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NYC - CHI

$32 Find cheap flights from New York to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from New York to Chicago departing on 8/21. 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 8/24
Sat 8/31

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.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from New York to Chicago.
In the last 7 days travelers have searched 50,552,696 times on KAYAK, and here is why:

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Cheap flight deals from New York to Chicago (NYC-CHI)

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
9:21 pm - 10:58 pmEWR-ORD
2h 37mnonstop
5:03 pm - 8:21 pmORD-EWR
2h 18mnonstop
$74Spirit Airlines
Find Deal
Wed, Aug 14 - Tue, Aug 20
9:21 pm - 10:58 pmEWR-ORD
2h 37mnonstop
5:03 pm - 8:21 pmORD-EWR
2h 18mnonstop
$75Spirit Airlines
Find Deal
Tue, Aug 20 - Tue, Aug 27
3:20 pm - 5:16 pmJFK-ORD
2h 56mnonstop
7:05 am - 10:31 amORD-JFK
2h 26mnonstop
$108Delta
Find Deal
Thu, Sep 5 - Mon, Sep 9
3:20 pm - 5:16 pmJFK-ORD
2h 56mnonstop
7:05 am - 10:31 amORD-JFK
2h 26mnonstop
$110Delta
Find Deal
Thu, Sep 5 - Mon, Sep 9
3:20 pm - 5:15 pmJFK-ORD
2h 55mnonstop
9:25 am - 12:50 pmORD-JFK
2h 25mnonstop
$132JetBlue
Find Deal
Sat, Sep 7 - Sat, Sep 21
3:20 pm - 5:15 pmJFK-ORD
2h 55mnonstop
6:20 pm - 9:51 pmORD-JFK
2h 31mnonstop
$148JetBlue
Find Deal
Thu, Sep 5 - Mon, Sep 9
9:25 am - 3:24 pmJFK-ORD
6h 59m1 stop
9:40 am - 2:50 pmORD-JFK
4h 10m1 stop
$155American Airlines
Find Deal
Sat, Aug 10 - Mon, Aug 12
3:45 pm - 5:36 pmJFK-ORD
2h 51mnonstop
11:33 am - 2:50 pmORD-JFK
2h 17mnonstop
$157American Airlines
Find Deal
Wed, Aug 14 - Tue, Aug 27
7:00 am - 8:35 amEWR-ORD
2h 35mnonstop
6:00 am - 9:14 amORD-EWR
2h 14mnonstop
$159United Airlines
Find Deal
Tue, Aug 13 - Tue, Aug 27
8:20 pm - 9:58 pmLGA-ORD
2h 38mnonstop
6:00 am - 9:14 amORD-LGA
2h 14mnonstop
$198United Airlines
Find Deal
Fri, Aug 9 - Sun, Aug 11

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 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.
Our data shows that the cheapest route for a one-way flight from New York to Chicago cost $53 and was between Newark Airport and Chicago O'Hare Intl Airport. On average, the best prices are found if you fly from New York LaGuardia Airport to Chicago Midway Airport. The average price for a return flight for this route is $90.

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 clicked on KAYAK for each day over the last 12 months.
For New York to Chicago, Tuesday is the cheapest day to fly on average and Sunday is the most expensive. Flying from Chicago back to New York, the best deals are generally found on Wednesday, with Sunday being the most expensive.

What is the cheapest month to fly from New York to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from New York to Chicago, 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 is January, where tickets cost $196 on average. On the other hand, the most expensive months are December and October, where the average cost of tickets is $287 and $286 respectively.

Can I save money by flying with a layover from New York to Chicago?

The average price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.
Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $338 on average

How far in advance should I book a flight from New York to Chicago?

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, 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, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 160 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.
In the past 3 days, the cheapest one-way tickets to Chicago from New York were found on Spirit Airlines ($32) and JetBlue ($48), and the lowest round-trip tickets were found on Spirit Airlines ($74) and Frontier ($102).

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 (181 flights per week), American Airlines (99 flights per week), and Delta (84 flights per week).

Which airlines fly non-stop between New York and Chicago?

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.
There are 6 airlines that fly nonstop from New York to Chicago. They are: American Airlines, Delta, JetBlue, Southwest, Spirit Airlines and United Airlines. The cheapest price of all airlines flying this route was found with Spirit Airlines at $44 for a one-way flight. On average, the best prices for this route can be found at Spirit Airlines.

