Cheap Flights from New York to Chicago

Compare New York to Chicago flight deals

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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 Rs44,629. Find the lowest prices on one-way and return tickets right here.

Chicago.Rs22,858 per passenger.Departing Wed, 5 Aug.One-way flight with jetBlue.Outbound direct flight with jetBlue departs from New York John F. Kennedy on Wed, 5 Aug, arriving in Chicago O'Hare International.Price includes taxes and charges.From Rs22,858, select.

Chicago.Rs22,912 per passenger.Departing Wed, 22 Jul.One-way flight with jetBlue.Outbound direct flight with jetBlue departs from New York John F. Kennedy on Wed, 22 Jul, arriving in Chicago O'Hare International.Price includes taxes and charges.From Rs22,912, select.

Chicago.Rs22,918 per passenger.Departing Tue, 8 Sep.One-way flight with jetBlue.Outbound direct flight with jetBlue departs from New York John F. Kennedy on Tue, 8 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From Rs22,918, select.

Chicago.Rs23,759 per passenger.Departing Tue, 1 Dec.One-way flight with United.Outbound direct flight with United departs from New York Newark on Tue, 1 Dec, arriving in Chicago O'Hare International.Price includes taxes and charges.From Rs23,759, select.

Chicago.Rs23,759 per passenger.Departing Sat, 3 Oct.One-way flight with Delta.Outbound direct flight with Delta departs from New York LaGuardia on Sat, 3 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From Rs23,759, select.

Chicago.Rs23,759 per passenger.Departing Wed, 4 Nov.One-way flight with United.Outbound direct flight with United departs from New York Newark on Wed, 4 Nov, arriving in Chicago O'Hare International.Price includes taxes and charges.From Rs23,759, select.

Chicago.Rs28,764 per passenger.Departing Sat, 6 Mar.One-way flight with Delta.Outbound direct flight with Delta departs from New York LaGuardia on Sat, 6 Mar, arriving in Chicago O'Hare International.Price includes taxes and charges.From Rs28,764, select.

Chicago.Rs28,764 per passenger.Departing Fri, 5 Feb.One-way flight with Delta.Outbound direct flight with Delta departs from New York John F. Kennedy on Fri, 5 Feb, arriving in Chicago O'Hare International.Price includes taxes and charges.From Rs28,764, select.

Chicago.Rs28,764 per passenger.Departing Thu, 28 Jan.One-way flight with Delta.Outbound direct flight with Delta departs from New York John F. Kennedy on Thu, 28 Jan, arriving in Chicago O'Hare International.Price includes taxes and charges.From Rs28,764, select.

Chicago.Rs28,767 per passenger.Departing Sat, 3 Apr.One-way flight with Delta.Outbound direct flight with Delta departs from New York LaGuardia on Sat, 3 Apr, arriving in Chicago O'Hare International.Price includes taxes and charges.From Rs28,767, select.

Chicago.Rs28,767 per passenger.Departing Thu, 13 May.One-way flight with Delta.Outbound direct flight with Delta departs from New York LaGuardia on Thu, 13 May, arriving in Chicago O'Hare International.Price includes taxes and charges.From Rs28,767, select.

Chicago.Rs40,226 per passenger.Departing Tue, 1 Jun.One-way flight with United.Outbound direct flight with United departs from New York Newark on Tue, 1 Jun, arriving in Chicago O'Hare International.Price includes taxes and charges.From Rs40,226, 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 August.

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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	Rs22,858
Cheapest month to fly	August
Average flight time	2 hrs, 47 mins
Most popular airline	American Airlines
Average flights per week	1,613

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 Rs44,629. 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 47 minutes is the average flight time from New York to Chicago.

Which airlines fly direct from New York to Chicago?

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

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

As of July 2026, there are 1,613 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 August.

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 Rs44,629.

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 Tuesday, 11 August 2026.

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

Yes – the average flight time is 2 hours and 47 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 July, 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 jetBlue .

