NYC - CHI

C$ 97 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 22/10. 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
1 adult, Economy

KAYAK searches 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
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Booking Insights
Flight Deals

Cheap Flights 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 for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from New York to Chicago

Wed, 8 Oct - Wed, 8 Oct
Spirit Airlines Logo
3:29 p.m. - 5:13 p.m.LGA-ORD
2h 44mdirect
Spirit Airlines Logo
6:58 p.m. - 9:00 a.m.ORD-LGA
13h 02m1 stop
C$ 181Spirit Airlines
Find Deal
Mon, 20 Oct - Wed, 22 Oct
Spirit Airlines Logo
3:29 p.m. - 5:13 p.m.LGA-ORD
2h 44mdirect
Spirit Airlines Logo
11:13 a.m. - 2:08 p.m.ORD-LGA
1h 55mdirect
C$ 183Spirit Airlines
Find Deal
Wed, 1 Oct - Wed, 1 Oct
United Airlines Logo
7:28 a.m. - 9:05 a.m.LGA-ORD
2h 37mdirect
United Airlines Logo
5:00 p.m. - 8:17 p.m.ORD-LGA
2h 17mdirect
C$ 184United Airlines
Find Deal
Wed, 8 Oct - Wed, 15 Oct
American Airlines Logo
2:06 p.m. - 3:58 p.m.LGA-ORD
2h 52mdirect
American Airlines Logo
7:00 a.m. - 10:08 a.m.ORD-LGA
2h 08mdirect
C$ 186American Airlines
Find Deal
Wed, 8 Oct - Wed, 15 Oct
Spirit Airlines Logo
5:55 a.m. - 9:33 p.m.LGA-ORD
16h 38m1 stop
Spirit Airlines Logo
6:58 p.m. - 9:00 a.m.ORD-LGA
13h 02m1 stop
C$ 190Spirit Airlines
Find Deal
Wed, 1 Oct - Wed, 1 Oct
Southwest Logo
6:00 a.m. - 12:45 p.m.LGA-ORD
7h 45m1 stop
Southwest Logo
3:10 p.m. - 9:00 p.m.ORD-LGA
4h 50m1 stop
C$ 193Southwest
Find Deal
Sat, 11 Oct - Sun, 12 Oct
United Airlines Logo
6:25 a.m. - 8:02 a.m.LGA-ORD
2h 37mdirect
United Airlines Logo
8:00 a.m. - 11:16 a.m.ORD-LGA
2h 16mdirect
C$ 195United Airlines
Find Deal
Tue, 7 Oct - Tue, 14 Oct
Southwest Logo
7:20 a.m. - 3:20 p.m.LGA-ORD
9h 00m1 stop
Southwest Logo
7:30 a.m. - 9:50 p.m.ORD-LGA
13h 20m1 stop
C$ 200Southwest
Find Deal
Sat, 25 Oct - Mon, 27 Oct
Delta Logo
2:55 p.m. - 4:34 p.m.LGA-ORD
2h 39mdirect
Delta Logo
7:00 a.m. - 10:11 a.m.ORD-LGA
2h 11mdirect
C$ 205Delta
Find Deal
Tue, 28 Oct - Wed, 5 Nov
Delta Logo
8:45 p.m. - 10:26 p.m.LGA-ORD
2h 41mdirect
Delta Logo
6:00 a.m. - 9:07 a.m.ORD-LGA
2h 07mdirect
C$ 218Delta
Find Deal

Everything you should know

Our travellers' advice
AI-generated summary based on content written by travel experts and KAYAK users
Choose Main Cabin Extra on American for early boarding.
Avoid carry-on roller bags on United from Newark.
Expert advice
Expert advice
+1
+1
Expert advice
Expert advice
+1
Top airlines
Spirit Airlines
Cheapest • from C$ 181 (round-trip)
Spirit Airlines
Best reviews • 6.3 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
JFK-ORD
Cheapest • 39% average savings
LGA-ORD
Most popular
Insights
Insights
Insights
Insights
When to book
3 weeks
in advance
Our data shows that travellers who book at least 3 weeks in advance save around 39% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
January
Cheapest • 24% price drop
August
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
C$ 181
Overall average: C$ 337
Spirit Airlines
Wed 8/10Wed 8/10
LGA - ORD • Direct
Cheapest direct flights
C$ 183
Typical prices: C$ 234-500
Spirit Airlines
Mon 20/10Wed 22/10
LGA - ORD • Direct
Start a new search
KAYAK searches hundreds of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Expert advice

Expert advice for your flight from New York to Chicago

 
Snippets provided in this section are AI-generated based on a summarisation of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
American Airlines

Consider Main Cabin Extra for early boarding and complimentary drinks on short flights.


