Flaut.Travel was designed and developed by a team dedicated to making the process of searching, comparing and booking airline tickets as easy and convenient as possible. Our service helps travelers to find and buy the cheapest flights from New York to Chicago. We have connected more than 40 airlines and airline ticketing agencies to help you find the most suitable and affordable flight option.
In different months, ticket prices from New York to Chicago vary: minimum — $93 (January 2027), maximum — $219 (September 2027). Typically, the flight costs $110–$134.
A non-stop flight is the most convenient and comfortable way to fly from New York to Chicago, despite the fact that sometimes flights with transfers can cost significantly less.
All 4 airlines on the New York — Chicago route operate on a daily basis: United Airlines, JetBlue Airways, Southwest Airlines, and American Airlines fly every day.
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Answers to questions about the route that travelers are most interested in.
We keep tight track on airlines' pre-holidays sales and other special offers occurences all the time to let you save maximum amount of funds while traveling to your family or just going out on vacation.
Tickets from New York to Chicago are getting more expensive each month. From November 2026 to September 2027, the increase reached 107%, with prices now at $219. It's unlikely to get cheaper than the current level.
The most significant price increase was from January 2027 to September 2027 — up 136%. The best time to fly is December 2026–January 2027, when the average price is $98. In May 2027–September 2027, tickets cost around $195.
Given the rising prices, it's best not to delay your purchase. Flying in December 2026–January 2027 can save you up to 50% compared to the most expensive months.
Price variation across months on this route is 32%. Your choice of departure month significantly affects the total flight cost.
The route New York — Chicago is served by many carriers — 6 in total, including American Airlines, Southwest Airlines, Frontier Airlines, Allegiant Air, JetBlue Airways, and United Airlines. This gives passengers wide opportunities: from finding the lowest fare (from $103) to selecting flights by schedule or service class. Our service aggregates data from multiple booking systems so you can compare offers in one place. This saves time and money: no need to check dozens of sites — just pick the right option and book online.
starting at $110
starting at $145
starting at $103
starting at $123
starting at $134
starting at $208
New York — Chicago
11/09/2026
Departure
Direct flight
AA2541
starting at $110
New York — Chicago
11/25/2026
Departure
Direct flight
AA1667
starting at $134
New York — Chicago
12/25/2026
Departure
Direct flight
WN2579
starting at $145
New York — Chicago
01/01/2027
Departure
Direct flight
AA2586
starting at $145
New York — Chicago
12/29/2026
Departure
Direct flight
AA2819
starting at $153
New York — Chicago
03/04/2027
Departure
Direct flight
AA3002
starting at $162
New York — Chicago
12/18/2026
Departure
Direct flight
AA2501
starting at $164
New York — Chicago
12/24/2026
Departure
Direct flight
AA3163
starting at $166
New York — Chicago
12/26/2026
Departure
Direct flight
WN2579
starting at $166
New York — Chicago
11/07/2026
Departure
Direct flight
AA504
starting at $168
United Airlines
Every day
starting at $157
JetBlue Airways
Every day
starting at $144
Southwest Airlines
Every day
starting at $141
American Airlines
Every day
starting at $149
The cheapest flight ticket from New York to Chicago according to data for the last 48 hours costs $103
Often the best time to buy tickets from New York to Chicago is 2 months before departure.
Based on statistics over the past years, the lowest prices for flights from New York to Chicago can be found flying in these months: January, December, February.
The fastest flights from New York to Chicago start from 2 hours 30 minutes in the air.
The following airlines operate direct flights on the route New York — Chicago: American Airlines, Southwest Airlines
All airports
The cheapest one-way flight from New York to Chicago departs on 12/09/2026, is operated by Frontier Airlines and costs $103
The cheapest roundtrip flight from New York to Chicago departs on 12/02/2026, is operated by Frontier Airlines and costs $187
Fastest flight from New York to Chicago takes 2h 30m
There are direct flights on this route 6 days a week: Mo, Tu, We, Th, Fr, and Sa
The distance between New York and Chicago is 1144km (709 miles). The average flight duration is 2h 20m. There are 456 direct flights from New York to Chicago. The time difference between New York and Chicago is 1h. Flights from New York begin at 5:31 AM. The latest flight from New York departs at 10:11 PM
We couldn't find any special offers for flights from New York to Chicago