How many flights are there between New York and Chicago per day?

Each day, there are between 48 and 68 nonstop flights that take off from New York and land in Chicago, with an average flight time of 2h 36m. The most common departure time is 6:00 am and most flights take off in the morning, while the most flights land at Chicago O'Hare Intl Airport. Each week, there are 445 flights. The most frequent day of departure is Tuesday, 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?

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 4 cabin class options for the route. These are First, Business, Economy and Prem 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?

Direct flights cover the 711 miles separating New York to Chicago in about 2h 32m.

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

Early birds can take the earliest flight from New York at 5:51 am and will be landing in Chicago at 7:20 am.

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 jets off at 10:50 pm and lands at 12:26 am.

Good to know

Low season

January

High season

August

Cheapest flight

$32
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly with an average 10% increase in price.
Flight from Newark Liberty Airport to Chicago O'Hare Airport

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 round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips 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 flights from New York to Chicago

  • Is there public transportation from Chicago Midway International Airport (MDW) to downtown Chicago?

    Chicago Midway International Airport (MDW) is located approximately 11.2 miles from the city center of Chicago. The easiest way to get there is via the Orange Line train service, which connects the two destinations in about 25 minutes.

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

    Chicago Midway (MDW) is closer to downtown Chicago, and as a smaller airport, it can be less busy and easier to navigate. However, due to the 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 Airport (ORD) to downtown Chicago?

    Request a ride with Uber to travel from ORD to Chicago city center. The trip typically takes 40 minutes, covering a distance of approximately 18 miles. The price for an Uber trip from ORD to Chicago city center usually starts around $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 Airport (ORD)?

    Chicago O'Hare International Airport (ORD) offers a cell phone lot for individuals wishing to pick up arriving passengers. The lot features a flight information display to alert those waiting when their passengers have arrived. Stopping in front of the terminal is not permitted except for immediate pickup of passengers. Therefore, the cell phone lot serves as an excellent option for those awaiting arriving passengers.

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

    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 in Astoria and then grab a taxi or Uber to the airport. The ferry offers both alcoholic and non-alcoholic drinks as well as a variety of snacks on board, making it a comfortable journey overall.

  • Are there car rentals from O'Hare International Airport (ORD) to downtown Chicago?

    You'll find several rental car companies at O'Hare International Airport (ORD) to suit your needs. You can pick up your rental car from Suite 830 or at Routes Car & Truck Rentals, located at 3901 Mannheim Rd, Schiller Park. It's helpful to make a booking in advance.

  • Are there any services for passengers with limited mobility at the Chicago airports upon their arrival?

    You’ll receive special services for passengers with disabilities and mobility limitations at any of the airports in Chicago, including ORD and MDW. However, it may be best to make early arrangements with your carrier. Services include wheelchairs and guidance for those with communication challenges.

  • Which is the best arrival airport if I want to visit the Museum of Science and Industry?

    The nearest airport to the Museum of Science and Industry is Chicago Midway (MDW) Airport, which is 8.3 miles away. Chicago O'Hare (ORD) is the main airport serving Chicago. The Museum of Science and Industry is located about 24.2 miles from ORD, and there are several transportation options to get you there. Bus line 6 connects the two points in about 1 hour and 18 minutes, while bus line 28 takes around an hour longer. Alternatively, you can use the subway, which takes about 1 hour and 17 minutes.

  • What is the cheapest flight from New York to Chicago?

    In the last 3 days, the lowest price for a flight from New York to Chicago was $32 for a one-way ticket and $74 for a round-trip.

  • Do I need a passport to fly between New York and Chicago?

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

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

    On your way to Chicago, you’ll fly out from one of these New York airports: Newark, New York John F Kennedy Intl, or New York LaGuardia. You’ll be landing in one of Chicago’s 2 airports: Chicago Midway or Chicago O'Hare Intl.

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

    American Airlines, JetBlue, and Delta 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 nonstop flights from New York to Chicago on a daily basis.

  • Which is the best airline for flights from New York to Chicago, Southwest or Delta?

    The two airlines most popular with KAYAK users for flights from New York to Chicago are Southwest and Delta. With an average price for the route of $281 and an overall rating of 8.1, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $263 and an overall rating of 8.0.

