American Airlines flights from Chicago to Naples

Recent searches for flights from Chicago to Naples

Aug 2026
From$903*
Updated: 22 hours ago
Round tripIEconomy
Sep 2026
From$974*
Updated: 2 hours ago
Round tripIEconomy
Oct 2026
From$877*
Updated: 30 minutes ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $903
cmp-daily-histogram-bars-legend-max-price-aria-label $1.6K
Displaying fares for August-2026
  • ORD–NAP, 08/12/26 – 08/19/26: From $903
    12

    We

    AUG

  • ORD–NAP, 08/13/26 – 08/20/26: From $953
    13

    Th

  • ORD–NAP, 08/14/26 – 08/21/26: From $953
    14

    Fr

  • ORD–NAP, 08/15/26 – 08/22/26: From $1,003
    15

    Sa

  • ORD–NAP, 08/16/26 – 08/23/26: From $957
    16

    Su

  • ORD–NAP, 08/17/26 – 08/24/26: From $957
    17

    Mo

  • ORD–NAP, 08/18/26 – 08/25/26: From $907
    18

    Tu

  • ORD–NAP, 08/19/26 – 08/26/26: From $907
    19

    We

  • ORD–NAP, 08/20/26 – 08/27/26: From $957
    20

    Th

  • ORD–NAP, 08/21/26 – 08/28/26: From $961
    21

    Fr

  • ORD–NAP, 08/22/26 – 08/29/26: From $1,011
    22

    Sa

  • ORD–NAP, 08/23/26 – 08/30/26: From $953
    23

    Su

  • ORD–NAP, 08/24/26 – 08/31/26: From $957
    24

    Mo

  • ORD–NAP, 08/25/26 – 09/01/26: From $1,008
    25

    Tu

  • ORD–NAP, 08/26/26 – 09/02/26: From $1,004
    26

    We

  • ORD–NAP, 08/27/26 – 09/03/26: From $1,058
    27

    Th

  • ORD–NAP, 08/28/26 – 09/04/26: From $1,223
    28

    Fr

  • ORD–NAP, 08/29/26 – 09/05/26: From $1,114
    29

    Sa

  • ORD–NAP, 08/30/26 – 09/06/26: From $1,072
    30

    Su

  • ORD–NAP, 08/31/26 – 09/07/26: From $1,072
    31

    Mo

  • ORD–NAP, 09/01/26 – 09/08/26: From $1,203
    01

    Tu

    SEP

  • ORD–NAP, 09/02/26 – 09/09/26: From $1,159
    02

    We

  • ORD–NAP, 09/03/26 – 09/10/26: From $1,441
    03

    Th

  • ORD–NAP, 09/04/26 – 09/11/26: From $1,177
    04

    Fr

  • ORD–NAP, 09/05/26 – 09/12/26: From $1,489
    05

    Sa

  • ORD–NAP, 09/06/26 – 09/13/26: From $1,557
    06

    Su

  • ORD–NAP, 09/07/26 – 09/21/26: From $1,214
    07

    Mo

  • ORD–NAP, 09/08/26 – 09/17/26: From $985
    08

    Tu

  • ORD–NAP, 09/09/26 – 09/16/26: From $985
    09

    We

  • ORD–NAP, 09/10/26 – 09/17/26: From $1,045
    10

    Th

  • ORD–NAP, 09/11/26 – 09/18/26: From $1,130
    11

    Fr

    • range$903-$1,557

    DisclaimerFares displayed have been collected within the last 24hrs and may no longer be available at time of booking. Modifying this information may result in a different fare. To find the most updated fare, please visit aa.com. Fares listed may be Basic Economy, which class is subject to additional terms and conditions. Additional baggage fees and charges for optional products and services may apply.

    Find deals on Chicago to Naples flights

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    Chicago (ORD)to

    Naples (NAP)
    12/09/26 - 12/16/26

    Round trip

    Economy

    from
    $738Fare subject to changes
    Updated: 2 hours ago

    Chicago (ORD)to

    Naples (NAP)
    12/01/26 - 12/08/26

    Round trip

    Economy

    from
    $738Fare subject to changes
    Updated: 2 hours ago

    Chicago (ORD)to

    Naples (NAP)
    12/06/26 - 12/13/26

    Round trip

    Economy

    from
    $777Fare subject to changes
    Updated: 2 hours ago

    Chicago (ORD)to

    Naples (NAP)
    12/08/26 - 12/15/26

    Round trip

    Economy

    from
    $798Fare subject to changes
    Updated: 2 hours ago

    Chicago (ORD)to

    Naples (NAP)
    12/10/26 - 12/17/26

    Round trip

    Economy

    from
    $849Fare subject to changes
    Updated: 2 hours ago

    Chicago (ORD)to

    Naples (NAP)
    10/14/26 - 10/21/26

    Round trip

    Economy

    from
    $877Fare subject to changes
    Updated: 30 minutes ago

    Chicago (ORD)to

    Naples (NAP)
    10/13/26 - 10/20/26

    Round trip

    Economy

    from
    $881Fare subject to changes
    Updated: 2 hours ago

    Chicago (ORD)to

    Naples (NAP)
    10/14/26 - 10/21/26

    Round trip

    Economy

    from
    $881Fare subject to changes
    Updated: 2 hours ago

    *Fares displayed have been collected within the last 24hrs and may no longer be available at time of booking. Some fares listed may include one or more connections that are Basic Economy, which class is subject to additional terms and conditions. Modifying this information may result in a different fare. To find the most updated fare, please visit aa.com. Additional baggage fees and charges for optional products and services may apply.

    Finding cheap flights from Chicago to Naples

    Looking for lower fares on your trip from Chicago to Naples? Here are a few ways to save.

    • Book early: Booking 1 to 3 months ahead can help you find lower fares
    • Be flexible with dates: Midweek travel, like Tuesdays and Wednesdays, can be more affordable
    • Travel during less busy periods: Flying outside peak travel times can help find lower fares and avoid crowds

    Earn up to $500 back on your next American Airlines flight plus, 30,000 bonus miles. Offers vary elsewhere. Opens another site in a new window that may not meet accessibility guidelines.

    Upgrade your flight with Main Cabin Extra

    Make your trip more comfortable with Main Cabin Extra. Enjoy benefits like:

    • Extra legroom: More space with seats at the front of the Main Cabin or in exit rows.
    • Early boarding: Preferred Group 5 boarding allows easier access to overhead bins.
    • Complimentary drinks: Enjoy beer, wine and spirits on flights with full beverage service.

    Discover how Main Cabin Extra can enhance your trip.

    American Airlines flights from Chicago to Naples