Cheap Flights from New York to Chicago

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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

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Flight deals from New York to Chicago

Looking for a cheap last-minute deal or the best return flight from New York to Chicago? If you want to travel next month, return fares start from SAR 592. Find the lowest prices on one-way and return tickets right here.

Chicago.SAR 589 per passenger.Departing Sat, 26 Sep, returning Thu, 1 Oct.Return flight with KLM.Outbound direct flight with KLM departs from New York LaGuardia on Sat, 26 Sep, arriving in Chicago O'Hare International.Inbound direct flight with KLM departs from Chicago O'Hare International on Thu, 1 Oct, arriving in New York LaGuardia.Price includes taxes and charges.From SAR 589, select.

Chicago.SAR 590 per passenger.Departing Tue, 13 Oct, returning Wed, 14 Oct.Return flight with jetBlue.Outbound direct flight with jetBlue departs from New York John F. Kennedy on Tue, 13 Oct, arriving in Chicago O'Hare International.Inbound direct flight with jetBlue departs from Chicago O'Hare International on Wed, 14 Oct, arriving in New York John F. Kennedy.Price includes taxes and charges.From SAR 590, select.

Chicago.SAR 591 per passenger.Departing Wed, 9 Sep, returning Wed, 16 Sep.Return flight with jetBlue.Outbound direct flight with jetBlue departs from New York John F. Kennedy on Wed, 9 Sep, arriving in Chicago O'Hare International.Inbound direct flight with jetBlue departs from Chicago O'Hare International on Wed, 16 Sep, arriving in New York John F. Kennedy.Price includes taxes and charges.From SAR 591, select.

Chicago.SAR 596 per passenger.Departing Wed, 28 Oct, returning Mon, 2 Nov.Return flight with United.Outbound direct flight with United departs from New York LaGuardia on Wed, 28 Oct, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Mon, 2 Nov, arriving in New York LaGuardia.Price includes taxes and charges.From SAR 596, select.

Chicago.SAR 596 per passenger.Departing Tue, 15 Dec, returning Tue, 15 Dec.Return flight with American Airlines.Outbound direct flight with American Airlines departs from New York Newark on Tue, 15 Dec, arriving in Chicago O'Hare International.Inbound direct flight with American Airlines departs from Chicago O'Hare International on Tue, 15 Dec, arriving in New York Newark.Price includes taxes and charges.From SAR 596, select.

Chicago.SAR 596 per passenger.Departing Sat, 14 Nov, returning Wed, 18 Nov.Return flight with American Airlines.Outbound direct flight with American Airlines departs from New York John F. Kennedy on Sat, 14 Nov, arriving in Chicago O'Hare International.Inbound direct flight with American Airlines departs from Chicago O'Hare International on Wed, 18 Nov, arriving in New York Newark.Price includes taxes and charges.From SAR 596, select.

Chicago.SAR 597 per passenger.Departing Mon, 23 Nov, returning Mon, 7 Dec.Return flight with United.Outbound direct flight with United departs from New York LaGuardia on Mon, 23 Nov, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Mon, 7 Dec, arriving in New York LaGuardia.Price includes taxes and charges.From SAR 597, select.

Chicago.SAR 597 per passenger.Departing Tue, 5 Jan, returning Sat, 9 Jan.Return flight with United.Outbound direct flight with United departs from New York Newark on Tue, 5 Jan, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Sat, 9 Jan, arriving in New York Newark.Price includes taxes and charges.From SAR 597, select.

Chicago.SAR 597 per passenger.Departing Sat, 6 Feb, returning Thu, 11 Feb.Return flight with United.Outbound direct flight with United departs from New York Newark on Sat, 6 Feb, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Thu, 11 Feb, arriving in New York Newark.Price includes taxes and charges.From SAR 597, select.

Chicago.SAR 597 per passenger.Departing Tue, 15 Dec, returning Tue, 5 Jan.Return flight with United.Outbound direct flight with United departs from New York Newark on Tue, 15 Dec, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Tue, 5 Jan, arriving in New York Newark.Price includes taxes and charges.From SAR 597, select.

Chicago.SAR 631 per passenger.Departing Mon, 31 Aug, returning Thu, 10 Sep.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from New York Newark on Mon, 31 Aug, arriving in Chicago O'Hare International.Inbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Thu, 10 Sep, arriving in New York Newark.Price includes taxes and charges.From SAR 631, select.

Chicago.SAR 648 per passenger.Departing Sat, 30 Jan, returning Mon, 1 Feb.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from New York LaGuardia on Sat, 30 Jan, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 1 Feb, arriving in New York LaGuardia.Price includes taxes and charges.From SAR 648, select.

