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C$ 158+ 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 5/2. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
7 Feb — 14 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 8 January 2026.

Sat 21/211:00 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sat 28/212:45 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 7/1C$ 254
Sat 31/111:00 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 2/211:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 6/1C$ 256
Sun 8/22:30 p.m.YTZ - MDW
Nonstop1h 50mMultiple Airlines
Tue 10/211:00 a.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 6/1C$ 257
Thu 5/29:00 a.m.YYZ - ORD
Nonstop2h 06mLufthansa
Sun 8/26:28 p.m.ORD - YYZ
Nonstop1h 53mLufthansa
Deal found 7/1C$ 258
Sat 7/211:00 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 8/211:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 7/1C$ 258
Fri 13/39:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 15/34:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 6/1C$ 260
Thu 12/39:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 15/34:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 7/1C$ 263
Wed 8/42:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sat 11/412:45 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 6/1C$ 264
Wed 21/19:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Thu 22/111:05 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 7/1C$ 265
Sat 14/211:00 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sat 21/212:45 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 6/1C$ 267
Wed 21/19:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Fri 23/111:05 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 7/1C$ 268
Mon 23/29:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 24/211:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 7/1C$ 270

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 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

Sat 31/1

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

Nonstop1h 50m

Chicago Midway

Mon 2/2

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

Nonstop1h 42m

C$ 256

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 8/2

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

Sat 7/2

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

Nonstop1h 50m

Chicago Midway

Sun 8/2

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

Nonstop1h 42m

C$ 258

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 13/3

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

Nonstop1h 50m

Chicago Midway

Sun 15/3

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

Nonstop1h 42m

C$ 260

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 13/3

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

Nonstop1h 50m

Chicago Midway

Mon 16/3

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

Nonstop1h 42m

C$ 261

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 16/3

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$ 263

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 12/3

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

Nonstop1h 50m

Chicago Midway

Sun 15/3

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

Nonstop1h 42m

C$ 263

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 13/2

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

Nonstop1h 50m

Chicago Midway

Tue 17/2

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

Nonstop1h 42m

C$ 264

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 9/3

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

Nonstop1h 50m

Chicago Midway

Wed 11/3

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

Nonstop1h 42m

C$ 264

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 21/1

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

Nonstop1h 50m

Chicago Midway

Thu 22/1

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

Nonstop1h 42m

C$ 265

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/1

Showing 1-10 of 51 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 8 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
8.0
Very good
406 reviews
Check prices

Crew

8.6

Comfort

7.9

Boarding

8.2

Food

7.6

Overall

8.0

Entertainment

7.0

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
406 reviews
Porter Airlines
8.0
Very good
406 reviews
Check prices

Crew

8.6

Comfort

7.9

Boarding

8.2

Food

7.6

Overall

8.0

Entertainment

7.0

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
7.7
Good
491 reviews
Porter Airlines
8.0
Very good
406 reviews
Check prices

Crew

8.6

Comfort

7.9

Boarding

8.2

Food

7.6

Overall

8.0

Entertainment

7.0

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
9,139 reviews
Porter Airlines
8.0
Very good
406 reviews
Check prices

Crew

8.6

Comfort

7.9

Boarding

8.2

Food

7.6

Overall

8.0

Entertainment

7.0

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
11,095 reviews
Porter Airlines
8.0
Very good
406 reviews
Check prices

Crew

8.6

Comfort

7.9

Boarding

8.2

Food

7.6

Overall

8.0

Entertainment

7.0

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
10,603 reviews
Porter Airlines
8.0
Very good
406 reviews
Check prices

Crew

8.6

Comfort

7.9

Boarding

8.2

Food

7.6

Overall

8.0

Entertainment

7.0

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$ 454. If you're looking for a direct round-trip flight to Chicago, you can expect to pay around C$ 1,185.

  • 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$ 1,366.

See more FAQs

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