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C$ 190+ 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 15/8. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
16 Aug — 23 Aug1
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 17 July 2026.

Wed 2/91:45 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Wed 16/93:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 14/7C$ 284
Fri 27/1110:10 a.m.
YTZ
-
ORD
Nonstop1h 55m
Porter Airlines
Mon 30/116:10 p.m.
ORD
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 16/7C$ 284
Thu 27/88:55 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Tue 1/93:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 13/7C$ 285
Fri 14/88:55 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sun 16/83:15 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 16/7C$ 286
Sat 28/114:35 p.m.
YTZ
-
ORD
Nonstop1h 55m
Porter Airlines
Mon 30/116:10 p.m.
ORD
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 16/7C$ 286
Thu 6/88:55 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Tue 11/810:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 13/7C$ 288
Thu 20/810:45 a.m.
YTZ
-
ORD
1 stop4h 59m
Air Canada
Mon 24/87:25 a.m.
ORD
-
YTZ
Nonstop1h 53m
Air Canada
Deal found 12/7C$ 288
Sat 10/101:45 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Tue 13/1011:45 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 17/7C$ 289
Thu 10/912:15 p.m.
YTZ
-
ORD
Nonstop2h 06m
Air Canada
Wed 16/97:25 a.m.
ORD
-
YTZ
Nonstop1h 42m
Air Canada
Deal found 16/7C$ 289
Wed 5/88:55 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Tue 11/810:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 13/7C$ 291
Thu 3/97:35 p.m.
YTZ
-
ORD
Nonstop2h 06m
Air Canada
Sun 6/97:25 a.m.
ORD
-
YTZ
Nonstop1h 42m
Air Canada
Deal found 15/7C$ 291
Sat 8/88:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Tue 11/810:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 13/7C$ 292

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 17 July 2026.

Round-trip from

C$ 284

One-way from

C$ 190

Popular in

June

Cheapest in

September

Average price

C$ 375

Good round-trip deal

C$ 297 or less

Good one-way deal

C$ 179 or less
Porter Airlines
  • Porter Airlines
  • 2/9-16/9
  • Nonstop
  • 3h 30m total
  • Toronto to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 15/8
  • Nonstop
  • 1h 50m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 3% potential increase in price (C$ 14 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 July 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 17 July 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

Fri 9/10

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

Nonstop1h 50m

Chicago Midway

Mon 12/10

11:45 a.m.-2:25 p.m.

Nonstop1h 40m

C$ 292

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 22/8

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

Nonstop1h 50m

Chicago Midway

Sun 23/8

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

Nonstop1h 40m

C$ 306

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 7/8

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

Nonstop1h 50m

Chicago Midway

Sun 9/8

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

Nonstop1h 40m

C$ 322

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 7/8

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

Nonstop1h 50m

Chicago Midway

Mon 17/8

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

Nonstop1h 40m

C$ 329

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 10/8

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$ 329

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 13/8

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

Nonstop1h 50m

Chicago Midway

Mon 17/8

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

Nonstop1h 40m

C$ 329

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 24/8

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

Nonstop1h 50m

Chicago Midway

Wed 26/8

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

Nonstop1h 40m

C$ 329

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 22/8

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

Nonstop1h 50m

Chicago Midway

Tue 25/8

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

Nonstop1h 40m

C$ 333

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sat 24/10

10:45 a.m.-2:52 p.m.

1 stop5h 07m

Chicago O'Hare Intl

Fri 30/10

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

Nonstop1h 41m

C$ 336

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 20/8

2:24 p.m.-8:30 p.m.

1 stop7h 06m

Chicago O'Hare Intl

Mon 24/8

5:20 p.m.-11:03 p.m.

1 stop4h 43m

C$ 351

Flights are sorted by cheapest round-trip flights first.

Deals found on 15/7

Showing 1-10 of 60 resultsSorted by cheapest first
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6

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 6 hours 17 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 Friday (79 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (43 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$ 123
United Airlines
United Airlines
From C$ 149
Porter Airlines
Porter Airlines
From C$ 199
WestJet
WestJet
From C$ 178

What are the cheapest airlines that fly to Chicago?

The cheapest airlines flying from Toronto to Chicago are Air Canada, Porter Airlines 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 11 July 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 17 July 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
445 reviews
Check prices

Entertainment

6.9

Boarding

8.2

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.5

Reviews

1 / 20
6.0
Good

Shannon,Jul 2026

YQT - YOW

Seats need to be a bit bigger & I'm not impressed that you have to pay to change seats
Porter Airlines
8.0
Very good
445 reviews
Porter Airlines
8.0
Very good
445 reviews
Check prices

Entertainment

6.9

Boarding

8.2

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.5

Reviews

1 / 20
6.0
Good

Shannon,Jul 2026

YQT - YOW

Seats need to be a bit bigger & I'm not impressed that you have to pay to change seats
Air Transat
7.8
Good
565 reviews
Porter Airlines
8.0
Very good
445 reviews
Check prices

Entertainment

6.9

Boarding

8.2

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.5

Reviews

1 / 20
6.0
Good

Shannon,Jul 2026

YQT - YOW

Seats need to be a bit bigger & I'm not impressed that you have to pay to change seats
United Airlines
7.4
Good
10,006 reviews
Porter Airlines
8.0
Very good
445 reviews
Check prices

Entertainment

6.9

Boarding

8.2

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.5

Reviews

1 / 20
6.0
Good

Shannon,Jul 2026

YQT - YOW

Seats need to be a bit bigger & I'm not impressed that you have to pay to change seats
American Airlines
7.1
Good
11,826 reviews
Porter Airlines
8.0
Very good
445 reviews
Check prices

Entertainment

6.9

Boarding

8.2

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.5

Reviews

1 / 20
6.0
Good

Shannon,Jul 2026

YQT - YOW

Seats need to be a bit bigger & I'm not impressed that you have to pay to change seats
Air Canada
7.1
Good
11,352 reviews
Porter Airlines
8.0
Very good
445 reviews
Check prices

Entertainment

6.9

Boarding

8.2

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.5

Reviews

1 / 20
6.0
Good

Shannon,Jul 2026

YQT - YOW

Seats need to be a bit bigger & I'm not impressed that you have to pay to change seats

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, Air Canada is rated the highest out of the airlines that fly to Chicago.

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

    Chicago Midway is currently the cheapest airport to fly to in Chicago. One-way flights to Chicago Midway typically cost C$ 153, while round-trip flights cost around C$ 189.

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

    A round-trip flight to Chicago will typically cost around C$ 755, however they can be found for as little as C$ 189.

  • 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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