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Find cheap flights from New York to Chicago from £44

This is the cheapest return flight price found by a KAYAK user in the last 72 hours by searching for a flight from New York to Chicago departing on 10/4. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Sat 27/4
Sat 4/5

Search hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from New York to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from New York to Chicago, as well as popular online travel agencies
In the last 7 days, travellers have searched 47,584,047 times on KAYAK, and here's why:

Save 24% or moreCompare multiple travel sites with one search.

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Cheap flight deals from New York to Chicago

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from New York to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
20:03 - 21:43LGA-ORD
2h 40mdirect
17:09 - 20:24ORD-LGA
2h 15mdirect
£44Spirit Airlines
Find Deal
Wed, 10 Apr - Tue, 16 Apr
08:37 - 10:14LGA-ORD
2h 37mdirect
17:36 - 07:42ORD-LGA
13h 06m1 stop
£61Spirit Airlines
Find Deal
Wed, 10 Apr - Tue, 16 Apr
09:55 - 20:09LGA-ORD
11h 14m1 stop
17:36 - 07:42ORD-LGA
13h 06m1 stop
£78Spirit Airlines
Find Deal
Wed, 10 Apr - Tue, 16 Apr
06:00 - 00:56LGA-ORD
19h 56m2 stops
17:36 - 07:42ORD-LGA
13h 06m1 stop
Wed, 10 Apr - Tue, 16 Apr
08:00 - 09:56JFK-ORD
2h 56mdirect
10:45 - 14:08ORD-JFK
2h 23mdirect
£101JetBlue
Find Deal
Tue, 7 May - Sat, 11 May
08:00 - 09:56JFK-ORD
2h 56mdirect
17:32 - 21:00ORD-JFK
2h 28mdirect
£117JetBlue
Find Deal
Thu, 2 May - Wed, 8 May
20:30 - 22:11EWR-ORD
2h 41mdirect
17:00 - 20:06ORD-EWR
2h 06mdirect
£160American Airlines
Find Deal
Fri, 26 Apr - Fri, 3 May
21:40 - 23:17EWR-ORD
2h 37mdirect
21:40 - 01:00ORD-EWR
2h 20mdirect
£177United Airlines
Find Deal
Mon, 1 Jul - Wed, 3 Jul
20:30 - 22:11EWR-ORD
2h 41mdirect
19:03 - 22:15ORD-EWR
2h 12mdirect
£181American Airlines
Find Deal
Wed, 24 Apr - Thu, 25 Apr
19:20 - 23:30EWR-ORD
5h 10m1 stop
06:00 - 09:17ORD-EWR
2h 17mdirect
£185United Airlines
Find Deal
Mon, 6 May - Sat, 11 May

Flights from New York to Chicago - Travel Insights & Trends

Get data-powered insights and trends into flights from New York to Chicago to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest New York to Chicago O'Hare Intl Airport flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for one-way flights from New York to Chicago O'Hare Intl Airport.
Our data shows that the cheapest route for a one-way flight from New York to Chicago O'Hare Intl Airport cost £28 and was between New York LaGuardia Airport and Chicago O'Hare Intl Airport. On average, the best prices are found if you fly from Newark Airport to Chicago O'Hare Intl Airport. The average price for a return flight for this route is £119.

What’s the cheapest day of the week to fly from New York to Chicago?

The average price of all flights from New York to Chicago O'Hare Intl Airport clicked on KAYAK for each day over the last 12 months.
If your flying dates are flexible, you should consider flying to Chicago on a Tuesday, as we generally find the cheapest rates on that day for this route. On the other hand, Friday is the most expensive day to fly from New York to Chicago. For your return ticket, we recommend flying on a Monday and avoiding Tuesdays for the best deals.

What is the cheapest month to fly from New York to Chicago O'Hare Intl Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from New York to Chicago O'Hare Intl Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from New York to Chicago O'Hare Intl Airport is February, where tickets cost £177 on average. On the other hand, the most expensive months are June and July, where the average cost of tickets is £295 and £269 respectively.

