Cheap Flights from New York to Chicago

Compare New York to Chicago flight deals

Find the cheapest month or even day of the year to fly to Chicago

Book the best Chicago fare with no extra fees

Flight deals from New York to Chicago

Looking for a cheap last-minute deal or the best return flight from New York to Chicago? Find the lowest prices on one-way and return tickets right here.

Don’t miss a great deal

Stay one step ahead. Find the best value travel with the latest deals, tips and news.

You can unsubscribe at any time. Read our Privacy Policy for more info.

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 May.

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 found£31
Cheapest month to flyMay
Average flight time2 hrs, 43 mins
Most popular airlineUnited
Average flights per week1,696

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 return flight from New York to Chicago is £31. 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.
As of May 2024, there are 1,696 flights per week flying from New York to Chicago.
The cheapest month to fly from New York to Chicago is usually May.
If you're flying from New York, the cheapest airport near Chicago is Chicago O'Hare International – which is 15.8 miles away from the centre of Chicago. We've found flights into this airport from £31.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from New York to Chicago on Wednesday, 29 May 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.
The cheapest airline that flies to Chicago is Spirit Airlines .

This information is correct as of February 2016

Airlines that fly from New York to Chicago

There’s a good selection of airlines providing direct flights from New York to Chicago. There are Delta, United, American Airlines and Spirit Airlines flights from LaGuardia Airport. United and American Airlines also offer flights from New York Newark Airport and both Delta and American Airlines also fly from New York John F. Kennedy Airport. All of these flights arrive to Chicago O’Hare International Airport.

Terminal Information

New York LaGuardia Airport

LaGuardia is located north of Queens, 12 miles from New York city centre. There are four terminals at the airport, all connected by walkways and buses. Delta flights to Chicago depart from Terminal A whilst all other flights to Chicago depart from Terminal B.

In Terminal A there are convenience stores, WorldBean and Yankee Clipper food outlets, device charging stations and cash machines. Terminal B is much bigger and has a greater selection of food, drink and shopping venues. There’s Auntie Anne’s, Figs Café, Metro Burger Bar and MexiJoe’s for a bite to eat, and Lacoste, Desigual, Hudson and a duty free store for a little retail therapy. Complimentary Wi-Fi for up to 30 minutes is available throughout both terminals.  

New York John F. Kennedy Airport

New York John F. Kennedy Airport is located in Queens, 12 miles southeast of Lower Manhattan. There are six terminals at the airport. Delta depart from Terminal 2 and American Airlines depart from Terminal 8. Free Wi-Fi is available throughout both terminals for up to 30 minutes. There’s an extensive selection of food and shopping options available in both terminals, although Terminal 8 is the bigger of the two and has slightly more choice.

New York Newark Airport

New York Newark Airport is located 15 miles southwest of Midtown Manhattan. There are three terminals at the airport with American Airlines flights departing from Terminal A and United flights departing from Terminal C. Complimentary Wi-Fi connection is available throughout all terminals for up to 30 minutes. In both terminals you’ll also find a great range of shops and food outlets along with cash machines and device charging stations.

Chicago O’Hare International Airport

Chicago O’Hare International Airport is located 17 miles northwest of Chicago city centre. The airport has four terminals. United flights arrive to Terminal 1, Delta flights arrive to Terminal 2, and both Spirit Airways and American Airlines flights arrive to Terminal 3.

The arrivals hall in all terminals offers an airport information desk, cash machines and convenience stores. If you’re looking to hire a car from the airport, you can take the car hire shuttle from outside each of the terminals. This shuttle will take you to the relevant company’s car hire office. Taxis also depart from outside each terminal building.

Public transport options from the airport to the city include both trains and buses. O’Hare Blue Line train station is located on the lower level of Terminal 2, which can be accessed by the ATS (Airport Transit System) if you need to travel between terminals. Shuttle buses to the city centre depart from the Bus/Shuttle Center, which can be found in the main car park outside Terminal 1.

Practical Information

If you’re a British citizen travelling to the US for a tourist visit of 90 days or less you will not need a visa thanks to the US Visa Waiver Programme. You will need to apply for authorisation to travel through the ESTA before your flight.

What to Expect in Chicago

The “Windy City” isn’t actually the windiest city in the US but it does get breezes coming off Lake Michigan. Temperatures in New York and Chicago are largely the same but Chicago can experience heavier snowfall and colder weather in winter months. During the summer, temperatures rise into the low thirties and there are regular thunderstorms.

The cost of living and travelling in Chicago is generally cheaper than in New York. You can expect to pay around $65.00 for a mid-range three course meal for two, $6.00 for a bottle of beer and $2.25 for a one-way ticket on public transport.

New York is one hour ahead of Chicago.


More flight options

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