How far in advance should I book tickets for a flight with American Airlines from New York to Chicago?

Generally, when trying to get a below average price for your ticket, try to book around 7 days before departure. For the cheapest possible price, our data suggests booking 92 days before departure.

Is American Airlines the cheapest airline to fly with from New York to Chicago?

With an average price of $273 return, American Airlines is not the cheapest airline to fly from New York to Chicago with. Instead, for the lowest price, our data suggests flying with Spirit Airlines, where a return flight costs $146 on average.

What is the cheapest American Airlines flight from New York to Chicago?

In the last 3 days, the lowest price for a flight with American Airlines from New York to Chicago was $79 for a return flight and $47 for a one-way flight.

Does American Airlines fly direct to Chicago from New York?

Yes, American Airlines does offer direct flights for the route, with around 40 flights per week.

What’s the cheapest day of the week to fly from New York to Chicago with American Airlines?

On average, the cheapest day of the week to fly from New York to Chicago with American Airlines is Monday, when prices are around $62. The most expensive day is generally Saturday, where the average price is around $85.

What’s the cheapest month to fly from New York to Chicago with American Airlines?

The cheapest month for American Airlines flights to Chicago from New York is generally September, where plane tickets cost $103 on average. If possible, try to avoid the most expensive months of December and May, where tickets cost $166 and $168 respectively.

$73 Cheap American Airlines Flights from New York to Chicago

NYC - CHI

Search hundreds of travel sites at once for deals on American Airlines flights from New York to Chicago

...and more

Travelers love KAYAK

41,299,237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Cheap American Airlines Flight Deals from New York to Chicago

Here are some of the best deals found on KAYAK recently from American Airlines for round-trip flights from New York to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Round-trip

One-way

Last minute

Direct

Recent round-trip American Airlines flight deals from New York to Chicago

Recommended round-trip American Airlines deals departing in the coming months from New York to Chicago.

Discover the best prices and deals for you by selecting your travel dates.

Choose your dates

7:05 am - 8:48 amEWR-ORD

2h 43mnonstop

5:59 pm - 8:57 pmORD-EWR

1h 58mnonstop

$139American Airlines

Find Deal

Wed, Feb 26 - Wed, Mar 5

3:50 pm - 5:42 pmJFK-ORD

2h 52mnonstop

4:14 pm - 7:30 pmORD-JFK

2h 16mnonstop

$147American Airlines

Find Deal

Fri, Feb 28 - Mon, Mar 3

6:00 am - 7:49 amLGA-ORD

2h 49mnonstop

7:22 am - 10:30 amORD-LGA

2h 08mnonstop

$147American Airlines

Find Deal

Sun, Feb 23 - Wed, Feb 26

3:50 pm - 5:42 pmJFK-ORD

2h 52mnonstop

11:45 am - 2:55 pmORD-JFK

2h 10mnonstop

$148American Airlines

Find Deal

Thu, Feb 20 - Mon, Feb 24

9:20 am - 10:59 amLGA-ORD

2h 39mnonstop

7:22 am - 10:31 amORD-LGA

2h 09mnonstop

$148American Airlines

Find Deal

Thu, Feb 20 - Mon, Feb 24

3:50 pm - 5:38 pmJFK-ORD

2h 48mnonstop

4:14 pm - 7:30 pmORD-JFK

2h 16mnonstop

$157American Airlines

Find Deal

Wed, Feb 12 - Sun, Feb 16

6:00 am - 7:36 amLGA-ORD

2h 36mnonstop

8:45 pm - 11:59 pmORD-LGA

2h 14mnonstop

$163American Airlines

Find Deal

Mon, Apr 7 - Thu, May 1

7:10 am - 8:58 amEWR-ORD

2h 48mnonstop

7:04 am - 10:21 amORD-EWR

2h 17mnonstop

$164American Airlines

Find Deal

Wed, Apr 9 - Sun, Apr 13

7:00 am - 8:46 amEWR-ORD

2h 46mnonstop

9:40 am - 12:48 pmORD-EWR

2h 08mnonstop

$167American Airlines

Find Deal

Tue, Feb 11 - Sun, Feb 16

3:59 pm - 5:43 pmJFK-ORD

2h 44mnonstop

4:42 pm - 8:00 pmORD-JFK

2h 18mnonstop

$168American Airlines

Find Deal

Tue, Apr 8 - Wed, May 28

Low season	January
High season	August
Cheapest flight	$73
Average price round-trip	$196

Best time to beat the crowds with an average 14% drop in price.

Most popular time to fly and prices are also 0% lower on average.