  • 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 travelers 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 round-trip 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? 25% of our users found flights on this route for $108 or less one-way and $202 or less round-trip.
  • If you choose to fly aboard American Airlines from New York to Chicago, please note that the airline's hub is located at O'Hare International Airport (ORD). Additionally, you can find alternative flight options to ORD from other airports in New York.
  • If you're planning to reserve a flight from New York to Chicago, you'll have more options available when flying to Chicago's main airport, ORD. The majority of direct flights departing from New York to Chicago arrive at this airport.
  • If you are looking for a budget-friendly way to get from Chicago O'Hare International Airport (ORD) to downtown Chicago, look no further than a ride on the EL Train. The trip costs just a few dollars and takes you directly into downtown Chicago. It's important to note that this option may be challenging if you are traveling with more than one or two bags.
  • If you do not want to deal with the hustle and bustle of downtown Chicago, there are many hotels located near Chicago O'Hare International (ORD) that will suit any traveler’s taste and budget. The SpringHill Suites by Marriott Chicago O'Hare offers 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 perfect for you as it has an indoor pool and kids’ menus.
  • Several fabulous hotels lie next to major airports in New York and are known for their courtesy shuttles to and from the airport. Those departing from John F. Kennedy International (JFK) should consider booking a room at the elegant Fairfield Inn By Marriott JFK Airport or the majestic Five Towns Inn – JFK Airport. Spending a night at any of these hotels is convenient for those with morning flights.
  • If man's best friend will also be traveling on your flights from New York to Chicago, each terminal at Newark Liberty International Airport (EWR) offers a pet relief station. The areas in Terminals B and C are pre-security, while the area in Terminal A is post-security.
  • The Amex Centurion Lounge at New York LaGuardia (LGA) 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 crafted by one of the nation's top mixologists. The lounge is located pre-security, on the 3rd floor between Terminals B and C.
  • Before catching your flight from any of the New York airports, take the time to explore the various attractions within the airport. If you’re departing from Newark Liberty International (EWR), why not stop at Terminal C and browse the boutiques? Relax with a chair massage or get your nails done at a salon in Terminal C, Gate 92.
  • If you'll be arriving at O'Hare International Airport (ORD), don't miss the opportunity to explore the unique public art displayed throughout the airport. Head to concourses B and C to browse the sculptures, murals and paintings depicting the region's hidden art. If you're looking to get your blood pumping, step into the gym in Terminal 2 and freshen up. Also, be sure to check out the expansion of O'Hare Airport's Terminal 5, which includes 19 new artworks by Chicago artists.
  • 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 in New York's John F. Kennedy International Airport (JFK). Shake Shack offers burgers, chicken sandwiches, hot dogs and, of course, amazing shakes.
See more tips

Prefer to fly non-stop from New York to Chicago?

Find which airlines fly direct from New York to Chicago, which days they fly and book direct flights.

Nonstop departures

New York to Chicago

Monday

ANA, Air Europa, Air France, +31 more

ANA, Air Europa, +32 more

Tuesday

ANA, Aerolineas Argentinas, Air Europa, +33 more

ANA, Aerolineas Argentinas, +34 more

Wednesday

ANA, Air Europa, Air France, +31 more

ANA, Air Europa, +32 more

Thursday

ANA, Air Europa, Air France, +31 more

ANA, Air Europa, +32 more

Friday

ANA, Aerolineas Argentinas, Air Europa, +32 more

ANA, Aerolineas Argentinas, +33 more

Saturday

ANA, Air Europa, Air France, +31 more

ANA, Air Europa, +32 more

Sunday

ANA, Aerolineas Argentinas, Air Europa, +33 more

ANA, Aerolineas Argentinas, +34 more

See more direct flights

Nonstop returns

Chicago to New York

Monday

ANA, Aerolineas Argentinas, Air Europa, +33 more

ANA, Aerolineas Argentinas, +34 more

Tuesday

ANA, Aerolineas Argentinas, Air Europa, +32 more

ANA, Aerolineas Argentinas, +33 more

Wednesday

ANA, Aerolineas Argentinas, Air Europa, +33 more

ANA, Aerolineas Argentinas, +34 more

Thursday

ANA, Aerolineas Argentinas, Air Europa, +32 more

ANA, Aerolineas Argentinas, +33 more

Friday

ANA, Aerolineas Argentinas, Air Europa, +32 more

ANA, Aerolineas Argentinas, +33 more

Saturday

ANA, Aerolineas Argentinas, Air Europa, +32 more

ANA, Aerolineas Argentinas, +33 more

Sunday

ANA, Aerolineas Argentinas, Air Europa, +32 more

ANA, Aerolineas Argentinas, +33 more

See more direct flights
See more direct flights

Top 5 airlines serving from New York to Chicago

 
See real verified KAYAK customer reviews for airlines flying from New York to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
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 verified KAYAK customer reviews.
8.0
DeltaOverall score based on 9630 reviews
7.9Comfort
8.6Crew
8.2Boarding
7.4Food
8.0Entertainment
Airline reviews

Older plane and it came with Fleas and flea bites!

