Cheap Flights from New York, NY to Chicago, IL from $29
On Cheapflightsplus.com you will find 58 direct and 756 connecting flights from New York to Chicago. You can compare airfare deals from 18 airlines and multiple travel sites from $29, book and save on cheap plane tickets and last minute offers. Also check out NYC-CHI flight schedule to find best flight time, convenient departure and arrival airports.
Flight Information
Below we will explain in detail what the flights cost on the destination from New York to Chicago depends on and how to choose the most interesting flight option for you.
Distance between New York and Chicago is 1144 miles. Time difference between the cities is 1h. Airplanes depart 01:20 to 23:45 from 16 New York airports and arrive 01:20 to 23:45 to 7 Chicago airports. Average flight time is 2h 37m.
- The fastest flight 2h 20m
- Average flight time 2h 37m
- The earliest flight 01:20
- The latest flight 23:45
- Distance 711 ml
Best Flights from New York to Chicago Today
| Price | Departure | Arrival | Flight Duration | Airline | Flight |
|---|---|---|---|---|---|
| from $29 | 11:00 New York John F Kennedy Intl | 12:45 Chicago O'Hare International | 2h 45m | Frontier Airlines | F91043 |
| from $50 | 15:29 New York La Guardia | 17:13 Chicago O'Hare International | 2h 44m | Spirit Airlines | NK494 |
| from $73 | 06:25 New York La Guardia | 08:02 Chicago O'Hare International | 2h 37m | United Airlines | UA2330 |
| from $43 | 11:59 New York La Guardia | 18:38 Chicago O'Hare International | 7h 39m layover 1h 19m - Miami | Spirit Airlines | NK374 NK1225 |
| from $69 | 19:59 New York La Guardia | 09:22+1 день Chicago O'Hare International | 14h 23m layover 7h 50m - Miami | Spirit Airlines | NK394 NK1530 |
The cheapest months to travel to Chicago are october (from 29 $), september (from 111 $), august (from 111 $).
The most expensive months are june (from 123 $), july (from 115 $), august (from 111 $).
What is the lowest airfare New York to Chicago?
The cheapest plane ticket found by our users is $29. This airfare is for economy class on one-way F91043 flight by Frontier Airlines for October 22, 2025 which leaves John F Kennedy Intl in New York at 11:00 am and arrives at Chicago O'Hare International at 12:45.
Flight Schedule New York (New York) to Chicago (Illinois)
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Popular Airlines on the Route
The flight New York — Chicago is served by 18 regular airlines and 7 low-cost airlines. Most of the flights on this route are operated by American Airlines - 220 departures per week at the price of from $ 236 . And the most expensive tickets are offered by Qatar Airways airline - from $ 9094.
Direct flights
There are 58 nonstop flights on the route. The fastest direct flight is WN4429 by Southwest Airlines takes 2h 20m and the cheapest is F91043 by Frontier Airlines for $29.
- AA - American Airlinesfrom $236Find
- F9 - Frontier Airlinesfrom $29Find
- B6 - JetBluefrom $214Find
- WN - Southwest Airlinesfrom $235Find
- DL - Delta Air Lines Inc.from $229Find
- UA - United Airlinesfrom $73Find
- NK - Spirit Airlinesfrom $50Find
Connecting Flights
There are 756 flights with layovers on the route. The fastest connecting flight is AA4719 by American Airlines takes 3h 53m and the cheapest is F91043 by Frontier Airlines for $43.
- AA - American Airlinesfrom $248Find
- QR - Qatar Airwaysfrom $9094Find
- AC - Air Canadafrom $669Find
- FI - Icelandairfrom $1401Find
- DL - Delta Air Lines Inc.from $270Find
- UA - United Airlinesfrom $94Find
- VB - VivaAerobusfrom $648Find
- AM - Aeromexicofrom $698Find
- LX - SWISS International Air Linesfrom $5516Find
- AS - Alaska Airlinesfrom $778Find
- F9 - Frontier Airlinesfrom $75Find
- B6 - JetBluefrom $357Find
Airports
You can fly from New York to Chicago from 16 airports (39th Street Ferry, Newyork Airport, Newyork Airport, La Guardia, Westchester County, World Trade Center, Pier 11/Wall St. SPB, John F Kennedy Intl, Flushing, East 34th St Heliport, West 30th St Heliport, Downtown Manhattan H/p, East 60th Street H/P, Battery Pk City/N. Cov, East 34th St Landing, Marine Air Terminal).
New York airports
- 39th Street Ferry-XNYFind
- Newyork Airport-NWKFind
- Newyork Airport-NYPFind
- La Guardia-LGAfrom $43Find
- Westchester County-HPNFind
- World Trade Center-WTCFind
- Pier 11/Wall St. SPB-NWSFind
- John F Kennedy Intl-JFKfrom $29Find
- Flushing-FLUFind
- East 34th St Heliport-TSSFind
- West 30th St Heliport-JRAFind
- Downtown Manhattan H/p-JRBFind
- East 60th Street H/P-JREFind
- Battery Pk City/N. Cov-NBPFind
- East 34th St Landing-NESFind
- Marine Air Terminal-QNYFind
Chicago airports
- O'Hare International-ORDFind
- Midway-MDWFind
- Dupage County-DPAFind
- Chicago FSS-CHIFind
- Merrill C Meigs (closed)-CGXFind
- Pal-Waukee-PWKFind
- Chicago NAS-NOHFind
Airplanes
There are flights to Chicago from New York by 18 airlines that use 10 aircraft brands. They range from huge modern airplanes to small-sized.
- Boeing 737 MAX 8from $73Find
- Airbus A318/319/320/321from $162Find
- Boeing 737-800from $235Find
- Boeing 737from $235Find
- Embraer 175 (short wing)from $236Find
- Airbus A319from $237Find
- Canadair Regional Jet 900from $248Find
- Airbus A321from $260Find
- Canadair 900from $266Find
- A220-100from $266Find
Top Domestic Destinations from New York
You may also consider searching for discounted plane tickets to some other popular places from New York within United States.
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Top International Destinations from New York
Our state-of-the art metasearch will definitely provide you with the best airfare on international flights. We’re proud to partner with many reliable travel suppliers located outside the US what gives us an opportunity to offer the most competitive prices on far destinations.
- from $65Find
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How to book a plane ticket yourself?
- Fill in the search parameters — cities of departure and destination, departure and return dates and click «Find flights»
- Select the best flight that you like. Please, check the airports of departure and arrival. Select the best fare, but pay attention to the following flight details - airports of departure and arrival, flight duration and layovers. Please use filters and sort to find the best flight.
- Click «Buy» when you are ready — our system will redirect you to the site that sells the selected flight ticket.
- Fill in all passenger and payment information — passport and contact information, please double check all passengers’ names and make a payment for your itinerary.
- That's it — you will receive an email with your e-ticket usually within 10 minutes after your flight is confirmed. Please, print the e-ticket and have it with you at the airport. You would need to have only a passport and/or a required form of ID to travel. Please, check your Visa requirements if you travel outside of the United States or Canada.
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