Southwest® flights from Boston to Chicago (O'Hare)

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Low fares from Boston to Chicago (O'Hare)

$

Boston (BOS)to

Chicago (Midway) (MDW)
Depart: 10/28/2026

One-way

Basic

From
$104
Seen: 14 hrs ago

Boston (BOS)to

Chicago (Midway) (MDW)
Depart: 09/26/2026

One-way

Basic

From
$104
Seen: 15 hrs ago

Boston (BOS)to

Chicago (Midway) (MDW)
Depart: 09/15/2026

One-way

Basic

From
$104
Seen: 16 hrs ago

Boston (BOS)to

Chicago (Midway) (MDW)
Depart: 09/22/2026

One-way

Basic

From
$104
Seen: 8 hrs ago

Boston (BOS)to

Chicago (Midway) (MDW)
Depart: 09/16/2026

One-way

Basic

From
$104
Seen: 7 hrs ago

Boston (BOS)to

Chicago (Midway) (MDW)
Depart: 10/27/2026

One-way

Basic

From
$104
Seen: 12 hrs ago

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Explore flights from Boston to Chicago (O'Hare)

Aug 2026
From$128*
Seen: 5 hrs ago
One Way/Basic
Sep 2026
From$104*
Seen: 7 hrs ago
One Way/Basic
Oct 2026
From$104*
Seen: 14 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $123
cmp-daily-histogram-bars-legend-max-price-aria-label $276
Displaying fares for August-2026
  • BOS–MDW, 08/05/2026: From $194
    05

    Wed

    AUG

  • BOS–MDW, 08/06/2026: From $184
    06

    Thu

  • BOS–MDW, 08/07/2026: From $233
    07

    Fri

  • BOS–MDW, 08/08/2026: From $234
    08

    Sat

  • BOS–MDW, 08/09/2026: From $276
    09

    Sun

  • BOS–MDW, 08/10/2026: From $204
    10

    Mon

  • BOS–MDW, 08/11/2026: From $199
    11

    Tue

  • BOS–MDW, 08/12/2026: From $159
    12

    Wed

  • BOS–MDW, 08/13/2026: From $159
    13

    Thu

  • BOS–MDW, 08/14/2026: From $159
    14

    Fri

  • BOS–MDW, 08/15/2026: From $199
    15

    Sat

  • BOS–MDW, 08/16/2026: From $194
    16

    Sun

  • BOS–MDW, 08/17/2026: From $159
    17

    Mon

  • BOS–MDW, 08/18/2026: From $128
    18

    Tue

  • BOS–MDW, 08/19/2026: From $128
    19

    Wed

  • BOS–MDW, 08/20/2026: From $128
    20

    Thu

  • BOS–MDW, 08/21/2026: From $128
    21

    Fri

  • BOS–MDW, 08/22/2026: From $128
    22

    Sat

  • BOS–MDW, 08/23/2026: From $128
    23

    Sun

  • BOS–MDW, 08/24/2026: From $128
    24

    Mon

  • BOS–MDW, 08/25/2026: From $128
    25

    Tue

  • BOS–MDW: cmp-view-offers-disclaimer. Find Offers
    26

    Wed

  • BOS–MDW, 08/27/2026: From $128
    27

    Thu

  • BOS–MDW, 08/28/2026: From $128
    28

    Fri

  • BOS–MDW, 08/29/2026: From $128
    29

    Sat

  • BOS–MDW, 08/30/2026: From $128
    30

    Sun

  • BOS–MDW, 08/31/2026: From $128
    31

    Mon

  • BOS–MDW, 09/01/2026: From $123
    01

    Tue

    SEP

  • BOS–MDW, 09/02/2026: From $128
    02

    Wed

  • BOS–MDW, 09/03/2026: From $128
    03

    Thu

  • BOS–MDW, 09/04/2026: From $128
    04

    Fri

    • Range$123-$276

    *Fares displayed have been collected within the last 24 hours and may no longer be available at time of booking. Additional fees and charges for optional products and services may apply. Modifying this information may result in a different fare. To find the most updated fare, please visit Southwest.com. Fares listed are Basic, which are subject to additional terms and conditions.

    Flight Details

    Departing from:
    Logan International Airport
    Arriving at:
    O'Hare International Airport
    Distance:
    867 miles

    Route Information

    74† Weekly flights

    † Weekly flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025. Note: route may not operate every day of the week.

    ‡ Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025.

    Questions we hear the most

    There are 74 weekly flights from Boston to Chicago (O'Hare) on Southwest Airlines.
    To find the lowest fares by day and time to fly Boston to Chicago (O'Hare) with Southwest, check out our Low Fare Calendar.
    You can rent a car at O'Hare International Airport book yours with your flight.
    Yes! Flights from Boston to Chicago (O'Hare)—or from here or there to anywhere—can be changed with no change fees. Fare difference may apply.
    Check the status of your upcoming Southwest flight.
    Check out the Southwest Airlines® Help Center for answers about everything Southwest.

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