New York to Chicago flights
Round trip · Economy · Prices per person in USD
Prices updated
Prices are low right now
$231 is $55 (19%) below the usual $286 for New York → Chicago.
Buy now or wait? We're still learning this route. We have 1 day of prices so far and need about a week to say whether to book or wait.
Not ready to book? Get an email when New York → Chicago drops below your price.Cheapest round trip by month
Lowest fare found per departure month| Month | Cheapest round trip |
|---|---|
| September 2026 | $253 |
| October 2026 | $231 (cheapest month) |
| November 2026 | $243 |
| December 2026 | $295 |
| January 2027 | $284 |
| February 2027 | No fares found yet |
| March 2027 | $293 |
| April 2027 | $287 |
Cheapest dates in the next 4 months
Round trip, per person-
Oct 28 – 31 3 nights · leave Wed$231 −19% vs usual$231 −19% vs usual Book
Frontier Airlines 1 stop · 5h 00m -
Oct 14 – 21 7 nights · leave Wed$243 −15% vs usual$243 −15% vs usual Book
Frontier Airlines 1 stop · 5h 08m
-
Nov 11 – 15 4 nights · leave Wed$243 −15% vs usual$243 −15% vs usual Book
Frontier Airlines 1 stop · 5h 00m
-
Nov 4 – 14 10 nights · leave Wed$247 −14% vs usual$247 −14% vs usual Book
Frontier Airlines 1 stop · 5h 00m
-
Oct 17 – 23 6 nights · leave Sat$248 −13% vs usual$248 −13% vs usual Book
United Airlines Nonstop · 2h 43m -
Oct 1 – 3 2 nights · leave Thu$249 −13% vs usual$249 −13% vs usual Book
Frontier Airlines 1 stop · 6h 00m
-
Nov 20 – 26 6 nights · leave Fri$249 −13% vs usual$249 −13% vs usual Book
Frontier Airlines 1 stop · 4h 54m
-
Oct 7 – 14 7 nights · leave Wed$250 −13% vs usual$250 −13% vs usual Book
Frontier Airlines 1 stop · 5h 03m
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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Airport transfer to Chicago
Fixed prices from ORD on KiwitaxiTo see transfer prices here, turn on partner content in .
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Plan the rest of your trip
Chicago · Oct 28 – 31Travel insurance · EKTA Airport transfer · Kiwitaxi
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Good to know
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New York to Chicago: questions
How much is a flight from New York to Chicago?
The cheapest round trip we have found right now is $231, leaving October 28 and returning October 31. The usual price on this route is about $286, so this fare is 19% less. Prices are per person, economy, in USD.
What is the cheapest month to fly from New York to Chicago?
October 2026, with round trips from $231. The most expensive month in our data is December (from $295). Based on the 7 months ahead we have prices for.
Are there nonstop flights from New York to Chicago?
Yes. Nonstop from $248 round trip. 16% of the 37 date combinations we track are nonstop.
What is the cheapest day to fly from New York to Chicago?
Leaving on a Wednesday. Typical fare $253, vs $271 across all days.
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 $231, departing October 28 and returning October 31, about 19% below the usual $286. Right now we're following 37 upcoming date combinations on this route. The cheapest month to fly in our data is October, from $231. Prices are per person and were correct when found; the final price is set by the airline or booking site when you book.