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

The price you pay for your flight to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 35 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to fly to Chicago?

Currently, the cheapest month for flights to Chicago is August . The most expensive month for flights is March . The cheapest prices are shown above but prices will vary according to departure times, airlines, class and how early you book.

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, Spirit Airlines 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 $25, while round-trip flights cost around $39.

How much is a round-trip flight to Chicago?

A round-trip flight to Chicago will typically cost around $935, however they can be found for as little as $67.

Where does the fastest flight to Chicago depart from?

For those looking to save time traveling to Chicago, Muskegon offers the quickest one-way flight (0 hours 50 minutes).

Which airport is closest to Aragon Ballroom?

If being close to Aragon Ballroom 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 mi away from Chicago O'Hare Intl).

When is the cheapest time to fly to Chicago?

Users looking for the lowest fares to Chicago should consider flying on Tuesday mornings, when prices are typically cheapest. Budget-minded travelers will want to avoid Sunday at noon, when prices are usually at their highest.

What are the most popular airlines that fly to Chicago?

The most popular airlines flying from New York to Chicago are United Airlines, American Airlines and Spirit Airlines.

How long is the flight to Chicago?

On average, a flight from New York to Chicago takes 7 hours 25 minutes. Flights to Chicago from other popular cities in USA will vary in length. Below are a few examples of popular routes and their flight times.

Weekly flight availability to Chicago

The most flights from New York to Chicago are scheduled on a Friday (196 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (83 on average).

What are the cheapest airlines that fly to Chicago?

The cheapest airlines flying from New York to Chicago are Spirit Airlines, Frontier and JetBlue.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

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 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

$70+ Flights to Chicago, Illinois

Popular in	August
Cheapest in	January
Average price	$185
Round-trip from	$127
One-way from	$70
Good round-trip deal	$68 or less
Good one-way deal	$44 or less

American Airlines' Main Cabin Extra provides more legroom than standard economy.

American Airlines' Flagship Business offers lie-flat seats on select transcontinental flights.

$70+ 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 1/29. Fares are subject to change and may not be available on all flights or dates of travel.

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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 2,558,603 searches and data was last updated on September 5, 2025.

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Cheapest flights to ChicagoExplore the most affordable flight options available to Chicago. Find the lowest fares based on data from user searches, with prices last updated on September 5, 2025.

Explore the most affordable flight options available to Chicago. Find the lowest fares based on data from user searches, with prices last updated on September 5, 2025.

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The best insider tips for flights to Chicago

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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.

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 New York to Chicago. Price data was last updated on August 29, 2025.

How long is the flight to Chicago?

When is the cheapest time to fly to Chicago?

Use this chart to determine the cheapest time to fly round-trip from New York to Chicago. Price data was last updated on December 16, 2024.

Weekly flight availability to Chicago

What are the most popular airlines that fly to Chicago?

What are the cheapest airlines that fly to Chicago?

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

Reviews of airlines servicing Chicago

Read reviews from past customers who have flown Southwest, Delta, and United Airlines to the United States. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.

FAQs about flying to Chicago

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

What is the best airline to fly to Chicago?

What is the cheapest airport to fly to in Chicago?

How much is a round-trip flight to Chicago?

Where does the fastest flight to Chicago depart from?

Which airport is closest to Aragon Ballroom?

Does Chicago O'Hare Intl have rental cars?

Are there hotels close to Chicago O'Hare Intl?

Traveling to a place near Chicago?

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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 September 5, 2025.