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C$ 161+ 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 21/1. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
14 Jan — 21 Jan1
1 adult
1 adult, Economy, 0 bags

Flights to Chicago in 2025

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 15 December 2025.

Wed 31/126:40 p.m.YYZ - ORD
1 stop5h 55mUnited Airlines
Sat 28/311:11 a.m.ORD - YYZ
Nonstop1h 50mUnited Airlines
Deal found 14/12C$ 369
Mon 29/129:00 a.m.YYZ - ORD
Nonstop2h 05mUnited Airlines
Sun 5/44:43 p.m.ORD - YYZ
Nonstop1h 54mUnited Airlines
Deal found 13/12C$ 381
Wed 31/126:40 p.m.YYZ - ORD
1 stop5h 55mUnited Airlines
Tue 24/31:06 p.m.ORD - YYZ
1 stop4h 51mUnited Airlines
Deal found 14/12C$ 383
Wed 31/126:40 p.m.YYZ - ORD
1 stop5h 55mUnited Airlines
Fri 27/34:30 p.m.ORD - YYZ
1 stop5h 50mUnited Airlines
Deal found 14/12C$ 388
Wed 31/126:40 p.m.YYZ - ORD
1 stop5h 55mUnited Airlines
Sun 4/18:46 p.m.ORD - YYZ
1 stop10h 49mUnited Airlines
Deal found 14/12C$ 401
Wed 31/127:40 p.m.YYZ - ORD
1 stop5h 04mUnited Airlines
Sat 4/43:00 p.m.ORD - YYZ
Nonstop1h 58mUnited Airlines
Deal found 13/12C$ 409
Tue 30/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Fri 2/14:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/12C$ 419
Wed 31/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 4/111:05 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 14/12C$ 424
Thu 25/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Thu 15/111:05 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 13/12C$ 425
Wed 31/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sat 4/412:45 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 13/12C$ 432
Mon 29/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Wed 25/311:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 14/12C$ 435
Wed 31/126:40 p.m.YYZ - ORD
1 stop5h 55mUnited Airlines
Thu 26/36:00 a.m.ORD - YYZ
1 stop6h 43mUnited Airlines
Deal found 14/12C$ 439

Find flight deals to Chicago

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 15 December 2025.

Round-trip from

C$ 246

One-way from

C$ 164

Popular in

December

Cheapest in

July

Average price

C$ 442

Good round-trip deal

C$ 245 or less

Good one-way deal

C$ 152 or less
Porter Airlines
  • Porter Airlines
  • 20/2-23/2
  • Nonstop
  • 3h 32m total
  • Toronto to Chicago
Search Deals
Air Canada
  • Air Canada
  • 7/2
  • Nonstop
  • 1h 55m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 9% potential increase in price (C$ 37 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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 15 December 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

Fri 20/2

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

Nonstop1h 50m

Chicago Midway

Mon 23/2

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

Nonstop1h 42m

C$ 246

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sun 8/2

11:00 a.m.-12:08 p.m.

Nonstop2h 08m

Chicago O'Hare Intl

Mon 16/2

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

Nonstop1h 53m

C$ 256

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 29/1

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

Nonstop1h 50m

Chicago Midway

Thu 5/2

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

Nonstop1h 42m

C$ 256

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 24/2

10:51 a.m.-12:00 p.m.

Nonstop2h 09m

Chicago O'Hare Intl

Fri 27/2

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

Nonstop1h 53m

C$ 256

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 9/2

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

Nonstop2h 05m

Chicago O'Hare Intl

Mon 16/2

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

Nonstop1h 44m

C$ 256

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 5/2

3:30 p.m.-4:40 p.m.

Nonstop2h 10m

Chicago O'Hare Intl

Sun 8/2

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

Nonstop1h 55m

C$ 256

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 4/2

3:30 p.m.-4:28 p.m.

Nonstop1h 58m

Chicago O'Hare Intl

Fri 6/2

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

Nonstop1h 44m

C$ 256

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 18/1

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

Nonstop1h 50m

Chicago Midway

Wed 21/1

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

Nonstop1h 42m

C$ 273

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 25/1

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

Nonstop1h 50m

Chicago Midway

Wed 28/1

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

Nonstop1h 42m

C$ 275

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Thu 5/2

10:45 a.m.-2:55 p.m.

1 stop5h 10m

Chicago O'Hare Intl

Sun 8/2

7:15 a.m.-2:25 p.m.

1 stop6h 10m

C$ 282

Flights are sorted by cheapest round-trip flights first.

Deals found on 15/12

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 12 December 2025.

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 8 hours 40 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 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 (64 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (18 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$ 174
Porter Airlines
Porter Airlines
From C$ 188

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).

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 15 December 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
399 reviews
Check prices

Overall

8.0

Comfort

7.9

Entertainment

7.0

Food

7.6

Boarding

8.2

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
399 reviews
Porter Airlines
8.0
Very good
399 reviews
Check prices

Overall

8.0

Comfort

7.9

Entertainment

7.0

Food

7.6

Boarding

8.2

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
482 reviews
Porter Airlines
8.0
Very good
399 reviews
Check prices

Overall

8.0

Comfort

7.9

Entertainment

7.0

Food

7.6

Boarding

8.2

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
9,092 reviews
Porter Airlines
8.0
Very good
399 reviews
Check prices

Overall

8.0

Comfort

7.9

Entertainment

7.0

Food

7.6

Boarding

8.2

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
11,051 reviews
Porter Airlines
8.0
Very good
399 reviews
Check prices

Overall

8.0

Comfort

7.9

Entertainment

7.0

Food

7.6

Boarding

8.2

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
10,525 reviews
Porter Airlines
8.0
Very good
399 reviews
Check prices

Overall

8.0

Comfort

7.9

Entertainment

7.0

Food

7.6

Boarding

8.2

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$ 49, while round-trip flights cost around C$ 54.

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

    A round-trip flight to Chicago will typically cost around C$ 345, however they can be found for as little as C$ 54.

  • 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).

  • 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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