How do most travelers feel about American Airlines?

The average rating from 624 American Airlines reviews by Cheapflights users is 7.5 (out of a maximum rating of 10). If you are considering flying NYC-CHI with Cheapflights, apply your desired dates to the form above to see our best pricing for your trip to Chicago with American Airlines.

Can I get a flight from New York to Chicago on American Airlines for under $300?

Cheapflights users have found 50 American Airlines flights for under $300 on the NYC-CHI route. Prices on flights to Chicago from New York can vary based on many factors including dates. To look at price based on your preferred dates, click here.

Fly American Airlines from New York to Chicago as low as $84

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NYC — CHI

Jun 13 — Jun 201

Round-tripOne-way

1 adult, Economy

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Cheapflights users flying from New York to Chicago on American Airlines typically fly into Chicago O'Hare Intl and depart from New York John F Kennedy Intl. Select your dates above for pricing.

American Airlines information for flights from New York to Chicago

One-Way Flights From	$84
Round Trip Flights From	$168

The average one-way flight costs $125

The average round trip flight costs $212

Those looking to travel from New York to Chicago on American Airlines should know that there are other options for airports to fly into when visiting Chicago. When arriving in Chicago, most people land at Chicago O'Hare Intl, but that is not the only available airport that American Airlines flies to. Many people choose to land at Chicago Midway depending on where there are traveling to in the area. If you are looking for a closer or different airport to depart from in New York, American Airlines also flies out of Newark when traveling to Chicago.

