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C$ 146+ 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 14/11. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
19 Aug — 26 Aug1
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 August 2025.

Round-trip from

C$ 203

One-way from

C$ 146

Popular in

December

Cheapest in

July

Average price

C$ 356

Good round-trip deal

C$ 216 or less

Good one-way deal

C$ 128 or less
Air Canada
  • Air Canada
  • 6/11-10/11
  • Nonstop
  • 3h 34m total
  • Toronto to Chicago
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American Airlines
  • American Airlines
  • 14/11
  • Nonstop
  • 2h 00m total
  • Toronto to Chicago
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Highest demand for flights based on searches. 8% potential increase in price (C$ 43 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease (C$ 8 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Toronto to Chicago.
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Price to beat on a one-way flight from Toronto to Chicago.
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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 14 August 2025.

Thu 6/112:15 p.m.YYZ - ORD
Nonstop1h 55mAir Canada
Mon 10/113:55 p.m.ORD - YYZ
Nonstop1h 39mAir Canada
Deal found 13/8C$ 203
Fri 7/119:00 p.m.YYZ - ORD
Nonstop2h 05mUnited Airlines
Mon 10/119:20 p.m.ORD - YYZ
Nonstop1h 39mUnited Airlines
Deal found 12/8C$ 204
Sat 1/115:30 p.m.YYZ - ORD
Nonstop2h 09mUnited Airlines
Fri 7/119:20 p.m.ORD - YYZ
Nonstop1h 39mUnited Airlines
Deal found 12/8C$ 208
Sun 12/102:10 p.m.YYZ - ORD
Nonstop1h 54mAir Canada
Sun 30/118:00 a.m.ORD - YYZ
Nonstop1h 40mAir Canada
Deal found 14/8C$ 219
Thu 2/106:35 p.m.YYZ - ORD
Nonstop1h 54mAir Canada
Sun 5/108:25 p.m.ORD - YYZ
Nonstop1h 43mAir Canada
Deal found 13/8C$ 222
Thu 2/104:40 p.m.YYZ - ORD
Nonstop1h 53mAir Canada
Mon 6/108:25 p.m.ORD - YYZ
Nonstop1h 43mAir Canada
Deal found 12/8C$ 225
Wed 1/1012:20 p.m.YYZ - ORD
Nonstop1h 54mAir Canada
Sat 4/103:50 p.m.ORD - YYZ
Nonstop1h 43mAir Canada
Deal found 14/8C$ 229
Sun 5/1012:20 p.m.YYZ - ORD
Nonstop1h 54mAir Canada
Fri 17/108:25 p.m.ORD - YYZ
Nonstop1h 43mAir Canada
Deal found 12/8C$ 237
Fri 5/93:35 p.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Mon 8/99:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/8C$ 240
Fri 26/97:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Tue 30/95:20 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 14/8C$ 241
Thu 2/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Sun 5/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/8C$ 243
Wed 3/97:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Tue 23/95:20 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 13/8C$ 247

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 August 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

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 1/11

8:55 a.m.-10:00 a.m.

Nonstop2h 05m

Chicago O'Hare Intl

Sat 8/11

1:19 p.m.-4:02 p.m.

Nonstop1h 43m

C$ 208

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 29/10

2:15 p.m.-3:10 p.m.

Nonstop1h 55m

Chicago O'Hare Intl

Thu 6/11

8:15 p.m.-10:54 p.m.

Nonstop1h 39m

C$ 208

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 6/11

7:40 p.m.-11:43 p.m.

1 stop5h 03m

Chicago O'Hare Intl

Mon 10/11

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

Nonstop1h 53m

C$ 223

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 2/10

2:10 p.m.-3:04 p.m.

Nonstop1h 54m

Chicago O'Hare Intl

Sun 5/10

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

Nonstop1h 43m

C$ 229

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 7/10

2:10 p.m.-3:04 p.m.

Nonstop1h 54m

Chicago O'Hare Intl

Tue 21/10

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

Nonstop1h 43m

C$ 237

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 8/10

6:35 p.m.-7:29 p.m.

Nonstop1h 54m

Chicago O'Hare Intl

Sun 19/10

3:50 p.m.-6:33 p.m.

Nonstop1h 43m

C$ 237

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 7/10

6:35 p.m.-7:29 p.m.

Nonstop1h 54m

Chicago O'Hare Intl

Thu 9/10

2:00 p.m.-4:43 p.m.

Nonstop1h 43m

C$ 237

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 24/10

4:40 p.m.-5:33 p.m.

Nonstop1h 53m

Chicago O'Hare Intl

Sun 26/10

3:55 p.m.-6:34 p.m.

Nonstop1h 39m

C$ 237

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 11/10

6:35 p.m.-7:29 p.m.

Nonstop1h 54m

Chicago O'Hare Intl

Tue 14/10

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

Nonstop1h 43m

C$ 237

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 8/10

6:35 p.m.-7:29 p.m.

Nonstop1h 54m

Chicago O'Hare Intl

Wed 22/10

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

Nonstop1h 43m

C$ 237

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/8

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 8 August 2025.

To ensure you get the cheapest price possible for a flight to Chicago, you should look to book at least 85 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 7 hours 35 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 20 October 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 Thursday (65 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (44 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$ 131
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 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 14 August 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
332 reviews
Check prices

Crew

8.7

Boarding

8.2

Comfort

8.0

Entertainment

7.0

Overall

8.0

Food

7.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Porter Airlines
8.0
Very good
332 reviews
Porter Airlines
8.0
Very good
332 reviews
Check prices

Crew

8.7

Boarding

8.2

Comfort

8.0

Entertainment

7.0

Overall

8.0

Food

7.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Air Transat
7.7
Good
427 reviews
Porter Airlines
8.0
Very good
332 reviews
Check prices

Crew

8.7

Boarding

8.2

Comfort

8.0

Entertainment

7.0

Overall

8.0

Food

7.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
United Airlines
7.4
Good
8,915 reviews
Porter Airlines
8.0
Very good
332 reviews
Check prices

Crew

8.7

Boarding

8.2

Comfort

8.0

Entertainment

7.0

Overall

8.0

Food

7.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
American Airlines
7.2
Good
10,000 reviews
Porter Airlines
8.0
Very good
332 reviews
Check prices

Crew

8.7

Boarding

8.2

Comfort

8.0

Entertainment

7.0

Overall

8.0

Food

7.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Air Canada
7.1
Good
9,956 reviews
Porter Airlines
8.0
Very good
332 reviews
Check prices

Crew

8.7

Boarding

8.2

Comfort

8.0

Entertainment

7.0

Overall

8.0

Food

7.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience

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 Midway is currently the cheapest airport to fly to in Chicago. One-way flights to Chicago Midway typically cost C$ 63, while round-trip flights cost around C$ 103.

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

    A round-trip flight to Chicago will typically cost around C$ 220, however they can be found for as little as C$ 75.

  • 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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