Question 1

When is the best time to book a flight to Chicago?

Accepted Answer

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.

Question 2

Can I find cheaper flights to Chicago if I am willing to have layovers?

Accepted Answer

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.

Question 3

What is the best airline to fly to Chicago?

Accepted Answer

Based on reviews from Cheapflights users, Porter Airlines is rated the highest out of the airlines that fly to Chicago.

Question 4

What is the cheapest airport to fly to in Chicago?

Accepted Answer

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$ 62, while round-trip flights cost around C$ 122.

Question 5

How much is a round-trip flight to Chicago?

Accepted Answer

A round-trip flight to Chicago will typically cost around C$ 367, however they can be found for as little as C$ 122.

Question 6

Where does the fastest flight to Chicago depart from?

Accepted Answer

For those looking to save time traveling to Chicago, Toronto offers the quickest one-way flight (1 hour 50 minutes).

Question 7

Which airport is closest to Wrigley Field?

Accepted Answer

If being close to Wrigley Field is important to you, you’ll want to land at Chicago O'Hare Intl Airport.

Question 8

Does Chicago O'Hare Intl have rental cars?

Accepted Answer

Yes. Those touching down at Chicago O'Hare Intl can take advantage of the rental car services offered upon their arrival.

Question 9

Are there hotels close to Chicago O'Hare Intl?

Accepted Answer

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).

Question 10

When is the cheapest time to fly to Chicago?

Accepted Answer

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

Question 11

What are the most popular airlines that fly to Chicago?

Accepted Answer

The most popular airlines flying from Toronto to Chicago are Air Canada, United Airlines and Porter Airlines.

Question 12

How long is the flight to Chicago?

Accepted Answer

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.

Question 13

Weekly flight availability to Chicago

Accepted Answer

The most flights from Toronto to Chicago are scheduled on a Thursday (70 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (25 on average).

Question 14

What are the cheapest airlines that fly to Chicago?

Accepted Answer

The cheapest airlines flying from Toronto to Chicago are Porter Airlines, American Airlines and Air Canada.

Question 15

E

Accepted Answer

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.

Question 16

E

Accepted Answer

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).

Question 17

What is good to know if travelling to Chicago?

Accepted Answer

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&#8217;t expose skin to the wind; in summer, be sure to drink plenty of water and use sunscreen.

Round-trip from	C$ 272
One-way from	C$ 171
Popular in	March
Cheapest in	July
Average price	C$ 346
Good round-trip deal	C$ 293 or less
Good one-way deal	C$ 264 or less

Flights to Chicago in 2026

Find the latest flights to Chicago in 2026, 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 2 April 2026.

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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 2 April 2026.

Explore the most affordable flight options available to Chicago. Find the lowest fares based on data from user searches, with prices last updated on 2 April 2026.

Best flights to Chicago
Discover carefully curated flight deals to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 2 April 2026.

Discover carefully curated flight deals to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 2 April 2026.

Direct flights to Chicago
Explore direct flight options to Chicago based on user searches, and compare prices and availability for your desired travel dates. Data last updated 2 April 2026.

Explore direct flight options to Chicago based on user searches, and compare prices and availability for your desired travel dates. Data last updated 2 April 2026.

Last-minute flights to Chicago
Discover last-minute flight deals to Chicago. Data last updated 2 April 2026 and is based on user searches.

Discover last-minute flight deals to Chicago. Data last updated 2 April 2026 and is based on user searches.

One-way flights to Chicago
Search for one-way flight options to Chicago. Find affordable one-way fares based on user searches. Data last updated 2 April 2026.

Search for one-way flight options to Chicago. Find affordable one-way fares based on user searches. Data last updated 2 April 2026.

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