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Book $48 Cheap American Airlines flights from New York City (NYC) to Chicago (CHI)

Flight deals from New York City to Chicago

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Prices shown below were available within the past 3 days for the period specified and should not be considered the final price offered. Please note that availability and prices are subject to change.

American Airlines flight deals from New York City to Chicago

New York City Chicago
BEST
DEAL
Mon, 13 Jan JFK - ORD
-21 %
$61 $48
Prime price per passenger
Newark - Nj Chicago
BEST
DEAL
Sun, 09 Feb EWR - ORD
$76 $72
Prime price per passenger
Philadelphia Chicago
BEST
DEAL
Wed, 08 Jan PHL - ORD
$93 $89
Prime price per passenger
Philadelphia Chicago
BEST
DEAL
Tue, 24 Dec PHL - ORD
Wed, 25 Dec ORD - PHL
$228 $224
Prime price per passenger
New York City Chicago
BEST
DEAL
Fri, 20 Dec LGA - ORD
Sat, 21 Dec ORD - LGA
$251 $243
Prime price per passenger
New York City Chicago
BEST
DEAL
Sat, 21 Dec LGA - ORD
Sat, 21 Dec ORD - LGA
$368 $357
Prime price per passenger
westchester, NY Chicago
BEST
DEAL
Mon, 30 Dec HPN - ORD
$420 $411
Prime price per passenger
Philadelphia Chicago
BEST
DEAL
Fri, 20 Dec PHL - MDW
Sun, 22 Dec MDW - PHL
$493 $483
Prime price per passenger
Newark - Nj Chicago
BEST
DEAL
Fri, 20 Dec EWR - ORD
Mon, 23 Dec ORD - EWR
$506 $493
Prime price per passenger
Newark - Nj Chicago
BEST
DEAL
Fri, 20 Dec EWR - ORD
Sun, 22 Dec ORD - EWR
$508 $495
Prime price per passenger
westchester, NY Chicago
BEST
DEAL
Mon, 23 Dec HPN - ORD
Wed, 25 Dec ORD - HPN
$519 $511
Prime price per passenger
westchester, NY Chicago
BEST
DEAL
Tue, 24 Dec HPN - ORD
Wed, 25 Dec ORD - HPN
$687 $679
Prime price per passenger

Best flight offers from other airlines

Islip, NY Chicago
BEST
DEAL
Fri, 20 Dec ISP - MDW
Mon, 23 Dec MDW - ISP
$237 $230
Prime price per passenger
Philadelphia Chicago
BEST
DEAL
Tue, 24 Dec PHL - MDW
Tue, 24 Dec MDW - PHL
$300 $291
Prime price per passenger
Philadelphia Chicago
BEST
DEAL
Sun, 22 Dec PHL - MDW
Tue, 24 Dec MDW - PHL
$301 $291
Prime price per passenger
New York City Chicago
BEST
DEAL
Wed, 25 Dec LGA - ORD
Wed, 25 Dec ORD - LGA
$312 $302
Prime price per passenger
New York City Chicago
BEST
DEAL
Wed, 25 Dec LGA - ORD
Wed, 25 Dec ORD - LGA
$318 $310
Prime price per passenger
Philadelphia Chicago
BEST
DEAL
Fri, 20 Dec PHL - MDW
Mon, 23 Dec MDW - PHL
$319 $309
Prime price per passenger

Get your flight with American Airlines to Chicago from New York City starting at $48

The Best New York City to Chicago Flight Deals with American Airlines

With eDreams, finding the best American Airlines deals for your trip from New York City to Chicago couldn’t be easier. Imagine this: exclusive discounts, intuitive booking tools, and plenty of helpful perks—all at your fingertips! Say goodbye to the hassle of planning and hello to the excitement of your upcoming adventure in Chicago.

Whether you’re looking for unbeatable prices, a custom-fit itinerary, or some extra perks, eDreams is your all-in-one travel partner for every part of the New York City (NYC) to Chicago (CHI) journey. Stick around to find out why booking with eDreams is the best way to kick off your trip.

Flying from New York City to Chicago with American Airlines

Flying from New York City (NYC) to Chicago (CHI) with American Airlines (AA) is all about comfort and convenience. From check-in to touchdown, American Airlines ensures a smooth experience, so you can just sit back and relax. You’ll find fast check-ins, extra legroom, and attentive service designed for a stress-free trip.

Once onboard, the friendly crew will make sure you have everything you need. Many routes offer in-flight Wi-Fi, so you can stay connected, binge-watch shows, or catch up on work if you need to. Feeling hungry? American Airlines has a great selection of snacks and meals to keep you satisfied mid-flight. And if you want a bit more luxury, you can treat yourself to upgrades and priority boarding, adding a personal touch to your journey. With great service and a focus on a smooth, enjoyable flight, American Airlines makes your trip from New York City to Chicago easy and fun.

Book Your Flight with eDreams and Enjoy the Perks

Booking affordable flights from New York City (NYC) to Chicago (CHI) with eDreams isn’t just about getting a great deal—it’s about making travel planning effortless. With eDreams, you get awesome perks that make your journey easier and more enjoyable:

Your Journey from New York City to Chicago with American Airlines

The journey from New York City (NYC) to Chicago (CHI) is all about getting you to your destination comfortably and quickly, so your adventure can start as soon as you land. This direct route offers plenty of options, whether you prefer a quick non-stop flight or more flexibility with layovers. Whatever your style, there’s a schedule that fits.

Departing from New York City and Arriving at Chicago: What to Expect

When departing from New York City, enjoy easy airport access, clear signage, and quick check-ins for a stress-free start. You’ll breeze through security, leaving plenty of time to relax before takeoff.

When you land in Chicago, you’ll be greeted by a modern terminal with plenty of transportation options like taxis, buses, and shuttles to get you on your way. Whether heading to your hotel or diving into sightseeing, everything you need is right there.

Best Time to Book Your New York City — Chicago Trip with American Airlines

For the best American Airlines flight deals from New York City to Chicago, timing is everything! Booking in advance often means lower fares, especially during off-peak seasons when Chicago is quieter and flights are more budget-friendly. Check the climate to plan for the ideal weather to suit your trip—whether for mild outdoor adventures or cultural explorations. With a bit of planning, you’re set for an unforgettable getaway!

American Airlines New York City-Chicago flights FAQ's

Which airports does American Airlines fly between New York City and Chicago?
For flights between New York City and Chicago, American Airlines operates the following airport routes: For flights between New York City and Chicago, American Airlines operates from the following airport routes: La Guardia (LGA) to O hare International Airport (ORD) ; La Guardia (LGA) to O hare International Airport (ORD)
What do American Airlines flights from New York City to Chicago cost?
One of American Airlines cheapest prices for a New York City to Chicago flight we have right now is $48. On average though, flights with American Airlines cost $350.85 for the route New York City to Chicago, but it mostly depends on the season and how far in advance you book your tickets.
Cheapest Ticket Price $48 The most affordable rate found in the last 72 hours for flights operated by American Airlines leaving from New York City and going to Chicago, according to our customers' bookings.
Flight Time 2 h and 45 m The American Airlines flight duration between New York City and Chicago is around 2 h and 45 m, however it could be affected by other circumstances.
Departure Airport John F Kennedy Intl Airport Your departure will be from John F Kennedy Intl Airport, when flying with American Airlines from New York City to Chicago.
Arrival Airport O'hare International Airport When flying with American Airlines from New York City to Chicago, your arrival airport will be John F Kennedy Intl Airport.

Plan your trip

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