Travelling from New York to Chicago: what you need to know

Kick off your journey at one of New York's main airports, New York John F. Kennedy Airport (JFK) or New York Newark Airport (EWR). Explore your options for booking a flight from New York to Chicago taking off from either of these.
When it comes to landing in Chicago, Chicago O'Hare International Airport (ORD) is a key hub. Chicago Midway Airport (MDW) is another.
The average length of a direct New York to Chicago flight is 2 hours 40 minutes.
Chicago is one hour behind New York and is in the UTC-6 timezone.
Choose from 61 services a week between New York John F. Kennedy Airport (JFK) and Chicago O'Hare International Airport (ORD). JFK to ORD is the most popular route when booking flights from New York to Chicago.
For a relaxed travel experience, arrive at the airport two hours ahead of international flights and an hour before domestic departures. This ensures you have enough time to board your New York to Chicago flight.
You can expect longer lines during popular months like July. Arriving up to four hours ahead of an international flight and two hours for domestic departures is a wise move.

How to find the cheapest flights from New York to Chicago

To find cheap New York to Chicago flights, book in advance. Airlines tend to offer their most competitively priced fares when flights first go on sale.
The 'Whole month' tool will show you the cheapest plane tickets from New York to Chicago across every month. It's an easy way to snap up a bargain if your travel dates aren't set in stone.
Cut down on the time spent looking for cheap flights from New York to Chicago by creating a Price Alert. We'll send you an email or notification on the app when a special offer becomes available.
Tailor your flights using filters. Pick your preferred departure and arrival times, total journey duration and airlines. You can also sort the results by 'Fastest,' 'Best' or 'Cheapest' New York to Chicago flights.

Flying from New York

New York John F. Kennedy Airport (JFK)

You can catch a direct flight from New York to Chicago leaving from New York John F. Kennedy Airport (JFK). Start your trip at JFK and land at Chicago O'Hare International Airport (ORD).
You'll have your choice of airlines that offer direct New York to Chicago plane tickets out of JFK. Let one of these carriers take you there:
The journey from central New York to JFK takes around 50 minutes by public transport. If you drive, ride-share or take a taxi, you'll cover the 21 kilometres in 45 minutes or so, depending on traffic conditions.
After a leisurely start to your journey? Stay near New York John F. Kennedy Airport. Whether you're taking an early flight from New York to Chicago or just don't want to be rushed, these hotels are just the thing:
When it comes to New York John F. Kennedy Airport's on-time performance, 73% of flights stick to their scheduled arrival time.
JFK is located at JFK Airport.

New York Newark Airport (EWR)

Searching for a direct flight from New York to Chicago leaving from New York Newark Airport (EWR)? Skip the connections and fly straight from EWR to Chicago O'Hare International Airport (ORD) and Chicago Midway Airport (MDW).
You can take your pick of airlines offering direct New York to Chicago plane tickets from EWR. Set off with any of these carriers and travel straight to your destination:
You can get to EWR from central New York in about 35 minutes by car, depending on traffic conditions. The ride by public transport takes roughly 1 hour to cover the 14 kilometres or so.
Want to enjoy an extra night away before boarding your flight from New York to Chicago? Kick back in a hotel near New York Newark Airport before your trip officially begins. Here's where you can stay:
71% of flights taking off from New York Newark Airport arrive according to schedule.
The address for EWR is Building 1, Conrad Road.

New York LaGuardia Airport (LGA)

Arrive sooner with a direct flight from New York to Chicago. From New York LaGuardia Airport (LGA), you can fly nonstop to Chicago O'Hare International Airport (ORD) or Chicago Midway Airport (MDW).
These airlines offer direct New York to Chicago plane tickets with departures from LGA. Simply choose your carrier and get ready to take off:
From central New York, LGA is around 13 kilometres away. It'll take you roughly 30 minutes to get to the airport by car and 55 minutes or so if you're on public transport.
Make catching an early New York to Chicago flight the easiest part of your journey. Stay at one of these accommodation options close to New York LaGuardia Airport and get to the check-in counter with plenty of time to spare:
Flights that depart from LGA arrive at their final stop as scheduled 69% of the time.
You'll find New York LaGuardia Airport at Hangar 7 Centre.

