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Find cheap American Airlines flights to Chicago from $64

1 adult
0 bags
Fri 5/31
Fri 6/7

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Good to know

Low season

January

High season

June

Cheapest flight

$64

Average price round-trip

$266
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly with an average 27% increase in price.
Flight from New York John F Kennedy Airport to Chicago O'Hare Airport
(price for this month)

When to book flights with American Airlines to Chicago

Average price per month
Flight prices as travel date approaches

FAQs for flying to Chicago with American Airlines

  • Is American Airlines cheaper than other airlines flying to Chicago?

    With an average return price of $591, American Airlines is cheaper than United Airlines and Alaska Airlines when it comes to flights to Chicago. However, the cheapest airline flying to Chicago is Allegiant Air, with an average return price of $93.

  • Which other airlines fly to Chicago?

    Along with American Airlines, you can also fly to Chicago with Southern / Mokulele, Delta, Frontier, Allegiant Air, Contour, United Airlines, Southwest, Avelo Airlines, Alaska Airlines, Delta, Frontier, Allegiant Air, Contour, United Airlines and Avelo Airlines.

  • How much is a flight to Chicago with American Airlines?

    On average, American Airlines flights to Chicago cost $314 for one-way and $591 return.

  • Which airport do American Airlines flights to Chicago fly into?

    American Airlines flights to Chicago will fly into either Chicago O'Hare Airport, Chicago Midway Airport and Chicago Greater Rockford.

  • Are there any other airlines in oneworld that fly to Chicago?

    The only other oneworld airline flying to Chicago is Alaska Airlines.

See more FAQs

Top tips for your flights to Chicago with American Airlines

  • Looking to fly from the United States to Chicago with American Airlines? 25% of our users found flights for the following prices or less: From White Plains $183 one-way, $425 round-trip; from La Crosse $300 one-way, $529 round-trip.
  • The cheapest flight to Chicago with American Airlines found on KAYAK in the last 2 weeks departed from White Plains and cost $99.

American Airlines customer reviews

7.3
GoodBased on 14,815 verified guest reviews
7.1Entertainment
8.0Crew
7.2Comfort
7.6Boarding
6.6Food

Pros +
Cons -

Traveler rating:
Sort by:
A
6.0 Okay
Pros:1/ That it was a direct flight to Dublin. 2/ The price of ticket.
Cons:1/ flight was 3 1/2 hours late leaving JFK - thankfully they made up about 45 minutes en route. Otherwise we would have missed our connecting flight. 2/ food was not good. 3/ there were no individual screens for entertainment. 4/ my husband was in business and his seat did not recline!!
A
2.0 Poor
Pros:Nothing
Cons:Seat 17F is very short on leg room for a 6 foot man. Flight attendants didn't care and rough landing; pilot needs more practice.
A
2.0 Poor
Cons:This flight never happened due to an airport and schedule shift caused by the first leg being cancelled.
A
2.0 Poor
Pros:Absolutely nothing
Cons:Our flight to Nashville AND our flight back to Dallas were both delayed due to "maintenance". Each time was a delay of a couple of hours causing us to miss both of our original layover flights. As a result, we missed TWO very important business meetings that ended up costing us over $10,000! We were unable to provide paychecks to employees! After spending 2 entire days sitting in the airport waiting, we were offered a "food voucher" for $30, were advised to go pick up our luggage first, but they failed to mention we would be unable to get back through DFW airport security just to eat!! We had to take a taxi back to our hotel for over $100 and they didn't offer help with that or anything else. This airline is the worst!!! Unless there is significant compensation offered, I will do anything and everything to destroy their reputation further. I'm in the marketing industry and am very capable of getting the word out to millions. American Airlines... 9/11...Never Forget.
A
4.3 Mediocre
Cons:Upon boarding the aircraft, the attendant at the gate told me to check the size of my carryon bag against the test dimensions, which I did. My bag fit but I had to press the side in slightly to make it fit. She said it had to slide in without me pressing on it and proceeded to make me remove items from the bag in order to board the plane. I walked down the ramp with my extra pair of shoes and a book in my hands. As a result, I had to place my bag far from my seat due to the added time. My bag easily fit in the overhead compartment with room to spare and my being made an example was a completely pointless exercise.
A
4.0 Mediocre
Cons:inflight entertainment wasn't working on my seat only which made my 6 hour flight seem even longer :(
A
10.0 Wonderful
Pros:The crew is so friendly. Perfect landing. Perfect flight!
J
4.0 Mediocre
Pros:Nothing.
Cons:Actually having a flight to Charlotte. They delayed flight without much warning... actually, they were delaying/cancelling many flights without warning most of the day. Long story short, I had to get a ride to LaGuardia, to catch a different flight. That flight got delayed when boarding
A
2.0 Poor
Pros:My 17 year old daughter flew American Airlines to attend a wedding. She recently had spinal surgery and is not able to lift more than 5lbs. After being assured by the airline that staff would help her with her carryon luggage, she was abandoned and ignored by both flight attendants. Each flight attendant referred het to the next, so she is walking back and forth tor their amusement. Tears rolling down her face, finally an elderly passenger helped her. Then the staff gave her attitude the entire flight. She may appear healthy, but she was cut from her neck to her waist and had two rods inserted along with bone grafts. I just cannot believe how awful she was treated.
Cons:The customer service was terroble. My daughter was humiliated.
A
7.6 Good
Cons:Overall the flight was great. I was carrying a suit in a hanging bag and asked the flight attendant in first class if there was a place I could hang it. She politely offered to hang it behind the last row of first class since none were in use. When getting off the plane, I grabbed my bag as I walked off and the other flight attendant said "you can't put your bag there, it isn't for you" to which I replied that I was told I could use the hanger. She then said "well you shouldn't have been given permission, and don't do it again, it isn't for you." The tone was a bit rude, and maybe the consistency should be reviewed.

