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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 18/1. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
15 Jan — 22 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 16 December 2025.

Fri 20/29:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 23/211:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 13/12C$ 246
Sat 24/16:45 p.m.YYZ - ORD
Nonstop2h 00mAir Canada
Sun 1/28:40 p.m.ORD - YYZ
Nonstop1h 39mAir Canada
Deal found 14/12C$ 248
Sun 18/19:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Wed 21/111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 14/12C$ 248
Thu 5/23:30 p.m.YYZ - ORD
Nonstop2h 10mUnited Airlines
Sun 8/211:15 a.m.ORD - YYZ
Nonstop1h 46mUnited Airlines
Deal found 16/12C$ 256
Thu 29/19:15 a.m.YTZ - MDW
Nonstop1h 50mMultiple Airlines
Thu 5/211:05 a.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 14/12C$ 256
Sat 17/111:00 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Thu 5/211:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 16/12C$ 257
Thu 12/211:38 a.m.YYZ - ORD
Nonstop1h 55mAmerican Airlines
Mon 16/28:14 a.m.ORD - YYZ
Nonstop1h 42mAmerican Airlines
Deal found 14/12C$ 263
Fri 30/14:50 p.m.YYZ - ORD
Nonstop1h 58mAir Canada
Fri 6/28:40 p.m.ORD - YYZ
Nonstop1h 39mAir Canada
Deal found 15/12C$ 267
Thu 29/14:50 p.m.YYZ - ORD
Nonstop1h 58mAir Canada
Thu 5/28:00 a.m.ORD - YYZ
Nonstop1h 40mAir Canada
Deal found 15/12C$ 270
Sat 24/111:00 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 25/111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 15/12C$ 272
Fri 16/16:40 p.m.YYZ - ORD
Nonstop2h 00mAir Canada
Sun 18/18:00 a.m.ORD - YYZ
Nonstop1h 40mAir Canada
Deal found 16/12C$ 274
Thu 15/16:45 p.m.YYZ - ORD
Nonstop2h 00mAir Canada
Sat 17/18:40 p.m.ORD - YYZ
Nonstop1h 39mAir Canada
Deal found 15/12C$ 275

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 16 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

Thu 15/1

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

Nonstop1h 50m

Chicago Midway

Sun 18/1

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

Nonstop1h 42m

C$ 252

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 16/1

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

Nonstop1h 50m

Chicago Midway

Fri 23/1

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

Nonstop1h 42m

C$ 255

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 5/2

9:00 a.m.-10:06 a.m.

Nonstop2h 06m

Chicago O'Hare Intl

Sun 8/2

7:10 a.m.-9:58 a.m.

Nonstop1h 48m

C$ 256

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 10/2

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

Nonstop1h 55m

Chicago O'Hare Intl

Sun 15/2

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

Nonstop1h 39m

C$ 256

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 29/1

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

Nonstop1h 50m

Chicago Midway

Thu 5/2

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

Nonstop1h 42m

C$ 256

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sun 1/2

9:00 a.m.-10:06 a.m.

Nonstop2h 06m

Chicago O'Hare Intl

Tue 3/2

1:13 p.m.-4:02 p.m.

Nonstop1h 49m

C$ 256

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 15/1

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

Nonstop2h 00m

Chicago O'Hare Intl

Sat 17/1

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

Nonstop1h 39m

C$ 275

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 25/1

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

Nonstop1h 50m

Chicago Midway

Wed 28/1

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

Nonstop1h 42m

C$ 275

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 10/1

6:50 a.m.-8:05 a.m.

Nonstop2h 15m

Chicago O'Hare Intl

Sun 11/1

4:50 p.m.-7:45 p.m.

Nonstop1h 55m

C$ 281

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 31/12

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

Nonstop2h 05m

Chicago O'Hare Intl

Sat 31/1

7:10 a.m.-9:58 a.m.

Nonstop1h 48m

C$ 281

Flights are sorted by cheapest round-trip flights first.

Deals found on 15/12

Showing 1-10 of 43 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 16 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

Food

7.6

Entertainment

7.0

Boarding

8.2

Comfort

7.9

Overall

8.0

Crew

8.6

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

Food

7.6

Entertainment

7.0

Boarding

8.2

Comfort

7.9

Overall

8.0

Crew

8.6

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
483 reviews
Porter Airlines
8.0
Very good
399 reviews
Check prices

Food

7.6

Entertainment

7.0

Boarding

8.2

Comfort

7.9

Overall

8.0

Crew

8.6

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
9,094 reviews
Porter Airlines
8.0
Very good
399 reviews
Check prices

Food

7.6

Entertainment

7.0

Boarding

8.2

Comfort

7.9

Overall

8.0

Crew

8.6

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
11,048 reviews
Porter Airlines
8.0
Very good
399 reviews
Check prices

Food

7.6

Entertainment

7.0

Boarding

8.2

Comfort

7.9

Overall

8.0

Crew

8.6

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
10,527 reviews
Porter Airlines
8.0
Very good
399 reviews
Check prices

Food

7.6

Entertainment

7.0

Boarding

8.2

Comfort

7.9

Overall

8.0

Crew

8.6

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$ 480. If you're looking for a direct round-trip flight to Chicago, you can expect to pay around C$ 1,213.

  • 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$ 820.

See more FAQs

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