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C$ 191+ Cheap flights to Chicago

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 19/7. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
23 Jul — 30 Jul1
1 adult
1 adult, Economy, 0 bags

Flights to Chicago in 2026

Enter your travel dates to find the best prices.

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 23 June 2026.

Fri 10/78:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Fri 17/73:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 22/6C$ 288
Thu 9/71:45 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 13/73:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 22/6C$ 289
Sat 5/91:00 p.m.
YYZ
-
ORD
Nonstop2h 05m
Multiple Airlines
Mon 7/99:50 a.m.
ORD
-
YYZ
Nonstop1h 45m
Multiple Airlines
Deal found 22/6C$ 290
Mon 6/78:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Thu 9/73:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 22/6C$ 290
Sat 10/101:40 p.m.
YTZ
-
ORD
Nonstop1h 55m
Porter Airlines
Thu 15/1011:45 a.m.
ORD
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 22/6C$ 290
Thu 2/712:25 p.m.
YYZ
-
ORD
Nonstop1h 57m
Air Canada
Sun 5/79:50 a.m.
ORD
-
YYZ
Nonstop1h 45m
Air Canada
Deal found 18/6C$ 292
Mon 6/71:45 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Wed 8/710:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 19/6C$ 292
Sat 10/101:40 p.m.
YTZ
-
ORD
Nonstop1h 55m
Porter Airlines
Wed 14/107:00 a.m.
ORD
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 22/6C$ 292
Wed 5/88:05 a.m.
YYZ
-
ORD
Nonstop1h 55m
Air Canada
Wed 12/82:15 p.m.
ORD
-
YYZ
Nonstop1h 46m
Air Canada
Deal found 21/6C$ 293
Sat 4/78:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sun 5/710:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 20/6C$ 293
Fri 14/87:25 p.m.
YTZ
-
ORD
Nonstop2h 04m
Air Canada
Tue 18/82:00 p.m.
ORD
-
YTZ
Nonstop1h 42m
Air Canada
Deal found 20/6C$ 293
Thu 9/72:00 p.m.
YYZ
-
ORD
Nonstop1h 55m
Air Canada
Sun 12/72:15 p.m.
ORD
-
YYZ
Nonstop1h 46m
Air Canada
Deal found 21/6C$ 295

Find flight deals to Chicago

Find the latest flights to Chicago in 2026, with up-to-date prices and availability. In the last 7 days, Cheapflights users made a total of 629,999 searches and data was last updated on 23 June 2026.

Round-trip from

C$ 288

One-way from

C$ 191

Popular in

May

Cheapest in

September

Average price

C$ 401

Good round-trip deal

C$ 296 or less

Good one-way deal

C$ 176 or less
Porter Airlines
  • Porter Airlines
  • 10/7-17/7
  • Nonstop
  • 3h 30m total
  • Toronto to Chicago
Search Deals
Air Canada
  • Air Canada
  • 19/7
  • Nonstop
  • 1h 55m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 5% potential increase in price (C$ 20 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease (C$ 3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2026
Search Deals
Price to beat on a round-trip flight from Toronto to Chicago.
Search Deals
Price to beat on a one-way flight from Toronto to Chicago.
Search Deals

Cheapflights Fare Finder

 
Locate flights to Chicago that fit your budget, with regularly updated fares and availability. In the last 7 days, Cheapflights users made a total of 629,999 searches and data was last updated on 23 June 2026.
Use the filters below to find and compare flights to Chicago that are best for you.

Fly from

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 3/8

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

Nonstop1h 50m

Chicago Midway

Fri 7/8

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

Nonstop1h 40m

C$ 293

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 17/7

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

Nonstop1h 50m

Chicago Midway

Sun 19/7

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

Nonstop1h 40m

C$ 293

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 5/7

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

Nonstop1h 50m

Chicago Midway

Wed 8/7

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

Nonstop1h 40m

C$ 295

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 3/8

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

Nonstop1h 50m

Chicago Midway

Sun 9/8

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

Nonstop1h 40m

C$ 296

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 9/7

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

Nonstop1h 50m

Chicago Midway

Mon 13/7

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

Nonstop1h 40m

C$ 299

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 10/7

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

Nonstop1h 50m

Chicago Midway

Mon 13/7

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

Nonstop1h 40m

C$ 302

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 18/7

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

Nonstop2h 00m

Chicago O'Hare Intl

Mon 17/8

5:53 p.m.-8:44 p.m.

Nonstop1h 51m

C$ 307

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 20/8

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

Nonstop1h 50m

Chicago Midway

Thu 27/8

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

Nonstop1h 40m

C$ 307

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 18/7

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

Nonstop1h 50m

Chicago Midway

Sun 19/7

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

Nonstop1h 40m

C$ 307

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 11/9

8:00 p.m.-12:28 a.m.

1 stop5h 28m

Chicago O'Hare Intl

Sun 13/9

9:50 a.m.-12:35 p.m.