How far in advance should I book a flight from New York to Chicago O'Hare Intl Airport?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from New York to Chicago O'Hare Intl Airport, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from New York to Chicago O'Hare Intl Airport, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 77 days before departure.

Which airlines provide the cheapest flights from New York to Chicago?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The best deals for a one-way ticket found by KAYAK users over the last 3 days were on JetBlue (£51) and Delta (£51). The cheapest round-trip tickets were found on Spirit Airlines (£44) and JetBlue (£101).

Which airlines fly most frequently between New York and Chicago?

New York and Chicago are connected by different airlines. The airlines that fly that route the most regularly are United Airlines (25 flights per day), Delta (20 flights per day), and American Airlines (15 flights per day).

Which airlines fly direct between New York and Chicago O'Hare Intl Airport?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from New York to Chicago O'Hare Intl Airport.
There are 5 airlines that fly direct from New York to Chicago O'Hare Intl Airport. They are: American Airlines, Delta, JetBlue, Spirit Airlines and United Airlines. The cheapest price of all airlines flying this route was found with Delta at £179 for a one-way flight. On average, the best prices for this route can be found at American Airlines.

How many flights are there between New York and Chicago O'Hare Intl Airport per day?

Each day, there are between 55 and 70 nonstop flights that take off from New York and land in Chicago O'Hare Intl Airport, with an average flight time of 2h 44m. The most common departure time is 06:00 and most flights take off in the morning. Each week, there are 453 flights. The most frequent day of departure is Friday, when 15% of all weekly flights depart. The fewest flights depart on a Saturday.

Which cabin class options are there for flights between New York and Chicago O'Hare Intl Airport?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There are 3 cabin class options for the route. These are First, Business and Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How long does a flight from New York to Chicago take?

The duration of a direct flight to Chicago from New York is typically 2h 33m. The journey crosses a distance of 725 miles.

What’s the earliest departure time from New York to Chicago?

Early birds can take the earliest flight from New York at 05:45 and will be landing in Chicago O'Hare Intl Airport at 07:27.

What’s the latest departure time from New York to Chicago?

If you prefer to fly at night, the latest flight from New York to Chicago O'Hare Intl Airport jets off at 21:00 and lands at 22:41.

Good to know - Cheap tickets from New York to Chicago

Low season

January

High season

June

Cheapest flight

£44
Best time to beat the crowds (22% less expensive on average)
Most popular time to fly (30% more expensive on average)
Flight from New York LaGuardia Airport to Chicago

When to book flights from New York to Chicago

Are your dates flexible? Find out the best times to travel from New York to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated return price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or returns with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking New York to Chicago flights

  • When looking for flights from New York to Chicago which Chicago airport should I choose?

    Chicago Midway is closer to downtown Chicago, and since it is a smaller airport it can be less busy and easier to navigate; however, because of the airport size difference, Chicago O'Hare International tends to have more flights and is served by more carriers.

  • What is the cost of an Uber from Chicago O'Hare International to downtown Chicago?

    Rides start at $38 but can, of course, be higher depending on the time of day and traffic conditions.

  • What is the best way for someone to pick me up at Chicago O'Hare International?

    Chicago O'Hare International utilizes a cell phone lot for those wishing to pick up arriving passengers. The lot has a flight information display to let those waiting know when you have arrived. The airport does not allow stopping in front of the terminal except for immediate pickup of passengers, so the cell phone lot is an excellent option for those waiting for arriving passengers.

  • What is the fastest way to get to New York LaGuardia airport?

    One very convenient and unique way to get to New York LaGuardia is via the New York City Ferry. You can take the ferry from New York to the last stop at Astoria and then get a taxi or Uber to the airport. The ferry offers alcoholic and non-alcoholic drinks as well as a variety of snacks on board, making it a comfortable journey overall.

  • What is the cheapest flight from New York to Chicago O'Hare Intl Airport?

    In the last 3 days, the lowest price for a flight from New York to Chicago O'Hare Intl Airport was £64 for a one-way ticket and £56 for a return.

