American Airlines flights from Chicago to Naples

Recent searches for flights from Chicago to Naples

Sep 2026
From$975*
Updated: 3 hours ago
Round tripIEconomy
Oct 2026
From$878*
Updated: 3 hours ago
Round tripIEconomy
Nov 2026
From$1,175*
Updated: 3 hours ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $975
cmp-daily-histogram-bars-legend-max-price-aria-label $2.3K
Displaying fares for September-2026
  • ORD–NAP, 09/02/26 – 09/07/26: From $1,627
    02

    We

    SEP

  • ORD–NAP, 09/03/26 – 09/07/26: From $1,571
    03

    Th

  • ORD–NAP, 09/04/26 – 09/11/26: From $1,348
    04

    Fr

  • ORD–NAP, 09/05/26 – 09/12/26: From $2,272
    05

    Sa

  • ORD–NAP, 09/06/26 – 09/13/26: From $1,269
    06

    Su

  • ORD–NAP, 09/07/26 – 09/14/26: From $1,169
    07

    Mo

  • ORD–NAP, 09/08/26 – 09/15/26: From $1,109
    08

    Tu

  • ORD–NAP, 09/09/26 – 09/16/26: From $1,107
    09

    We

  • ORD–NAP, 09/10/26 – 09/17/26: From $1,167
    10

    Th

  • ORD–NAP, 09/11/26 – 09/18/26: From $1,167
    11

    Fr

  • ORD–NAP, 09/12/26 – 09/19/26: From $1,499
    12

    Sa

  • ORD–NAP, 09/13/26 – 09/20/26: From $1,221
    13

    Su

  • ORD–NAP, 09/14/26 – 09/21/26: From $1,187
    14

    Mo

  • ORD–NAP, 09/15/26 – 09/22/26: From $1,107
    15

    Tu

  • ORD–NAP, 09/16/26 – 09/23/26: From $1,109
    16

    We

  • ORD–NAP, 09/17/26 – 09/24/26: From $1,175
    17

    Th

  • ORD–NAP, 09/18/26 – 09/25/26: From $1,265
    18

    Fr

  • ORD–NAP, 09/19/26 – 10/10/26: From $1,353
    19

    Sa

  • ORD–NAP, 09/20/26 – 09/27/26: From $1,441
    20

    Su

  • ORD–NAP, 09/21/26 – 09/28/26: From $1,433
    21

    Mo

  • ORD–NAP, 09/22/26 – 09/29/26: From $1,161
    22

    Tu

  • ORD–NAP, 09/23/26 – 09/30/26: From $1,127
    23

    We

  • ORD–NAP, 09/24/26 – 10/01/26: From $1,173
    24

    Th

  • ORD–NAP, 09/25/26 – 10/02/26: From $1,163
    25

    Fr

  • ORD–NAP, 09/26/26 – 10/03/26: From $1,313
    26

    Sa

  • ORD–NAP, 09/27/26 – 10/04/26: From $1,333
    27

    Su

  • ORD–NAP, 09/28/26 – 10/05/26: From $1,163
    28

    Mo

  • ORD–NAP, 09/29/26 – 10/06/26: From $1,103
    29

    Tu

  • ORD–NAP, 09/30/26 – 10/07/26: From $975
    30

    We

  • ORD–NAP, 10/01/26 – 10/08/26: From $1,035
    01

    Th

    OCT

    • range$975-$2,272

    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)
    02/14/27 - 02/21/27

    Round trip

    Economy

    from
    $796Fare subject to changes
    Updated: 20 hours ago

    Chicago (ORD)to

    Naples (NAP)
    04/14/27 - 04/21/27

    Round trip

    Economy

    from
    $812Fare subject to changes
    Updated: 10 hours ago

    Chicago (ORD)to

    Naples (NAP)
    02/13/27 - 02/21/27

    Round trip

    Economy

    from
    $846Fare subject to changes
    Updated: 21 hours ago

    Chicago (ORD)to

    Naples (NAP)
    02/12/27 - 02/21/27

    Round trip

    Economy

    from
    $846Fare subject to changes
    Updated: 20 hours ago

    Chicago (ORD)to

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

    Round trip

    Economy

    from
    $741Fare subject to changes
    Updated: 3 hours ago

    Chicago (ORD)to

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

    Round trip

    Economy

    from
    $780Fare subject to changes
    Updated: 3 hours ago

    Chicago (ORD)to

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

    Round trip

    Economy

    from
    $801Fare subject to changes
    Updated: 3 hours ago

    Chicago (ORD)to

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

    Round trip

    Economy

    from
    $805Fare subject to changes
    Updated: 3 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