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 13 September 2026.

Tue 6/1012:25 p.m. -

Nonstop1h 58m

Sat 10/109:55 a.m. -

Nonstop1h 45m

Deal found 12/9C$ 275

Fri 25/911:00 a.m. -

Nonstop2h 00m

Sun 27/99:55 a.m. -

Nonstop1h 45m

Deal found 11/9C$ 284

Sat 3/101:45 p.m. -

Nonstop1h 50m

Mon 5/103:20 p.m. -

Nonstop1h 40m

Deal found 11/9C$ 284

Sat 10/106:50 p.m. -

Nonstop1h 58m

Sat 17/103:45 p.m. -

Nonstop1h 46m

Deal found 10/9C$ 286

Fri 2/101:45 p.m. -

Nonstop1h 50m

Sun 4/103:20 p.m. -

Nonstop1h 40m

Deal found 9/9C$ 286

Sat 24/1012:15 p.m. -

Nonstop2h 10m

Sat 31/101:55 p.m. -

Nonstop1h 47m

Deal found 9/9C$ 286

Thu 24/911:00 a.m. -

Nonstop2h 00m

Sun 27/97:09 a.m. -

Nonstop1h 45m

Deal found 9/9C$ 287

Thu 24/910:10 a.m. -

Nonstop1h 50m

Sun 27/911:45 a.m. -

Nonstop1h 40m

Deal found 9/9C$ 287

Thu 24/97:35 p.m. -

Nonstop2h 06m

Sun 27/97:25 a.m. -

Nonstop1h 42m

Deal found 10/9C$ 287

Wed 23/91:45 p.m. -

Nonstop1h 50m

Mon 28/911:45 a.m. -

Nonstop1h 40m

Deal found 9/9C$ 288

Thu 24/97:35 p.m. -

Nonstop2h 06m

Mon 28/97:25 a.m. -

Nonstop1h 42m

Deal found 10/9C$ 288

Mon 26/108:20 a.m. -

Nonstop2h 03m

Mon 2/114:30 p.m. -

Nonstop1h 40m

Deal found 10/9C$ 290

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-MDW

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

Quickest round-trip

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Sun 4/10

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$ 182

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Thu 1/10

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 182

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Tue 6/10

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 182

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Thu 24/9

8:05 a.m.-9:00 a.m.

Nonstop1h 55m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 183

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Tue 20/10

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 183

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Wed 23/9

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$ 183

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Wed 28/10

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$ 183

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Sun 25/10

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$ 184

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Fri 16/10

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 184

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Tue 29/9

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 184

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 60 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

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

7.4

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

7.1

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.

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.

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$ 444. If you're looking for a direct round-trip flight to Chicago, you can expect to pay around C$ 712.
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 Toronto Pearson Intl Airport. A round-trip direct flight from Toronto Pearson Intl Airport to Chicago typically costs around C$ 629.

See more FAQs

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