American Airlines flights from Pensacola to Chicago

Recent searches for flights from Pensacola to Chicago

Sep 2026
From$359*
Updated: 2 hours ago
Round tripIEconomy
Oct 2026
From$329*
Updated: 2 hours ago
Round tripIEconomy
Nov 2026
From$319*
Updated: 2 hours ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $339
cmp-daily-histogram-bars-legend-max-price-aria-label $610
Displaying fares for September-2026
  • PNS–ORD, 09/12/26 – 09/14/26: From $569
    12

    Sa

    SEP

  • PNS–ORD, 09/13/26 – 09/20/26: From $610
    13

    Su

  • PNS–ORD, 09/14/26 – 09/21/26: From $549
    14

    Mo

  • PNS–ORD, 09/15/26 – 09/22/26: From $506
    15

    Tu

  • PNS–ORD, 09/16/26 – 09/23/26: From $506
    16

    We

  • PNS–ORD, 09/17/26 – 09/24/26: From $549
    17

    Th

  • PNS–ORD, 09/18/26 – 09/20/26: From $449
    18

    Fr

  • PNS–ORD, 09/19/26 – 09/26/26: From $414
    19

    Sa

  • PNS–ORD, 09/20/26 – 09/27/26: From $414
    20

    Su

  • PNS–ORD, 09/21/26 – 09/28/26: From $464
    21

    Mo

  • PNS–ORD, 09/22/26 – 09/29/26: From $414
    22

    Tu

  • PNS–ORD, 09/23/26 – 09/30/26: From $414
    23

    We

  • PNS–ORD, 09/24/26 – 10/01/26: From $414
    24

    Th

  • PNS–ORD, 09/25/26 – 10/02/26: From $414
    25

    Fr

  • PNS–ORD, 09/26/26 – 10/03/26: From $359
    26

    Sa

  • PNS–ORD, 09/27/26 – 10/04/26: From $359
    27

    Su

  • PNS–ORD, 09/28/26 – 10/05/26: From $359
    28

    Mo

  • PNS–ORD, 09/29/26 – 10/06/26: From $359
    29

    Tu

  • PNS–ORD, 09/30/26 – 10/07/26: From $359
    30

    We

  • PNS–ORD, 10/01/26 – 10/08/26: From $464
    01

    Th

    OCT

  • PNS–ORD, 10/02/26 – 10/09/26: From $359
    02

    Fr

  • PNS–ORD, 10/03/26 – 10/10/26: From $339
    03

    Sa

  • PNS–ORD, 10/04/26 – 10/11/26: From $444
    04

    Su

  • PNS–ORD, 10/05/26 – 10/12/26: From $548
    05

    Mo

  • PNS–ORD, 10/06/26 – 10/13/26: From $339
    06

    Tu

  • PNS–ORD, 10/07/26 – 10/14/26: From $339
    07

    We

  • PNS–ORD, 10/08/26 – 10/15/26: From $443
    08

    Th

  • PNS–ORD, 10/09/26 – 10/16/26: From $359
    09

    Fr

  • PNS–ORD: cmp-view-offers-disclaimer. Find Offers
    10

    Sa

  • PNS–ORD: cmp-view-offers-disclaimer. Find Offers
    11

    Su

    • range$339-$610

    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 Pensacola to Chicago flights

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    Pensacola (PNS)to

    Chicago (ORD)
    12/02/26 - 12/09/26

    Round trip

    Economy

    from
    $319Fare subject to changes
    Updated: 2 hours ago

    Pensacola (PNS)to

    Chicago (ORD)
    12/05/26 - 12/12/26

    Round trip

    Economy

    from
    $319Fare subject to changes
    Updated: 2 hours ago

    Pensacola (PNS)to

    Chicago (ORD)
    12/06/26 - 12/13/26

    Round trip

    Economy

    from
    $319Fare subject to changes
    Updated: 2 hours ago

    Pensacola (PNS)to

    Chicago (ORD)
    11/25/26 - 12/02/26

    Round trip

    Economy

    from
    $319Fare subject to changes
    Updated: 2 hours ago

    Pensacola (PNS)to

    Chicago (ORD)
    11/04/26 - 11/11/26

    Round trip

    Economy

    from
    $319Fare subject to changes
    Updated: 2 hours ago

    Pensacola (PNS)to

    Chicago (ORD)
    11/06/26 - 11/13/26

    Round trip

    Economy

    from
    $319Fare subject to changes
    Updated: 2 hours ago

    Pensacola (PNS)to

    Chicago (ORD)
    11/12/26 - 11/19/26

    Round trip

    Economy

    from
    $319Fare subject to changes
    Updated: 2 hours ago

    Pensacola (PNS)to

    Chicago (ORD)
    12/03/26 - 12/10/26

    Round trip

    Economy

    from
    $319Fare 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 Pensacola to Chicago

    Looking for lower fares on your trip from Pensacola to Chicago? 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

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    American Airlines flights from Pensacola to Chicago