Cheap Flights from New York, NY to Chicago, IL from $29

Return flight: Chicago – New York

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

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.

Economy class
$29
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Business class
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First class
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Flight Schedule New York (New York) to Chicago (Illinois)

05:55 — 07:33
2h 38m flight time
Find flight
from$253
New York — Chicago
AA462 American Airlines
06:25 — 08:02
2h 37m flight time
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from$73
New York — Chicago
UA2330 United Airlines
07:28 — 09:05
2h 37m flight time
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from$73
New York — Chicago
UA2389 United Airlines
07:28 — 09:05
2h 37m flight time
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from$112
New York — Chicago
UA2440 United Airlines
08:25 — 10:02
2h 37m flight time
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from$73
New York — Chicago
UA1554 United Airlines
08:25 — 10:02
2h 37m flight time
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from$111
New York — Chicago
UA2479 United Airlines
09:18 — 10:55
2h 37m flight time
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from$73
New York — Chicago
UA623 United Airlines
10:20 — 11:57
2h 37m flight time
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from$73
New York — Chicago
UA1310 United Airlines
10:20 — 11:57
2h 37m flight time
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from$112
New York — Chicago
UA561 United Airlines
11:00 — 12:45
2h 45m flight time
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from$29
New York — Chicago
F91043 Frontier Airlines
11:20 — 12:57
2h 37m flight time
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from$73
New York — Chicago
UA705 United Airlines
12:24 — 14:04
2h 40m flight time
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from$273
New York — Chicago
AA512 American Airlines
13:18 — 14:55
2h 37m flight time
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from$73
New York — Chicago
UA2199 United Airlines
14:20 — 15:57
2h 37m flight time
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from$73
New York — Chicago
UA2360 United Airlines
15:25 — 17:02
2h 37m flight time
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from$73
New York — Chicago
UA1504 United Airlines
15:29 — 17:13
2h 44m flight time
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from$50
New York — Chicago
NK494 Spirit Airlines
16:28 — 18:05
2h 37m flight time
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from$73
New York — Chicago
UA1842 United Airlines
17:19 — 18:55
2h 36m flight time
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from$83
New York — Chicago
UA2299 United Airlines
18:30 — 20:07
2h 37m flight time
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from$73
New York — Chicago
UA1952 United Airlines
19:30 — 21:07
2h 37m flight time
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from$83
New York — Chicago
UA1582 United Airlines
20:30 — 22:07
2h 37m flight time
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from$73
New York — Chicago
UA2181 United Airlines
21:30 — 23:07
2h 37m flight time
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from$73
New York — Chicago
UA541 United Airlines
Full flight schedule will help you in detecting at what time planes fly from New York to Chicago. You can also specify the concrete flights and airlines on the route and how long the flight actually is. Use the calendar for today, tomorrow or other specific date as some flights are available only on certain days of the week.
*Departure and arrival times - local. Updated on October 18, 2025.

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 Frontier Airlines - 55 departures per week at the price of from $ 29 . 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 Airlines
    from $236
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  • F9 - Frontier Airlines
    from $29
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  • B6 - JetBlue
    from $214
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  • WN - Southwest Airlines
    from $235
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  • DL - Delta Air Lines Inc.
    from $229
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  • UA - United Airlines
    from $73
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  • NK - Spirit Airlines
    from $50
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See more direct flights

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.

  • F9 - Frontier Airlines
    from $75
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  • AA - American Airlines
    from $248
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  • QR - Qatar Airways
    from $9094
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  • AC - Air Canada
    from $669
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  • FI - Icelandair
    from $1401
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  • DL - Delta Air Lines Inc.
    from $270
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  • UA - United Airlines
    from $94
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  • VB - VivaAerobus
    from $648
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  • AM - Aeromexico
    from $698
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  • LX - SWISS International Air Lines
    from $5516
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  • AS - Alaska Airlines
    from $778
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  • B6 - JetBlue
    from $357
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See more connecting flights

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-XNY
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  • Newyork Airport-NWK
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  • Newyork Airport-NYP
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  • La Guardia-LGA
    from $43
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  • Westchester County-HPN
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  • World Trade Center-WTC
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  • Pier 11/Wall St. SPB-NWS
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  • John F Kennedy Intl-JFK
    from $29
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  • Flushing-FLU
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  • East 34th St Heliport-TSS
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  • West 30th St Heliport-JRA
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  • Downtown Manhattan H/p-JRB
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  • East 60th Street H/P-JRE
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  • Battery Pk City/N. Cov-NBP
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  • East 34th St Landing-NES
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  • Marine Air Terminal-QNY
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Chicago airports

  • O'Hare International-ORD
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  • Midway-MDW
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  • Dupage County-DPA
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  • Chicago FSS-CHI
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  • Merrill C Meigs (closed)-CGX
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  • Pal-Waukee-PWK
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  • Chicago NAS-NOH
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How to book a plane ticket yourself?

How to book an air 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.

    To find a plane ticket, please select dates.

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