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C$ 203+ 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 19/3. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
22 Jan — 29 Jan1
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 17 January 2025.

Round-trip from

C$ 339

One-way from

C$ 208

Popular in

December

Cheapest in

April

Average price

C$ 410
Porter Airlines
  • Porter Airlines
  • 19/2-25/2
  • Nonstop
  • 3h 32m total
  • Toronto to Chicago
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Porter Airlines
  • Porter Airlines
  • 24/3
  • Nonstop
  • 1h 50m total
  • Toronto to Chicago
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High demand for flights, 7% potential price rise
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Best time to find cheap flights, 1% potential price drop
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Average for round-trip flights in January 2025
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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 17 January 2025.

Fri 14/211:20 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 16/21:05 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 15/1C$ 339
Thu 6/27:15 a.m.YYZ - ORD
1 stop8h 37mMultiple Airlines
Sun 9/26:15 p.m.ORD - YYZ
1 stop16h 10mMultiple Airlines
Deal found 16/1C$ 344
Thu 6/29:00 a.m.YYZ - ORD
Nonstop2h 10mUnited Airlines
Mon 10/22:05 p.m.ORD - YYZ
Nonstop1h 41mUnited Airlines
Deal found 15/1C$ 356
Fri 7/23:25 p.m.YTZ - ORD
1 stop5h 30mAir Canada
Sun 9/27:20 a.m.ORD - YTZ
1 stop6h 30mAir Canada
Deal found 15/1C$ 362
Fri 7/22:05 p.m.YYZ - ORD
1 stop5h 33mAir Canada
Mon 10/210:53 a.m.ORD - YYZ
Nonstop1h 49mAir Canada
Deal found 16/1C$ 365
Thu 20/211:20 a.m.YTZ - MDW
Nonstop1h 50mAir Transat
Sun 23/21:05 p.m.MDW - YTZ
Nonstop1h 42mAir Transat
Deal found 16/1C$ 366
Fri 7/26:20 p.m.YYZ - ORD
Nonstop2h 00mBritish Airways
Sun 9/28:11 a.m.ORD - YYZ
Nonstop1h 40mBritish Airways
Deal found 16/1C$ 369
Thu 10/41:15 p.m.YYZ - ORD
Nonstop1h 55mAmerican Airlines
Sat 12/46:45 a.m.ORD - YYZ
1 stop7h 34mAmerican Airlines
Deal found 16/1C$ 377
Wed 19/210:10 a.m.YYZ - ORD
1 stop3h 45mDelta
Mon 24/22:35 p.m.ORD - YYZ
1 stop8h 04mDelta
Deal found 16/1C$ 385
Fri 7/26:00 a.m.YYZ - MDW
1 stop3h 51mDelta
Sun 9/25:05 p.m.MDW - YYZ
1 stop4h 44mDelta
Deal found 14/1C$ 391
Thu 6/212:20 p.m.YYZ - ORD
1 stop7h 18mLufthansa
Sun 9/24:00 p.m.ORD - YYZ
1 stop5h 15mLufthansa
Deal found 16/1C$ 397
Thu 6/21:05 p.m.YTZ - ORD
2 stops21h 34mMultiple Airlines
Sun 9/25:35 a.m.ORD - YTZ
2 stops13h 30mMultiple Airlines
Deal found 15/1C$ 410

Find flights to Chicago within your budget

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 January 2025.

Fly from

Any airport

Route

Depart

Return

Price

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 14/2

11:20 a.m.-12:10 p.m.

Nonstop1h 50m

Chicago Midway

Sun 16/2

1:05 p.m.-3:47 p.m.

Nonstop1h 42m

C$ 339

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 6/2

7:15 a.m.-2:52 p.m.

1 stop8h 37m

Chicago O'Hare Intl

Sun 9/2

6:15 p.m.-11:25 a.m.

1 stop16h 10m

C$ 344

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 5/2

6:20 p.m.-7:20 p.m.

Nonstop2h 00m

Chicago O'Hare Intl

Wed 12/2

8:11 a.m.-10:51 a.m.

