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C$ 168+ 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 13/12. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
24 Dec — 31 Dec1
1 adult
1 adult, Economy, 0 bags

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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 24 November 2025.

Fri 19/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 29/1211:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 24/11C$ 257
Wed 31/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 6/111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 22/11C$ 262
Sat 6/126:00 a.m.YYZ - ORD
Nonstop2h 15mAmerican Airlines
Sat 13/128:20 a.m.ORD - YYZ
1 stop6h 39mAmerican Airlines
Deal found 22/11C$ 266
Tue 23/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 4/14:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 23/11C$ 266
Tue 30/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 6/111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 22/11C$ 268
Mon 22/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 29/124:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 24/11C$ 269
Tue 23/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Thu 1/14:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 23/11C$ 271
Wed 24/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 30/124:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 24/11C$ 272
Mon 8/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Thu 11/124:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 24/11C$ 274
Fri 12/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 15/1211:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 23/11C$ 275
Tue 9/124:50 p.m.YYZ - ORD
Nonstop1h 58mAir Canada
Sun 14/128:00 a.m.ORD - YYZ
Nonstop1h 40mAir Canada
Deal found 23/11C$ 276
Fri 5/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 7/1211:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 21/11C$ 278

Flights to Chicago in 2025

Find the latest flights to Chicago in 2025, 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 24 November 2025.

Round-trip from

C$ 255

One-way from

C$ 168

Popular in

November

Cheapest in

July

Average price

C$ 409

Good round-trip deal

C$ 348 or less

Good one-way deal

C$ 199 or less
Porter Airlines
  • Porter Airlines
  • 5/1-6/1
  • Nonstop
  • 3h 32m total
  • Toronto to Chicago
Search Deals
Air Canada
  • Air Canada
  • 13/12
  • 1 total stop
  • 5h 18m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 10% potential increase in price (C$ 40 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
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 24 November 2025.
Use the filters below to find and compare flights to Chicago that are best for you.

Fly from

Toronto

Route

Depart

Return

Price

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 7/1

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

Wed 14/1

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 255

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 19/12

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

Chicago Midway

Mon 29/12

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 257

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 23/12

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

Thu 1/1

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

Nonstop1h 42m

C$ 257

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sun 1/2

9:00 a.m.-10:06 a.m.

Nonstop2h 06m

Chicago O'Hare Intl

Wed 4/2

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

Nonstop1h 44m

C$ 258

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 3/4

1:00 p.m.-2:01 p.m.

Nonstop2h 01m

Chicago O'Hare Intl

Sun 5/4

9:05 a.m.-11:49 a.m.

Nonstop1h 44m

C$ 258

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 26/2

3:30 p.m.-4:39 p.m.

Nonstop2h 09m

Chicago O'Hare Intl

Sun 8/3

7:10 a.m.-9:58 a.m.

Nonstop1h 48m

C$ 258

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 6/1

9:00 a.m.-10:05 a.m.

Nonstop2h 05m

Chicago O'Hare Intl

Tue 13/1

4:50 p.m.-7:45 p.m.

Nonstop1h 55m

C$ 258

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 8/1

5:30 p.m.-6:50 p.m.

Nonstop2h 20m

Chicago O'Hare Intl

Sun 11/1

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

Nonstop1h 44m

C$ 259

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 23/12

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

Sun 4/1

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

Nonstop1h 42m

C$ 266

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 30/12

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

Thu 1/1

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

Nonstop1h 42m

C$ 269

Flights are sorted by cheapest round-trip flights first.

Deals found on 24/11

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 21 November 2025.

To ensure you get the cheapest price possible for a flight to Chicago, you should look to book at least 77 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 8 hours 41 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 16 December 2024.

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

Weekly flight availability to Chicago

The most flights from Toronto to Chicago are scheduled on a Monday (64 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (45 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$ 152
United Airlines
United Airlines
From C$ 185
Porter Airlines
Porter Airlines
From C$ 193
WestJet
WestJet
From C$ 180

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 24 November 2025.
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
393 reviews
Check prices

Boarding

8.2

Entertainment

7.0

Food

7.6

Comfort

8.0

Overall

8.0

Crew

8.6

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

Boarding

8.2

Entertainment

7.0

Food

7.6

Comfort

8.0

Overall

8.0

Crew

8.6

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
7.8
Good
478 reviews
Porter Airlines
8.0
Very good
393 reviews
Check prices

Boarding

8.2

Entertainment

7.0

Food

7.6

Comfort

8.0

Overall

8.0

Crew

8.6

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
9,043 reviews
Porter Airlines
8.0
Very good
393 reviews
Check prices

Boarding

8.2

Entertainment

7.0

Food

7.6

Comfort

8.0

Overall

8.0

Crew

8.6

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
11,040 reviews
Porter Airlines
8.0
Very good
393 reviews
Check prices

Boarding

8.2

Entertainment

7.0

Food

7.6

Comfort

8.0

Overall

8.0

Crew

8.6

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
10,469 reviews
Porter Airlines
8.0
Very good
393 reviews
Check prices

Boarding

8.2

Entertainment

7.0

Food

7.6

Comfort

8.0

Overall

8.0

Crew

8.6

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, 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 O'Hare Intl is currently the cheapest airport to fly to in Chicago. One-way flights to Chicago O'Hare Intl typically cost C$ 61, while round-trip flights cost around C$ 63.

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

    A round-trip flight to Chicago will typically cost around C$ 329, however they can be found for as little as C$ 63.

  • 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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