Nonstop1h 45m

C$ 312

Flights are sorted by cheapest round-trip flights first.

Deals found on 19/6

Showing 1-10 of 60 resultsSorted by cheapest first
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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.
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.

Cheapflights Insights

Everything you need to know about your flight to Chicago

How long is the flight to Chicago?

On average, a flight from Toronto to Chicago takes 5 hours 14 minutes. Flights to Chicago from other popular cities in Canada will vary in length. Below are a few examples of popular routes and their flight times.

Weekly flight availability to Chicago

The most flights from Toronto to Chicago are scheduled on a Monday (78 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (61 on average).

What are the most popular airlines that fly to Chicago?

The most popular airlines flying from Toronto to Chicago are Air Canada, United Airlines and Porter Airlines.

Air Canada
Air Canada
From C$ 124
United Airlines
United Airlines
From C$ 153
Porter Airlines
Porter Airlines
From C$ 116
WestJet
WestJet
From C$ 179

What are the cheapest airlines that fly to Chicago?

The cheapest airlines flying from Toronto to Chicago are Porter Airlines, Air Canada and American Airlines.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago when rainfall is around 43.0 mm.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

When is the best time to book a flight to Chicago?

To ensure you get the cheapest price possible for a flight to Chicago, you should look to book at least 87 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

When is the cheapest time to fly to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Toronto to Chicago. Price data was last updated on 20 June 2026.

Users looking for the lowest fares to Chicago should consider flying on Wednesday afternoons, when prices are typically cheapest. Budget-minded travellers will want to avoid Monday evenings, when prices are usually at their highest.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated 23 June 2026.
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
439 reviews
Check prices

Comfort

7.9

Entertainment

6.9

Crew

8.6

Boarding

8.2

Overall

8.0

Food

7.5

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
8.0
Very good
439 reviews
Porter Airlines
8.0
Very good
439 reviews
Check prices

Comfort

7.9

Entertainment

6.9

Crew

8.6

Boarding

8.2

Overall

8.0

Food

7.5

Reviews

1 / 20
6.0
Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.
Air Transat
7.8
Good
558 reviews
Porter Airlines
8.0
Very good
439 reviews
Check prices

Comfort

7.9

Entertainment

6.9

Crew

8.6

Boarding

8.2

Overall

8.0

Food

7.5

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
9,874 reviews
Porter Airlines
8.0
Very good
439 reviews
Check prices

Comfort

7.9

Entertainment

6.9

Crew

8.6

Boarding

8.2

Overall

8.0

Food

7.5

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
11,744 reviews
Porter Airlines
8.0
Very good
439 reviews
Check prices

Comfort

7.9

Entertainment

6.9

Crew

8.6

Boarding

8.2

Overall

8.0

Food

7.5

Reviews

1 / 20
6.0
Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.
Air Canada
7.1
Good
11,242 reviews
Porter Airlines
8.0
Very good
439 reviews
Check prices

Comfort

7.9

Entertainment

6.9

Crew

8.6

Boarding

8.2

Overall

8.0

Food

7.5

Reviews

1 / 20
6.0
Good

Justin,May 2026

YYZ - MCO

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

FAQs about flying to Chicago

  • What is good to know if travelling to Chicago?

    One of the biggest challenges for visitors to Chicago can be the weather. Fiercely hot in the summer, the city is bitterly cold and windy in the winter. In the winter, wear layers and don’t expose skin to the wind; in summer, be sure to drink plenty of water and use sunscreen.

  • Can I find cheaper flights to Chicago if I am willing to have layovers?

    Yes, flights with layovers are often cheaper than direct flights. Keep an eye out for flight deals to Chicago on Cheapflights that require 1 or 2 stops for potential cost savings.

  • What is the best airline to fly to Chicago?

    Based on reviews from Cheapflights users, Porter Airlines is rated the highest out of the airlines that fly to Chicago.

  • What is the cheapest airport to fly to in Chicago?

    Chicago O'Hare Intl is currently the cheapest airport to fly to in Chicago. One-way flights to Chicago O'Hare Intl typically cost C$ 133, while round-trip flights cost around C$ 168.

  • How much is a round-trip flight to Chicago?

    A round-trip flight to Chicago will typically cost around C$ 234, however they can be found for as little as C$ 168.

  • Where does the fastest flight to Chicago depart from?

    For those looking to save time traveling to Chicago, Toronto offers the quickest one-way flight (1 hour 50 minutes).

  • Does Chicago O'Hare Intl have rental cars?

    Yes. Those touching down at Chicago O'Hare Intl can take advantage of the rental car services offered upon their arrival.

  • Are there hotels close to Chicago O'Hare Intl?

    Yes. Chicago O'Hare Intl has hotels nearby for those requiring accommodations. Hilton Chicago O'Hare Airport is the closest property to Chicago O'Hare Intl (0.0 km away from Chicago O'Hare Intl).

See more FAQs

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