4.0 OkayMichael, Jul 2024LGA - ORF
Read more about Delta reviews

Older plane and it came with Fleas and flea bites!

All good on Delta's part. Passengers could be a little more courteous to each other.

The fight was about 2 1/2 hours delayed, but that was weather related. The flight was also overbooked. But we were in Comfort plus so the flight was fine for us.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

I'm a larger, athletic guy (6'2", 260lbs powerlifter) and I found the seats incredibly uncomfortable with minimal leg room, especially in a window seat. Now, I full understand that being smaller may change my view but even if I was 80lbs less, my legs would be the same size and I was sandwiched between my seat and the seat in front of me.

Seat back monitors and outlets were dead and not working.

I usually have a positive experience with Delta. Complimentary upgrades are always nice!

Service was good for such a short flight. Small plane but smooth flight.

The flight was delayed but we got to our final destination.

Uncomfortable seats on 14 hour flight. Mediocre food. On time and great crew.

I volunteered to let them put my carry on suitcase in the baggage storage area. But when we landed I was told it was being unloaded IN A DIFFERENT TERMINAL! I had to walk (painful for me) a long way to retrieve my bag and my ride had to move from the waiting area they were in to a totally different one. Not happy.

Over 2 hour delay for a 50-minute flight is unacceptable, especially in normal weather. Very poor communication via app

The flight was excellent. The crew was welcoming and attentive.

Going through JFK’s security is a mess. The TSA security said no shoes on the bins. So, we place our shoes in the belt and they came out all over the belt. Boarding was delayed and Flight as well.

There were multiple delays but JetBlue tried to make the boarding and departure process as quick and efficient as possible. The crew was as detached from reality as could be, meaning: not very friendly and just doing things by the numbers.

40 minute delay before take off after boarding flight. Bright lights throughout night flight due Issues with light panels. In flight Entertainment nonfunctional

Another horrible Jet Blue experience. This airline has suffered the biggest decline of all from best to worst. TVs didn’t work (again). internet was temperamental. Boarded late and couldn’t get organized to serve snacks.

I hate their constant delays! It’s as if I cannot confidently make plans for timing when I'm traveling with them. I slept through it, so all I can say is it was good.

There was no wheelchair or wheelchair escort at the gate..unacceptable

From bag drop to boarding, it was great. In-flight is a little different. The seats were a little uncomfortable for that long of a flight. The rest of the cabin crew except for Eva was wonderful. Eva was not friendly at all. I've had to personally encounter her twice in-flight. First time was when I had to go to the lavatory in the back of the plane, and since it was the first for me to board such tiny plane, I didn't know we were using the crew toilet. She was giving me an attitude while telling me where and how to open it since it's not the regular push to open type of door. The second one was when I had to throw trash then use the lavatory again. I asked where to throw them, and unfortunately she was the only crew in the back doodling on her phone, she had to point it out to me with an attitude then told me to wait on the carpet, which I understand because I didn't realize that, but she could have been nicer. After all, I'm a paying customer, and assisting a passenger who isn't knowledgeable about the aircraft is one of the things she's there for. The rest of the experience and crew from bag drop to in-flight were excellent except for her.

The new Airbus A231neo has neat tech but the economy seats are so tight together that I always had my shoulders against one passenger or the other. I was very miffed that Basic Economy REQUIRES check-in of bags other than your personal carry-on; if you want to offer low-cost airline prices and then add services for a fee, just let me carry on my duffel. Hell, I could have put my carry on IN the duffel and called it a day but the gate agent would not let me; I ended up paying $40 for the risk of losing my bag. Not the worst flight, but far from the best.

It is a modern tragedy that any airline expects you to travel for 14 hours in such discomfort and that the only way to add comfort is exorbitant prices. I was in pain by the time we landed. Shameful.

