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Cheap Flights from New York to Chicago

2-5 hours direct flight. Airlines: American Airlines, United, Delta +2 more. Fares from $150.

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New York to Chicago Flight Overview

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Flight Details

  • Duration: 2-5 hours direct
  • Direct Flights: Yes
  • From: JFK, LGA, EWR
  • To: ORD or MDW
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Typical Prices

  • Economy: $150-500 roundtrip
  • Cheapest: January, February, September
  • Priciest: June, July, December

Airlines Flying New York to Chicago

American AirlinesUnitedDeltaSouthwestJetBlue
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Tips for Cheap New York to Chicago Flights

1Midway (MDW) beats O'Hare for speed and price. Southwest dominates Midway with frequent cheap flights from JFK, LaGuardia, and Newark. It's closer to downtown Chicago and has shorter security lines than massive O'Hare.
2Book the earliest flight for business rates. Morning departures cater to business travelers but often cost less than afternoon flights when leisure travelers fly. A 6am JFK departure can save you $50-80 roundtrip.
3Winter flights are dirt cheap if you can handle cold. January and February see $99 roundtrip deals because nobody wants to visit Chicago in freezing temps, but museums and restaurants are just as good indoors.
4Fly on Tuesdays or Wednesdays for best fares. This business-heavy route sees huge price swings based on day of week. Weekend flights cost 40-60% more than midweek when corporate travelers stay home.
5Check both JFK and Newark prices. United dominates Newark to Chicago with hub connections, while American and Delta prefer JFK. Compare both airports since fares can differ by $100+ on the same dates.

💡Savings tip: Book 6-8 weeks ahead for the best New York to Chicago fares. Flexibility with dates can save you 20-30%.

FAQs About Flights to New York to Chicago

Direct flights take 2.5-3 hours from JFK, LaGuardia, or Newark to O'Hare or Midway. It's one of the shortest cross-country flights, making it perfect for a long weekend trip without burning a full day traveling.

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