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Find cheap American Airlines flights to Chicago from $58

1 adult
0 bags
Thu 6/27
Thu 7/4

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Good to know

Low season

January

High season

June

Cheapest flight

$58

Average price round-trip

$2,615

Good deal round-trip

$1,481
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 17% increase in price.
Flight from Boston 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 $595, American Airlines is the most expensive airline flying into Chicago. The cheapest airline flying to Chicago is Allegiant Air.

  • 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, Denver Air Connection, Contour, United Airlines, Southwest, Avelo Airlines, Delta, Frontier, Allegiant Air, Contour and United Airlines.

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

    On average, American Airlines flights to Chicago cost $345 for one-way and $595 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?

    Unfortunately, there are no other airlines in oneworld that fly to Chicago.

See more FAQs

Top tips for your flights to Chicago with American Airlines

  • The cheapest flight to Chicago with American Airlines found on KAYAK in the last 2 weeks departed from Lansing and cost $124.

American Airlines customer reviews

7.3
GoodBased on 14,316 verified guest reviews
6.6Food
7.1Entertainment
7.6Boarding
7.2Comfort
8.0Crew

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
8.0 Very good
Pros:On time
Cons:No gluten free food available
A
10.0 Wonderful
Pros:good attention
A
10.0 Wonderful
Pros:Early arrival
M
10.0 Wonderful
Pros:Free movies and tv
Cons:Nothing
A
5.0 Fair
Pros:Andres was so nice. Amazing actually
Cons:They boarded us then we had to switch planes. Delayed an hour
S
4.0 Mediocre
Cons:Delays, seats are cramped and uncomfortable
A
2.0 Poor
Cons:Had to reschedule to a later flight.
N
6.0 Okay
Cons:Films, TV screens did not work

Book Cheap flights with American Airlines to Chicago

Recent round-trip flight deals

6/26Wed
nonstopAmerican Airlines
2h 57mJFK-ORD
7/3Wed
nonstopAmerican Airlines
2h 20mORD-JFK
$127
7/9Tue
nonstopAmerican Airlines
2h 40mLGA-ORD
7/16Tue
nonstopAmerican Airlines
2h 04mORD-LGA
$127
6/26Wed
nonstopAmerican Airlines
2h 57mJFK-ORD
6/29Sat
nonstopAmerican Airlines
2h 25mORD-JFK
$128
6/26Wed
nonstopAmerican Airlines
2h 57mJFK-ORD
7/3Wed
nonstopAmerican Airlines
2h 20mORD-JFK
$129
6/26Wed
nonstopAmerican Airlines
2h 57mJFK-ORD
7/3Wed
nonstopAmerican Airlines
2h 20mORD-JFK
$130
8/13Tue
nonstopAmerican Airlines
2h 55mBOS-ORD
8/17Sat
nonstopAmerican Airlines
2h 18mORD-BOS
$147
7/4Thu
nonstopAmerican Airlines
2h 51mJFK-ORD
7/9Tue
nonstopAmerican Airlines
2h 38mORD-JFK
$148
7/23Tue
nonstopAmerican Airlines
2h 40mLGA-ORD
7/26Fri
nonstopAmerican Airlines
2h 21mORD-LGA
$148
9/4Wed
nonstopAmerican Airlines
4h 03mSEA-ORD
9/11Wed
nonstopAmerican Airlines
4h 38mORD-SEA
$149
7/1Mon
nonstopAmerican Airlines
2h 57mJFK-ORD
7/2Tue
nonstopAmerican Airlines
2h 26mORD-JFK
$150
6/19Wed
nonstopAmerican Airlines
2h 57mJFK-ORD
6/25Tue
nonstopAmerican Airlines
2h 26mORD-JFK
$157
6/7Fri
nonstopAmerican Airlines
2h 55mBOS-ORD
6/11Tue
nonstopAmerican Airlines
2h 26mORD-BOS
$160
7/10Wed
nonstopAmerican Airlines
2h 54mJFK-ORD
7/16Tue
nonstopAmerican Airlines
2h 38mORD-JFK
$161
8/28Wed
nonstopAmerican Airlines
2h 44mJFK-ORD
9/3Tue
nonstopAmerican Airlines
2h 21mORD-JFK
$167
6/15Sat
nonstopAmerican Airlines
2h 56mBOS-ORD
6/16Sun
nonstopAmerican Airlines
2h 25mORD-BOS
$167
7/5Fri
nonstopAmerican Airlines
2h 56mBOS-ORD
7/8Mon
nonstopAmerican Airlines
2h 27mORD-BOS
$168
9/14Sat
nonstopAmerican Airlines
2h 41mJFK-ORD
9/17Tue
nonstopAmerican Airlines
2h 15mORD-JFK
$169
9/5Thu
nonstopAmerican Airlines
2h 14mDCA-ORD
9/7Sat
nonstopAmerican Airlines
1h 47mORD-DCA
$169
6/18Tue
nonstopAmerican Airlines
2h 34mEWR-ORD
6/25Tue
nonstopAmerican Airlines
2h 09mORD-EWR
$169
11/14Thu
nonstopAmerican Airlines
2h 40mLGA-ORD
11/17Sun
nonstopAmerican Airlines
2h 06mORD-LGA
$169

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Recent one-way flight deals

6/18Tue
nonstopAmerican Airlines
2h 55mBOS-ORD
$58
6/26Wed
nonstopAmerican Airlines
2h 57mJFK-ORD
$64
6/25Tue
nonstopAmerican Airlines
2h 34mLGA-ORD
$64
6/26Wed
nonstopAmerican Airlines
2h 57mJFK-ORD
$65
7/3Wed
nonstopAmerican Airlines
2h 55mBOS-ORD
$69
9/6Fri
nonstopAmerican Airlines
3h 03mMCO-ORD
$70
8/27Tue
nonstopAmerican Airlines
4h 09mSEA-ORD
$75
8/17Sat
nonstopAmerican Airlines
2h 53mBOS-ORD
$79
6/4Tue
nonstopAmerican Airlines
3h 04mBOS-ORD
$82
7/1Mon
nonstopAmerican Airlines
2h 57mJFK-ORD
$85
7/2Tue
nonstopAmerican Airlines
2h 15mDCA-ORD
$85
6/18Tue
nonstopAmerican Airlines
2h 40mEWR-ORD
$85
7/29Mon
nonstopAmerican Airlines
2h 43mLGA-ORD
$85
10/24Thu
nonstopAmerican Airlines
2h 42mJFK-ORD
$86
10/24Thu
nonstopAmerican Airlines
2h 43mEWR-ORD
$86
7/22Mon
nonstopAmerican Airlines
2h 44mLGA-ORD
$86
7/19Fri
nonstopAmerican Airlines
2h 56mBOS-ORD
$89
7/9Tue
nonstopAmerican Airlines
4h 13mSFO-ORD
$90
7/17Wed
nonstopAmerican Airlines
2h 54mJFK-ORD
$94
8/7Wed
nonstopAmerican Airlines
2h 20mDCA-ORD
$95

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Flights to Chicago - American Airlines

Return flight deals:

Chicago - United States

Cabin classes:

$360
$419
$234
$43

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