Chicago.SAR 686 per passenger.Departing Mon, 31 Aug, returning Mon, 14 Sep.Return flight with United.Outbound direct flight with United departs from New York LaGuardia on Mon, 31 Aug, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Mon, 14 Sep, arriving in New York LaGuardia.Price includes taxes and charges.From SAR 686, select.

Chicago.SAR 762 per passenger.Departing Wed, 3 Mar, returning Thu, 1 Apr.Return flight with United.Outbound direct flight with United departs from New York Newark on Wed, 3 Mar, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Thu, 1 Apr, arriving in New York Newark.Price includes taxes and charges.From SAR 762, select.

Chicago.SAR 779 per passenger.Departing Tue, 18 Aug, returning Tue, 25 Aug.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from New York Newark on Tue, 18 Aug, arriving in Chicago O'Hare International.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Tue, 25 Aug, arriving in New York Newark.Price includes taxes and charges.From SAR 779, select.

Chicago.SAR 780 per passenger.Departing Sat, 26 Sep, returning Sun, 8 Nov.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from New York Newark on Sat, 26 Sep, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Sun, 8 Nov, arriving in New York Newark.Price includes taxes and charges.From SAR 780, select.

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 October.

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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	SAR 589
Cheapest month to fly	September
Average flight time	2 hrs, 49 mins
Most popular airline	American Airlines
Average flights per week	1,496

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

How many airports are there in Chicago?

There are 3 airports in Chicago: Chicago Midway, Chicago O'Hare International and Chicago Rockford.

How much are return flights from New York to Chicago?

The best price we found for a return flight from New York to Chicago is SAR 589. 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.

How long does it take to fly from New York to Chicago?

2 hours and 48 minutes is the average flight time from New York to Chicago.

Which airlines fly direct from New York to Chicago?

American Airlines, United and Southwest Airlines fly direct from New York to Chicago.

How many flights are there a week from New York to Chicago?

As of August 2026, there are 1,496 flights per week flying from New York to Chicago.

When is the cheapest time to fly from New York to Chicago?

The cheapest month to fly from New York to Chicago is usually September.

Which is the cheapest airport to fly into in Chicago?

If you're flying from New York, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.5 km away from the centre of Chicago. We've found flights into this airport from SAR 589.

Which upcoming date is cheapest to fly from New York to Chicago on?

After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from New York to Chicago on Saturday, 26 September 2026.

Can I get a direct flight from New York to Chicago?

Yes – the average flight time is 2 hours and 48 minutes.

How can I get the best flight deal from New York to Chicago?

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.

When is the best time to book flights to Chicago?

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.

What’s the weather like in Chicago?

In August, the average temperature is usually around 22°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.

Which is the cheapest airline to fly from New York to Chicago with?

The cheapest airline that flies to Chicago is KLM .

How to find cheap flights to Chicago from New York

Looking for cheap tickets from New York to Chicago? Here are a few tips on how to secure the best flight price and make your journey as smooth as possible.

Simply hit 'search'. From British Airways to international carriers like Emirates, we compare all major airlines along with the most popular online travel agents to find the cheapest plane tickets from New York to Chicago. And with us there are no hidden fees - what you see is what you pay.
Compare flight deals to Chicago from New York from over 1,000 providers. Then choose the cheapest or fastest plane tickets.
Flex your dates to find the best New York-Chicago ticket prices. If you are flexible when it comes to your travel dates, use Skyscanner's 'Whole month' tool to find the cheapest month, and even day to fly to Chicago from New York.
Set up a Price Alert. You can easily track the fare of your cheap New York-Chicago flights by creating an alert. Whenever prices go down or up, you'll get an email or push notification to help make sure you get the best possible flight deal.
Fly without stops. Only interested in direct flights between New York and Chicago? Make sure to tick 'Direct flights only' when performing a search. If there are direct flights available on the route, these will appear in the results.
Find the cheapest Business class flights from New York and Chicago. We scour the internet for the best Business, Premium Economy and First Class flight fares to Chicago, too. Check the difference in price as you search – you might just chance upon a last-minute low fare. Note that not all cabin classes are available for every destination or airline.
Include nearby airports in your search. Widen your search for New York to Chicago flight deals by selecting the "add nearby airports" option. This will allow you to see flight prices for all the nearest airports at your departure point and your destination and could help you save next time you travel.

Combine your flight to Chicago from New York with hotels and car hire

Once you've secured your cheap flight ticket from New York to Chicago, discover the best prices and exclusive rates for hotels in Chicago or nearby. You can also compare hundreds of car hire companies in one go so that you get the best car hire price for your trip.