starting at $79
starting at $86
starting at $93
starting at $94
starting at $119
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.
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.
None of the 5 airlines on the New York — Chicago route fly every day: Spirit Airlines, Frontier Airlines, Southwest Airlines, American Airlines, and United Airlines fly every day except Sunday.
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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.
The route New York — Chicago is served by many carriers — 5 in total, including Southwest Airlines, JetBlue Airways, American Airlines, United Airlines, and Frontier Airlines. This gives passengers wide opportunities: from finding the lowest fare (from $79) 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 $79
starting at $86
starting at $93
starting at $94
starting at $119
New York — Chicago
08/31/2026
Departure
Direct flight
WN2411
starting at $79
New York — Chicago
08/24/2026
Departure
Direct flight
WN2411
starting at $83
New York — Chicago
08/17/2026
Departure
Direct flight
B6405
starting at $86
New York — Chicago
07/15/2026
Departure
Direct flight
B6405
starting at $87
New York — Chicago
07/15/2026
Departure
Direct flight
WN2469
starting at $88
New York — Chicago
07/26/2026
Departure
Direct flight
B6805
starting at $89
New York — Chicago
06/20/2026
Departure
Direct flight
B6805
starting at $89
New York — Chicago
06/17/2026
Departure
Direct flight
WN3016
starting at $90
New York — Chicago
07/21/2026
Departure
Direct flight
WN1095
starting at $91
New York — Chicago
07/22/2026
Departure
Direct flight
WN291
starting at $91
Spirit Airlines
Mo, Tu, We, Th, Fr, and Sa
starting at $52
Frontier Airlines
Mo, Tu, We, Th, Fr, and Sa
starting at $33
Southwest Airlines
Mo, Tu, We, Th, Fr, and Sa
starting at $132
American Airlines
Mo, Tu, We, Th, Fr, and Sa
starting at $136
United Airlines
Mo, Tu, We, Th, Fr, and Sa
starting at $150
The cheapest one-way flight from New York to Chicago departs on 08/31/2026, is operated by Southwest Airlines and costs $79
The cheapest roundtrip flight from New York to Chicago departs on 06/26/2026, is operated by Southwest Airlines and costs $129
Fastest flight from New York to Chicago takes
There are direct flights on this route 5 days a week: Su, Mo, Tu, We, and Sa
The distance between New York and Chicago is 1144km (709 miles). The average flight duration is 2h 41m. There are 421 direct flights from New York to Chicago. The time difference between New York and Chicago is 1h. Flights from New York begin at 6:00 AM. The latest flight from New York departs at 10:54 PM
We couldn't find any special offers for flights from New York to Chicago
The cheapest flight ticket from New York to Chicago according to data for the last 48 hours costs $79
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: August, July, June.
The fastest flights from New York to Chicago start from 2 hours 15 minutes in the air.
The following airlines operate direct flights on the route New York — Chicago: Southwest Airlines, JetBlue Airways
In different months, ticket prices from New York to Chicago vary: minimum — $79 (August 2026), maximum — $128 (December 2026). Typically, the flight costs $99–$195.
Flight costs from New York to Chicago climb toward the middle of the period, then start to drop. By choosing the right dates, you can save noticeably.
Prices rise from August 2026 to December 2026 (+61%), then decline from June 2026 to August 2026 (11%). The cheapest tickets are in July 2026–August 2026 (averaging $83), while the priciest are in December 2026–January 2027 ($120).
For savings, plan your flight for July 2026–August 2026 — you could save up to 30%. Try to avoid December 2026–January 2027 when possible: prices are at their highest then.
Price spread on this route is 13.8%. Costs depend heavily on the season, so flexibility in choosing your departure month is especially valuable here.