Cheap flights from New York to Chicago
Travel > North America > United States > New York to Chicago flights
Founded in the early 1800s, Chicago is positioned between civilization and wilderness and many aspects of modern life had their start here. Chicago really does have it all, with less infrastructural problems than its coastal rivals.... (read more in our Chicago Travel Guide)
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Cheapest flights found for the next 6 months
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Check our newest flight offers to Chicago:
- $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 - $120 Frontier Airlines
cheapoair.com check priceFrom To Departure Time New York, NY (LGA) Chicago, IL (ORD) 04/15/2025 10:00 pm Chicago, IL (ORD) New York, NY (LGA) 04/29/2025 12:46 pm - $135
Multiple Airlines
cheapoair.com check priceFrom To Departure Time New York, NY (LGA) Chicago, IL (ORD) 04/15/2025 10:00 pm Chicago, IL (ORD) New York, NY (LGA) 04/29/2025 08:12 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 - $700 Frontier Airlines
cheapoair.com check priceFrom To Departure Time Buffalo, NY (BUF) Chicago, IL (MDW) 05/27/2025 10:02 am Chicago, IL (MDW) Buffalo, NY (BUF) 06/04/2025 06:15 am
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