Cheap Flights from New York to Chicago

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Find the cheapest month to fly from New York to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like New York to Chicago flights are currently cheapest in June.

Direct flights from New York to Chicago

Alternative New York to Chicago routes

Looking for the cheapest, fastest or easiest route from New York to Chicago? You could fly into the following airports instead.

New York to Chicago: Flight information

The things to know before you go.
Cheapest flight foundAED 184
Cheapest month to flyJune
Average flight time2 hrs, 43 mins
Most popular airlineUnited
Average flights per week1,488

Finding cheap flights from New York to Chicago: Frequently asked questions

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a round-trip flight from New York to Chicago is AED 184. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
2 hours and 43 minutes is the average flight time from New York to Chicago.
United, American Airlines and WestJet fly direct from New York to Chicago.
There are 1,573 flights per week flying from New York to Chicago, as of May 2024.
The cheapest month to fly from New York to Chicago is usually June.
If you're flying from New York, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the center of Chicago. We've found flights to this airport from AED 184.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from New York to Chicago on Tuesday, June 4, 2024.
Yes – the average flight time is 2 hours and 43 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar, and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
In May, the average temperature is usually around 13°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.

Three airports in New York offer direct flights to Chicago - New York JFK Airport, the main airport in New York, as well as New York LaGuardia and New York Newark Airport. Flights from New York land at two airports in Chicago - Chicago O'Hara International AIrport, the main airport and the world’s sixth busiest airport, and Midway International Airport which mostly offers domestic flights. Chicago O’Hare International Airport has seven airlines operating flights to and from New York - American Airlines, Delta Connection, Delta Air Lines, JetBlue Airways, Spirit Airlines, United Airlines and United Express, the shuttle service to United Airlines. Midway International Airport offers flights to and from New York via Southwest Airlines.

* This information is correct as of June 2017

Airport Information - Arriving

Chicago O’Hare International Airport, often shortened to O’Hare Airport, is 27km (17 miles) outside of Chicago. It offers a wide variety of amenities for travelers to enjoy. Alongside a large selection of shops where you can buy everything you need for your trip, the airport offers a sizeable range of places to eat and drink including restaurants, cafes and bars. Once you have arrived in Chicago you can easily reach the city from the airport on the CTA Blue Line in around 40-50 minutes.

Midway International Airport is mainly a domestic airport set within a single terminal complex. All of the facilities and services you would expect can be found including a range shops and places to eat and drink, so you won’t be lacking in options. As the airport is only 10km (6 miles) from Chicago the journey into the city is quick and convenient, with the fastest route being on the CTA Orange Line train.

Airport Information - Departing

New York JFK Airport is the busiest airport serving New York made up of 6 passenger terminals. Getting to the airport is possible on the JFK AirTrain which also allows you to easily travel between terminals. There are a wide range of shops to browse through at the airport including the latest designer and luxury goods as well as other essential shops to pick up all your basics. You will also find many different dining and drinking establishments available at the airport serving up a variety of cuisine for you to fill up before your flight.

New York Newark Airport is New York’s secondary airport handling around 40 million travelers per year. You can travel to the airport from the city on the AirTrain Newark if you don’t have your own vehicle and want to use public transport. The airport offers all of the amenities and services you would need for a pleasant stay including different places to eat and drink and shops to buy everything for your journey.

New York LaGuardia is comprised of four passenger terminals and is mainly a domestic airport. At the airport you will find everything you would need whether it’s shops to browse through or somewhere to sit down and enjoy a meal or a drink. Travelers can also enjoy free Wi-Fi for a period up to 30 minutes so you can stay connected.

What to Expect in Chicago

In Chicago the climate can change from warm and sunny over the summer to freezing and snowy winters so be sure to pack appropriately. As you will be flying on a domestic route within the US you won’t need to get a visa, but you still need to bring all of your essential travel documents along with you. Remember that Chicago is 1 hour behind New York so be sure to wind back your clocks when you land. Check out the top hotels in Chicago to make sure you get the most out of your trip.


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Prices shown on this page are estimated lowest prices only. Found in the last 45 days.