Find flights
Deals
Airlines

C$ 163+ 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 24/2. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
7 Jan — 14 Jan1
1 adult
1 adult, Economy, 0 bags

Find flight deals to Chicago

Enter your travel dates to find the best prices.

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 8 December 2025.

Thu 29/18:15 a.m.YYZ - ORD
Nonstop1h 58mAir Canada
Sun 1/210:00 a.m.ORD - YYZ
Nonstop1h 40mAir Canada
Deal found 7/12C$ 239
Thu 22/19:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Thu 29/111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 8/12C$ 240
Tue 20/19:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 27/111:05 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 6/12C$ 245
Sat 24/12:15 p.m.YYZ - ORD
Nonstop1h 55mAir Canada
Sun 1/22:00 p.m.ORD - YYZ
Nonstop1h 39mAir Canada
Deal found 6/12C$ 246
Wed 21/16:45 p.m.YYZ - ORD
Nonstop2h 00mAir Canada
Wed 28/18:45 p.m.ORD - YYZ
Nonstop1h 35mAir Canada
Deal found 7/12C$ 249
Fri 20/29:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 24/211:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 6/12C$ 249
Thu 29/19:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 1/211:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 7/12C$ 251
Wed 21/19:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Wed 28/111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 5/12C$ 254
Thu 22/12:15 p.m.YYZ - ORD
Nonstop1h 55mAir Canada
Thu 29/12:00 p.m.ORD - YYZ
Nonstop1h 39mAir Canada
Deal found 8/12C$ 256
Fri 13/29:00 p.m.YYZ - ORD
Nonstop2h 04mUnited Airlines
Mon 16/29:14 p.m.ORD - YYZ
Nonstop1h 45mUnited Airlines
Deal found 7/12C$ 257
Tue 3/27:04 p.m.YYZ - ORD
Nonstop2h 00mAmerican Airlines
Sun 8/26:31 p.m.ORD - YYZ
Nonstop1h 52mAmerican Airlines
Deal found 7/12C$ 264
Thu 5/26:00 a.m.YYZ - ORD
Nonstop2h 15mAmerican Airlines
Thu 26/29:47 a.m.ORD - YYZ
Nonstop1h 45mAmerican Airlines
Deal found 6/12C$ 268

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 8 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

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 29/1

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

Nonstop2h 05m

Chicago O'Hare Intl

Sun 1/2

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

Nonstop1h 53m

C$ 246

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 22/1

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

Nonstop1h 50m

Chicago Midway

Thu 29/1

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

Nonstop1h 42m

C$ 247

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 18/2

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

Nonstop1h 50m

Chicago Midway

Sun 22/2

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

Nonstop1h 42m

C$ 249

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 19/2

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

Nonstop1h 50m

Chicago Midway

Mon 23/2

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

Nonstop1h 42m

C$ 249

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 19/2

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

Nonstop1h 50m

Chicago Midway

Sun 22/2

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

Nonstop1h 42m

C$ 249

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 18/2

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

Nonstop1h 50m

Chicago Midway

Mon 23/2

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

Nonstop1h 42m

C$ 249

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 18/2

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

Nonstop1h 50m

Chicago Midway

Tue 24/2

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

Nonstop1h 42m

C$ 249

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 20/2

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

Nonstop1h 50m

Chicago Midway

Sun 22/2

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

Nonstop1h 42m

C$ 249

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 20/2

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

Nonstop1h 50m

Chicago Midway

Mon 23/2

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

Nonstop1h 42m

C$ 249

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 20/2

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

Nonstop1h 50m

Chicago Midway

Fri 20/3

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

Nonstop1h 42m

C$ 275

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/12

Showing 1-10 of 42 results
1
2
3
...
5

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 8 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
397 reviews
Check prices

Crew

8.6

Boarding

8.2

Entertainment

7.0

Food

7.6

Comfort

8.0

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
397 reviews
Porter Airlines
8.0
Very good
397 reviews
Check prices

Crew

8.6

Boarding

8.2

Entertainment

7.0

Food

7.6

Comfort

8.0

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
480 reviews
Porter Airlines
8.0
Very good
397 reviews
Check prices

Crew

8.6

Boarding

8.2

Entertainment

7.0

Food

7.6

Comfort

8.0

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
9,089 reviews
Porter Airlines
8.0
Very good
397 reviews
Check prices

Crew

8.6

Boarding

8.2

Entertainment

7.0

Food

7.6

Comfort

8.0

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
11,045 reviews
Porter Airlines
8.0
Very good
397 reviews
Check prices

Crew

8.6

Boarding

8.2

Entertainment

7.0

Food

7.6

Comfort

8.0

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
10,514 reviews
Porter Airlines
8.0
Very good
397 reviews
Check prices

Crew

8.6

Boarding

8.2

Entertainment

7.0

Food

7.6

Comfort

8.0

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$ 517. If you're looking for a direct round-trip flight to Chicago, you can expect to pay around C$ 818.

  • 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$ 845.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Direct flights to Illinois

Book a non-stop flight to one of these other cities located in Illinois.
Direct flights to St. Louis

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.