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C$ 166+ 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 15/6. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
20 Feb — 27 Feb1
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 21 January 2026.

Tue 10/211:00 a.m.
YYZ
-
ORD
Nonstop2h 08m
United Airlines
Tue 17/26:28 p.m.
ORD
-
YYZ
Nonstop1h 53m
United Airlines
Deal found 20/1C$ 261
Thu 19/23:30 p.m.
YYZ
-
ORD
Nonstop2h 09m
United Airlines
Mon 23/29:15 p.m.
ORD
-
YYZ
Nonstop1h 44m
United Airlines
Deal found 21/1C$ 263
Tue 3/29:20 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Tue 10/211:05 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 19/1C$ 264
Thu 5/29:20 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Tue 10/211:05 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 19/1C$ 271
Wed 18/29:20 a.m.
YTZ
-
MDW
Nonstop1h 50m
Air Transat
Wed 25/211:05 a.m.
MDW
-
YTZ
Nonstop1h 42m
Air Transat
Deal found 20/1C$ 274
Wed 25/21:10 p.m.
YYZ
-
ORD
Nonstop2h 00m
American Airlines
Fri 27/25:00 a.m.
ORD
-
YYZ
1 stop5h 13m
American Airlines
Deal found 20/1C$ 275
Thu 12/29:20 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Thu 19/211:05 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 18/1C$ 275
Thu 19/26:00 a.m.
YYZ
-
ORD
Nonstop2h 15m
American Airlines
Mon 23/26:08 a.m.
ORD
-
YYZ
1 stop4h 43m
American Airlines
Deal found 21/1C$ 277
Sat 14/211:05 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 16/24:15 p.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 19/1C$ 277
Thu 19/29:20 a.m.
YTZ
-
MDW
Nonstop1h 50m
Air Transat
Mon 23/211:05 a.m.
MDW
-
YTZ
Nonstop1h 42m
Air Transat
Deal found 19/1C$ 278
Wed 11/210:59 a.m.
YYZ
-
ORD
1 stop8h 35m
American Airlines
Sun 15/29:46 a.m.
ORD
-
YYZ
Nonstop1h 44m
American Airlines
Deal found 20/1C$ 282
Thu 19/210:59 a.m.
YYZ
-
ORD
1 stop5h 18m
American Airlines
Sat 28/29:46 a.m.
ORD
-
YYZ
Nonstop1h 44m
American Airlines
Deal found 19/1C$ 283

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 21 January 2026.

Round-trip from

C$ 261

One-way from

C$ 166

Popular in

January

Cheapest in

July

Average price

C$ 405

Good round-trip deal

C$ 283 or less

Good one-way deal

C$ 196 or less
United Airlines
  • United Airlines
  • 10/2-17/2
  • Nonstop
  • 4h 01m total
  • Toronto to Chicago
Search Deals
Air Canada
  • Air Canada
  • 15/6
  • Nonstop
  • 2h 00m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 11% potential increase in price (C$ 44 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 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 21 January 2026.
Use the filters below to find and compare flights to Chicago that are best for you.

Fly from

Toronto

Route

Depart

Return

Price

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 12/2

6:45 a.m.-8:00 a.m.

Nonstop2h 15m

Chicago O'Hare Intl

Tue 17/2

9:15 p.m.-11:59 p.m.

Nonstop1h 44m

C$ 261

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 11/2

6:50 a.m.-8:05 a.m.

Nonstop2h 15m

Chicago O'Hare Intl

Wed 18/2

6:28 p.m.-9:21 p.m.

Nonstop1h 53m

C$ 261

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 12/2

6:45 a.m.-8:00 a.m.

Nonstop2h 15m

Chicago O'Hare Intl

Sat 14/2

6:28 p.m.-9:21 p.m.

Nonstop1h 53m

C$ 261

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 19/2

9:20 a.m.-10:10 a.m.

Nonstop1h 50m

Chicago Midway

Sun 22/2

4:15 p.m.-6:57 p.m.

