New York to Chicago flights (JFK → ORD)

Looking for New York to Chicago flights? Cheapest round-trip I’ve found: US$297 on JetBlue, 1 stop(s), departing 2026-10-16. That’s US$5 below the typical price for this route. Cheap flights from New York to Chicago change daily — I re-check this route three times a day.

Deal score: Higher than usual — cheaper than 3% of prices I’ve seen on this route.

Best months to fly New York to Chicago

How to book this fare

I don’t sell tickets — I track prices and point you to where to look. To book New York to Chicago flights:

1. Search New York to Chicago on Google Flights for the dates shown above (Oct 2026) — the fare I found is usually still available there.
2. Compare the same dates on metasearch sites like Skyscanner or KAYAK to confirm you’re seeing the lowest price.
3. Book directly with the airline when you can — it’s often the same price and makes changes or cancellations much easier.

Fares change constantly. If the price has moved, check back — I re-check this route daily.

Other New York to … flights

• New York to Gold Coast flights — US$1,390
• New York to Wellington flights — US$1,471
• New York to Sydney flights — US$1,339
• New York to Buenos Aires flights — US$925
• New York to Bali flights — US$831
• New York to Brasilia flights — US$680
• New York to Lima flights — US$676
• New York to Paris flights — US$567

All flights to Chicago · All flights from New York

Prices last checked: 2026-09-25, 6:10:50 a.m.. Prices are indicative and change quickly — confirm on the airline site before booking. See how I find these deals.