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 10 April 2026.

Fri 12/68:50 a.m.

YTZ

-

MDW

Nonstop1h 50m

Porter Airlines

Mon 15/610:25 a.m.

MDW

-

YTZ

Nonstop1h 40m

Porter Airlines

Deal found 5/4C$ 274

Fri 11/910:05 a.m.

YTZ

-

ORD

Nonstop1h 55m

Porter Airlines

Mon 14/93:20 p.m.

ORD

-

YTZ

Nonstop1h 40m

Porter Airlines

Deal found 5/4C$ 274

Thu 30/71:45 p.m.

YTZ

-

MDW

Nonstop1h 50m

Air Transat

Sun 2/810:25 a.m.

MDW

-

YTZ

Nonstop1h 40m

Air Transat

Deal found 6/4C$ 275

Wed 5/87:20 p.m.

YTZ

-

ORD

Nonstop1h 56m

Air Canada

Sun 9/82:00 p.m.

ORD

-

YTZ

Nonstop1h 41m

Air Canada

Deal found 6/4C$ 275

Fri 22/51:55 p.m.

YYZ

-

ORD

Nonstop2h 00m

Air Canada

Tue 26/58:35 p.m.

ORD

-

YYZ

Nonstop1h 43m

Air Canada

Deal found 6/4C$ 281

Mon 4/51:45 p.m.

YTZ

-

MDW

Nonstop1h 50m

Air Transat

Wed 6/510:30 a.m.

MDW

-

YTZ

Nonstop1h 40m

Air Transat

Deal found 9/4C$ 281

Sat 9/56:40 p.m.

YYZ

-

ORD

Nonstop2h 00m

Air Canada

Mon 11/58:35 p.m.

ORD

-

YYZ

Nonstop1h 43m

Air Canada

Deal found 6/4C$ 282

Thu 30/71:45 p.m.

YTZ

-

MDW

Nonstop1h 50m

Air Transat

Sat 1/810:25 a.m.

MDW

-

YTZ

Nonstop1h 40m

Air Transat

Deal found 7/4C$ 282

Wed 29/712:25 p.m.

YYZ

-

ORD

Nonstop1h 57m

Air Canada

Tue 4/83:45 p.m.

ORD

-

YYZ

Nonstop1h 45m

Air Canada

Deal found 7/4C$ 284

Sun 10/58:55 a.m.

YTZ

-

MDW

Nonstop1h 50m

Air Transat

Sun 17/510:30 a.m.

MDW

-

YTZ

Nonstop1h 40m

Air Transat

Deal found 10/4C$ 284

Wed 29/49:25 a.m.

YTZ

-

MDW

Nonstop1h 50m

Porter Airlines

Wed 6/53:20 p.m.

MDW

-

YTZ

Nonstop1h 40m

Porter Airlines

Deal found 6/4C$ 285

Fri 11/911:00 a.m.

YYZ

-

ORD

Nonstop2h 00m

United Airlines

Mon 14/99:15 p.m.

ORD

-

YYZ

Nonstop1h 44m

United Airlines

Deal found 5/4C$ 286

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-MDW

YTZ-ORD

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

YTZ - ORD

YTZORD

Toronto Island

Mon 10/8

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

Nonstop1h 55m

Chicago O'Hare Intl

Sat 15/8

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

Nonstop1h 41m

C$ 275

Quickest round-trip

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 26/5

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

Nonstop1h 50m

Chicago Midway

Thu 28/5

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

Nonstop1h 40m

C$ 286

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Fri 24/7

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

Nonstop1h 55m

Chicago O'Hare Intl

Sun 26/7

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

Nonstop1h 41m

C$ 286

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 8/8

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

Nonstop2h 00m

Chicago O'Hare Intl

Sat 8/8

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

Nonstop1h 44m

C$ 289

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 30/4

2:45 p.m.-3:43 p.m.

Nonstop1h 58m

Chicago O'Hare Intl

Sun 3/5

9:04 a.m.-11:49 a.m.

Nonstop1h 45m

C$ 292

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 24/4

1:00 p.m.-2:01 p.m.

Nonstop2h 01m

Chicago O'Hare Intl

Mon 27/4

9:05 a.m.-11:49 a.m.

Nonstop1h 44m

C$ 293

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 25/7

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

Nonstop1h 50m

Chicago Midway

Wed 29/7

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

Nonstop1h 40m

C$ 296

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Mon 8/6

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

Nonstop1h 56m

Chicago O'Hare Intl

Wed 10/6

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

Nonstop1h 41m

C$ 297

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Wed 29/7

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

Nonstop1h 56m

Chicago O'Hare Intl

Mon 3/8

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

Nonstop1h 41m

C$ 300

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 29/7

12:25 p.m.-1:22 p.m.

Nonstop1h 57m

Chicago O'Hare Intl

Sat 1/8

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

Nonstop1h 46m

C$ 303

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/4

Showing 1-10 of 60 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$ 512. If you're looking for a direct round-trip flight to Chicago, you can expect to pay around C$ 1,038.
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$ 719.

See more FAQs

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