Download the American Airlines app for in-flight entertainment on domestic flights.

United Airlines

Upgrade to Economy Plus for up to 15 cm more legroom on short domestic flights.


Consider Priority Boarding to ensure overhead bin space for your carry-on.

Spirit Airlines

Opt for the Big Front Seat for more legroom and comfort on budget flights.


Bring your own snacks to save money on Spirit flights.

Airports
EWR

For a quick commute to NYC, take the AirTrain to NJ Transit or Amtrak for a 35-60 minute ride to Penn Station.

Read more about EWRby Stefanie Waldek
LGA

LGA's Terminal C offers hands-free bag drop and Digital ID screening, expediting security for a smoother departure.

Read more about LGAby Laura Ratliff
ORD

Take the CTA Blue Line from ORD to downtown Chicago in about 45 minutes, avoiding traffic delays.

Read more about ORDby Stefanie Waldek
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet Baskas

Harriet Baskas

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines, ORD and EWR

Stefanie Waldek

Stefanie Waldek

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Joe Cortez

Joe Cortez

Expert on Spirit Airlines

Joe Cortez

Joe Cortez

Joe Cortez is a seasoned managing editor in aviation with over a decade of industry experience. His work has been featured on prominent platforms such as FlyerTalk and TripSavvy, establishing him as a respected voice in aviation journalism.

Read more
Laura Ratliff

Laura Ratliff

Expert on LGA

Laura Ratliff

Laura Ratliff

Laura Ratliff is a New York-based writer and editor. She lives in downtown Brooklyn with her husband and their beloved dogs. Originally from Texas, she now considers New York City her home. She typically spends more than 200,000 miles on a plane each year and stays in plenty of hotels.

Read more
Booking Insights

KAYAK's insights & trends for New York to Chicago flights

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?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from New York to Chicago costs C$ 134 on the route between New York John F Kennedy Intl Airport (JFK) and Chicago O'Hare Intl Airport (ORD). Over the past month, this route was, on average, 39% cheaper than other New York-Chicago routes. The most popular route is between New York LaGuardia Airport (LGA) and Chicago O'Hare Intl Airport (ORD).

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 round-trip 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 C$ 251 (return) on average. On the other hand, the most expensive months are August and June, where the average cost of round-trip tickets is C$ 388 and C$ 384 respectively.

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

The average round-trip 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.

No, with an average price for the route of C$ 323, prices are generally cheapest when you fly direct.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip 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 week.

To get a below average price on the flight from New York to Chicago, you should book around 3 weeks before departure, which saves you about 39% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 7 weeks before departure.

Good to know

Low seasonJanuary
Best time to beat the crowds (24% less expensive on average)
Most popular time to fly (18% more expensive on average)

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.

Flights from New York to Chicago: the best tips from KAYAK users' own experiences

Insights shared by verified travellers who flew the route from New York to Chicago 
StephenFlew with United AirlinesEWR-ORDJan 2025
Don't bring a carry on roller bag. It won't fit. They will gate check it. It will take forever.
SheenaFlew with SouthwestLGA-MDWJun 2024
Get to the airport early. NY airports are always busy, even when you have TSA pre check
yvgeniFlew with United AirlinesEWR-ORDJan 2024
Check the weather before flying , and don’t rely on getting on time to your destination

FAQs for booking flights from New York to Chicago

  • 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?

    In the last 3 days, the lowest price for a flight from New York to Chicago was C$ 70 for a one-way ticket and C$ 131 for a round-trip.

  • 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, Star Alliance, and SkyTeam 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.

  • 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.

KAYAK’s 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 C$ 467 or less one-way and C$ 355 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.

Prefer to fly direct from New York to Chicago?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from New York to Chicago.
Find which airlines fly direct from New York to Chicago, which days they fly and book direct flights.

