Find flights
Deals
Airlines

C$ 138+ 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 20/10. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
19 Jul — 26 Jul1
1 adult

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 14 July 2025.

Round-trip from

C$ 199

One-way from

C$ 138

Popular in

December

Cheapest in

June

Average price

C$ 349

Good round-trip deal

C$ 216 or less

Good one-way deal

C$ 135 or less
Porter Airlines
  • Porter Airlines
  • 20/8-21/8
  • Nonstop
  • 3h 32m total
  • Toronto to Chicago
Search Deals
Air Canada
  • Air Canada
  • 20/10
  • 1 total stop
  • 5h 57m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 7% potential increase in price (C$ 42 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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

Find flight deals to Chicago

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 14 July 2025.

Thu 4/96:15 a.m.YYZ - ORD
1 stop4h 36mAir Canada
Sun 7/910:40 a.m.ORD - YYZ
1 stop5h 44mAir Canada
Deal found 14/7C$ 200
Sun 17/87:55 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 19/89:40 a.m.MDW - YTZ
Nonstop1h 40mPorter Airlines
Deal found 13/7C$ 204
Sun 26/106:52 a.m.YYZ - ORD
Nonstop2h 05mUnited Airlines
Sun 2/117:10 a.m.ORD - YYZ
Nonstop1h 48mUnited Airlines
Deal found 14/7C$ 207
Wed 27/83:25 p.m.YTZ - ORD
1 stop5h 51mAir Canada
Wed 3/910:40 a.m.ORD - YTZ
1 stop6h 05mAir Canada
Deal found 13/7C$ 207
Thu 4/97:00 a.m.YYZ - ORD
Nonstop1h 59mMultiple Airlines
Sun 7/98:25 p.m.ORD - YYZ
Nonstop1h 43mMultiple Airlines
Deal found 14/7C$ 211
Thu 4/97:30 a.m.YTZ - MDW
Nonstop1h 49mAir Transat
Sun 7/99:15 a.m.MDW - YTZ
Nonstop1h 42mAir Transat
Deal found 11/7C$ 220
Fri 26/93:11 p.m.YYZ - ORD
Nonstop1h 54mAmerican Airlines
Sun 28/96:10 a.m.ORD - YYZ
1 stop9h 23mAmerican Airlines
Deal found 13/7C$ 233
Tue 5/87:55 a.m.YTZ - MDW
Nonstop1h 50mMultiple Airlines
Fri 8/89:40 a.m.MDW - YTZ
Nonstop1h 40mMultiple Airlines
Deal found 13/7C$ 233
Sat 25/1012:15 p.m.YYZ - MDW
1 stop7h 21mDelta
Sat 1/115:59 p.m.MDW - YYZ
1 stop3h 59mDelta
Deal found 14/7C$ 279
Fri 8/86:30 p.m.YYZ - MDW
2 stops16h 06mWestJet
Wed 10/99:15 a.m.MDW - YYZ
2 stops14h 16mWestJet
Deal found 12/7C$ 352
Thu 4/96:00 a.m.YKF - ORD
1 stop11h 43mMultiple Airlines
Sun 7/95:30 p.m.ORD - YKF
1 stop10h 45mMultiple Airlines
Deal found 14/7C$ 446
Fri 8/86:00 a.m.YHM - ORD
3 stops25h 03mMultiple Airlines
Mon 11/87:08 a.m.ORD - YHM
2 stops16h 33mMultiple Airlines
Deal found 12/7C$ 472

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 14 July 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

Thu 24/7

7:55 a.m.-8:45 a.m.

Nonstop1h 50m

Chicago Midway

Mon 28/7

9:40 a.m.-12:20 p.m.

Nonstop1h 40m

C$ 199

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 4/9

6:15 a.m.-9:51 a.m.

1 stop4h 36m

Chicago O'Hare Intl

Sun 7/9

10:40 a.m.-5:24 p.m.

1 stop5h 44m

C$ 200

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sun 26/10

6:52 a.m.-7:57 a.m.

Nonstop2h 05m

Chicago O'Hare Intl

Sun 2/11

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

Nonstop1h 48m

C$ 207

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Wed 27/8

3:25 p.m.-8:16 p.m.