  • Which airports will I be using when flying from New York to Chicago?

    When flying out of New York you will be using one of these airports: Newark, New York John F Kennedy Intl, or New York LaGuardia. You will be landing at Chicago O'Hare Intl.

  • Which airlines offer Wi-Fi service onboard planes from New York to Chicago?

    American Airlines, Delta, and JetBlue offer inflight Wi-Fi service on the New York to Chicago flight route.

  • Which aircraft models fly most regularly from New York to Chicago?

    The Boeing 737-800 is the aircraft model that flies most regularly on the New York to Chicago flight route.

  • Which airline alliances offer flights from New York to Chicago?

    oneworld, SkyTeam, and Star Alliance are the airline alliances operating flights between New York and Chicago, with SkyTeam being the most commonly used for this route.

  • On which days can I fly direct from New York to Chicago?

    There are direct flights from New York to Chicago on a daily basis.

  • Which is the best airline for flights from New York to Chicago, United Airlines or American Airlines?

    The two airlines most popular with KAYAK users for flights from New York to Chicago are United Airlines and American Airlines. With an average price for the route of £252 and an overall rating of 7.4, United Airlines is the most popular choice. American Airlines is also a great choice for the route, with an average price of £208 and an overall rating of 7.3.

  • How does KAYAK find such low prices on flights from New York to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from New York to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from New York to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from New York is likely to change within 7 days, so travellers know whether to wait or book now.

  • What is the Hacker Fare option on flights from New York to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional return ticket. You could then fly to Chicago with an airline and back to New York with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from New York to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from New York up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding a cheap flight from New York to Chicago

  • Looking for a cheap flight from Chicago to New York? 25% of our users found flights on this route for £67 or less one-way and £190 or less round-trip.
  • Passengers find that when hunger strikes before flights from New York to Chicago, a great place to eat is the New York classic Shake Shack located at Terminal 4 at New York John F. Kennedy International. Shake Shack offers burgers, chicken sandwiches, hot dogs, and, of course, amazing shakes.
  • If man's best friend will also be traveling on your flights from New York to Chicago, each terminal at Newark International offers a pet relief station. The areas at Terminal B and C are pre-security while the area at Terminal A is after security.
  • The Centurion Lounge at New York LaGuardia is a great place to spend some time before flights from New York to Chicago. The lounge offers a dining menu created by one of Zagat’s top 30 under 30 chefs and a cocktail selection created by on the nation's top mixologists.
  • If you do not want to bother with the hustle and bustle of downtown Chicago, there are many hotels located near Chicago O'Hare International that will suit any traveler’s taste and budget. The SpringHill Suites Chicago O'Hare has top-rated service, a convenient location near the airport, and a free airport shuttle. If your whole family is making the trip, the Hilton Garden Inn Chicago O'Hare Airport is just for you, as it includes an indoor pool and kids’ menus.
  • If you are looking for a budget-friendly way to get from Chicago O'Hare International to downtown Chicago, look no further than a ride on the EL Train. The trip costs just a few dollars and will take you right into downtown Chicago. It should be noted that this can be a difficult choice if you are traveling with more than just one or two bags.
See more tips

Prefer to fly direct from New York to Chicago?

Find which airlines fly direct from New York to O'Hare Intl, which days they fly and book direct flights.