Direct departures

New York to Chicago

Monday

American Airlines,Delta,Frontier, +4 more

American Airlines,Delta, +5 more

Tuesday

American Airlines,Delta,Frontier, +4 more

American Airlines,Delta, +5 more

Wednesday

American Airlines,Delta,Frontier, +4 more

American Airlines,Delta, +5 more

Thursday

American Airlines,Delta,Frontier, +4 more

American Airlines,Delta, +5 more

Friday

American Airlines,Delta,Frontier, +4 more

American Airlines,Delta, +5 more

Saturday

American Airlines,Delta,Frontier, +4 more

American Airlines,Delta, +5 more

Sunday

American Airlines,Delta,JetBlue, +4 more

American Airlines,Delta, +5 more

See more nonstop flights

Direct returns

Chicago to New York

Monday

American Airlines,Delta,Frontier, +4 more

American Airlines,Delta, +5 more

Tuesday

American Airlines,Delta,Frontier, +4 more

American Airlines,Delta, +5 more

Wednesday

American Airlines,Delta,Frontier, +4 more

American Airlines,Delta, +5 more

Thursday

American Airlines,Delta,Frontier, +4 more

American Airlines,Delta, +5 more

Friday

American Airlines,Delta,Frontier, +4 more

American Airlines,Delta, +5 more

Saturday

American Airlines,Delta,Frontier, +4 more

American Airlines,Delta, +5 more

Sunday

American Airlines,Delta,JetBlue, +4 more

American Airlines,Delta, +5 more

See more nonstop flights

Reviews of the top airline flying 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.
6.3
Spirit AirlinesOverall score based on 8023 reviews
6.6Boarding
5.0Entertainment
5.1Food
7.0Crew
5.9Comfort
Airline reviews

Everything was fine. I'm average height and I pack light. I'm ready for my Spirit flight.

10.0 ExcellentRonald, Sep 2025LGA - FLL
Read more Spirit Airlines reviews

Everything was fine. I'm average height and I pack light. I'm ready for my Spirit flight.

Just total easy flight experience!! What could you do better..? Hmmm..? There was nothing I can remember. Spirit was a far more comfortable and easy process than American, United & Delta. I'll always look for Spirit and I've told a few people about, since flying this past trip!! I'm a SPIRIT FAN!! Thank You, SPIRIT AIRLINES!! Very, VERY well done, 100%!! See you...SOON!! -Best, Linda R.

Spirit is a very uncomfortable travel experience. It’s cheap but you are squeezed into the seats like canned meat.

The seat belt was lengthy enough that I did not need an extender. Courteous and helpful flight attendants.

As expected. Nothing jumps out at me as bad or wrong, but the flight was fine. No complaints with pilot or crew. The flight left on time and arrived earlier than stated. Overall, I will continue to plan on flying with Spirit.

Horrible considering I didn’t go and I bought travel insurance and I didn’t receive a refund.

While on the flight we had a delay and had to sit on the plane while maintenance fixed it. It’s ended up taking an hour and a half longer to leave than expected. I had an unruly passenger sitting behind me that vaped during the flight and was rude and loud for the majority of the flight.

Spirit is by far the worst airline to travel with, period. Seats are cardboard, flight attendants need anger management and if you ask for water, you’re basically a criminal. I don’t care how much it costs but I will travel with an airline who actually cares about their customers. Oh and one more thing, the next time your gate agent puts his foot on someone’s baggage's scale, I hope they get what’s coming next, a viral video of your scams. You suck Spirit, do better.

I mean, it’s Spirit. But it was frustrating to have our flight canceled, get bumped to a later flight, and then Spirit was unwilling to check our bag until 4 hours before our flight… tell us we could not sit in the waiting area’s chairs… and really negative experience getting checked in and dropping the bag.

Not having it be changed after we bought the flight tickets from a direct flight getting in at a reasonable time to a connecting flight red eye of 9 hours, so that we would lose our 35 dollars in nonrefundable insurance would've been great! Our country really does need low-cost carrier options, but this type of "service" ain't it. Fortunately, had a little better success with them flying to and from San Juan PR last month at least.

Everything you need to know for your flight from New York to Chicago

Cabin class types available on flights from New York to Chicago

Cabin classes available on flights from New York to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability are not guaranteed.

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