Book Cheap flights with American Airlines to Chicago

Recent round-trip flight deals

7/16Tue
nonstopAmerican Airlines
2h 40mLGA-ORD
7/24Wed
nonstopAmerican Airlines
2h 04mORD-LGA
$137
5/29Wed
nonstopAmerican Airlines
2h 56mBOS-ORD
6/15Sat
nonstopAmerican Airlines
2h 25mORD-BOS
$137
6/11Tue
nonstopAmerican Airlines
2h 57mJFK-ORD
6/13Thu
nonstopAmerican Airlines
2h 26mORD-JFK
$148
8/7Wed
nonstopAmerican Airlines
2h 41mLGA-ORD
8/13Tue
nonstopAmerican Airlines
2h 05mORD-LGA
$148
5/29Wed
nonstopAmerican Airlines
2h 56mBOS-ORD
6/1Sat
nonstopAmerican Airlines
2h 26mORD-BOS
$153
5/30Thu
nonstopAmerican Airlines
2h 57mBOS-ORD
6/8Sat
nonstopAmerican Airlines
2h 29mORD-BOS
$159
6/5Wed
nonstopAmerican Airlines
2h 55mBOS-ORD
6/10Mon
nonstopAmerican Airlines
2h 25mORD-BOS
$163
5/27Mon
nonstopAmerican Airlines
2h 35mLGA-ORD
5/31Fri
nonstopAmerican Airlines
2h 03mORD-LGA
$167
5/22Wed
nonstopAmerican Airlines
3h 02mJFK-ORD
5/29Wed
nonstopAmerican Airlines
2h 13mORD-JFK
$168
10/9Wed
nonstopAmerican Airlines
2h 42mJFK-ORD
10/15Tue
nonstopAmerican Airlines
2h 30mORD-JFK
$169
6/11Tue
nonstopAmerican Airlines
2h 11mDCA-ORD
6/18Tue
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1h 49mORD-DCA
$169
6/11Tue
nonstopAmerican Airlines
2h 37mEWR-ORD
6/15Sat
nonstopAmerican Airlines
2h 11mORD-EWR
$169
10/7Mon
nonstopAmerican Airlines
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10/9Wed
nonstopAmerican Airlines
4h 33mORD-SEA
$169
8/29Thu
nonstopAmerican Airlines
2h 30mLGA-ORD
9/1Sun
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$169
9/25Wed
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2h 39mEWR-ORD
10/3Thu
nonstopAmerican Airlines
2h 02mORD-EWR
$170
5/22Wed
nonstopAmerican Airlines
3h 02mJFK-ORD
6/11Tue
nonstopAmerican Airlines
2h 26mORD-JFK
$171
5/21Tue
nonstopAmerican Airlines
2h 35mLGA-ORD
5/24Fri
nonstopAmerican Airlines
2h 04mORD-LGA
$171
7/2Tue
nonstopAmerican Airlines
2h 57mJFK-ORD
7/9Tue
nonstopAmerican Airlines
2h 38mORD-JFK
$172
10/21Mon
nonstopAmerican Airlines
2h 30mEWR-ORD
10/26Sat
nonstopAmerican Airlines
2h 18mORD-EWR
$172
5/29Wed
nonstopAmerican Airlines
2h 56mBOS-ORD
6/5Wed
nonstopAmerican Airlines
2h 25mORD-BOS
$177

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Recent one-way flight deals

6/11Tue
nonstopAmerican Airlines
2h 57mJFK-ORD
$64
6/18Tue
nonstopAmerican Airlines
2h 34mLGA-ORD
$64
6/26Wed
nonstopAmerican Airlines
2h 56mBOS-ORD
$64
8/14Wed
nonstopAmerican Airlines
2h 56mBOS-ORD
$65
6/1Sat
nonstopAmerican Airlines
3h 02mJFK-ORD
$69
8/6Tue
nonstopAmerican Airlines
2h 30mLGA-ORD
$69
5/29Wed
nonstopAmerican Airlines
4h 12mSEA-ORD
$70
5/30Thu
nonstopAmerican Airlines
2h 58mBOS-ORD
$70
8/10Sat
nonstopAmerican Airlines
2h 53mBOS-ORD
$74
6/11Tue
nonstopAmerican Airlines
4h 15mSEA-ORD
$75
9/24Tue
nonstopAmerican Airlines
2h 50mJFK-ORD
$80
5/26Sun
nonstopAmerican Airlines
2h 37mEWR-ORD
$84
5/23Thu
nonstopAmerican Airlines
2h 40mJFK-ORD
$85
5/22Wed
nonstopAmerican Airlines
2h 15mDCA-ORD
$85
6/25Tue
nonstopAmerican Airlines
2h 37mEWR-ORD
$85
7/2Tue
nonstopAmerican Airlines
2h 34mLGA-ORD
$85
8/19Mon
nonstopAmerican Airlines
2h 37mEWR-ORD
$86
6/7Fri
nonstopAmerican Airlines
2h 57mJFK-ORD
$90
7/21Sun
nonstopAmerican Airlines
2h 35mEWR-ORD
$90
5/15Wed
nonstopAmerican Airlines
3h 04mBOS-ORD
$90

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Flights to Chicago - American Airlines

Return flight deals:

Chicago - United States

Cabin classes:

$274
$293
$219
$38

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