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C$ 190+ 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 24/7. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
21 Jul — 28 Jul1
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 June 2026.

Thu 2/712:25 p.m.
YYZ
-
ORD
Nonstop1h 57m
Air Canada
Sun 5/79:50 a.m.
ORD
-
YYZ
Nonstop1h 45m
Air Canada
Deal found 18/6C$ 292
Mon 6/71:45 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Wed 8/710:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 19/6C$ 292
Sat 4/78:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sun 5/710:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 20/6C$ 293
Mon 12/108:40 p.m.
YTZ
-
ORD
Nonstop1h 55m
Porter Airlines
Sat 17/103:20 p.m.
ORD
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 16/6C$ 293
Sat 11/78:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 13/73:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 20/6C$ 294
Sat 18/77:25 p.m.
YTZ
-
ORD
Nonstop2h 04m
Air Canada
Sun 19/72:00 p.m.
ORD
-
YTZ
Nonstop1h 42m
Air Canada
Deal found 20/6C$ 294
Fri 3/78:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sun 5/710:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 19/6C$ 296
Fri 3/712:25 p.m.
YYZ
-
ORD
Nonstop1h 57m
Air Canada
Sun 5/79:50 a.m.
ORD
-
YYZ
Nonstop1h 45m
Air Canada
Deal found 19/6C$ 297
Fri 3/77:25 p.m.
YTZ
-
ORD
Nonstop2h 04m
Air Canada
Mon 6/72:00 p.m.
ORD
-
YTZ
Nonstop1h 42m
Air Canada
Deal found 19/6C$ 297
Sun 5/78:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Tue 7/73:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 19/6C$ 299
Thu 9/71:45 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 13/710:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 19/6C$ 300
Fri 3/712:25 p.m.
YYZ
-
ORD
Nonstop1h 57m
Air Canada
Wed 8/73:50 p.m.
ORD
-
YYZ
Nonstop1h 44m
Air Canada
Deal found 17/6C$ 301

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 June 2026.
Use the filters below to find and compare direct flights to Chicago that are best for you.

Fly from

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 5/7

8:50 a.m.-9:40 a.m.

Nonstop1h 50m

Chicago Midway

Wed 8/7

10:25 a.m.-1:05 p.m.

Nonstop1h 40m

C$ 294

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Thu 2/7

7:25 p.m.-8:29 p.m.

Nonstop2h 04m

Chicago O'Hare Intl

Sat 4/7

2:00 p.m.-4:42 p.m.

Nonstop1h 42m

C$ 297

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Wed 1/7

7:25 p.m.-8:29 p.m.

Nonstop2h 04m

Chicago O'Hare Intl

Mon 6/7

2:00 p.m.-4:42 p.m.

Nonstop1h 42m

C$ 297

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Fri 14/8

12:15 p.m.-1:19 p.m.

Nonstop2h 04m

Chicago O'Hare Intl

Sun 16/8

7:25 a.m.-10:07 a.m.

Nonstop1h 42m

C$ 297

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Thu 6/8

7:25 p.m.-8:29 p.m.

Nonstop2h 04m

Chicago O'Hare Intl

Sun 9/8

2:00 p.m.-4:42 p.m.

Nonstop1h 42m

C$ 297

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 16/7

8:50 a.m.-9:40 a.m.

Nonstop1h 50m

Chicago Midway

Sat 18/7

10:25 a.m.-1:05 p.m.

Nonstop1h 40m

C$ 299

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 2/8

8:50 a.m.-9:40 a.m.

Nonstop1h 50m

Chicago Midway

Sun 9/8

3:15 p.m.-5:55 p.m.

Nonstop1h 40m

C$ 300

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 10/7

8:50 a.m.-9:40 a.m.

Nonstop1h 50m

Chicago Midway

Mon 13/7

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

C$ 301

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 4/7

11:00 a.m.-12:00 p.m.

Nonstop2h 00m

Chicago O'Hare Intl

Sun 5/7

7:09 a.m.-9:54 a.m.

Nonstop1h 45m

C$ 307

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 21/7

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

Chicago Midway

Sat 25/7

10:25 a.m.-1:05 p.m.

Nonstop1h 40m

C$ 308

Flights are sorted by cheapest round-trip flights first.

Deals found on 16/6

Showing 1-10 of 60 resultsSorted by cheapest first
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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 June 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
438 reviews
Check prices

Entertainment

6.9

Boarding

8.2

Food

7.6

Crew

8.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
6.0
Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.
Porter Airlines
8.0
Very good
438 reviews
Porter Airlines
8.0
Very good
438 reviews
Check prices

Entertainment

6.9

Boarding

8.2

Food

7.6

Crew

8.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
6.0
Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.
Air Transat
7.8
Good
556 reviews
Porter Airlines
8.0
Very good
438 reviews
Check prices

Entertainment

6.9

Boarding

8.2

Food

7.6

Crew

8.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
6.0
Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.
United Airlines
7.4
Good
9,866 reviews
Porter Airlines
8.0
Very good
438 reviews
Check prices

Entertainment

6.9

Boarding

8.2

Food

7.6

Crew

8.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
6.0
Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.
American Airlines
7.1
Good
11,723 reviews
Porter Airlines
8.0
Very good
438 reviews
Check prices

Entertainment

6.9

Boarding

8.2

Food

7.6

Crew

8.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
6.0
Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.
Air Canada
7.1
Good
11,229 reviews
Porter Airlines
8.0
Very good
438 reviews
Check prices

Entertainment

6.9

Boarding

8.2

Food

7.6

Crew

8.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
6.0
Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.

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$ 354. If you're looking for a direct round-trip flight to Chicago, you can expect to pay around C$ 607.

  • Which airlines fly direct to Chicago?

    At the moment, Air Canada, United Airlines, Porter Airlines, American Airlines, WestJet, Delta 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, September is worth consideration, as prices are usually at their lowest, on average. February 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 Montreal Pierre Elliott Trudeau Intl Airport. A round-trip direct flight from Montreal Pierre Elliott Trudeau Intl Airport to Chicago typically costs around C$ 622.

See more FAQs

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