Nonstop1h 42m

C$ 277

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 19/2

9:20 a.m.-10:10 a.m.

Nonstop1h 50m

Chicago Midway

Mon 23/2

11:05 a.m.-1:47 p.m.

Nonstop1h 42m

C$ 278

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 2/2

9:20 a.m.-10:10 a.m.

Nonstop1h 50m

Chicago Midway

Thu 5/2

11:05 a.m.-1:47 p.m.

Nonstop1h 42m

C$ 286

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 3/2

9:20 a.m.-10:10 a.m.

Nonstop1h 50m

Chicago Midway

Fri 6/2

11:05 a.m.-1:47 p.m.

Nonstop1h 42m

C$ 288

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 3/2

9:20 a.m.-10:10 a.m.

Nonstop1h 50m

Chicago Midway

Sun 8/2

4:15 p.m.-6:57 p.m.

Nonstop1h 42m

C$ 288

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 12/2

6:00 a.m.-1:29 p.m.

1 stop8h 29m

Chicago O'Hare Intl

Sun 15/2

6:30 a.m.-4:10 p.m.

1 stop8h 40m

C$ 296

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 12/2

6:45 a.m.-8:00 a.m.

Nonstop2h 15m

Chicago O'Hare Intl

Thu 19/2

7:07 a.m.-9:58 a.m.

Nonstop1h 51m

C$ 301

Flights are sorted by cheapest round-trip flights first.

Deals found on 21/1

Showing 1-10 of 60 results
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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

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

Use this chart to determine the optimal time to book a round-trip flight from Toronto to Chicago. Price data was last updated on 16 January 2026.

To ensure you get the cheapest price possible for a flight to Chicago, you should look to book at least 78 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.

How long is the flight to Chicago?

On average, a flight from Toronto to Chicago takes 5 hours 27 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.

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 17 January 2026.

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

Weekly flight availability to Chicago

The most flights from Toronto to Chicago are scheduled on a Monday (65 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (54 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$ 149
United Airlines
United Airlines
From C$ 166
WestJet
WestJet
From C$ 175
Porter Airlines
Porter Airlines
From C$ 189

What are the cheapest airlines that fly to Chicago?

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

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).

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 21 January 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
7.9
Good
412 reviews
Check prices

Overall

7.9

Comfort

7.9

Crew

8.6

Entertainment

6.9

Food

7.5

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
Porter Airlines
7.9
Good
412 reviews
Porter Airlines
7.9
Good
412 reviews
Check prices

Overall

7.9

Comfort

7.9

Crew

8.6

Entertainment

6.9

Food

7.5

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
Air Transat
7.7
Good
499 reviews
Porter Airlines
7.9
Good
412 reviews
Check prices

Overall

7.9

Comfort

7.9

Crew

8.6

Entertainment

6.9

Food

7.5

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
United Airlines
7.4
Good
9,191 reviews
Porter Airlines
7.9
Good
412 reviews
Check prices

Overall

7.9

Comfort

7.9

Crew

8.6

Entertainment

6.9

Food

7.5

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
American Airlines
7.2
Good
11,174 reviews
Porter Airlines
7.9
Good
412 reviews
Check prices

Overall

7.9

Comfort

7.9

Crew

8.6

Entertainment

6.9

Food

7.5

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
Air Canada
7.1
Good
10,646 reviews
Porter Airlines
7.9
Good
412 reviews
Check prices

Overall

7.9

Comfort

7.9

Crew

8.6

Entertainment

6.9

Food

7.5

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out

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, Delta 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$ 104, while round-trip flights cost around C$ 120.

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

    A round-trip flight to Chicago will typically cost around C$ 1,043, however they can be found for as little as C$ 120.

  • 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 49 minutes).

  • Which airport is closest to Wrigley Field?

    If being close to Wrigley Field is important to you, you’ll want to land at Chicago O'Hare Intl Airport.

  • 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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