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C$ 191+ 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 15/8. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
12 Aug — 19 Aug1
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 13 July 2026.

Fri 14/88:55 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sun 16/810:20 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 12/7C$ 290
Mon 27/78:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Thu 30/73:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 13/7C$ 292
Wed 19/87:35 p.m.
YTZ
-
ORD
Nonstop2h 06m
Air Canada
Tue 25/87:25 a.m.
ORD
-
YTZ
Nonstop1h 53m
Air Canada
Deal found 12/7C$ 292
Thu 23/78:05 a.m.
YYZ
-
ORD
Nonstop1h 55m
Air Canada
Mon 27/79:50 a.m.
ORD
-
YYZ
Nonstop1h 45m
Air Canada
Deal found 9/7C$ 293
Sat 25/78:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Wed 29/73:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 10/7C$ 293
Tue 11/87:35 p.m.
YTZ
-
ORD
Nonstop2h 06m
Air Canada
Sat 22/87:25 a.m.
ORD
-
YTZ
Nonstop1h 53m
Air Canada
Deal found 8/7C$ 293
Mon 3/81:45 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sun 9/83:15 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 12/7C$ 294
Wed 12/87:35 p.m.
YTZ
-
ORD
Nonstop2h 06m
Air Canada
Mon 17/87:25 a.m.
ORD
-
YTZ
Nonstop1h 53m
Air Canada
Deal found 11/7C$ 294
Fri 7/86:55 p.m.
YYZ
-
ORD
Nonstop1h 57m
Air Canada
Thu 13/82:15 p.m.
ORD
-
YYZ
Nonstop1h 46m
Air Canada
Deal found 12/7C$ 296
Thu 20/81:45 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sat 22/810:20 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 9/7C$ 296
Tue 15/912:15 p.m.
YTZ
-
ORD
Nonstop2h 06m
Air Canada
Fri 18/92:00 p.m.
ORD
-
YTZ
Nonstop1h 42m
Air Canada
Deal found 11/7C$ 296
Sat 25/78:05 a.m.
YYZ
-
ORD
Nonstop1h 55m
Air Canada
Wed 29/73:45 p.m.
ORD
-
YYZ
Nonstop1h 44m
Air Canada
Deal found 8/7C$ 297

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 13 July 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

Tue 11/8

8:55 a.m.-9:45 a.m.

Nonstop1h 50m

Chicago Midway

Mon 17/8

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

Nonstop1h 40m

C$ 293

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Thu 6/8

7:35 p.m.-8:41 p.m.

Nonstop2h 06m

Chicago O'Hare Intl

Sun 9/8

7:25 a.m.-10:18 a.m.

Nonstop1h 53m

C$ 293

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 2/9

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

Nonstop2h 00m

Chicago O'Hare Intl

Tue 8/9

9:29 p.m.-12:13 a.m.

Nonstop1h 44m

C$ 306

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 18/8

7:00 a.m.-8:00 a.m.

Nonstop2h 00m

Chicago O'Hare Intl

Tue 18/8

2:15 p.m.-5:01 p.m.

Nonstop1h 46m

C$ 306

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 1/9

7:00 a.m.-8:00 a.m.

Nonstop2h 00m

Chicago O'Hare Intl

Tue 8/9

9:29 p.m.-12:13 a.m.

Nonstop1h 44m

C$ 306

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 12/8

7:00 a.m.-8:00 a.m.

Nonstop2h 00m

Chicago O'Hare Intl

Sun 23/8

9:50 a.m.-12:35 p.m.

Nonstop1h 45m

C$ 306

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 17/8

8:55 a.m.-9:45 a.m.

Nonstop1h 50m

Chicago Midway

Thu 20/8

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

Nonstop1h 40m

C$ 306

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 4/9

7:00 a.m.-8:00 a.m.

Nonstop2h 00m

Chicago O'Hare Intl

Wed 9/9

2:52 p.m.-5:56 p.m.

Nonstop2h 04m

C$ 306

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 2/8

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

Nonstop1h 50m

Chicago Midway

Tue 11/8

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

Nonstop1h 40m

C$ 309

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 7/8

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

Nonstop1h 50m

Chicago Midway

Sun 16/8

10:20 a.m.-1:00 p.m.

Nonstop1h 40m

C$ 313

Flights are sorted by cheapest round-trip flights first.

Deals found on 13/7

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 13 July 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
443 reviews
Check prices

Food

7.5

Crew

8.6

Boarding

8.2

Entertainment

6.9

Overall

8.0

Comfort

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
443 reviews
Porter Airlines
8.0
Very good
443 reviews
Check prices

Food

7.5

Crew

8.6

Boarding

8.2

Entertainment

6.9

Overall

8.0

Comfort

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
564 reviews
Porter Airlines
8.0
Very good
443 reviews
Check prices

Food

7.5

Crew

8.6

Boarding

8.2

Entertainment

6.9

Overall

8.0

Comfort

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
9,987 reviews
Porter Airlines
8.0
Very good
443 reviews
Check prices

Food

7.5

Crew

8.6

Boarding

8.2

Entertainment

6.9

Overall

8.0

Comfort

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
11,810 reviews
Porter Airlines
8.0
Very good
443 reviews
Check prices

Food

7.5

Crew

8.6

Boarding

8.2

Entertainment

6.9

Overall

8.0

Comfort

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
11,335 reviews
Porter Airlines
8.0
Very good
443 reviews
Check prices

Food

7.5

Crew

8.6

Boarding

8.2

Entertainment

6.9

Overall

8.0

Comfort

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$ 692. If you're looking for a direct round-trip flight to Chicago, you can expect to pay around C$ 1,280.

  • Which airlines fly direct to Chicago?

    At the moment, Air Canada, United Airlines, Porter Airlines, American Airlines, WestJet, 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, January 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 Toronto Pearson Intl Airport. A round-trip direct flight from Toronto Pearson Intl Airport to Chicago typically costs around C$ 2,609.

See more FAQs

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