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C$ 175+ 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 8/6. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
25 Jun — 2 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 26 May 2026.

Wed 24/68:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Fri 26/63:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 22/5C$ 275
Wed 23/91:40 p.m.
YTZ
-
ORD
Nonstop1h 55m
Porter Airlines
Sat 26/93:20 p.m.
ORD
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 21/5C$ 276
Wed 9/910:05 a.m.
YTZ
-
ORD
Nonstop1h 55m
Porter Airlines
Tue 15/93:20 p.m.
ORD
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 23/5C$ 277
Thu 11/61:45 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sun 14/610:15 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 25/5C$ 279
Sun 14/68:45 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 15/63:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 24/5C$ 280
Thu 15/108:40 p.m.
YTZ
-
ORD
Nonstop1h 55m
Porter Airlines
Sun 18/103:20 p.m.
ORD
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 20/5C$ 280
Fri 18/98:40 p.m.
YTZ
-
ORD
Nonstop1h 55m
Porter Airlines
Sun 20/911:45 a.m.
ORD
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 25/5C$ 282
Mon 8/68:45 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 15/610:15 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 25/5C$ 283
Sun 13/98:40 p.m.
YTZ
-
ORD
Nonstop1h 55m
Porter Airlines
Thu 17/911:45 a.m.
ORD
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 22/5C$ 283
Fri 12/611:00 a.m.
YYZ
-
ORD
Nonstop2h 00m
United Airlines
Sun 14/69:20 p.m.
ORD
-
YYZ
Nonstop1h 39m
United Airlines
Deal found 21/5C$ 284
Sat 6/68:45 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sat 13/610:15 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 23/5C$ 284
Tue 1/98:40 p.m.
YTZ
-
ORD
Nonstop1h 55m
Porter Airlines
Tue 8/911:45 a.m.
ORD
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 24/5C$ 284

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 26 May 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

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Wed 23/9

1:40 p.m.-2:35 p.m.

Nonstop1h 55m

Chicago O'Hare Intl

Sat 26/9

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

Nonstop1h 40m

C$ 279

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Tue 8/9

8:40 p.m.-9:35 p.m.

Nonstop1h 55m

Chicago O'Hare Intl

Sun 13/9

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

Nonstop1h 40m

C$ 284

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 25/6

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

Nonstop1h 50m

Chicago Midway

Sun 28/6

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

Nonstop1h 40m

C$ 291

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Mon 15/6

7:20 p.m.-8:16 p.m.

Nonstop1h 56m

Chicago O'Hare Intl

Wed 17/6

7:25 a.m.-10:06 a.m.

Nonstop1h 41m

C$ 306

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 26/6

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

Nonstop1h 50m

Chicago Midway

Sun 28/6

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

Nonstop1h 40m

C$ 323

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 2/7

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

Nonstop1h 50m

Chicago Midway

Sat 4/7

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

Nonstop1h 40m

C$ 323

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Thu 25/6

7:20 p.m.-8:16 p.m.

Nonstop1h 56m

Chicago O'Hare Intl

Thu 2/7

7:25 a.m.-10:06 a.m.

Nonstop1h 41m

C$ 329

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Fri 24/7

7:20 p.m.-8:16 p.m.

Nonstop1h 56m

Chicago O'Hare Intl

Mon 27/7

7:25 a.m.-10:06 a.m.

Nonstop1h 41m

C$ 341

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 12/6

8:45 a.m.-9:35 a.m.

Nonstop1h 50m

Chicago Midway

Sun 14/6

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

Nonstop1h 40m

C$ 341

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Tue 15/9

1:40 p.m.-2:35 p.m.

Nonstop1h 55m

Chicago O'Hare Intl

Thu 17/9

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

Nonstop1h 40m

C$ 341

Flights are sorted by cheapest round-trip flights first.

Deals found on 25/5

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 26 May 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
439 reviews
Check prices

Entertainment

7.0

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.6

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
Porter Airlines
8.0
Very good
439 reviews
Porter Airlines
8.0
Very good
439 reviews
Check prices

Entertainment

7.0

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.6

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
Air Transat
7.8
Good
553 reviews
Porter Airlines
8.0
Very good
439 reviews
Check prices

Entertainment

7.0

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.6

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
United Airlines
7.4
Good
9,749 reviews
Porter Airlines
8.0
Very good
439 reviews
Check prices

Entertainment

7.0

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.6

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
American Airlines
7.1
Good
11,629 reviews
Porter Airlines
8.0
Very good
439 reviews
Check prices

Entertainment

7.0

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.6

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
Air Canada
7.1
Good
11,090 reviews
Porter Airlines
8.0
Very good
439 reviews
Check prices

Entertainment

7.0

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.6

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.

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$ 461. If you're looking for a direct round-trip flight to Chicago, you can expect to pay around C$ 1,147.

  • Which airlines fly direct to Chicago?

    At the moment, Air Canada, United Airlines, Porter Airlines, WestJet, 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, 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 Toronto Pearson Intl Airport. A round-trip direct flight from Toronto Pearson Intl Airport to Chicago typically costs around C$ 1,311.

See more FAQs

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