Direct flights to Chicago | Cheapflights

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Best

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 14 February 2026.

Fri 24/49:15 a.m.

YTZ

-

MDW

Nonstop1h 50m

Porter Airlines

Sun 26/411:00 a.m.

MDW

-

YTZ

Nonstop1h 42m

Porter Airlines

Deal found 10/2C$ 259

Sun 29/312:05 p.m.

YYZ

-

ORD

Nonstop2h 00m

Air Canada

Sun 5/49:50 a.m.

ORD

-

YYZ

Nonstop1h 36m

Air Canada

Deal found 11/2C$ 261

Wed 18/39:15 a.m.

YTZ

-

MDW

Nonstop1h 50m

Porter Airlines

Thu 19/34:15 p.m.

MDW

-

YTZ

Nonstop1h 42m

Porter Airlines

Deal found 11/2C$ 261

Fri 27/312:05 p.m.

YYZ

-

ORD

Nonstop1h 56m

Air Canada

Fri 3/44:15 p.m.

ORD

-

YYZ

Nonstop1h 42m

Air Canada

Deal found 10/2C$ 263

Wed 18/39:15 a.m.

YTZ

-

MDW

Nonstop1h 50m

Porter Airlines

Wed 25/311:00 a.m.

MDW

-

YTZ

Nonstop1h 42m

Porter Airlines

Deal found 13/2C$ 263

Thu 5/38:15 a.m.

YYZ

-

ORD

Nonstop1h 58m

Air Canada

Sun 8/38:40 p.m.

ORD

-

YYZ

Nonstop1h 39m

Air Canada

Deal found 9/2C$ 264

Sun 8/32:30 p.m.

YTZ

-

MDW

Nonstop1h 50m

Porter Airlines

Fri 13/311:00 a.m.

MDW

-

YTZ

Nonstop1h 42m

Porter Airlines

Deal found 10/2C$ 264

Sat 14/311:00 a.m.

YTZ

-

MDW

Nonstop1h 50m

Porter Airlines

Mon 23/311:00 a.m.

MDW

-

YTZ

Nonstop1h 42m

Porter Airlines

Deal found 13/2C$ 267

Sat 28/311:00 a.m.

YTZ

-

MDW

Nonstop1h 50m

Porter Airlines

Sat 4/412:45 p.m.

MDW

-

YTZ

Nonstop1h 42m

Porter Airlines

Deal found 11/2C$ 271

Sat 9/58:50 a.m.

YTZ

-

MDW

Nonstop1h 50m

Porter Airlines

Mon 11/510:25 a.m.

MDW

-

YTZ

Nonstop1h 40m

Porter Airlines

Deal found 10/2C$ 272

Wed 3/612:15 p.m.

YTZ

-

ORD

Nonstop1h 55m

Air Canada

Fri 5/67:25 a.m.

ORD

-

YTZ

Nonstop1h 41m

Air Canada

Deal found 13/2C$ 272

Fri 6/38:15 a.m.

YYZ

-

ORD

Nonstop1h 58m

Air Canada

Sun 8/38:40 p.m.

ORD

-

YYZ

Nonstop1h 39m

Air Canada

Deal found 13/2C$ 274

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

YTZ - MDW

YTZMDW

Toronto Island

Tue 17/3

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

Nonstop1h 50m

Chicago Midway

Thu 19/3

4:15 p.m.-6:57 p.m.

Nonstop1h 42m

C$ 261

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$ 263

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 14/3

11:00 a.m.-11:50 a.m.

Nonstop1h 50m

Chicago Midway

Mon 23/3

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

Nonstop1h 42m

C$ 267

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 17/4

6:30 p.m.-7:25 p.m.

Nonstop1h 55m

Chicago O'Hare Intl

Fri 8/5

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

Nonstop1h 40m

C$ 272

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 2/4

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

Nonstop2h 03m

Chicago O'Hare Intl

Sun 5/4

10:52 a.m.-1:42 p.m.

Nonstop1h 50m

C$ 272

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 3/4

11:00 a.m.-12:03 p.m.

Nonstop2h 03m

Chicago O'Hare Intl

Mon 6/4

5:57 p.m.-8:44 p.m.

Nonstop1h 47m

C$ 272

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 9/5

4:00 p.m.-4:59 p.m.

Nonstop1h 59m

Chicago O'Hare Intl

Sat 16/5

8:20 p.m.-11:03 p.m.

Nonstop1h 43m

C$ 272

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Wed 3/6

12:15 p.m.-1:10 p.m.

Nonstop1h 55m

Chicago O'Hare Intl

Fri 5/6

7:25 a.m.-10:06 a.m.

Nonstop1h 41m

C$ 272

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 28/3

11:00 a.m.-11:50 a.m.

Nonstop1h 50m

Chicago Midway

Sat 4/4

12:45 p.m.-3:27 p.m.

Nonstop1h 42m

C$ 274

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 21/5

4:00 p.m.-4:50 p.m.

Nonstop1h 50m

Chicago Midway

Sun 24/5

10:25 a.m.-1:05 p.m.

Nonstop1h 40m

C$ 274

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/2

Showing 1-10 of 60 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

7.9

Good

Reviews

1 / 20

2.0

Mediocre

Milad,Feb 2026

LIR - YYZ

Not helpful staff at Liberia airport at the check-in counter. Extremely poor skill people and not willing to help the passenger.

Porter Airlines

7.9

Good

Porter Airlines

7.9

Good

Reviews

1 / 20

2.0

Mediocre

Milad,Feb 2026

LIR - YYZ

Not helpful staff at Liberia airport at the check-in counter. Extremely poor skill people and not willing to help the passenger.

7.7

Good

Porter Airlines

7.9

Good

Reviews

1 / 20

2.0

Mediocre

Milad,Feb 2026

LIR - YYZ

Not helpful staff at Liberia airport at the check-in counter. Extremely poor skill people and not willing to help the passenger.

United Airlines

7.4

Good

Porter Airlines

7.9

Good

Reviews

1 / 20

2.0

Mediocre

Milad,Feb 2026

LIR - YYZ

Not helpful staff at Liberia airport at the check-in counter. Extremely poor skill people and not willing to help the passenger.

American Airlines

7.2

Good

Porter Airlines

7.9

Good

Reviews

1 / 20

2.0

Mediocre

Milad,Feb 2026

LIR - YYZ

Not helpful staff at Liberia airport at the check-in counter. Extremely poor skill people and not willing to help the passenger.

7.1

Good

Porter Airlines

7.9

Good

Reviews

1 / 20

2.0

Mediocre

Milad,Feb 2026

LIR - YYZ

Not helpful staff at Liberia airport at the check-in counter. Extremely poor skill people and not willing to help the passenger.

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$ 399. If you're looking for a direct round-trip flight to Chicago, you can expect to pay around C$ 789.
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 Toronto Pearson Intl Airport. A round-trip direct flight from Toronto Pearson Intl Airport to Chicago typically costs around C$ 710.

See more FAQs

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