Direct flights to Chicago | Cheapflights

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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 8 July 2026.

Tue 4/88:05 a.m.

YYZ

-

ORD

Nonstop1h 55m

Air Canada

Tue 11/83:45 p.m.

ORD

-

YYZ

Nonstop1h 45m

Air Canada

Deal found 7/7C$ 294

Wed 22/712:15 p.m.

YTZ

-

ORD

Nonstop2h 04m

Air Canada

Thu 30/72:00 p.m.

ORD

-

YTZ

Nonstop1h 42m

Air Canada

Deal found 7/7C$ 294

Fri 21/82:00 p.m.

YYZ

-

ORD

Nonstop1h 55m

Air Canada

Fri 28/88:50 p.m.

ORD

-

YYZ

Nonstop1h 46m

Air Canada

Deal found 7/7C$ 296

Mon 17/81:45 p.m.

YTZ

-

MDW

Nonstop1h 50m

Porter Airlines

Mon 24/83:15 p.m.

MDW

-

YTZ

Nonstop1h 40m

Porter Airlines

Deal found 3/7C$ 296

Fri 11/97:25 p.m.

YTZ

-

ORD

Nonstop2h 04m

Air Canada

Mon 28/97:25 a.m.

ORD

-

YTZ

Nonstop1h 42m

Air Canada

Deal found 5/7C$ 297

Wed 22/78:05 a.m.

YYZ

-

ORD

Nonstop1h 55m

Air Canada

Wed 22/72:15 p.m.

ORD

-

YYZ

Nonstop1h 46m

Air Canada

Deal found 7/7C$ 298

Sat 25/78:50 a.m.

YTZ

-

MDW

Nonstop1h 50m

Porter Airlines

Sat 1/810:20 a.m.

MDW

-

YTZ

Nonstop1h 40m

Porter Airlines

Deal found 7/7C$ 298

Fri 4/98:40 p.m.

YTZ

-

ORD

Nonstop1h 55m

Porter Airlines

Sat 5/97:00 a.m.

ORD

-

YTZ

Nonstop1h 40m

Porter Airlines

Deal found 5/7C$ 298

Thu 20/88:55 a.m.

YTZ

-

MDW

Nonstop1h 50m

Porter Airlines

Mon 24/83:15 p.m.

MDW

-

YTZ

Nonstop1h 40m

Porter Airlines

Deal found 7/7C$ 300

Thu 23/71:45 p.m.

YTZ

-

MDW

Nonstop1h 50m

Porter Airlines

Mon 27/73:20 p.m.

MDW

-

YTZ

Nonstop1h 40m

Porter Airlines

Deal found 8/7C$ 301

Wed 26/812:25 p.m.

YYZ

-

ORD

Nonstop1h 57m

Air Canada

Fri 28/88:50 p.m.

ORD

-

YYZ

Nonstop1h 46m

Air Canada

Deal found 7/7C$ 303

Sat 18/78:50 a.m.

YTZ

-

MDW

Nonstop1h 50m

Porter Airlines

Wed 22/73:20 p.m.

MDW

-

YTZ

Nonstop1h 40m

Porter Airlines

Deal found 3/7C$ 303

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

YTZ - ORD

YTZORD

Toronto Island

Fri 7/8

7:35 p.m.-8:41 p.m.

Nonstop2h 06m

Chicago O'Hare Intl

Mon 10/8

7:25 a.m.-10:18 a.m.

Nonstop1h 53m

C$ 294

Quickest round-trip

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 17/8

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

Nonstop1h 50m

Chicago Midway

Mon 24/8

3:15 p.m.-5:55 p.m.

Nonstop1h 40m

C$ 296

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 23/7

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

Nonstop1h 50m

Chicago Midway

Sat 25/7

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

Nonstop1h 40m

C$ 303

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 16/9

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

Nonstop2h 06m

Chicago O'Hare Intl

Wed 23/9

9:29 p.m.-12:13 a.m.

Nonstop1h 44m

C$ 307

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 14/8

8:50 a.m.-9:53 a.m.

Nonstop2h 03m

Chicago O'Hare Intl

Sun 16/8

4:35 p.m.-7:37 p.m.

Nonstop2h 02m

C$ 307

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 24/7

11:00 a.m.-12:00 p.m.

Nonstop2h 00m

Chicago O'Hare Intl

Sun 26/7

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

Nonstop1h 39m

C$ 307

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 9/10

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

Nonstop2h 00m

Chicago O'Hare Intl

Tue 13/10

9:18 p.m.-11:59 p.m.

Nonstop1h 41m

C$ 318

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 11/8

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

Nonstop1h 50m

Chicago Midway

Sat 15/8

10:20 a.m.-1:00 p.m.

Nonstop1h 40m

C$ 325

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 4/8

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

Nonstop1h 50m

Chicago Midway

Tue 11/8

3:15 p.m.-5:55 p.m.

Nonstop1h 40m

C$ 328

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Thu 13/8

7:25 p.m.-8:29 p.m.

Nonstop2h 04m

Chicago O'Hare Intl

Wed 19/8

2:00 p.m.-4:42 p.m.

Nonstop1h 42m

C$ 330

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/7

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

7.9

Good

Reviews

1 / 20

6.0

Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.

Porter Airlines

7.9

Good

Porter Airlines

7.9

Good

Reviews

1 / 20

6.0

Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.

7.8

Good

Porter Airlines

7.9

Good

Reviews

1 / 20

6.0

Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.

United Airlines

7.4

Good

Porter Airlines

7.9

Good

Reviews

1 / 20

6.0

Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.

American Airlines

7.1

Good

Porter Airlines

7.9

Good

Reviews

1 / 20

6.0

Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.

7.1

Good

Porter Airlines

7.9

Good

Reviews

1 / 20

6.0

Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.

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$ 517. If you're looking for a direct round-trip flight to Chicago, you can expect to pay around C$ 1,249.
Which airlines fly direct to Chicago?
At the moment, Air Canada, United Airlines, Porter Airlines, American Airlines, WestJet, Delta 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 Toronto Pearson Intl Airport. A round-trip direct flight from Toronto Pearson Intl Airport to Chicago typically costs around C$ 2,275.

See more FAQs

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