Arriving in Chicago

Chicago O'Hare International Airport (ORD)

Chicago O'Hare International Airport (ORD) to central Chicago takes about 30 minutes by car. The centre is roughly 26 kilometres away.
It typically takes 45 minutes to get there on public transport.
The last thing you need is a long journey to your hotel if you're landing late on a flight from New York to Chicago. Book one of these accommodation options near ORD instead:
Pick up a Chicago O'Hare International Airport rental car and explore Chicago and beyond with your own set of wheels. Routes Car Rentals, Dollar and Budget are popular providers you can book with here.
To get the best deal, reserve your vehicle from Chicago O'Hare International Airport around four weeks in advance of your New York to Chicago flight.
The street address for ORD is 10000 West O'Hare.

Chicago Midway Airport (MDW)

Central Chicago is about 14 kilometres from Chicago Midway Airport (MDW). Once your flight from New York to Chicago has hit the runway and you've made your way to arrivals, expect a drive of about 25 minutes.
Public transport will get you there in approximately 30 minutes.
You'll find some comfortable places ready to welcome you near MDW. Kick back after your New York to Chicago flight at one of these well-located options:
No need to worry about public transport schedules or long taxi queues. Grab a Chicago Midway Airport rental car and let the journey unfold your way. Compare availability and rates from Dollar, Hertz and Budget.
Get first dibs on the best options. Reserving your ride from MDW four weeks in advance often means better deals and a wider range of vehicles.
You can find Chicago Midway Airport at 5700 South Cicero.

Chicago Rockford Airport (RFD)

Make your way to the city centre after your flight from New York to Chicago has arrived. Central Chicago is about 129 kilometres from Chicago Rockford Airport (RFD) and takes roughly 1 hour 40 minutes to reach by car.
Public transport can take you there in about 2 hours.
Begin your journey without stressing about how to reach your destination with a Chicago Rockford Airport rental car. You can book with reliable suppliers here like Budget, Alamo and National.
Booking at least a few weeks ahead of your flight from New York to Chicago is a smart move. As well as better prices, you'll get a better selection of vehicle makes and models at RFD.
The address for Chicago Rockford Airport is 2 Airport Cir.

Best time to go to Chicago

March is the quietest month for flights from New York to Chicago, while July is the most popular. Figure out the best time to go to Chicago based on whether you prefer a bustling atmosphere or a more laid-back vibe.
Book a New York to Chicago ticket departing in July if you want to explore the city during its warmest month. Expect temperatures in Chicago to range from 16ºC to 28ºC.
Look for cheap flights from New York to Chicago in January if you want to travel in cooler conditions. Temperatures are at their lowest then, ranging between -12ºC and 3ºC on average.

More about Chicago

Start your Chicago trip right by choosing the perfect place to stay. Once you've booked your flight from New York to Chicago, check out our selection of accommodation options including:
Millennium Park and The Art Institute of Chicago are just two of the popular attractions to put on your Chicago itinerary. Keep the sightseeing going at Willis Tower.

Explore more of the United States

You've visited Chicago, now it's time to discover other corners of the United States. Travel about 451 kilometres southeast to Columbus to tick off its popular sights. From Franklin Park Conservatory and Botanical Gardens to Columbus Park of Roses and Ohio Theatre, you'll have a packed itinerary ahead.
Around 257 kilometres southeast of Chicago, Indianapolis is another favourite stop in the United States. No visit is complete without checking out Lucas Oil Stadium, Eiteljorg Museum of American Indians and Western Art and The Children's Museum of Indianapolis.