Cheap flights from New York to Chicago
Fares from $95 in January 2027. Compare every month below, then book with the site you like.
Search New York → Chicago flightsCheapest New York to Chicago fares by month
Lowest price per person found in recent searches. Prices change often and are checked when you book.
- October 2026Oct 31 · one way · American Airlines · Direct$266See deal
- November 2026Nov 21 · one way · Frontier · 1 stop$108See deal
- December 2026Dec 9 · one way · Frontier · 1 stop$105See deal
- January 2027Jan 6 · one way · Frontier · 1 stop$95See deal
- February 2027Feb 9 · one way · Frontier · 1 stop$106See deal
- March 2027Mar 3 · one way · Frontier · 1 stop$113See deal
- April 2027Apr 14 · one way · American Airlines · Direct$173See deal
- May 2027May 16 · one way · American Airlines · Direct$175See deal
- September 2027Sep 24 · one way · United · Direct$223See deal
New York to Chicago at a glance
- Distance738 miles
- Nonstop flight timeabout 2h 15m
- Cheapest monthJanuary 2027
- Airport codesNYC → CHI
Plan your Chicago trip
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Frequently asked questions
- How much is a flight from New York to Chicago?
- The cheapest fare we found recently is $95 per person, departing Jan 6 on Frontier. Prices change daily, so search your dates to see today's fares.
- What is the cheapest month to fly from New York to Chicago?
- January 2027 is currently the cheapest month, from $95. October 2026 is the most expensive, from $266.
- Are there direct flights from New York to Chicago?
- Yes. Recent searches found nonstop fares from $173.
- Which airlines fly from New York to Chicago?
- The cheapest recent fares on this route were on American Airlines, Frontier, United.
- How long is the flight from New York to Chicago?
- New York and Chicago are about 738 miles apart, so a nonstop flight takes roughly 2h 15m. Flights with a stop take longer, depending on the connection.
- How do I find the cheapest flight from New York to Chicago?
- Search your dates on Gotoesy. We list fares from several booking sites sorted cheapest first, show nearby dates when your day has no saved fare, and send you straight to the seller to book.
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