Cheapest American Airlines flights from New York to Chicago

Jul 25 - Jul 26

LGA

New York LaGuardia

ORD

Chicago O'Hare Intl

Nonstop

2h 46m

ORD

Chicago O'Hare Intl

LGA

New York LaGuardia

Nonstop

2h 07m

$168

American Airlines

Pick Dates

Deal found 6/7

Jul 4 - Jul 4

JFK

New York John F Kennedy Intl

ORD

Chicago O'Hare Intl

Nonstop

3h 02m

ORD

Chicago O'Hare Intl

JFK

New York John F Kennedy Intl

1 stop

4h 33m

$197

American Airlines

Pick Dates

Deal found 6/7

Jul 22 - Jul 25

JFK

New York John F Kennedy Intl

ORD

Chicago O'Hare Intl

1 stop

7h 39m

ORD

Chicago O'Hare Intl

JFK

New York John F Kennedy Intl

Nonstop

2h 24m

$199

American Airlines

Pick Dates

Deal found 6/8

Direct flights from New York to Chicago on American Airlines

Sep 14 - Sep 18

JFK

New York John F Kennedy Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 49m

ORD

Chicago O'Hare Intl

JFK

New York John F Kennedy Intl

Nonstop

2h 30m

$168

American Airlines

Pick Dates

Deal found 6/7

Aug 8 - Aug 9

EWR

Newark

ORD

Chicago O'Hare Intl

Nonstop

2h 35m

ORD

Chicago O'Hare Intl

EWR

Newark

Nonstop

2h 08m

$168

American Airlines

Pick Dates

Deal found 6/7

Sep 14 - Sep 15

LGA

New York LaGuardia

ORD

Chicago O'Hare Intl

Nonstop

2h 34m

ORD

Chicago O'Hare Intl

LGA

New York LaGuardia

Nonstop

2h 09m

$168

American Airlines

Pick Dates

Deal found 6/6

Last minute deals on Cheapflights

Jun 17 - Jul 25

JFK

New York John F Kennedy Intl

ORD

Chicago O'Hare Intl

1 stop

5h 17m

ORD

Chicago O'Hare Intl

JFK

New York John F Kennedy Intl

Nonstop

2h 24m

$274

American Airlines

Pick Dates

Deal found 6/7

Jun 17 - Jul 25

LGA

New York LaGuardia

ORD

Chicago O'Hare Intl

1 stop

7h 21m

ORD

Chicago O'Hare Intl

LGA

New York LaGuardia

Nonstop

2h 12m

$274

American Airlines

Pick Dates

Deal found 6/7

Jun 16 - Jun 27

LGA

New York LaGuardia

ORD

Chicago O'Hare Intl

1 stop

5h 25m

ORD

Chicago O'Hare Intl

LGA

New York LaGuardia

Nonstop

2h 08m

$276

American Airlines

Pick Dates

Deal found 6/7

One-way American Airlines flights to Chicago from New York

Sep 5

JFK

New York John F Kennedy Intl

ORD

Chicago O'Hare Intl

Nonstop

3h 03m

$84

American Airlines

Pick Dates

Deal found 6/7

Aug 9

EWR

Newark

ORD

Chicago O'Hare Intl

Nonstop

2h 44m

$84

American Airlines

Pick Dates

Deal found 6/7

Aug 28

LGA

New York LaGuardia

ORD

Chicago O'Hare Intl

Nonstop

2h 36m

$84

American Airlines

Pick Dates

Deal found 6/7

Other American Airlines flights from New York

American Airlines flights from John F Kennedy Intl to Miami

American Airlines flights from Newark to Sky Harbor Intl

American Airlines flights from Newark to Dallas/Fort Worth

American Airlines flights from LaGuardia to Miami

American Airlines flights from John F Kennedy Intl to Montego Bay

American Airlines flights from John F Kennedy Intl to Punta Cana

American Airlines flights from John F Kennedy Intl to New Delhi

Popular flights with American Airlines

American Airlines flights from Los Angeles to Miami

American Airlines flights from Chicago to New York

American Airlines flights from Philadelphia to Los Angeles

American Airlines flights from Philadelphia to Las Vegas

American Airlines flights from Boston to Sky Harbor Intl

American Airlines flights from Washington, D.C. to Miami

American Airlines flights from Philadelphia to Miami

American Airlines flights from Dallas/Fort Worth to New York

American Airlines flights from Chicago to Cancún

American Airlines flights from John F Kennedy Intl to Miami

American Airlines flights from Los Angeles to Philadelphia

American Airlines flights from Philadelphia to Cancún

American Airlines flights from Dallas/Fort Worth to Cancún

American Airlines flights from San Francisco to Miami

American Airlines flights from Dallas/Fort Worth to Los Angeles

American Airlines flights from O'Hare Intl to Cancún

American Airlines flights from Miami to Cancún

American Airlines flights from Philadelphia to Tampa

American Airlines flights from Los Angeles to Dallas/Fort Worth

American Airlines flights from Austin to Las Vegas

American Airlines flights from Charlotte to Las Vegas

American Airlines flights from Raleigh to Miami

American Airlines flights from Newark to Sky Harbor Intl

American Airlines flights from Boston to Chicago

American Airlines flights from Philadelphia to Denver

American Airlines flights from Atlanta to Miami

American Airlines flights from Charlotte to Denver

American Airlines flights from O'Hare Intl to Sky Harbor Intl

American Airlines flights from Los Angeles to Puerto Vallarta

American Airlines flights from Miami to Mexico City

Other popular destinations in North America

Flights to Williamsport

Flights to San Francisco

Flights to Bullhead City

Flights to Klamath Falls

Flights to Los Angeles

Flights to Atlanta

Flights to Flagstaff

Flights to Portland

Flights to Indianapolis

Flights to New York

Flights to Tucson

Flights to Dayton

Fly from New York to Chicago on another airline

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See what others are saying about American Airlines

American Airlines

7.3

Good

19,415 reviews

Check prices

Overview

Recent reviews

7.9

Good|Sep 2021

A REVIEW BASED ON FACTUAL EXPERIENCES ON FORIGN CARRIERS AND THEIR SERVICE COMPARED TO AA and Other US CARRIERS, FIRST CLASS WHAT ? YOUR price for what not much more then a premium class seat AND ALL YOU OFFER IS a can of coke and a pkg of Fig Cookies ? Seriously. All 4 of my flights were first class, Joke of an offering, and each one sucked, I am American and I have flown over 800,000 miles and over 650 flights in 4 years, out of all these flights I've only flown US Carriers 12 times and I know that is a factual number. Jet Blue I will fly again, they act are a good and ran and they know how to take care of their guests AMERICAN AIRLINES JUST SUCKS Cathay pacific, Eva Air, Air Asia, Asiana, Korean Air, ANA, Thai Air ways and many more, I fly business class and every one of these airlines blows away these Sad Poorly ran US CARRIER'S, ,

5.9

Fair|Sep 2021

The boarding process was uneventful and normal. The plane was on the smaller side and a tight fit. Most people had to plane side check their luggage. The pilots seemed pleasant. We waited about an hour from leaving the gate to actually taking off with no information from the crew as to what was taking longer than normal. The flight attendants were informative but aggressive about the mask policy and spoke on the PA system often and for long periods of time. The attitude of the flight crew about several issues made the passengers tense. We arrived about 30 minutes behind schedule but safely.