After the morning frenzy of 35 min wait through CLT security at 4;30 AM, it was nice to have a smooth pleasant boarding experience. This 6:30 AM flight was not full. We were able to get seated swiftly and took off promptly. Nice touch they distributed the old fashioned headsets with 8 mm jacks. Snacks were decent and arrival was uneventful.

I had a great flight. Everything went smoothly and the flight arrived early.

The flight and boarding were easy peasy. I was traveling with my 4-year-old, so a smooth boarding experience was especially appreciated. My only piece of feedback is really about where our gate was in O'Hare. They've shoved four gates into a tiny corner of the B terminal and there isn't early enough room or seating for everyone. Not United's problem, but did dent the overall experience.

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

The flight was delayed instead of leaving at 11 it left at 12.20

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

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

It was freezing in there. When I asked about it, the response is “we would have to tell them” and then she just walked away and continued to serve beverages. Everyone was cold and they didn’t care at all.

I did not enjoy continuously being lied to about the amount of time we would circle Chicago before deciding to redirect to Milwaukee. Then the amount of time we would sit on the ground in Milwaukee waiting for gas, or to take off again. Or the amount of time it would then take to get to Chicago again, or sit on the runway waiting for a gate. The whole time continuously hopefully we would make our connecting flight that kept getting delayed as well. Only to scramble and miss it. Enough with the BS. Tell me the truth. "Sorry, things are backed up and your probably not going to make your flight. You should rebook on the next flight now rather than wait." You'll never hear those words from an airline. Speaking of which. If the flight has been redirected and/or is seriously delayed, how about making the WiFi free for everyone so they get to rebooking and reserving hotel rooms while still in the air. You've inconvenienced me already and now you want me to pay $20 for Internet so I can try to make other plans. Absolutely disgusting!

Great flight. The captain did a great job of minimizing some minor turbulence and in general it was a smooth flight. Early departure and early arrival at destination. Great service.

Our flight left on time and we arrived a few minutes early. Great service!

Our 9:10 am scheduled flight continued to get delayed all day with no information given from the agents as to why. It wasn’t until I went to the customer service desk and got us switched to another flight at 2:44 pm (that wasn’t nonstop like our booked flight) that the agent finally was able to find out it was due to a fuel leak. I don’t know if our original flight ever took off but I don’t find it acceptable to leave people sitting in an airport all day with no explanation.

I am very disappointed with american. We have flown American airlines numerous times, as well as other airlines and never had such an experience. My son's flight for Sunday afternoon was cancelled around 11 am. We were told not to do anything bec AA would. After an hour of not seeing a change in his flight status. I called AA. I was on hold for half hour then opted for a call back. That call back never came. So I called again, in meantime I started looking online at my options. No flights were leaving that day from AA. But other airlines were flying out. We needed our son in Chicago asap.i kept calling AA for a callback, but never received one. Finally i called back later in the afternoon and a representative answered the call. She told me there were no flights out till Tuesday morning. I asked how this is possible, I had seen flights from AA and other airlines leaving Monday. She said she checked all NYC airports and there were no AA flights till Tuesday AM. Then I asked about getting on another airline. She responded i would be responsible for that. When I asked how AA would reimburse. She became nasty and told me AA has not responsibility to reimburse anything they will put me in a flight for Tuesday morning. When i explained he must be there Monday by 8am, she told me there's nothing to do and practically hung up. At that point I just asked her to book the Tuesday morning flight. I had this experience with other airlines, cancelled due to weather and they and their reps were much more helpful. Either way Tuesday morning flight was delayed as well. Over an hour! I expect more from AA.

When you pay for Premium Economy on an 787 and you’re promised amenities for the extra money, you expect them to work. They didn’t. USB connector wouldn’t charge continuously. 120v outlet wouldn’t hold anything you plugged into it. The adapter would just fall out. The noise canceling headphones stopped noise cancelling in the first 15 minutes for EVERYONE. No one on the plane knew how to fix it so I couldn’t listen to any movies. I just put in my AirPods and went to sleep. Very unhappy with the crappy Panasonic entertainment system. I won’t buy premium again.

Our flight was delayed by 18 hours. Poor accommodations made and no apology.

This flight was awful all around. Delays on the tarmac at PHL before takeoff and at the tarmac in Chicago caused me to miss my final connection. This was completely avoidable, in my opinion.

Internet service was erratic. Crew service was poor and slow. My luggage on this non-stop flight was lost and not recovered

Would have been better if I would’ve made it on my flight but it was delayed twice and then canceled and now I’m stuck till Monday which was and extra 5 days I did not count on .

