New York to Chicago flights
The cheapest round trip we found from New York to Chicago is $208 (Dec 2 – 9, 1 stop), 37% below the usual $332.
NYC to CHI · Round trip · Economy · Prices per person in USD · Price found (3 days ago)
Cheapest found
Cheapest round trip by month
Lowest fare found per departure month| Month | Cheapest round trip |
|---|---|
| November 2026 | $300 |
| December 2026 | $208 (cheapest month) |
| January 2027 | $312 |
| February 2027 | $316 |
| March 2027 | No fares found yet |
| April 2027 | $332 |
| May 2027 | No fares found yet |
| June 2027 | No fares found yet |
| July 2027 | $344 |
| August 2027 | No fares found yet |
| September 2027 | $367 |
| October 2027 | $760 |
Cheapest dates in the next 4 months
Round trip, per person-
Dec 2 – 9 7 nights · leave Wed$208 −37% vs usual$208 −37% vs usual Book
Frontier Airlines 1 stop · 5h 06m -
Dec 9 – 16 7 nights · leave Wed$211 −36% vs usual$211 −36% vs usual Book
Frontier Airlines 1 stop · 6h 13m
-
Dec 7 – 11 4 nights · leave Mon$242 −27% vs usual$242 −27% vs usual Book
American Airlines 1 stop · 4h 06m -
Dec 16 – 19 3 nights · leave Wed$290 −13% vs usual$290 −13% vs usual Book
Frontier Airlines 1 stop · 6h 13m
-
Nov 21 – 24 3 nights · leave Sat$300 −10% vs usual$300 −10% vs usual Book
Frontier Airlines 1 stop · 4h 34m
-
Jan 3 – 5, 2027 2 nights · leave Sun$312 −6% vs usual$312 −6% vs usual Book
American Airlines 1 stop · 3h 00m
-
Feb 18 – 21, 2027 3 nights · leave Thu$316 −5% vs usual$316 −5% vs usual Book
Frontier Airlines 1 stop · 5h 20m
-
Dec 21 – 25 4 nights · leave Mon$320$320 Book
United Airlines Nonstop · 2h 52m
Prices change often. The booking site shows the final price before you pay. Other dates? Set an alert
Things to do in Chicago
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Go City prices checked Oct 23, 2026; the final price is on Go City. Partner links: we may earn a commission if you book, at no extra cost to you.
Plan the rest of your trip
Chicago · Dec 2 – 9Partner links: we may earn a commission if you book, at no extra cost to you.
Good to know
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New York to Chicago: questions
How much does a flight from New York to Chicago cost?
The cheapest round trip we have found right now is $208, leaving December 2 and returning December 9. The usual price on this route is about $332, so this fare is 37% less. Prices are per person, economy, in USD.
What is the cheapest month to fly from New York to Chicago?
December 2026, with round trips from $208. The most expensive month in our data is October (from $760). Based on the 8 months ahead we have prices for.
Are there nonstop flights from New York to Chicago?
Yes. Nonstop from $320 round trip. 27% of the 15 date combinations we track are nonstop.
Which airports do New York to Chicago flights use?
New York airports include John F. Kennedy International (JFK), Newark Liberty International (EWR) and LaGuardia (LGA). Chicago airports include O'Hare International (ORD), Chicago Midway International (MDW) and Chicago Rockford International (RFD). The prices on this page cover every airport in both cities (NYC and CHI are the city codes).
About this route
We track round-trip economy fares from New York (United States) to Chicago (United States) using Travelpayouts / Aviasales data. The cheapest round trip we've found is $208, departing December 2 and returning December 9, about 37% below the usual $332. Right now we're following 15 upcoming date combinations on this route. The cheapest month to fly in our data is December, from $208. Prices are per person and were correct when found; the final price is set by the airline or booking site when you book.