Cheap flights from New York to Chicago
A good round-trip price from New York to Chicago is under $244. Over the last 2 days the lowest fare we found each day was usually around $244, and the lowest of all was $244, for travel in November 2026. The cheapest month to fly is November 2026, at around $244.
Join to get alerts- Good price
- $244
- under this is a deal · round trip
- Typical price
- $244
- the middle of what we saw · round trip
- Lowest we saw
- $244
- for November 2026 · round trip
- Nonstop
- 100%
- of the cheapest fares
Cheapest months to fly
The cheapest round trip for each departure month, from fares seen on November 11, 2026.
- Nov 26$244 (Cheapest)
- Dec 26$314
- Jan 27$324
- Feb 27$345
- Mar 27$359
- Apr 27$332
Price over the last 30 days
The lowest round-trip fare we found each day. Today: $244.
Deals on this route
Members get an alert when a fare on this route drops well under $244.
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Questions about this route
What is a good price to fly from New York to Chicago?
Under $244 round trip is a good price. Over the last 2 days the typical fare was $244 and the lowest was $244.
What is the cheapest month to fly from New York to Chicago?
November 2026, at $244 round trip, from the fares we found today. The most expensive month is March 2027, at $359.
Are there cheap nonstop flights from New York to Chicago?
100% of the cheapest daily fares we found were nonstop.
How far ahead should I book flights from New York to Chicago?
The cheapest quarter of fares we found were for trips about 2 days ahead. Deals also appear at short notice, which is why members get alerts.
How long is the flight from New York to Chicago?
About 2 h 57 min one way on the cheapest fares we found, including any stops.
Fares like these don't wait
Members get an alert when a fare from their city drops far below normal, with the dates and a link to book.
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Based on 2 days of fares we checked between November 10, 2026 and November 11, 2026. Prices change fast, so always check the final price before you book.