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C$ 167+ Direct flights to Chicago

This is the cheapest price on a non-stop flight to Chicago found by a Cheapflights user in the last 72 hours by searching for a flight departing on 26/4. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
27 Feb — 6 Mar1
1 adult
1 adult, Economy, 0 bags

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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 28 January 2026.

Thu 19/22:15 p.m.
YYZ
-
ORD
Nonstop1h 55m
Air Canada
Mon 23/28:00 a.m.
ORD
-
YYZ
Nonstop1h 40m
Air Canada
Deal found 26/1C$ 256
Thu 12/39:15 a.m.
YTZ
-
MDW
Nonstop1h 50m
Multiple Airlines
Thu 19/34:15 p.m.
MDW
-
YTZ
Nonstop1h 42m
Multiple Airlines
Deal found 26/1C$ 257
Fri 19/67:00 a.m.
YYZ
-
ORD
Nonstop2h 00m
United Airlines
Sun 21/69:15 p.m.
ORD
-
YYZ
Nonstop1h 44m
United Airlines
Deal found 27/1C$ 258
Thu 19/23:30 p.m.
YYZ
-
ORD
Nonstop2h 09m
United Airlines
Mon 23/26:28 p.m.
ORD
-
YYZ
Nonstop1h 53m
United Airlines
Deal found 26/1C$ 260
Fri 22/54:00 p.m.
YTZ
-
MDW
Nonstop1h 50m
Air Transat
Sun 24/510:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Air Transat
Deal found 26/1C$ 261
Wed 11/39:15 a.m.
YTZ
-
MDW
Nonstop1h 50m
Multiple Airlines
Wed 18/311:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Multiple Airlines
Deal found 25/1C$ 264
Thu 19/23:30 p.m.
YYZ
-
ORD
Nonstop2h 09m
Lufthansa
Mon 23/26:28 p.m.
ORD
-
YYZ
Nonstop1h 53m
Lufthansa
Deal found 26/1C$ 271
Sat 21/211:05 a.m.
YTZ
-
MDW
Nonstop1h 50m
Multiple Airlines
Tue 24/211:05 a.m.
MDW
-
YTZ
Nonstop1h 42m
Multiple Airlines
Deal found 26/1C$ 271
Thu 19/29:20 a.m.
YTZ
-
MDW
Nonstop1h 50m
Multiple Airlines
Mon 23/211:05 a.m.
MDW
-
YTZ
Nonstop1h 42m
Multiple Airlines
Deal found 27/1C$ 272
Mon 23/29:20 a.m.
YTZ
-
MDW
Nonstop1h 50m
Multiple Airlines
Wed 25/211:05 a.m.
MDW
-
YTZ
Nonstop1h 42m
Multiple Airlines
Deal found 27/1C$ 273
Sun 15/22:30 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sat 21/212:50 p.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 25/1C$ 276
Sun 15/22:30 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Tue 17/211:05 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 26/1C$ 277

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.
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.

Cheapflights Fare Finder

 
Use the slider to find non-stop flights to Chicago within your budget. Price data is based on user searches made on Cheapflights. Over the past seven days, Cheapflights users made 629,999 searches and data was last updated on 28 January 2026.
Use the filters below to find and compare direct flights to Chicago that are best for you.

Fly from

Toronto

Route

Depart

Return

Price

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 12/3

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$ 257

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 11/4

1:00 p.m.-2:03 p.m.

Nonstop2h 03m

Chicago O'Hare Intl

Tue 14/4

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

Nonstop1h 44m

C$ 258

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 20/6

9:00 p.m.-10:05 p.m.

Nonstop2h 05m

Chicago O'Hare Intl

Tue 23/6

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

Nonstop1h 44m

C$ 258

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 19/6

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

Nonstop2h 00m

Chicago O'Hare Intl

Sun 21/6

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

Nonstop1h 44m

C$ 258

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 26/3

8:45 a.m.-9:50 a.m.

Nonstop2h 05m

Chicago O'Hare Intl

Sun 29/3

9:05 a.m.-11:49 a.m.

Nonstop1h 44m

C$ 258

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 1/4

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

Nonstop2h 00m

Chicago O'Hare Intl

Wed 1/4

2:58 p.m.-5:56 p.m.

Nonstop1h 58m

C$ 258

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 6/5

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

Nonstop2h 00m

Chicago O'Hare Intl

Sat 9/5

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

Nonstop1h 44m

C$ 258

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 17/2

8:45 a.m.-9:50 a.m.

Nonstop2h 05m

Chicago O'Hare Intl

Tue 24/2

1:12 p.m.-4:02 p.m.

Nonstop1h 50m

C$ 258

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 13/3

12:05 p.m.-1:01 p.m.

Nonstop1h 56m

Chicago O'Hare Intl

Sun 15/3

3:55 p.m.-6:35 p.m.

Nonstop1h 40m

C$ 260

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 21/2

6:40 p.m.-7:45 p.m.

Nonstop2h 05m

Chicago O'Hare Intl

Tue 24/2

10:00 a.m.-12:40 p.m.

Nonstop1h 40m

C$ 260

Flights are sorted by cheapest round-trip flights first.

Deals found on 26/1

Showing 1-10 of 57 results
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Reviews of airlines flying non-stop to Chicago

Get insights into the airlines that provide direct flights to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated 28 January 2026.
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
412 reviews
Check prices

Overall

7.9

Comfort

7.9

Food

7.5

Entertainment

6.9

Crew

8.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
Porter Airlines
7.9
Good
412 reviews
Porter Airlines
7.9
Good
412 reviews
Check prices

Overall

7.9

Comfort

7.9

Food

7.5

Entertainment

6.9

Crew

8.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
Air Transat
7.7
Good
501 reviews
Porter Airlines
7.9
Good
412 reviews
Check prices

Overall

7.9

Comfort

7.9

Food

7.5

Entertainment

6.9

Crew

8.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
United Airlines
7.4
Good
9,206 reviews
Porter Airlines
7.9
Good
412 reviews
Check prices

Overall

7.9

Comfort

7.9

Food

7.5

Entertainment

6.9

Crew

8.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
American Airlines
7.2
Good
11,198 reviews
Porter Airlines
7.9
Good
412 reviews
Check prices

Overall

7.9

Comfort

7.9

Food

7.5

Entertainment

6.9

Crew

8.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
Air Canada
7.1
Good
10,660 reviews
Porter Airlines
7.9
Good
412 reviews
Check prices

Overall

7.9

Comfort

7.9

Food

7.5

Entertainment

6.9

Crew

8.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out

FAQ about direct flights to Chicago

Find answers to frequently asked questions about direct flights to Chicago to unlock the best deals on Cheapflights.

  • How much are direct flights to Chicago?

    On average, a one-way direct flight to Chicago will cost users approximately C$ 389. If you're looking for a direct round-trip flight to Chicago, you can expect to pay around C$ 1,361.

  • Which airlines fly direct to Chicago?

    At the moment, Air Canada, United Airlines, WestJet, Porter Airlines, 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, April 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$ 2,199.

See more FAQs

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