Direct departures

New York to Chicago O'Hare Intl

Monday

ANA, Air Europa, Air France, +30 more

ANA, Air Europa, +31 more

Tuesday

ANA, Aerolineas Argentinas, Air Europa, +32 more

ANA, Aerolineas Argentinas, +33 more

Wednesday

ANA, Air Europa, Air France, +29 more

ANA, Air Europa, +30 more

Thursday

ANA, Air Europa, Air France, +30 more

ANA, Air Europa, +31 more

Friday

ANA, Aerolineas Argentinas, Air Europa, +30 more

ANA, Aerolineas Argentinas, +31 more

Saturday

ANA, Air Europa, Air France, +28 more

ANA, Air Europa, +29 more

Sunday

ANA, Aerolineas Argentinas, Air Europa, +30 more

ANA, Aerolineas Argentinas, +31 more

See more direct flights

Direct returns

Chicago O'Hare Intl to New York

Monday

ANA, Aerolineas Argentinas, Air Europa, +32 more

ANA, Aerolineas Argentinas, +33 more

Tuesday

ANA, Aerolineas Argentinas, Air Europa, +31 more

ANA, Aerolineas Argentinas, +32 more

Wednesday

ANA, Aerolineas Argentinas, Air Europa, +32 more

ANA, Aerolineas Argentinas, +33 more

Thursday

ANA, Aerolineas Argentinas, Air Europa, +31 more

ANA, Aerolineas Argentinas, +32 more

Friday

ANA, Aerolineas Argentinas, Air Europa, +31 more

ANA, Aerolineas Argentinas, +32 more

Saturday

ANA, Aerolineas Argentinas, Air Europa, +31 more

ANA, Aerolineas Argentinas, +32 more

Sunday

ANA, Aerolineas Argentinas, Air Europa, +31 more

ANA, Aerolineas Argentinas, +32 more

See more direct flights
See more direct flights

Top airlines flying from New York to Chicago

Need help choosing which airline to fly with from New York to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to KAYAK reviews.
7.4
United AirlinesOverall score based on 11481 reviews
72comfort
77boarding
74overall
67food
71entertainment
81crew
Airline reviews

Good movies, iffy pay WiFi, food ok- on time though and that was great!

Read more about United Airlines

Good movies, iffy pay WiFi, food ok- on time though and that was great!

Awful…flight was delayed more than 12hrs, missed all connections to Fort Wayne, IN, had to get flight to another city 2 hours from my destination, flight was again delayed by 40 mins because they did not have enough fuel, again missed a connection, finally arrived in Indiana at 11pm…but before my 2 hour drive home, ay, no Five That Our Luggage Never Made On The plane and Still In Chicago

Boarding was friendly and quick. While the plane model was older with no live tv, the entertainment was full of movies and tv shows. All food was available. Pilots were very communicative with status of the flight. Flight landed on time.

The Palm Springs to Chicago O’Hare was on Time and Palm Springs airport is easier navigate. As our connection was only an approximately 50 minutes, we asked staff for insights for the Chicago airport in terms of transferring into the other terminal from which our flight left, and they were unhelpful. However, the United App was very helpful in terms of notifications and even providing directions. The Chicago to Detroit flight was significantly delayed which we all know does happen. However, there were very few updates or notifications as to why this was happening when we would actually arrive. It took nearly 30 minutes for bags to make it to baggage claim. We arrived nearly 1 hour late on a 40 minute flight.

Flight cancelled due to fog. No other flights available for 36 hours. Directed by United to book passage on another carrier, and submit receipts for reimbursement. Did that. United now states they will not reimburse. Currently out 2 grand.

The flight was delayed by 4 hours !!!!! It was very uncomfortable , and they told us only one our before departure

The flights from Ottawa to Albuquerque went smoothly enough though on on flight they didn't have how water for coffee or tea and on another there there was no ice. The return flights from Albuquerque were delayed by mechanical problems on both flights. Ottawa was a ground crew maintenance issue.

The male air hostess was rude and didn’t provide good customer service. Didn’t even offer me a drink

The staff was phenomenal. I can’t think of anything that could be better. Will be flying with UA again

Nothing bad to say about the actual crew or airline. It was nice to have a complimentary FULL can of soda, as well as a snack. Blankets and earbuds were also provided at no cost for this red eye flight. I especially appreciated the free WiFi and movie selection with the Bluetooth option. It helped the flight pass more quickly. No matter who you fly, boarding and disembarking are always SUCH a pain. As I mentioned, this is on the passengers and not the crew!!

The only problem experienced was a ground stop in Chicago due to weather. But the crew handled everything professionally. They prioritized rebooking those passengers who had connecting flights and then deplaning the other passengers. When the hold was lifted, they efficiently re-boarded all the passengers so that we could depart before our departure limit expired.

