Cheap flights from New York to Chicago
Travel > North America > United States > New York to Chicago flights
Though residents complain about the cold weather that lasts almost through the whole year, at least on a winter day, they can duck into such popular clubs as Andy's, where there's hot jazz even at noon. The best time to visit is between May and October when the weather is the most predictable. Then you could head out to ivy-covered Wrigley Field to catch baseball's Cubs in action, or take a cruise boat under the bridges of the Chicago River at sunset.... (read more in our Chicago Travel Guide)
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Check our newest flight offers to Chicago:
- $116
Spirit Airlines
cheapoair.com check priceFrom To Departure Time New York, NY (LGA) Chicago, IL (ORD) 01/13/2025 10:59 am Chicago, IL (ORD) New York, NY (LGA) 01/18/2025 05:06 pm - $142 Spirit Airlines
cheapoair.com check priceFrom To Departure Time New York, NY (LGA) Chicago, IL (ORD) 01/05/2025 08:35 am Chicago, IL (ORD) New York, NY (LGA) 01/14/2025 07:00 am - $151 Spirit Airlines
cheapoair.com check priceFrom To Departure Time New York, NY (LGA) Chicago, IL (ORD) 01/29/2025 10:59 am Chicago, IL (ORD) New York, NY (LGA) 02/07/2025 01:35 pm - $158
Multiple Airlines
cheapoair.com check priceFrom To Departure Time New York, NY (LGA) Chicago, IL (ORD) 01/05/2025 08:35 am Chicago, IL (ORD) New York, NY (LGA) 01/14/2025 03:00 pm - $208 Spirit Airlines
cheapoair.com check priceFrom To Departure Time Rochester, NY (ROC) Chicago, IL (ORD) 01/15/2025 07:55 am Chicago, IL (ORD) Rochester, NY (ROC) 01/26/2025 06:06 pm
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