Direct flights to Chicago | Cheapflights

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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 22 February 2026.

Tue 2/68:50 a.m.

YTZ

-

MDW

Nonstop1h 50m

Porter Airlines

Sat 6/610:25 a.m.

MDW

-

YTZ

Nonstop1h 40m

Porter Airlines

Deal found 20/2C$ 260

Fri 27/32:15 p.m.

YYZ

-

ORD

Nonstop1h 55m

Air Canada

Sun 29/38:20 p.m.

ORD

-

YYZ

Nonstop1h 43m

Air Canada

Deal found 19/2C$ 261

Wed 4/39:15 a.m.

YTZ

-

MDW

Nonstop1h 50m

Porter Airlines

Wed 11/311:00 a.m.

MDW

-

YTZ

Nonstop1h 42m

Porter Airlines

Deal found 18/2C$ 261

Wed 13/54:00 p.m.

YTZ

-

MDW

Nonstop1h 50m

Porter Airlines

Mon 18/510:25 a.m.

MDW

-

YTZ

Nonstop1h 40m

Porter Airlines

Deal found 20/2C$ 263

Thu 19/39:15 a.m.

YTZ

-

MDW

Nonstop1h 50m

Multiple Airlines

Thu 26/311:00 a.m.

MDW

-

YTZ

Nonstop1h 42m

Multiple Airlines

Deal found 18/2C$ 264

Mon 4/54:00 p.m.

YTZ

-

MDW

Nonstop1h 50m

Porter Airlines

Thu 7/55:35 p.m.

MDW

-

YTZ

Nonstop1h 40m

Porter Airlines

Deal found 20/2C$ 265

Sat 4/411:00 a.m.

YTZ

-

MDW

Nonstop1h 50m

Multiple Airlines

Sat 11/412:35 p.m.

MDW

-

YTZ

Nonstop1h 42m

Multiple Airlines

Deal found 18/2C$ 267

Fri 8/54:00 p.m.

YTZ

-

MDW

Nonstop1h 50m

Porter Airlines

Fri 15/55:35 p.m.

MDW

-

YTZ

Nonstop1h 40m

Porter Airlines

Deal found 21/2C$ 268

Sat 4/48:50 a.m.

YYZ

-

ORD

Nonstop2h 00m

Lufthansa

Mon 6/49:20 p.m.

ORD

-

YYZ

Nonstop1h 39m

Lufthansa

Deal found 20/2C$ 269

Fri 20/39:15 a.m.

YTZ

-

MDW

Nonstop1h 50m

Porter Airlines

Fri 10/44:05 p.m.

MDW

-

YTZ

Nonstop1h 42m

Porter Airlines

Deal found 18/2C$ 269

Fri 24/42:30 p.m.

YTZ

-

MDW

Nonstop1h 50m

Porter Airlines

Mon 27/411:00 a.m.

MDW

-

YTZ

Nonstop1h 42m

Porter Airlines

Deal found 18/2C$ 271

Wed 18/39:15 a.m.

YTZ

-

MDW

Nonstop1h 50m

Multiple Airlines

Wed 25/311:00 a.m.

MDW

-

YTZ

Nonstop1h 42m

Multiple Airlines

Deal found 18/2C$ 272

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

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

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 9/4

10:15 a.m.-11:18 a.m.

Nonstop2h 03m

Chicago O'Hare Intl

Mon 13/4

9:15 p.m.-11:59 p.m.

Nonstop1h 44m

C$ 261

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 6/6

12:25 p.m.-1:25 p.m.

Nonstop2h 00m

Chicago O'Hare Intl

Tue 9/6

3:45 p.m.-6:28 p.m.

Nonstop1h 43m

C$ 261

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 4/3

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

Wed 11/3

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 261

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sun 29/3

8:50 a.m.-9:50 a.m.

Nonstop2h 00m

Chicago O'Hare Intl

Sat 11/4

9:15 p.m.-11:59 p.m.

Nonstop1h 44m

C$ 261

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 6/5

1:55 p.m.-2:55 p.m.

Nonstop2h 00m

Chicago O'Hare Intl

Tue 12/5

9:55 a.m.-12:35 p.m.

Nonstop1h 40m

C$ 261

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sun 29/3

7:00 a.m.-8:03 a.m.

Nonstop2h 03m

Chicago O'Hare Intl

Fri 10/4

4:43 p.m.-7:37 p.m.

Nonstop1h 54m

C$ 261

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 6/6

11:00 a.m.-12:00 p.m.

Nonstop2h 00m

Chicago O'Hare Intl

Mon 8/6

7:09 a.m.-9:54 a.m.

Nonstop1h 45m

C$ 261

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 10/4

8:50 a.m.-9:50 a.m.

Nonstop2h 00m

Chicago O'Hare Intl

Sun 12/4

9:15 p.m.-11:59 p.m.

Nonstop1h 44m

C$ 261

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 5/6

8:50 a.m.-9:40 a.m.

Nonstop1h 50m

Chicago Midway

Tue 9/6

5:35 p.m.-8:15 p.m.

Nonstop1h 40m

C$ 265

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 20/3

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

Wed 25/3

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 268

Flights are sorted by cheapest round-trip flights first.

Deals found on 18/2

Showing 1-10 of 59 results

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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

10.0

Excellent

Anonymous,Feb 2026

YYJ - YYZ

Always great! The Flight Attendants are always polite and attentive! The Polite was great and reminded us all that it was Valentine's Day!

Porter Airlines

8.0

Very good

Porter Airlines

8.0

Very good

Reviews

1 / 20

10.0

Excellent

Anonymous,Feb 2026

YYJ - YYZ

Always great! The Flight Attendants are always polite and attentive! The Polite was great and reminded us all that it was Valentine's Day!

7.7

Good

Porter Airlines

8.0

Very good

Reviews

1 / 20

10.0

Excellent

Anonymous,Feb 2026

YYJ - YYZ

Always great! The Flight Attendants are always polite and attentive! The Polite was great and reminded us all that it was Valentine's Day!

United Airlines

7.4

Good

Porter Airlines

8.0

Very good

Reviews

1 / 20

10.0

Excellent

Anonymous,Feb 2026

YYJ - YYZ

Always great! The Flight Attendants are always polite and attentive! The Polite was great and reminded us all that it was Valentine's Day!

American Airlines

7.2

Good

Porter Airlines

8.0

Very good

Reviews

1 / 20

10.0

Excellent

Anonymous,Feb 2026

YYJ - YYZ

Always great! The Flight Attendants are always polite and attentive! The Polite was great and reminded us all that it was Valentine's Day!

7.1

Good

Porter Airlines

8.0

Very good

Reviews

1 / 20

10.0

Excellent

Anonymous,Feb 2026

YYJ - YYZ

Always great! The Flight Attendants are always polite and attentive! The Polite was great and reminded us all that it was Valentine's Day!

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$ 383. If you're looking for a direct round-trip flight to Chicago, you can expect to pay around C$ 806.
Which airlines fly direct to Chicago?
At the moment, Air Canada, United Airlines, Porter Airlines, WestJet, American Airlines, Delta, Air Transat 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 Montreal Pierre Elliott Trudeau Intl Airport. A round-trip direct flight from Montreal Pierre Elliott Trudeau Intl Airport to Chicago typically costs around C$ 650.

See more FAQs

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