Our second leg to Jackson WY was unable to land due to weather. We were flown back to Dallas after stopping in SLC. We were given hotel rooms and vouchers. We were told that we would be back on the same plane in the morning. Instead we were given a different flight with different seats. Not a good experience. No one knew what was going on.

Turn on the heat. Flight was way too cold from Arizona to Chicago.

Perfect flight. On time departure and early arrival. Smooth flight.

Overall pleasant was delayed and caused transportation issue when landing

The arriving flight was a few minutes late, but the gate crew helped to deplane and board our outgoing flight quickly and efficiently. We were able to depart quickly and arrive at ORD almost at the posted time. Great job.

Nothing, flight was supposed to leave at 758 am. My flight didn’t leave until 430 pm. Spent the whole day at the airport.

Despite a bumpy flight the pilot was great. The rest of the crew on the other hand couldn’t care less if a passenger would colapse and die. Horrible service, robot like, lifeless…

Biggest issue was original flight canceled and booked to another flight 6 hours earlier and received no notification

It was great. It was just a commuter so I splurged on first class and it was wonderful. Wish all seats were this spacious. Enjoyed it and will do it again.

Book cheap flights from New York to Chicago

Cheapest flights to Chicago from New York found in 2024

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from New York to Chicago found on KAYAK in the last 72 hours.
8/5Wed
directJetBlue
2h 56mJFK-ORD
£51
25/6Tue
directDelta
2h 50mLGA-ORD
£51
11/4Thu
1 stopFrontier
13h 23mLGA-ORD
£51
14/8Wed
directAmerican Airlines
2h 33mEWR-ORD
£55
10/5Fri
directSpirit Airlines
2h 39mLGA-ORD
£59
10/5Fri
1 stopSpirit Airlines
7h 59mLGA-ORD
£61
9/5Thu
directAmerican Airlines
2h 40mEWR-ORD
£71
2/7Tue
directUnited Airlines
2h 38mLGA-ORD
£78
1/6Sat
directUnited Airlines
2h 35mEWR-ORD
£88
8/5Wed
1 stopFrontier
7h 37mLGA-ORD
£95

Search by stops

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Last minute flights from New York to Chicago

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from New York to Chicago that are departing in the next 10 days.
2/4Tue
multi-stop
14h 41mLGA-ORD
4/4Thu
direct
2h 09mORD-LGA
£172
2/4Tue
directSpirit Airlines
2h 48mLGA-ORD
4/4Thu
directSpirit Airlines
2h 09mORD-LGA
£183
2/4Tue
directDelta
2h 40mLGA-ORD
9/4Tue
directDelta
2h 14mORD-LGA
£212
2/4Tue
multi-stopDelta
5h 08mJFK-ORD
10/4Wed
directDelta
2h 14mORD-JFK
£219
2/4Tue
directJetBlue
2h 51mJFK-ORD
3/4Wed
directJetBlue
2h 25mORD-JFK
£237
2/4Tue
directJetBlue
2h 51mJFK-ORD
13/4Sat
directJetBlue
2h 23mORD-JFK
£243
29/3Fri
multi-stopUnited Airlines
13h 55mEWR-ORD
30/3Sat
directUnited Airlines
2h 14mORD-EWR
£260
1/4Mon
directAmerican Airlines
3h 11mJFK-ORD
3/4Wed
directAmerican Airlines
2h 13mORD-JFK
£288
2/4Tue
multi-stopAmerican Airlines
5h 13mJFK-ORD
4/4Thu
directAmerican Airlines
2h 17mORD-JFK
£317
2/4Tue
directUnited Airlines
2h 39mEWR-ORD
15/4Mon
multi-stopUnited Airlines
5h 11mORD-EWR
£317

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New York - Chicago Flights

Destination:

Chicago (ORD)United States

Return flight deals:

Chicago - New York

Cabin classes:

£511
£448
£797
£119

Browse destinations:

  • Flights » 
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  • Chicago » 
  • Chicago O'Hare Airport