American Airlines flights from Pensacola to Chicago

Recent searches for flights from Pensacola to Chicago

Aug 2026
From$374*
Updated: 3 hours ago
Round tripIEconomy
Sep 2026
From$285*
Updated: 16 minutes ago
Round tripIEconomy
Oct 2026
From$289*
Updated: 5 hours ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $285
cmp-daily-histogram-bars-legend-max-price-aria-label $560
Displaying fares for August-2026
  • PNS–CHI, 08/23/26 – 08/29/26: From $459
    23

    Su

    AUG

  • PNS–ORD, 08/24/26 – 08/31/26: From $449
    24

    Mo

  • PNS–ORD, 08/25/26 – 09/01/26: From $446
    25

    Tu

  • PNS–ORD, 08/26/26 – 09/02/26: From $446
    26

    We

  • PNS–ORD, 08/27/26 – 09/03/26: From $459
    27

    Th

  • PNS–ORD, 08/28/26 – 09/04/26: From $449
    28

    Fr

  • PNS–ORD, 08/29/26 – 09/05/26: From $456
    29

    Sa

  • PNS–ORD, 08/30/26 – 09/06/26: From $374
    30

    Su

  • PNS–ORD, 08/31/26 – 09/07/26: From $560
    31

    Mo

  • PNS–CHI, 09/01/26 – 09/08/26: From $364
    01

    Tu

    SEP

  • PNS–CHI, 09/02/26 – 09/09/26: From $364
    02

    We

  • PNS–ORD, 09/03/26 – 09/10/26: From $364
    03

    Th

  • PNS–ORD, 09/04/26 – 09/11/26: From $364
    04

    Fr

  • PNS–CHI, 09/05/26 – 09/12/26: From $352
    05

    Sa

  • PNS–ORD, 09/06/26 – 09/13/26: From $309
    06

    Su

  • PNS–CHI, 09/07/26 – 09/14/26: From $409
    07

    Mo

  • PNS–ORD, 09/08/26 – 09/15/26: From $344
    08

    Tu

  • PNS–ORD, 09/09/26 – 09/16/26: From $319
    09

    We

  • PNS–CHI, 09/10/26 – 09/17/26: From $351
    10

    Th

  • PNS–CHI, 09/11/26 – 09/18/26: From $319
    11

    Fr

  • PNS–ORD, 09/12/26 – 09/19/26: From $319
    12

    Sa

  • PNS–ORD, 09/13/26 – 09/20/26: From $488
    13

    Su

  • PNS–CHI, 09/14/26 – 09/21/26: From $331
    14

    Mo

  • PNS–ORD, 09/15/26 – 09/22/26: From $299
    15

    Tu

  • PNS–ORD, 09/16/26 – 09/22/26: From $285
    16

    We

  • PNS–CHI, 09/17/26 – 09/24/26: From $299
    17

    Th

  • PNS–CHI, 09/18/26 – 09/25/26: From $299
    18

    Fr

  • PNS–CHI, 09/19/26 – 09/26/26: From $299
    19

    Sa

  • PNS–CHI: cmp-view-offers-disclaimer. Find Offers
    20

    Su

  • PNS–CHI: cmp-view-offers-disclaimer. Find Offers
    21

    Mo

  • PNS–CHI: cmp-view-offers-disclaimer. Find Offers
    22

    Tu

    • range$285-$560

    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)
    11/04/26 - 11/11/26

    Round trip

    Economy

    from
    $279Fare subject to changes
    Updated: 5 hours ago

    Pensacola (PNS)to

    Chicago (ORD)
    11/11/26 - 11/18/26

    Round trip

    Economy

    from
    $279Fare subject to changes
    Updated: 5 hours ago

    Pensacola (PNS)to

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

    Round trip

    Economy

    from
    $279Fare subject to changes
    Updated: 5 hours ago

    Pensacola (PNS)to

    Chicago (ORD)
    11/17/26 - 11/24/26

    Round trip

    Economy

    from
    $279Fare subject to changes
    Updated: 5 hours ago

    Pensacola (PNS)to

    Chicago (ORD)
    11/01/26 - 11/08/26

    Round trip

    Economy

    from
    $279Fare subject to changes
    Updated: 5 hours ago

    Pensacola (PNS)to

    Chicago (ORD)
    11/02/26 - 11/09/26

    Round trip

    Economy

    from
    $279Fare subject to changes
    Updated: 5 hours ago

    Pensacola (PNS)to

    Chicago (ORD)
    11/05/26 - 11/12/26

    Round trip

    Economy

    from
    $279Fare subject to changes
    Updated: 5 hours ago

    Pensacola (PNS)to

    Chicago (ORD)
    11/07/26 - 11/14/26

    Round trip

    Economy

    from
    $279Fare subject to changes
    Updated: 5 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

    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 Pensacola to Chicago