American Airlines flights from Cleveland to Chicago

Recent searches for flights from Cleveland to Chicago

Sep 2026
From$347*
Updated: 7 hours ago
Round tripIEconomy
Oct 2026
From$207*
Updated: 6 hours ago
Round tripIEconomy
Nov 2026
From$207*
Updated: 6 hours ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $207
cmp-daily-histogram-bars-legend-max-price-aria-label $573
Displaying fares for September-2026
  • CLE–ORD: cmp-view-offers-disclaimer. Find Offers
    14

    Mo

    SEP

  • CLE–ORD, 09/15/26 – 09/22/26: From $515
    15

    Tu

  • CLE–ORD, 09/16/26 – 09/17/26: From $509
    16

    We

  • CLE–ORD, 09/17/26 – 09/24/26: From $573
    17

    Th

  • CLE–ORD, 09/18/26 – 09/25/26: From $573
    18

    Fr

  • CLE–ORD, 09/19/26 – 09/20/26: From $476
    19

    Sa

  • CLE–ORD, 09/20/26 – 09/27/26: From $573
    20

    Su

  • CLE–ORD, 09/21/26 – 09/28/26: From $531
    21

    Mo

  • CLE–ORD, 09/22/26 – 09/29/26: From $502
    22

    Tu

  • CLE–ORD, 09/23/26 – 09/24/26: From $462
    23

    We

  • CLE–ORD, 09/24/26 – 10/01/26: From $531
    24

    Th

  • CLE–ORD, 09/25/26 – 10/02/26: From $531
    25

    Fr

  • CLE–ORD, 09/26/26 – 10/03/26: From $502
    26

    Sa

  • CLE–ORD, 09/27/26 – 10/04/26: From $531
    27

    Su

  • CLE–ORD, 09/28/26 – 09/29/26: From $347
    28

    Mo

  • CLE–ORD, 09/29/26 – 10/06/26: From $348
    29

    Tu

  • CLE–ORD, 09/30/26 – 10/07/26: From $348
    30

    We

  • CLE–ORD, 10/01/26 – 10/08/26: From $363
    01

    Th

    OCT

  • CLE–ORD, 10/02/26 – 10/09/26: From $378
    02

    Fr

  • CLE–ORD, 10/03/26 – 10/10/26: From $348
    03

    Sa

  • CLE–ORD, 10/04/26 – 10/11/26: From $449
    04

    Su

  • CLE–ORD, 10/05/26 – 10/12/26: From $237
    05

    Mo

  • CLE–ORD, 10/06/26 – 10/13/26: From $207
    06

    Tu

  • CLE–ORD, 10/07/26 – 10/14/26: From $207
    07

    We

  • CLE–ORD, 10/08/26 – 10/15/26: From $237
    08

    Th

  • CLE–ORD, 10/09/26 – 10/12/26: From $252
    09

    Fr

  • CLE–ORD, 10/10/26 – 10/17/26: From $207
    10

    Sa

  • CLE–ORD, 10/11/26 – 10/15/26: From $323
    11

    Su

  • CLE–ORD, 10/12/26 – 10/15/26: From $237
    12

    Mo

  • CLE–ORD: cmp-view-offers-disclaimer. Find Offers
    13

    Tu

    • range$207-$573

    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 Cleveland to Chicago flights

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    Cleveland (CLE)to

    Chicago (ORD)
    10/17/26 - 10/24/26

    Round trip

    Economy

    from
    $207Fare subject to changes
    Updated: 6 hours ago

    Cleveland (CLE)to

    Chicago (ORD)
    10/20/26 - 10/27/26

    Round trip

    Economy

    from
    $207Fare subject to changes
    Updated: 6 hours ago

    Cleveland (CLE)to

    Chicago (ORD)
    10/21/26 - 10/28/26

    Round trip

    Economy

    from
    $207Fare subject to changes
    Updated: 6 hours ago

    Cleveland (CLE)to

    Chicago (ORD)
    10/27/26 - 11/03/26

    Round trip

    Economy

    from
    $207Fare subject to changes
    Updated: 6 hours ago

    Cleveland (CLE)to

    Chicago (ORD)
    10/28/26 - 11/04/26

    Round trip

    Economy

    from
    $207Fare subject to changes
    Updated: 6 hours ago

    Cleveland (CLE)to

    Chicago (ORD)
    10/31/26 - 11/07/26

    Round trip

    Economy

    from
    $207Fare subject to changes
    Updated: 6 hours ago

    Cleveland (CLE)to

    Chicago (ORD)
    10/07/26 - 10/14/26

    Round trip

    Economy

    from
    $207Fare subject to changes
    Updated: 6 hours ago

    Cleveland (CLE)to

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

    Round trip

    Economy

    from
    $207Fare subject to changes
    Updated: 6 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 Cleveland to Chicago

    Looking for lower fares on your trip from Cleveland 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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    • 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 Cleveland to Chicago