Cheap flights from New York City to Chicago
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Travel tip: Visit Chicago on your holidays!Check our current prices for flights from New York City to Chicago. Please note that we also give you historical search data for this city connection. These are all airfares that people found in the past, in order to find more current flight information from New York City to Chicago, you will need to run a search below.
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Cheap Chicago airfares from $120/RT are provided by Cheapoair.com. Outbound flight is leaving on 04/22/2025, 11:00 am from New York Ny/newark Kennedy (JFK) airport and arrives at Chicago Midway (MDW) at 05:49 pm. The flight time is 6 hours and 49 minutes. The Returning flight departes on 04/29/2025, 12:46 pm (other return dates are also available). Date posted: 05 Jan 2025
Price evolution for flights From New York City To Chicago
Recent Deals on Flights from New York City to Chicago:Roundtrip / Oneway
- $120
Frontier Airlines
cheapoair.com check priceFrom To Departure Time New York, NY (JFK) Chicago, IL (MDW) 04/22/2025 11:00 am Chicago, IL (MDW) New York, NY (JFK) 04/29/2025 12:46 pm - $171
Spirit Airlines
cheapoair.com check priceFrom To Departure Time New York, NY (LGA) Chicago, IL (ORD) 04/22/2025 06:00 am Chicago, IL (ORD) New York, NY (LGA) 04/29/2025 08:12 pm - $49 Spirit Airlines
cheapoair.com check priceFrom To Departure Time New York, NY (LGA) Chicago, IL (ORD) 05/13/2025 05:40 pm - $60 Frontier Airlines
cheapoair.com check priceFrom To Departure Time New York, NY (JFK) Chicago, IL (MDW) 05/13/2025 11:00 am
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Know what to do when flying to Chicago?
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