5.6

Fair|Apr 2018

the connection time between flights was NOT adequate especially considering I had to go through customs! AA did page me and had a representative (I think his name was Brian) waiting for me to help me get to my connection. He gave me a bright red/orange tag. I still hit some barriers. I was stopped in security and my carry on was put aside to be searched. It sat and sat . I explained to the man I had to go. He said he was working alone, so I had to wait. I was ready to leave it and just run to catch the flight, but the security man said I wasn't allowed to do that. He finally called someone else to search my bag (nothing found) I did make it...barely!

1.9

Poor|Oct 2021

My direct flight was canceled and I had to go through Atlanta. I checked out my luggage through customs in Atlanta and checked them in to Philadelphia. I boarded on Friday, bags arrived on Monday at 6 Pm. The suitcases are bashed in, the contents spilled and ruined my expensive bags and shoes . I had to throw several cooked foods away because they had gone bad. My original ticket from Accra to London on Oct 6 was canceled without an explanation. Then the flight 24 hours later, was changed . It was a nightmare without any explanations or compensation.

2.0

Poor|Nov 2021

Absolutely horrible check in process leaving Aruba. Arrived 3 hours early. Line stretched from inside to out of airport. No movement in 1 hour. Two hours left. Much less than 1/2 to desk with one hour left and multiple security and customs checks (both Aruba and US). Two flights from Aruba leaving to Miami with American a only couple of hours apart. No one came through trying to determine who had the earlier flight to make sure no one missed it. If not for my “pushy” wife who moved us into “First Class” line to bypass others, we would have missed flight as obviously most people waiting around us did as they did not board the plane. Not enough American Airlines staff working at counters. Very slow check in process. The extensive Verifly process we did to document our immunizations and vaccines we were told was not working so they wanted to see documents. They wanted to charge us for checked bag despite we had a checked bag included. Same story from others who actually made the flight.

8.0

Very good|Jan 2022

I know it’s been 2 years and counting ,BUT your folks need to get more aggressive having everyone cover their noses in tight spaces on the bus and in the boarding areas. There are always a few “smart asses” who refuse to cover up. I suppose it would be difficult to “deputize” passengers, and you guys know the rules better than anyone. But how selfish are these people ? They should Immediately be removed from the lines, and at least held out to board last as an example. If airlines did something like this, it might help keeping us all safe from this ongoing problem! Please send my highest regards to all your employees! I am sure they never thought they would be put in this position but they should remember it’s keeping them and their families safe as well! Otherwise , the flight was great!

2.0

Poor|Dec 2021

The puddle jumper from Charlotte to Asheville often appears to be a low priority, if not for American Airlines then Charlotte International Airport. We had a tight connection (45 minutes), made worse by malfunction of gateway which took agonizing time to repair. I got no less than 3 gate changes, all in Concourse E, the farthest away from B where we landed. Fortunately airport people were great with a wheelchair for my wife, without which we would have missed the connection. Then, when we arrived at the resigned gate, the wheelchair attendant had to try times to get gate personnel to direct her to the right gate. Finally, when we went down stairs, we were redirected to a plane at least 300 yards from where we went down the stairs. If all that weren't enough, the two flight attendants appeared more interested in flirting with each other than paying any attention to the travelers. Avoid this connection if you can. Delta much better customer service.

7.6

Good|Apr 2018

Time of flight and on time flight

Lack of gluten free snack Cramped knee room

10.0

Wonderful|Mar 2018

Perfect

6.0

Okay|Apr 2018

longer hours due to the 2 stops

1 out of 6472

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American Airlines flights from New York to Chicago (NYC - CHI)

Cheapflights users flying from New York to Chicago on American Airlines typically fly into Chicago O'Hare Intl and depart from New York John F Kennedy Intl. Select your dates above for pricing.

American Airlines information for flights from New York to Chicago

One-Way Flights From

Round Trip Flights From

Can I get a flight from New York to Chicago on American Airlines for under $300?

Does American Airlines service alternative airports for NYC-CHI?

How do most travelers feel about American Airlines?

Cheapest American Airlines flights from New York to Chicago

Direct flights from New York to Chicago on American Airlines

Last minute deals on Cheapflights

One-way American Airlines flights to Chicago from New York

Other American Airlines flights from New York

Popular flights with American Airlines

Other popular destinations in North America

Fly from New York to Chicago on another airline

See what others are saying about American Airlines

Overview

Recent reviews

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