You get what you pay for, but those tickets weren't cheap, so I expected better, but Spirit is just one of those airlines.

Both flights were delayed. Flight from LGA to DTW caused serious anxiety as 3 people were removed from the aircraft before take off for disorderly conduct. Extremely uncomfortable to be in that situation. Staff handled themselves okay- definitely could’ve been more professional and deescalated the situation first. No apology for the delays at all. No water, no snack, no nothing. Not a good flight experience.

Cancelled the return flight moments before boarding, horrible customer service in assisting with any rebooking. Never again will I fly Spirit.

The flight was minimally delayed and after landing we needed to wait an hour, hungry, thirsty, and with other customers improper behavior. Flight was good and quick, boarding was delayed but quick. Thanks

Overall, poor. Boarding was extremely slow, which caused flight delays.

Flight got diwngraded last minute and left us stranded. I was told I’ll be given credit for my luggage and seat upgrades but haven’t got anything yet

Crew was nice, explained emergency protocol very well. Flight took off and arrived on time. Pilot explained the small delay that occurred with docking and providing updates. I would definitely fly spirit again.

The seat are terrible. Don’t even think of sleeping on a Spirit flight. The kids that run the plane aka flight attendants are pretty rude and straight forward. They get the job done but without class.

I had a death in my family and booked my flight on Spirit. My flight was cancelled the morning of my flight, no explanation, no help to rebook, nobody to talk to. The next available flight was 2days later !!!! Terrible airline, will NEVER fly with them again!

Book cheap flights from New York to Chicago

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.
8/21Wed
nonstopSpirit Airlines
2h 37mEWR-ORD
$32
8/20Tue
nonstopSpirit Airlines
2h 37mEWR-ORD
$37
8/20Tue
nonstopJetBlue
2h 53mJFK-ORD
$48
9/6Fri
nonstopAmerican Airlines
2h 36mLGA-ORD
$64
8/28Wed
nonstopJetBlue
2h 45mJFK-ORD
$64
9/3Tue
nonstopAmerican Airlines
2h 39mJFK-ORD
$68
8/28Wed
1 stopDelta
3h 33mEWR-MDW
$78
10/12Sat
1 stopDelta
5h 01mEWR-MDW
$79
8/5Mon
nonstopUnited Airlines
2h 35mLGA-ORD
$91
8/25Sun
1 stopUnited Airlines
4h 35mEWR-ORD
$94

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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.
7/30Tue
nonstopSpirit Airlines
2h 38mLGA-ORD
7/31Wed
nonstopSpirit Airlines
2h 16mORD-LGA
$97
7/30Tue
nonstopSpirit Airlines
2h 38mLGA-ORD
8/6Tue
nonstopSpirit Airlines
2h 18mORD-LGA
$98
7/30Tue
nonstopAmerican Airlines
2h 35mEWR-ORD
8/1Thu
nonstopAmerican Airlines
2h 10mORD-EWR
$181
7/30Tue
nonstopDelta
2h 58mLGA-ORD
8/1Thu
nonstopDelta
2h 14mORD-LGA
$181
7/30Tue
nonstopAmerican Airlines
2h 35mEWR-ORD
8/2Fri
nonstopAmerican Airlines
2h 04mORD-EWR
$194
7/30Tue
nonstopDelta
2h 58mLGA-ORD
8/2Fri
nonstopDelta
2h 19mORD-LGA
$194
7/30Tue
nonstopJetBlue
2h 53mJFK-ORD
8/6Tue
nonstopJetBlue
2h 18mORD-JFK
$194
7/30Tue
nonstopJetBlue
2h 53mJFK-ORD
8/2Fri
nonstopJetBlue
2h 25mORD-JFK
$269
7/30Tue
nonstopUnited Airlines
2h 35mEWR-ORD
8/19Mon
nonstopUnited Airlines
2h 29mORD-EWR
$302
7/26Fri
nonstopUnited Airlines
2h 35mEWR-ORD
8/5Mon
nonstopUnited Airlines
2h 20mORD-EWR
$322

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Flights to Chicago

Return flight deals:

Chicago - New York

Cabin classes:

$465
$250
$259
$90

Compare transportation modes for New York to Chicago

Average priceAverage duration
Flights$6242h 20m
Trains$23020h 45m
Buses$17721h 54m