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C$ 185+ 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 15/9. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
10 Sep — 17 Sep1
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 11 August 2026.

Thu 10/96:50 p.m. -
Nonstop1h 58m
Sun 13/98:40 p.m. -
Nonstop1h 46m
Deal found 7/8C$ 278
Wed 9/91:45 p.m. -
Nonstop1h 50m
Sun 13/93:20 p.m. -
Nonstop1h 40m
Deal found 7/8C$ 279
Thu 10/912:15 p.m. -
Nonstop2h 06m
Sun 13/97:25 a.m. -
Nonstop1h 42m
Deal found 7/8C$ 279
Sat 29/88:50 a.m. -
Nonstop1h 50m
Sat 12/911:45 a.m. -
Nonstop1h 40m
Deal found 7/8C$ 280
Tue 8/92:00 p.m. -
Nonstop1h 55m
Mon 14/99:55 a.m. -
Nonstop1h 45m
Deal found 8/8C$ 282
Fri 11/91:45 p.m. -
Nonstop1h 50m
Sun 13/911:45 a.m. -
Nonstop1h 40m
Deal found 10/8C$ 282
Sat 12/97:35 p.m. -
Nonstop2h 06m
Tue 15/97:25 a.m. -
Nonstop1h 42m
Deal found 7/8C$ 282
Tue 8/912:15 p.m. -
Nonstop2h 06m
Wed 9/92:00 p.m. -
Nonstop1h 42m
Deal found 10/8C$ 283
Fri 4/91:45 p.m. -
Nonstop1h 50m
Tue 8/911:45 a.m. -
Nonstop1h 40m
Deal found 7/8C$ 284
Thu 10/97:35 p.m. -
Nonstop2h 06m
Thu 24/97:25 a.m. -
Nonstop1h 42m
Deal found 6/8C$ 286
Fri 4/97:45 p.m. -
Nonstop2h 06m
Tue 8/92:00 p.m. -
Nonstop1h 42m
Deal found 6/8C$ 287
Tue 8/92:00 p.m. -
Nonstop1h 55m
Tue 15/99:55 a.m. -
Nonstop1h 45m
Deal found 9/8C$ 289

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 11 August 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 Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Fri 11/9

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

Nonstop1h 50m

Chicago Midway

Sat 12/9

11:45 a.m.-2:25 p.m.

Nonstop1h 40m

C$ 280

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Sat 19/9

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

Nonstop2h 06m

Chicago O'Hare Intl

Mon 21/9

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

Nonstop1h 42m

C$ 287

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Wed 23/9

12:15 p.m.-1:21 p.m.

Nonstop2h 06m

Chicago O'Hare Intl

Wed 30/9

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

Nonstop1h 42m

C$ 289

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Mon 14/9

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

Nonstop2h 06m

Chicago O'Hare Intl

Wed 16/9

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

Nonstop1h 42m

C$ 289

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Tue 8/9

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

Nonstop2h 00m

Chicago O'Hare Intl

Mon 14/9

9:18 p.m.-11:59 p.m.

Nonstop1h 41m

C$ 294

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Thu 3/9

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

Nonstop2h 00m

Chicago O'Hare Intl

Tue 8/9

9:18 p.m.-11:59 p.m.

Nonstop1h 41m

C$ 294

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Thu 10/9

10:10 a.m.-11:00 a.m.

Nonstop1h 50m

Chicago Midway

Sat 19/9

11:45 a.m.-2:25 p.m.

Nonstop1h 40m

C$ 305

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Fri 4/9

10:10 a.m.-11:00 a.m.

Nonstop1h 50m

Chicago Midway

Tue 8/9

11:45 a.m.-2:25 p.m.

Nonstop1h 40m

C$ 307

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Tue 8/9

10:10 a.m.-11:00 a.m.

Nonstop1h 50m

Chicago Midway

Mon 14/9

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

Nonstop1h 40m

C$ 314

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Wed 9/9

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

Nonstop1h 50m

Chicago Midway

Thu 10/9

11:45 a.m.-2:25 p.m.

Nonstop1h 40m

C$ 321

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/8

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 11 August 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
454 reviews
Check prices

Overall

8.0

Entertainment

6.9

Crew

8.6

Comfort

8.0

Food

7.6

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.
Porter Airlines
8.0
Very good
454 reviews
Porter Airlines
8.0
Very good
454 reviews
Check prices

Overall

8.0

Entertainment

6.9

Crew

8.6

Comfort

8.0

Food

7.6

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.
Air Transat
7.8
Good
572 reviews
Porter Airlines
8.0
Very good
454 reviews
Check prices

Overall

8.0

Entertainment

6.9

Crew

8.6

Comfort

8.0

Food

7.6

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.
United Airlines
7.4
Good
10,103 reviews
Porter Airlines
8.0
Very good
454 reviews
Check prices

Overall

8.0

Entertainment

6.9

Crew

8.6

Comfort

8.0

Food

7.6

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.
American Airlines
7.1
Good
11,902 reviews
Porter Airlines
8.0
Very good
454 reviews
Check prices

Overall

8.0

Entertainment

6.9

Crew

8.6

Comfort

8.0

Food

7.6

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.
Air Canada
7.1
Good
11,462 reviews
Porter Airlines
8.0
Very good
454 reviews
Check prices

Overall

8.0

Entertainment

6.9

Crew

8.6

Comfort

8.0

Food

7.6

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.

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$ 485. If you're looking for a direct round-trip flight to Chicago, you can expect to pay around C$ 1,262.

  • 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. 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$ 1,411.

See more FAQs

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