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C$ 166+ 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 15/6. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
20 Feb — 27 Feb1
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 21 January 2026.

Tue 10/211:00 a.m.
YYZ
-
ORD
Nonstop2h 08m
United Airlines
Tue 17/26:28 p.m.
ORD
-
YYZ
Nonstop1h 53m
United Airlines
Deal found 20/1C$ 261
Thu 19/23:30 p.m.
YYZ
-
ORD
Nonstop2h 09m
United Airlines
Mon 23/29:15 p.m.
ORD
-
YYZ
Nonstop1h 44m
United Airlines
Deal found 21/1C$ 263
Tue 3/29:20 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Tue 10/211:05 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 19/1C$ 264
Thu 5/29:20 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 9/211:05 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 19/1C$ 271
Wed 18/29:20 a.m.
YTZ
-
MDW
Nonstop1h 50m
Air Transat
Wed 25/211:05 a.m.
MDW
-
YTZ
Nonstop1h 42m
Air Transat
Deal found 20/1C$ 274
Thu 12/29:20 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Thu 19/211:05 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 18/1C$ 275
Sat 14/211:05 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 16/24:15 p.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 19/1C$ 277
Thu 19/29:20 a.m.
YTZ
-
MDW
Nonstop1h 50m
Air Transat
Mon 23/211:05 a.m.
MDW
-
YTZ
Nonstop1h 42m
Air Transat
Deal found 19/1C$ 278
Mon 2/29:20 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Thu 5/211:05 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 19/1C$ 286
Tue 3/29:20 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sun 8/24:15 p.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 20/1C$ 288
Mon 16/28:15 a.m.
YYZ
-
ORD
Nonstop1h 58m
Air Canada
Fri 20/210:00 a.m.
ORD
-
YYZ
Nonstop1h 40m
Air Canada
Deal found 19/1C$ 290
Tue 3/29:20 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Thu 5/211:05 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 19/1C$ 292

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 21 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

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 12/2

6:45 a.m.-8:00 a.m.

Nonstop2h 15m

Chicago O'Hare Intl

Tue 17/2

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

Nonstop1h 44m

C$ 261

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 11/2

3:30 p.m.-4:40 p.m.

Nonstop2h 10m

Chicago O'Hare Intl

Sun 15/2

11:11 a.m.-2:01 p.m.

Nonstop1h 50m

C$ 261

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 12/2

6:45 a.m.-8:00 a.m.

Nonstop2h 15m

Chicago O'Hare Intl

Sat 14/2

6:28 p.m.-9:21 p.m.

Nonstop1h 53m

C$ 261

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 14/2

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

Nonstop2h 00m

Chicago O'Hare Intl

Mon 16/2

8:00 a.m.-10:40 a.m.

Nonstop1h 40m

C$ 263

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 12/2

9:20 a.m.-10:10 a.m.

Nonstop1h 50m

Chicago Midway

Thu 19/2

11:05 a.m.-1:47 p.m.

Nonstop1h 42m

C$ 275

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 18/2

9:20 a.m.-10:10 a.m.

Nonstop1h 50m

Chicago Midway

Wed 25/2

11:05 a.m.-1:47 p.m.

Nonstop1h 42m

C$ 277

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 19/2

9:20 a.m.-10:10 a.m.

Nonstop1h 50m

Chicago Midway

Sun 22/2

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

Nonstop1h 42m

C$ 277

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 19/2

9:20 a.m.-10:10 a.m.

Nonstop1h 50m

Chicago Midway

Mon 23/2

11:05 a.m.-1:47 p.m.

Nonstop1h 42m

C$ 278

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 5/2

9:20 a.m.-10:10 a.m.

Nonstop1h 50m

Chicago Midway

Sun 8/2

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

Nonstop1h 42m

C$ 288

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 3/2

9:20 a.m.-10:10 a.m.

Nonstop1h 50m

Chicago Midway

Fri 6/2

11:05 a.m.-1:47 p.m.

Nonstop1h 42m

C$ 288

Flights are sorted by cheapest round-trip flights first.

Deals found on 20/1

Showing 1-10 of 56 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 21 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

Boarding

8.2

Overall

7.9

Comfort

7.9

Crew

8.6

Entertainment

6.9

Food

7.5

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

Boarding

8.2

Overall

7.9

Comfort

7.9

Crew

8.6

Entertainment

6.9

Food

7.5

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
499 reviews
Porter Airlines
7.9
Good
412 reviews
Check prices

Boarding

8.2

Overall

7.9

Comfort

7.9

Crew

8.6

Entertainment

6.9

Food

7.5

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
9,191 reviews
Porter Airlines
7.9
Good
412 reviews
Check prices

Boarding

8.2

Overall

7.9

Comfort

7.9

Crew

8.6

Entertainment

6.9

Food

7.5

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
11,173 reviews
Porter Airlines
7.9
Good
412 reviews
Check prices

Boarding

8.2

Overall

7.9

Comfort

7.9

Crew

8.6

Entertainment

6.9

Food

7.5

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
10,646 reviews
Porter Airlines
7.9
Good
412 reviews
Check prices

Boarding

8.2

Overall

7.9

Comfort

7.9

Crew

8.6

Entertainment

6.9

Food

7.5

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$ 441. If you're looking for a direct round-trip flight to Chicago, you can expect to pay around C$ 1,024.

  • 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$ 1,300.

See more FAQs

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