American Airlines flights from Boston to Chicago

Recent searches for flights from Boston to Chicago

Sep 2026
From$242*
Updated: 2 hours ago
Round tripIEconomy
Oct 2026
From$189*
Updated: 2 hours ago
Round tripIEconomy
Nov 2026
From$189*
Updated: 2 hours ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $189
cmp-daily-histogram-bars-legend-max-price-aria-label $443
Displaying fares for September-2026
  • BOS–ORD, 09/15/26 – 09/17/26: From $377
    15

    Tu

    SEP

  • BOS–ORD, 09/16/26 – 09/23/26: From $377
    16

    We

  • BOS–ORD, 09/17/26 – 09/20/26: From $377
    17

    Th

  • BOS–ORD, 09/18/26 – 09/20/26: From $377
    18

    Fr

  • BOS–ORD, 09/19/26 – 10/06/26: From $283
    19

    Sa

  • BOS–ORD, 09/20/26 – 09/27/26: From $377
    20

    Su

  • BOS–ORD, 09/21/26 – 09/28/26: From $377
    21

    Mo

  • BOS–ORD, 09/22/26 – 09/29/26: From $336
    22

    Tu

  • BOS–ORD, 09/23/26 – 09/30/26: From $336
    23

    We

  • BOS–ORD, 09/24/26 – 10/01/26: From $336
    24

    Th

  • BOS–ORD, 09/25/26 – 10/02/26: From $336
    25

    Fr

  • BOS–ORD, 09/26/26 – 10/03/26: From $336
    26

    Sa

  • BOS–ORD, 09/27/26 – 10/04/26: From $443
    27

    Su

  • BOS–ORD, 09/28/26 – 10/05/26: From $296
    28

    Mo

  • BOS–ORD, 09/29/26 – 10/06/26: From $242
    29

    Tu

  • BOS–ORD, 09/30/26 – 10/07/26: From $242
    30

    We

  • BOS–ORD, 10/01/26 – 10/04/26: From $295
    01

    Th

    OCT

  • BOS–ORD, 10/02/26 – 10/17/26: From $242
    02

    Fr

  • BOS–ORD, 10/03/26 – 10/10/26: From $242
    03

    Sa

  • BOS–ORD, 10/04/26 – 10/11/26: From $287
    04

    Su

  • BOS–ORD, 10/05/26 – 10/10/26: From $202
    05

    Mo

  • BOS–ORD, 10/06/26 – 10/13/26: From $189
    06

    Tu

  • BOS–ORD, 10/07/26 – 10/14/26: From $189
    07

    We

  • BOS–ORD, 10/08/26 – 10/10/26: From $283
    08

    Th

  • BOS–ORD, 10/09/26 – 10/15/26: From $397
    09

    Fr

  • BOS–ORD, 10/10/26 – 10/17/26: From $244
    10

    Sa

  • BOS–ORD, 10/11/26 – 10/15/26: From $255
    11

    Su

  • BOS–ORD, 10/12/26 – 10/14/26: From $281
    12

    Mo

  • BOS–ORD, 10/13/26 – 10/14/26: From $189
    13

    Tu

  • BOS–ORD, 10/14/26 – 10/16/26: From $215
    14

    We

    • range$189-$443

    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 Boston to Chicago flights

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    Boston (BOS)to

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

    Round trip

    Economy

    from
    $189Fare subject to changes
    Updated: 2 hours ago

    Boston (BOS)to

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

    Round trip

    Economy

    from
    $189Fare subject to changes
    Updated: 2 hours ago

    Boston (BOS)to

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

    Round trip

    Economy

    from
    $189Fare subject to changes
    Updated: 2 hours ago

    Boston (BOS)to

    Chicago (ORD)
    12/01/26 - 12/08/26

    Round trip

    Economy

    from
    $189Fare subject to changes
    Updated: 2 hours ago

    Boston (BOS)to

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

    Round trip

    Economy

    from
    $189Fare subject to changes
    Updated: 2 hours ago

    Boston (BOS)to

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

    Round trip

    Economy

    from
    $189Fare subject to changes
    Updated: 2 hours ago

    Boston (BOS)to

    Chicago (ORD)
    10/06/26 - 10/13/26

    Round trip

    Economy

    from
    $189Fare subject to changes
    Updated: 2 hours ago

    Boston (BOS)to

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

    Round trip

    Economy

    from
    $189Fare 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.

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