 p.m.

Nonstop2h 13m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 222

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Wed 2/12

12:00 p.m.-1:13 p.m.

Nonstop2h 13m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 222

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Fri 25/12

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$ 229

Flights are sorted by cheapest round-trip flights first.

Deals found on 25/10

Showing 1-10 of 46 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$ 685. If you're looking for a direct round-trip flight to Chicago, you can expect to pay around C$ 839.
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$ 649.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Popular United States destinations

Popular North America destinations

Popular Chicago routes

Airlines

United States origins

Direct flights to United States

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.