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 14 March 2026.

Mon 30/39:15 a.m.

YTZ

-

MDW

Nonstop1h 50m

Porter Airlines

Wed 1/411:00 a.m.

MDW

-

YTZ

Nonstop1h 42m

Porter Airlines

Deal found 9/3C$ 268

Thu 9/49:25 a.m.

YTZ

-

MDW

Nonstop1h 50m

Porter Airlines

Sat 11/412:55 p.m.

MDW

-

YTZ

Nonstop1h 42m

Porter Airlines

Deal found 9/3C$ 270

Thu 16/49:25 a.m.

YTZ

-

MDW

Nonstop1h 50m

Porter Airlines

Mon 20/411:00 a.m.

MDW

-

YTZ

Nonstop1h 42m

Porter Airlines

Deal found 8/3C$ 271

Fri 24/42:30 p.m.

YTZ

-

MDW

Nonstop1h 50m

Porter Airlines

Fri 1/53:20 p.m.

MDW

-

YTZ

Nonstop1h 40m

Porter Airlines

Deal found 10/3C$ 275

Thu 23/49:25 a.m.

YTZ

-

MDW

Nonstop1h 50m

Porter Airlines

Thu 30/411:00 a.m.

MDW

-

YTZ

Nonstop1h 42m

Porter Airlines

Deal found 9/3C$ 278

Sat 4/411:20 a.m.

YTZ

-

MDW

Nonstop1h 50m

Porter Airlines

Wed 8/411:00 a.m.

MDW

-

YTZ

Nonstop1h 42m

Porter Airlines

Deal found 10/3C$ 281

Tue 7/49:25 a.m.

YTZ

-

MDW

Nonstop1h 50m

Porter Airlines

Tue 14/411:00 a.m.

MDW

-

YTZ

Nonstop1h 42m

Porter Airlines

Deal found 10/3C$ 282

Sat 4/411:20 a.m.

YTZ

-

MDW

Nonstop1h 50m

Porter Airlines

Mon 6/411:00 a.m.

MDW

-

YTZ

Nonstop1h 42m

Porter Airlines

Deal found 10/3C$ 283

Thu 16/48:15 a.m.

YYZ

-

ORD

Nonstop1h 55m

Air Canada

Mon 20/44:15 p.m.

ORD

-

YYZ

Nonstop1h 43m

Air Canada

Deal found 10/3C$ 286

Mon 8/67:20 p.m.

YTZ

-

ORD

Nonstop1h 56m

Air Canada

Thu 11/62:00 p.m.

ORD

-

YTZ

Nonstop1h 41m

Air Canada

Deal found 10/3C$ 294

Sat 25/46:30 p.m.

YYZ

-

ORD

Nonstop1h 55m

Air Canada

Sun 26/44:15 p.m.

ORD

-

YYZ

Nonstop1h 43m

Air Canada

Deal found 12/3C$ 297

Mon 6/44:50 p.m.

YYZ

-

ORD

Nonstop2h 00m

Air Canada

Sun 12/47:55 a.m.

ORD

-

YYZ

Nonstop1h 36m

Air Canada

Deal found 9/3C$ 300

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

YTZ-MDW

YTZ-ORD

YYZ-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 - MDW

YTZMDW

Toronto Island

Sat 11/4

11:20 a.m.-12:10 p.m.

Nonstop1h 50m

Chicago Midway

Thu 23/4

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

Nonstop1h 42m

C$ 296

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 23/4

9:00 p.m.-10:03 p.m.

Nonstop2h 03m

Chicago O'Hare Intl

Thu 30/4

9:20 p.m.-11:59 p.m.

Nonstop1h 39m

C$ 307

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 1/4

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

Nonstop1h 50m

Chicago Midway

Tue 7/4

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

Nonstop1h 42m

C$ 313

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 17/4

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

Nonstop1h 50m

Chicago Midway

Mon 20/4

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

Nonstop1h 42m

C$ 315

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 1/4

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

Nonstop2h 00m

Chicago O'Hare Intl

Mon 6/4

7:04 a.m.-9:54 a.m.

Nonstop1h 50m

C$ 332

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 31/3

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

Nonstop2h 00m

Chicago O'Hare Intl

Sat 4/4

10:52 a.m.-1:42 p.m.

Nonstop1h 50m

C$ 332

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 10/4

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

Nonstop2h 01m

Chicago O'Hare Intl

Fri 17/4

5:57 p.m.-8:44 p.m.

Nonstop1h 47m

C$ 332

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 14/4

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

Nonstop2h 01m

Chicago O'Hare Intl

Wed 22/4

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

Nonstop1h 44m

C$ 332

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Mon 7/9

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

Nonstop1h 55m

Chicago O'Hare Intl

Mon 14/9

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

Nonstop1h 40m

C$ 342

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$ 343

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/3

Showing 1-10 of 57 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$ 638. If you're looking for a direct round-trip flight to Chicago, you can expect to pay around C$ 855.
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$ 873.

See more FAQs

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