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Find cheap American Airlines flights to Chicago from $64

1 adult
0 bags
lun. 5/27
lun. 6/3

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Good to know

Low season

January

High season

June

Cheapest flight

$64

Average price round-trip

$245

Good deal one-way

$437
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
(avg. price over the last 2 weeks)
or less

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 $580, American Airlines is cheaper than 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 $95.

  • Which other airlines fly to Chicago?

    Along with American Airlines, you can also fly to Chicago with Cape Air, Southern / Mokulele, Delta, Frontier, Allegiant Air, Contour, United Airlines, Southwest, 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 $308 for one-way and $580 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 $176 one-way, $421 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 Manchester, New Hampshire and cost $116.

American Airlines customer reviews

7.3
GoodBased on 14,875 verified guest reviews
7.2Comfort
7.6Boarding
8.0Crew
7.1Entertainment
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.
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Recent round-trip flight deals

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Flights to Chicago - American Airlines

Return flight deals:

Chicago - United States

Cabin classes:

$274
First Class flights to Chicago
$293
Business Class flights to Chicago
$217
$38

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