Flight from New York John F Kennedy Airport to Chicago O'Hare Airport

(price for this month)

When to Book Flights with American Airlines from New York to Chicago

Average price per month

Flight prices as travel date approaches

How far in advance should I book tickets for a flight with American Airlines from New York to Chicago?
Generally, when trying to get a below average price for your ticket, try to book around 7 days before departure. For the cheapest possible price, our data suggests booking 92 days before departure.
Is American Airlines the cheapest airline to fly with from New York to Chicago?
With an average price of $273 return, American Airlines is not the cheapest airline to fly from New York to Chicago with. Instead, for the lowest price, our data suggests flying with Spirit Airlines, where a return flight costs $146 on average.
What is the cheapest American Airlines flight from New York to Chicago?
In the last 3 days, the lowest price for a flight with American Airlines from New York to Chicago was $79 for a return flight and $47 for a one-way flight.
Does American Airlines fly direct to Chicago from New York?
Yes, American Airlines does offer direct flights for the route, with around 40 flights per week.
What’s the cheapest day of the week to fly from New York to Chicago with American Airlines?
On average, the cheapest day of the week to fly from New York to Chicago with American Airlines is Monday, when prices are around $62. The most expensive day is generally Saturday, where the average price is around $85.
What’s the cheapest month to fly from New York to Chicago with American Airlines?
The cheapest month for American Airlines flights to Chicago from New York is generally September, where plane tickets cost $103 on average. If possible, try to avoid the most expensive months of December and May, where tickets cost $166 and $168 respectively.

See more FAQs

7.2

GoodBased on 10,000 verified guest reviews

7.2Comfort

7.0Entertainment

8.0Crew

7.5Boarding

6.5Food

Pros +

Cons -

Show reviews that mention

2.0 Poor

Verified traveler, Jan 2025

HND-JFK

Random carry-on baggage inspection before boarding for NO REASON. The crew kept talking loudly the entire time, making it impossible to rest. When I asked the crew for something, they said they would come back later but never did. It was an EXTREMELY UNPLEASANT and UNCOMFORTABLE flight.

8.0 Very good

Verified traveler, Jan 2025

ORD-MSN

Good experience

10.0 Wonderful

Benjamin, Jan 2025

DFW-TUL

This was a pleasant, short flight and the crew was friendly.

4.0 Mediocre

Benjamin, Jan 2025

PHL-DFW

The temperature was too warm, which made it uncomfortable.

2.0 Poor

Virginia, Jan 2025

PHL-BTV

DELAYED

2.0 Poor

Virginia, Jan 2025

AUA-PHL

DELAYED!!

6.0 Okay

Dorothy, Jan 2025

PHL-SRQ

Very poor. Our special services attendant gave us incorrect information. I also was mishandled at landing. There was no wheelchair waiting. I fell deboarding the plane. Appalling!

8.0 Very good

Thurston, Jan 2025

ALB-DCA

It was good. It’s been a long time since my wife and I fly any where and things have changed. Our trip was to see our new grandson. We fly economy and that was not good for my bad back. It was a quick flight but uncomfortable.

10.0 Wonderful

Verified traveler, Jan 2025

JAX-PHL

Wonderful experience

8.0 Very good

Brandon, Jan 2025

SAN-PHX

I paid for what I got which was cheap, I brought my own entertainment. I knew what to expect, so I could be prepared. If you’re flying economy, check in early like me. I have no problems with my flight, was on time, staff were friendly, and overall good experience.

Everything you need to know for your flight from New York to Chicago

NYC - CHI

$73 Find Cheap American Airlines Flights from New York to Chicago

Search hundreds of travel sites at once for deals on American Airlines flights from New York to Chicago

Cheap American Airlines Flight Deals from New York to Chicago

Recent round-trip American Airlines flight deals from New York to Chicago

Recent one-way American Airlines flight deals from New York to Chicago

Recent last minute American Airlines flight deals from New York to Chicago

Recent direct American Airlines flight deals from New York to Chicago

Good to know

Low season

High season

Cheapest flight

Average price round-trip

When to Book Flights with American Airlines from New York to Chicago

FAQs for flying to Chicago with American Airlines

How far in advance should I book tickets for a flight with American Airlines from New York to Chicago?

Is American Airlines the cheapest airline to fly with from New York to Chicago?

What is the cheapest American Airlines flight from New York to Chicago?

Does American Airlines fly direct to Chicago from New York?

What’s the cheapest day of the week to fly from New York to Chicago with American Airlines?

What’s the cheapest month to fly from New York to Chicago with American Airlines?

American Airlines Customer Reviews

Pros +

Cons -

Traveler rating:

Sort by:

Everything you need to know for your flight from New York to Chicago

Other airlines flying from New York to Chicago

Flights from the other most popular airlines that fly from New York to Chicago according to KAYAK users. Prices are the lowest found on KAYAK over the last 7 days. Price and availability are not guaranteed.

Top American Airlines flights

The most popular destinations for flights with American Airlines according to clicks from KAYAK users. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

Cabin class types available on flights from New York to Chicago

Cabin classes available on flights from New York to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

Complete your trip to Chicago with a hotel stay or car rental

Flights to other popular destinations

The most popular flights on KAYAK according to clicks in the last 2 weeks. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

Find deals for your return flight