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C$ 160+ 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 25/1. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
21 Jan — 28 Jan1
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 22 December 2025.

Wed 4/28:15 a.m.YYZ - ORD
Nonstop1h 58mAir Canada
Wed 11/23:55 p.m.ORD - YYZ
Nonstop1h 39mAir Canada
Deal found 20/12C$ 251
Tue 17/29:20 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 23/211:05 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 20/12C$ 251
Thu 19/29:15 a.m.YTZ - MDW
Nonstop1h 50mMultiple Airlines
Tue 24/211:05 a.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 21/12C$ 252
Thu 22/19:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Fri 23/111:05 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 22/12C$ 255
Sun 18/12:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 25/14:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 21/12C$ 256
Mon 9/29:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 10/211:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 21/12C$ 257
Thu 15/112:05 p.m.YYZ - ORD
Nonstop1h 56mAir Canada
Sun 15/28:00 a.m.ORD - YYZ
Nonstop1h 40mAir Canada
Deal found 20/12C$ 259
Fri 16/19:20 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Fri 23/111:05 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 19/12C$ 259
Sun 15/212:05 p.m.YYZ - ORD
Nonstop1h 56mAir Canada
Mon 23/28:40 p.m.ORD - YYZ
Nonstop1h 39mAir Canada
Deal found 20/12C$ 266
Sat 24/111:00 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sat 31/112:45 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 21/12C$ 266
Thu 5/27:04 p.m.YYZ - ORD
Nonstop2h 00mAmerican Airlines
Sun 8/29:41 a.m.ORD - YYZ
Nonstop1h 53mAmerican Airlines
Deal found 22/12C$ 267
Sat 24/111:00 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Fri 30/111:05 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 21/12C$ 284

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 22 December 2025.
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

Tue 17/2

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

Nonstop1h 50m

Chicago Midway

Wed 25/2

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

Nonstop1h 42m

C$ 251

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 19/2

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

Nonstop1h 50m

Chicago Midway

Tue 24/2

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

Nonstop1h 42m

C$ 252

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 19/1

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

Nonstop1h 50m

Chicago Midway

Mon 26/1

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

Nonstop1h 42m

C$ 255

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 18/1

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

Chicago Midway

Sun 25/1

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

Nonstop1h 42m

C$ 256

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 9/2

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

Nonstop1h 50m

Chicago Midway

Tue 10/2

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

Nonstop1h 42m

C$ 257

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 15/1

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

Nonstop1h 50m

Chicago Midway

Mon 19/1

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

Nonstop1h 42m

C$ 259

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 20/2

2:15 p.m.-3:10 p.m.

Nonstop1h 55m

Chicago O'Hare Intl

Wed 25/2

2:00 p.m.-4:39 p.m.

Nonstop1h 39m

C$ 266

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 13/2

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

Nonstop2h 00m

Chicago O'Hare Intl

Thu 19/2

2:00 p.m.-4:39 p.m.

Nonstop1h 39m

C$ 266

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 24/2

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

Nonstop2h 00m

Chicago O'Hare Intl

Fri 27/2

8:40 p.m.-11:19 p.m.

Nonstop1h 39m

C$ 266

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 24/1

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

Nonstop1h 50m

Chicago Midway

Sat 31/1

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

Nonstop1h 42m

C$ 266

Flights are sorted by cheapest round-trip flights first.

Deals found on 22/12

Showing 1-10 of 49 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 22 December 2025.
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
399 reviews
Check prices

Entertainment

7.0

Boarding

8.2

Food

7.6

Comfort

7.9

Crew

8.6

Overall

8.0

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
8.0
Very good
399 reviews
Porter Airlines
8.0
Very good
399 reviews
Check prices

Entertainment

7.0

Boarding

8.2

Food

7.6

Comfort

7.9

Crew

8.6

Overall

8.0

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
7.8
Good
484 reviews
Porter Airlines
8.0
Very good
399 reviews
Check prices

Entertainment

7.0

Boarding

8.2

Food

7.6

Comfort

7.9

Crew

8.6

Overall

8.0

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
9,102 reviews
Porter Airlines
8.0
Very good
399 reviews
Check prices

Entertainment

7.0

Boarding

8.2

Food

7.6

Comfort

7.9

Crew

8.6

Overall

8.0

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
11,052 reviews
Porter Airlines
8.0
Very good
399 reviews
Check prices

Entertainment

7.0

Boarding

8.2

Food

7.6

Comfort

7.9

Crew

8.6

Overall

8.0

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
10,551 reviews
Porter Airlines
8.0
Very good
399 reviews
Check prices

Entertainment

7.0

Boarding

8.2

Food

7.6

Comfort

7.9

Crew

8.6

Overall

8.0

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$ 495. If you're looking for a direct round-trip flight to Chicago, you can expect to pay around C$ 1,198.

  • Which airlines fly direct to Chicago?

    At the moment, Air Canada, United Airlines, WestJet, Porter Airlines, American Airlines, Delta, Air Transat, Alaska Airlines 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$ 848.

See more FAQs

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