Direct flights to Chicago | Cheapflights

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Best

Last-minute

One-way

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 2 April 2026.

Thu 23/78:50 a.m.

YTZ

-

MDW

Nonstop1h 50m

Multiple Airlines

Fri 24/710:25 a.m.

MDW

-

YTZ

Nonstop1h 40m

Multiple Airlines

Deal found 29/3C$ 272

Fri 1/59:00 p.m.

YYZ

-

ORD

Nonstop2h 01m

United Airlines

Sat 2/57:09 a.m.

ORD

-

YYZ

Nonstop1h 45m

United Airlines

Deal found 29/3C$ 274

Wed 6/51:45 p.m.

YTZ

-

MDW

Nonstop1h 50m

Air Transat

Wed 13/53:20 p.m.

MDW

-

YTZ

Nonstop1h 40m

Air Transat

Deal found 29/3C$ 274

Wed 1/712:25 p.m.

YYZ

-

ORD

Nonstop1h 57m

Air Canada

Tue 22/93:45 p.m.

ORD

-

YYZ

Nonstop1h 45m

Air Canada

Deal found 1/4C$ 275

Sat 2/58:55 a.m.

YTZ

-

MDW

Nonstop1h 50m

Multiple Airlines

Tue 5/510:30 a.m.

MDW

-

YTZ

Nonstop1h 40m

Multiple Airlines

Deal found 30/3C$ 275

Thu 3/91:40 p.m.

YTZ

-

ORD

Nonstop1h 55m

Air Transat

Sun 6/911:45 a.m.

ORD

-

YTZ

Nonstop1h 40m

Air Transat

Deal found 2/4C$ 275

Wed 22/49:25 a.m.

YTZ

-

MDW

Nonstop1h 50m

Porter Airlines

Sat 2/510:30 a.m.

MDW

-

YTZ

Nonstop1h 40m

Porter Airlines

Deal found 31/3C$ 276

Sat 5/910:05 a.m.

YTZ

-

ORD

Nonstop1h 55m

Porter Airlines

Tue 8/911:45 a.m.

ORD

-

YTZ

Nonstop1h 40m

Porter Airlines

Deal found 30/3C$ 276

Wed 5/84:00 p.m.

YYZ

-

ORD

Nonstop1h 57m

Air Canada

Wed 30/98:40 p.m.

ORD

-

YYZ

Nonstop1h 46m

Air Canada

Deal found 31/3C$ 278

Mon 27/49:25 a.m.

YTZ

-

MDW

Nonstop1h 50m

Multiple Airlines

Thu 7/510:30 a.m.

MDW

-

YTZ

Nonstop1h 40m

Multiple Airlines

Deal found 2/4C$ 278

Mon 27/49:25 a.m.

YTZ

-

MDW

Nonstop1h 50m

Air Transat

Thu 7/510:30 a.m.

MDW

-

YTZ

Nonstop1h 40m

Air Transat

Deal found 2/4C$ 279

Fri 28/812:15 p.m.

YTZ

-

ORD

Nonstop1h 55m

Air Canada

Sun 30/87:25 a.m.

ORD

-

YTZ

Nonstop1h 41m

Air Canada

Deal found 29/3C$ 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.

YTO-CHI

YYZ-ORD

YTZ-ORD

YTZ-MDW

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.

Fly from

Route

Depart

Return

Price

Cheapest round-trip

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 3/6

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

Nonstop2h 00m

Chicago O'Hare Intl

Sun 7/6

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

Nonstop1h 45m

C$ 274

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 18/6

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

Nonstop2h 00m

Chicago O'Hare Intl

Sun 21/6

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

Nonstop1h 45m

C$ 274

Quickest round-trip

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 29/6

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

Nonstop1h 50m

Chicago Midway

Mon 6/7

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

Nonstop1h 40m

C$ 275

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Thu 3/9

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

Nonstop1h 55m

Chicago O'Hare Intl

Sun 6/9

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

Nonstop1h 40m

C$ 275

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 16/6

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

Nonstop1h 50m

Chicago Midway

Sat 20/6

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

Nonstop1h 40m

C$ 275

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sat 5/9

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

Nonstop1h 55m

Chicago O'Hare Intl

Tue 8/9

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

Nonstop1h 40m

C$ 276

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 27/4

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

Nonstop1h 50m

Chicago Midway

Thu 7/5

10:30 a.m.-1:10 p.m.

Nonstop1h 40m

C$ 279

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 17/4

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

Nonstop1h 50m

Chicago Midway

Sat 18/4

12:55 p.m.-3:37 p.m.

Nonstop1h 42m

C$ 286

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Thu 9/7

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

Nonstop1h 56m

Chicago O'Hare Intl

Mon 13/7

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

Nonstop1h 41m

C$ 289

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Tue 7/7

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

Nonstop1h 55m

Chicago O'Hare Intl

Sat 11/7

2:00 p.m.-4:41 p.m.

Nonstop1h 41m

C$ 289

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/4

Showing 1-10 of 56 resultsSorted by cheapest first

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6

Reviews of airlines flying non-stop to Chicago

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

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

Porter Airlines

8.0

Very good

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.

7.7

Good

Porter Airlines

8.0

Very good

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

Porter Airlines

8.0

Very good

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

Porter Airlines

8.0

Very good

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.

7.1

Good

Porter Airlines

8.0

Very good

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

How much are direct flights to Chicago?
On average, a one-way direct flight to Chicago will cost users approximately C$ 656. If you're looking for a direct round-trip flight to Chicago, you can expect to pay around C$ 1,039.
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, 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 Montreal Pierre Elliott Trudeau Intl Airport. A round-trip direct flight from Montreal Pierre Elliott Trudeau Intl Airport to Chicago typically costs around C$ 728.

See more FAQs

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