Nonstop1h 40m

C$ 346

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 7/2

8:00 a.m.-2:45 p.m.

1 stop7h 45m

Chicago O'Hare Intl

Mon 10/2

10:53 a.m.-1:42 p.m.

Nonstop1h 49m

C$ 352

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 6/2

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

Nonstop2h 10m

Chicago O'Hare Intl

Mon 10/2

2:05 p.m.-4:46 p.m.

Nonstop1h 41m

C$ 356

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Fri 7/2

3:25 p.m.-7:55 p.m.

1 stop5h 30m

Chicago O'Hare Intl

Sun 9/2

7:20 a.m.-2:50 p.m.

1 stop6h 30m

C$ 362

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 20/2

11:20 a.m.-12:10 p.m.

Nonstop1h 50m

Chicago Midway

Sun 23/2

1:05 p.m.-3:47 p.m.

Nonstop1h 42m

C$ 366

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 13/2

7:45 a.m.-12:55 p.m.

1 stop6h 10m

Chicago O'Hare Intl

Mon 17/2

6:59 a.m.-4:09 p.m.

1 stop8h 10m

C$ 391

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 7/2

6:00 a.m.-8:51 a.m.

1 stop3h 51m

Chicago Midway

Sun 9/2

5:05 p.m.-10:49 p.m.

1 stop4h 44m

C$ 391

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 6/2

12:20 p.m.-6:38 p.m.

1 stop7h 18m

Chicago O'Hare Intl

Sun 9/2

4:00 p.m.-10:15 p.m.

1 stop5h 15m

C$ 397

Flights are sorted by cheapest round-trip flights first.

Deals found on 15/1

Showing 1-10 of 39 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.

Travel insights for flights to Chicago

Get recent, data-driven insights about flights to Chicago including ideal travel times, pricing trends, and more.

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 10 January 2025.

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.

How long is the flight to Chicago?

On average, a flight from Toronto to Chicago takes 5 hours 38 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 (54 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (32 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$ 223

United Airlines

United Airlines

From C$ 249

Porter Airlines

Porter Airlines

From C$ 194

American Airlines

American Airlines

From C$ 250

What are the cheapest airlines that fly to Chicago?

The cheapest airlines flying from Toronto to Chicago are Porter Airlines, Air Canada and United 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 17 January 2025.
Get a feel of what it's like to fly with Air Canada, United Airlines and American Airlines to Chicago by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
8,511 reviews
Check prices

Food

7.3

Crew

8.6

Comfort

8.0

Entertainment

7.9

Boarding

8.2

Overall

8.0

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Delta
8.0
Very good
8,511 reviews
Delta
8.0
Very good
8,511 reviews
Check prices

Food

7.3

Crew

8.6

Comfort

8.0

Entertainment

7.9

Boarding

8.2

Overall

8.0

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Porter Airlines
7.9
Good
276 reviews
Delta
8.0
Very good
8,511 reviews
Check prices

Food

7.3

Crew

8.6

Comfort

8.0

Entertainment

7.9

Boarding

8.2

Overall

8.0

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

KLM
7.8
Good
1,339 reviews
Delta
8.0
Very good
8,511 reviews
Check prices

Food

7.3

Crew

8.6

Comfort

8.0

Entertainment

7.9

Boarding

8.2

Overall

8.0

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Air Transat
7.8
Good
381 reviews
Delta
8.0
Very good
8,511 reviews
Check prices

Food

7.3

Crew

8.6

Comfort

8.0

Entertainment

7.9

Boarding

8.2

Overall

8.0

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

United Airlines
7.4
Good
8,965 reviews
Delta
8.0
Very good
8,511 reviews
Check prices

Food

7.3

Crew

8.6

Comfort

8.0

Entertainment

7.9

Boarding

8.2

Overall

8.0

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

  • 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, American Airlines 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$ 68, while round-trip flights cost around C$ 113.

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

    A round-trip flight to Chicago will typically cost around C$ 571, however they can be found for as little as C$ 79.

  • 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).

  • 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).

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