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 81 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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, Frontier 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 $50.

How much is a round-trip flight to Chicago?

A round-trip flight to Chicago will typically cost around $138, however they can be found for as little as $50.

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 Wednesday evenings, 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 8 hours 50 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 Thursday (176 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (47 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).

Most accurate provider : Out of all of the providers offering Chicago flight deals, Cheapflights users have found CheapOair to have the most accurate pricing on Cheapflights vs. their site about >95% of the time, users can find the same price on Chicago flight deals on Cheapflights and CheapOair. This is based on searches made for Chicago flights over the past month.

Most trusted provider : CheapOair is the most trusted provider by Cheapflights users offering Chicago flight deals. With a user feedback rating of 3 out of 3 stars (3 being the best), CheapOair has received the most positive sentiment from Cheapflights users searching for flights to Chicago. This is based on data collected from Cheapflights searches made over the past month.

$55+ Cheap Flights to Chicago, Illinois

Popular in	August
Cheapest in	January
Average price	$182
Round-trip from	$85
One-way from	$55
Good round-trip deal	$148 or less
Good one-way deal	$105 or less

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy2 stars	Trust Score*3 stars
eDreams	Price Accuracy3 stars	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust Score*1 star
Ovago	Price Accuracy2 stars	Trust Score*2 stars
Cheapflightsfares	Price Accuracy3 stars	Trust Score*2 stars
Priceline	Price Accuracy1 star	Trust Score*3 stars
CheapOair	Price Accuracy3 stars	Trust Score*3 stars
Kiwi.com	Price Accuracy3 stars	Trust Score*3 stars
Justfly.com	Price Accuracy3 stars	Trust Score*3 stars
CheapTicketsDeal	Price Accuracy3 stars	Trust Score*3 stars

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

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

$55+ 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 4/7. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights to Chicago with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

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 2,558,603 searches and data was last updated on January 15, 2026.

Popular in

Cheapest in

Average price

Round-trip from

One-way from

Good round-trip deal

Good one-way deal

Find flight deals to Chicago

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 January 15, 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 January 15, 2026.

Cheapflights Fare Finder

Use the filters below to find and compare flights to Chicago that are best for you.

Compare providers for flights to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals to Chicago in January.

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 January 9, 2026.

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 January 10, 2026.

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.

The best insider tips for flights to Chicago

AI-powered summary based on content written by travel experts. AI can make mistakes.

Cheapflights partnered with top experts to bring you the best recommendations for your Chicago trip

Airlines

American Airlines

Alaska Airlines

Frontier

Delta

United Airlines

Spirit Airlines

Airports

ORD

MDW

Our travel experts

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?

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.

Find the best flight deals to Chicago

Some of the lowest fares we’ve come across for flights 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 January 15, 2026.