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C$ 170+ 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 29/4. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
18 Apr — 25 Apr1
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 19 March 2026.

Tue 21/49:25 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Tue 28/411:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 18/3C$ 264
Sat 2/58:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sat 9/510:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 17/3C$ 265
Wed 2/910:05 a.m.
YTZ
-
ORD
Nonstop1h 55m
Porter Airlines
Mon 7/97:00 a.m.
ORD
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 17/3C$ 266
Mon 8/61:45 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Wed 10/63:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 18/3C$ 268
Sat 11/411:20 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sat 18/412:55 p.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 18/3C$ 270
Mon 20/49:25 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 27/411:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 17/3C$ 272
Thu 23/49:25 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 27/411:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 17/3C$ 273
Sat 4/411:20 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Tue 7/411:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 17/3C$ 275
Tue 7/49:25 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Wed 8/411:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 16/3C$ 276
Thu 10/910:05 a.m.
YTZ
-
ORD
Nonstop1h 55m
Porter Airlines
Sun 13/911:45 a.m.
ORD
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 19/3C$ 276
Fri 10/42:30 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 20/411:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 16/3C$ 277
Wed 8/49:25 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sun 12/44:05 p.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 15/3C$ 279

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 19 March 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 3/6

12:15 p.m.-1:10 p.m.

Nonstop1h 55m

Chicago O'Hare Intl

Sun 7/6

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

Nonstop1h 41m

C$ 270

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Thu 4/6

12:15 p.m.-1:10 p.m.

Nonstop1h 55m

Chicago O'Hare Intl

Sun 7/6

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

Nonstop1h 41m

C$ 270

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 23/4

9:25 a.m.-10:15 a.m.

Nonstop1h 50m

Chicago Midway

Mon 27/4

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

Nonstop1h 42m

C$ 273

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 2/5

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

Nonstop1h 50m

Chicago Midway

Mon 4/5

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

Nonstop1h 40m

C$ 275

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 10/4

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

Chicago Midway

Sun 12/4

4:05 p.m.-6:47 p.m.

Nonstop1h 42m

C$ 277

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 4/6

5:15 p.m.-6:18 p.m.

Nonstop2h 03m

Chicago O'Hare Intl

Sun 7/6

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

Nonstop1h 45m

C$ 283

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Wed 9/9

10:05 a.m.-11:00 a.m.

Nonstop1h 55m

Chicago O'Hare Intl

Wed 16/9

7:00 a.m.-9:40 a.m.

Nonstop1h 40m

C$ 290

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 15/7

10:15 a.m.-11:21 a.m.

Nonstop2h 06m

Chicago O'Hare Intl

Wed 22/7

9:15 p.m.-11:59 p.m.

Nonstop1h 44m

C$ 301

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 28/4

9:25 a.m.-10:15 a.m.

Nonstop1h 50m

Chicago Midway

Wed 29/4

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

Nonstop1h 42m

C$ 308

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 25/6

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

Nonstop2h 05m

Chicago O'Hare Intl

Sun 28/6

5:55 p.m.-8:44 p.m.

Nonstop1h 49m

C$ 321

Flights are sorted by cheapest round-trip flights first.

Deals found on 18/3

Showing 1-10 of 59 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 19 March 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
425 reviews
Check prices

Overall

8.0

Boarding

8.2

Entertainment

7.0

Crew

8.6

Comfort

8.0

Food

7.6

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
425 reviews
Porter Airlines
8.0
Very good
425 reviews
Check prices

Overall

8.0

Boarding

8.2

Entertainment

7.0

Crew

8.6

Comfort

8.0

Food

7.6

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
7.7
Good
521 reviews
Porter Airlines
8.0
Very good
425 reviews
Check prices

Overall

8.0

Boarding

8.2

Entertainment

7.0

Crew

8.6

Comfort

8.0

Food

7.6

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
9,450 reviews
Porter Airlines
8.0
Very good
425 reviews
Check prices

Overall

8.0

Boarding

8.2

Entertainment

7.0

Crew

8.6

Comfort

8.0

Food

7.6

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
11,481 reviews
Porter Airlines
8.0
Very good
425 reviews
Check prices

Overall

8.0

Boarding

8.2

Entertainment

7.0

Crew

8.6

Comfort

8.0

Food

7.6

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
10,818 reviews
Porter Airlines
8.0
Very good
425 reviews
Check prices

Overall

8.0

Boarding

8.2

Entertainment

7.0

Crew

8.6

Comfort

8.0

Food

7.6

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$ 743. If you're looking for a direct round-trip flight to Chicago, you can expect to pay around C$ 1,198.

  • 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$ 1,210.

See more FAQs

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