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 25 March 2026.

Mon 25/58:50 a.m.

YTZ

-

MDW

Nonstop1h 50m

Porter Airlines

Fri 19/63:20 p.m.

MDW

-

YTZ

Nonstop1h 40m

Porter Airlines

Deal found 21/3C$ 265

Sat 2/58:55 a.m.

YTZ

-

MDW

Nonstop1h 50m

Porter Airlines

Mon 4/510:30 a.m.

MDW

-

YTZ

Nonstop1h 40m

Porter Airlines

Deal found 22/3C$ 270

Thu 18/67:20 p.m.

YTZ

-

ORD

Nonstop1h 56m

Air Canada

Sun 21/67:25 a.m.

ORD

-

YTZ

Nonstop1h 41m

Air Canada

Deal found 23/3C$ 271

Wed 24/67:20 a.m.

YYZ

-

ORD

Nonstop2h 12m

American Airlines

Wed 8/78:37 p.m.

ORD

-

YYZ

Nonstop1h 52m

American Airlines

Deal found 22/3C$ 272

Thu 10/910:05 a.m.

YTZ

-

ORD

Nonstop1h 55m

Porter Airlines

Sun 13/93:20 p.m.

ORD

-

YTZ

Nonstop1h 40m

Porter Airlines

Deal found 24/3C$ 276

Wed 9/98:40 p.m.

YTZ

-

ORD

Nonstop1h 55m

Porter Airlines

Wed 16/97:00 a.m.

ORD

-

YTZ

Nonstop1h 40m

Porter Airlines

Deal found 22/3C$ 279

Mon 25/51:55 p.m.

YYZ

-

ORD

Nonstop2h 00m

Air Canada

Fri 19/68:40 p.m.

ORD

-

YYZ

Nonstop1h 46m

Air Canada

Deal found 21/3C$ 282

Mon 4/58:55 a.m.

YTZ

-

MDW

Nonstop1h 50m

Porter Airlines

Wed 6/53:20 p.m.

MDW

-

YTZ

Nonstop1h 40m

Porter Airlines

Deal found 23/3C$ 282

Sat 6/611:00 a.m.

YYZ

-

ORD

Nonstop2h 00m

United Airlines

Sun 7/67:09 a.m.

ORD

-

YYZ

Nonstop1h 45m

United Airlines

Deal found 22/3C$ 283

Sat 18/411:20 a.m.

YTZ

-

MDW

Nonstop1h 50m

Porter Airlines

Tue 28/411:00 a.m.

MDW

-

YTZ

Nonstop1h 42m

Porter Airlines

Deal found 23/3C$ 283

Tue 21/49:25 a.m.

YTZ

-

MDW

Nonstop1h 50m

Multiple Airlines

Tue 28/411:00 a.m.

MDW

-

YTZ

Nonstop1h 42m

Multiple Airlines

Deal found 24/3C$ 286

Fri 10/712:15 p.m.

YTZ

-

ORD

Nonstop1h 55m

Air Canada

Tue 14/77:25 a.m.

ORD

-

YTZ

Nonstop1h 41m

Air Canada

Deal found 20/3C$ 287

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-ORD

YTZ-MDW

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 - ORD

YTZORD

Toronto Island

Thu 18/6

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

Nonstop1h 56m

Chicago O'Hare Intl

Sun 21/6

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

Nonstop1h 41m

C$ 271

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Fri 19/6

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

Nonstop1h 56m

Chicago O'Hare Intl

Mon 22/6

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

Nonstop1h 41m

C$ 271

Quickest round-trip

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 9/7

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

Nonstop1h 50m

Chicago Midway

Sun 12/7

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

Nonstop1h 40m

C$ 278

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 18/6

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

Nonstop2h 00m

Chicago O'Hare Intl

Sun 21/6

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

Nonstop1h 45m

C$ 283

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Fri 10/7

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$ 287

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Thu 9/7

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

Nonstop1h 56m

Chicago O'Hare Intl

Sun 12/7

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

Nonstop1h 41m

C$ 289

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Fri 24/7

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

Nonstop1h 56m

Chicago O'Hare Intl

Sun 26/7

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

Nonstop1h 41m

C$ 289

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

Fri 26/6

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

Nonstop1h 55m

Chicago O'Hare Intl

Sat 4/7

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

Nonstop1h 41m

C$ 298

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 9/7

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

Nonstop2h 03m

Chicago O'Hare Intl

Sun 12/7

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

Nonstop1h 45m

C$ 301

Flights are sorted by cheapest round-trip flights first.

Deals found on 20/3

Showing 1-10 of 51 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$ 761. If you're looking for a direct round-trip flight to Chicago, you can expect to pay around C$ 1,239.
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 Montreal Pierre Elliott Trudeau Intl Airport. A round-trip direct flight from Montreal Pierre Elliott Trudeau Intl Airport to Chicago typically costs around C$ 838.

See more FAQs

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