Cheap Flights from New York to Chicago Starting at $23
Helping travelers to find the best flight offers
Cheapest flights from New York to Chicago
Fly from New York to Chicago with confidence — our metasearch combs through over 700 airlines, 50+ agencies and more than 5 top booking systems to surface the best prices, schedules and travel conditions. Friendly and fast, we compare options so you can pick the ideal nonstop or connecting flight and book in seconds.
Remember that on average the ideal time to book flights is 2 months before departure!
In different months, ticket prices from New York to Chicago vary: minimum — $25 (October 2025), maximum — $138 (December 2025). Typically, the flight costs $81–$167.
Airlines operating on route
Direct Flights from New York to Chicago
Fly direct from New York to Chicago for the fastest, most convenient way to get between these two vibrant cities—no layovers, less hassle, and more time to enjoy your destination. While connecting flights can sometimes be cheaper, a nonstop trip saves hours and tends to be more comfortable, making it ideal for business or short getaways. Book now to lock in a smooth, time-saving journey.
Schedule of direct flights from New York to Chicago
A direct flight is the easiest way to get to your destination. The following airlines operate non-stop flights from New York to Chicago:
New York airports overview
Chicago airports overview
Frequently asked questions (FAQ)
Answers to questions about the route that travelers are most interested in.
Special offers and sales on air tickets from New York to Chicago
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.
Alternative routes
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Cheapest one way flight
$23
Spirit Airlines
Direct flight
2h 32m
11/12/2025
The cheapest one-way flight from New York to Chicago departs on 11/12/2025, is operated by Spirit Airlines and costs $23
Cheapest round trip flight
$55
Spirit Airlines
Direct flight
4h 40m
11/05/2025
The cheapest roundtrip flight from New York to Chicago departs on 11/05/2025, is operated by Spirit Airlines and costs $55
The fastest flight
2h 24m
Fastest flight from New York to Chicago takes 2h 24m
Direct flights
Every day
There are direct flights on this route 7 days a week: Su, Mo, Tu, We, Th, Fr, and Sa
Earliest flight
5:59 AM
Latest flight
10:00 PM
Average flight duration
2h 37m
Direct flights count
429
Distance
1144km
Timezone difference
1h
The distance between New York and Chicago is 1144km (709 miles). The average flight duration is 2h 37m. There are 429 direct flights from New York to Chicago. The time difference between New York and Chicago is 1h. Flights from New York begin at 5:59 AM. The latest flight from New York departs at 10:00 PM
October 2025
Lowest price
on average:
$25
December 2025
Highest price
on average:
$138
Avg Price
The route New York — Chicago is served by many carriers — 7 in total, including Spirit Airlines, Frontier Airlines, JetBlue Airways, United Airlines, American Airlines, Southwest Airlines, and Air Canada. This gives passengers wide opportunities: from finding the lowest fare (from $23) 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.
O'Hare International Airport (ORD) is Chicago's primary international hub, serving major global carriers and United's large operations alongside many international and legacy airlines. Flights can be competitive on price but often reflect hub status for premium routings. Located about 17 miles northwest of downtown, typical transfers to the Loop take 30–60 minutes depending on traffic; the CTA Blue Line rail runs to downtown in roughly 45 minutes with fares around $2.50–$3, while taxis or rideshares commonly cost in the $30–$60 range. Pros: extensive international connectivity and frequent flights; Cons: it can be busy and may require longer transit times between terminals.
How much is the cheapest flight ticket from New York to Chicago?
The cheapest flight ticket from New York to Chicago according to data for the last 48 hours costs $23
When is the best time to buy air tickets on the route New York — Chicago?
Often the best time to buy tickets from New York to Chicago is 2 months before departure.
When is the cheapest time of year to fly from New York to Chicago?
Based on statistics over the past years, the lowest prices for flights from New York to Chicago can be found flying in these months: October, November, January.
How long does it take to fly from New York to Chicago?
The fastest flights from New York to Chicago start from 2 hours 24 minutes in the air.
Which airline can fly direct from New York to Chicago?
The following airlines operate direct flights on the route New York — Chicago: Spirit Airlines, Frontier Airlines
John F. Kennedy International (JFK) is New York’s primary international gateway and a major transatlantic and transpacific hub, typically serving full-service carriers alongside many international and premium airlines. It’s about 15–20 miles from Midtown Manhattan; travelers usually allow 45–75 minutes by car depending on traffic. Public options include the AirTrain connecting to the Long Island Rail Road or NYC Subway (travel times to Manhattan commonly range 50–70 minutes; fares vary by operator), plus taxis and app rides that can be pricier. Pros: extensive long-haul connectivity and full-service amenities. Cons: can be crowded and subject to variable traffic and longer transfer times.
LaGuardia Airport (LGA) generally functions as New York’s domestic and short-haul regional airport, often favored by budget-conscious travelers and carriers focusing on U.S. routes. Located roughly 8–10 miles from Midtown, ground travel is usually 20–40 minutes by car when traffic is moderate. Transit options include buses and a short AirTrain-to-subway connection via the nearby transit network; fares are typically low but travel can be slower than driving. Pros: closer to Manhattan and convenient for short domestic hops. Cons: fewer international flights, more limited lounges, and potential congestion during peak hours.
Newark Liberty International (EWR) is an important international and domestic hub in the New York metro, commonly used by both legacy carriers and many international airlines. Situated in New Jersey about 16–20 miles from Midtown Manhattan, journey times by car are frequently 30–60 minutes depending on traffic and bridge/tunnel conditions. The AirTrain links to NJ Transit and Amtrak at Newark Liberty International Airport Station, with typical total travel times to Penn Station around 30–50 minutes and fares varying by service. Pros: strong transcontinental and international connections and extensive airline options. Cons: less convenient to some Manhattan destinations and can involve tolls and variable commute times.