1 stop5h 51m

Chicago O'Hare Intl

Wed 3/9

10:40 a.m.-5:45 p.m.

1 stop6h 05m

C$ 207

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 4/9

7:00 a.m.-7:59 a.m.

Nonstop1h 59m

Chicago O'Hare Intl

Sun 7/9

8:25 p.m.-11:08 p.m.

Nonstop1h 43m

C$ 211

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 1/10

3:35 p.m.-4:24 p.m.

Nonstop1h 49m

Chicago Midway

Sat 4/10

9:15 a.m.-11:57 a.m.

Nonstop1h 42m

C$ 226

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 26/9

3:11 p.m.-4:05 p.m.

Nonstop1h 54m

Chicago O'Hare Intl

Sun 28/9

6:10 a.m.-4:33 p.m.

1 stop9h 23m

C$ 233

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 5/8

7:55 a.m.-8:45 a.m.

Nonstop1h 50m

Chicago Midway

Fri 8/8

9:40 a.m.-12:20 p.m.

Nonstop1h 40m

C$ 233

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 25/10

12:15 p.m.-6:36 p.m.

1 stop7h 21m

Chicago Midway

Sat 1/11

5:59 p.m.-10:58 p.m.

1 stop3h 59m

C$ 279

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 8/8

6:30 p.m.-9:36 a.m.

2 stops16h 06m

Chicago Midway

Wed 10/9

9:15 a.m.-12:31 a.m.

2 stops14h 16m

C$ 352

Flights are sorted by cheapest round-trip flights first.

Deals found on 14/7

Showing 1-10 of 33 results
1
2
3
4

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 11 July 2025.

To ensure you get the cheapest price possible for a flight to Chicago, you should look to book at least 52 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 43 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 30 June 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 (65 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (57 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$ 108
United Airlines
United Airlines
From C$ 175
Porter Airlines
Porter Airlines
From C$ 137
WestJet
WestJet
From C$ 128

What are the cheapest airlines that fly to Chicago?

The cheapest airlines flying from Toronto to Chicago are American Airlines, Porter 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 14 July 2025.
Read through reviews of airlines serving the United States, such as Porter Airlines,Delta, andAir Transat. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
306 reviews
Check prices

Entertainment

7.1

Boarding

8.2

Crew

8.7

Overall

8.0

Comfort

8.1

Food

7.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Porter Airlines
8.0
Very good
306 reviews
Porter Airlines
8.0
Very good
306 reviews
Check prices

Entertainment

7.1

Boarding

8.2

Crew

8.7

Overall

8.0

Comfort

8.1

Food

7.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Delta
8.0
Very good
7,956 reviews
Porter Airlines
8.0
Very good
306 reviews
Check prices

Entertainment

7.1

Boarding

8.2

Crew

8.7

Overall

8.0

Comfort

8.1

Food

7.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Air Transat
7.8
Good
414 reviews
Porter Airlines
8.0
Very good
306 reviews
Check prices

Entertainment

7.1

Boarding

8.2

Crew

8.7

Overall

8.0

Comfort

8.1

Food

7.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
United Airlines
7.4
Good
8,858 reviews
Porter Airlines
8.0
Very good
306 reviews
Check prices

Entertainment

7.1

Boarding

8.2

Crew

8.7

Overall

8.0

Comfort

8.1

Food

7.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
American Airlines
7.2
Good
10,000 reviews
Porter Airlines
8.0
Very good
306 reviews
Check prices

Entertainment

7.1

Boarding

8.2

Crew

8.7

Overall

8.0

Comfort

8.1

Food

7.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!

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$ 54, while round-trip flights cost around C$ 107.

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

    A round-trip flight to Chicago will typically cost around C$ 161, however they can be found for as little as C$ 78.

  • 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights to Chicago?

Cheapflights makes it easy to find Chicago flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Why should you use Cheapflights to find cheap flight tickets to Chicago?

It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights to Chicago.

Can Cheapflights find flights to Chicago with no change fees?

Yes, we can. To see specific flights to Chicago with no change fees, users can toggle flexible booking options after using the search form above to find flights.

Can Cheapflights notify me if prices for flights to Chicago become cheaper?

Yes, Cheapflights offers price alerts on Chicago flights so you can book your flight when prices are ideal. Enable price alerts by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.