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: 09/15/2026

One-way

Basic

From
$109
Seen: 18 hrs ago

Boston (BOS)to

Chicago (Midway) (MDW)
Depart: 09/29/2026

One-way

Basic

From
$109
Seen: 21 hrs ago

Boston (BOS)to

Chicago (Midway) (MDW)
Depart: 10/05/2026

One-way

Basic

From
$109
Seen: 7 hrs ago

Boston (BOS)to

Chicago (Midway) (MDW)
Depart: 11/26/2026

One-way

Basic

From
$109
Seen: 5 hrs ago

Boston (BOS)to

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

One-way

Basic

From
$109
Seen: 3 hrs ago

Boston (BOS)to

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

One-way

Basic

From
$109
Seen: 2 hrs ago

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Explore flights from Boston to Chicago (O'Hare)

Aug 2026
From$169*
Seen: 5 hrs ago
One Way/Basic
Sep 2026
From$109*
Seen: 1 hour ago
One Way/Basic
Oct 2026
From$109*
Seen: 13 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $109
cmp-daily-histogram-bars-legend-max-price-aria-label $169
Displaying fares for August-2026
  • BOS–MDW, 08/25/2026: From $169
    25

    Tue

    AUG

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

    Wed

  • BOS–MDW, 08/27/2026: From $169
    27

    Thu

  • BOS–MDW, 08/28/2026: From $169
    28

    Fri

  • BOS–MDW, 08/29/2026: From $169
    29

    Sat

  • BOS–MDW, 08/30/2026: From $169
    30

    Sun

  • BOS–MDW, 08/31/2026: From $169
    31

    Mon

  • BOS–MDW, 09/01/2026: From $169
    01

    Tue

    SEP

  • BOS–MDW, 09/02/2026: From $169
    02

    Wed

  • BOS–MDW, 09/03/2026: From $169
    03

    Thu

  • BOS–MDW, 09/04/2026: From $169
    04

    Fri

  • BOS–MDW: cmp-view-offers-disclaimer. Find Offers
    05

    Sat

  • BOS–MDW, 09/06/2026: From $158
    06

    Sun

  • BOS–MDW, 09/07/2026: From $158
    07

    Mon

  • BOS–MDW, 09/08/2026: From $128
    08

    Tue

  • BOS–MDW: cmp-view-offers-disclaimer. Find Offers
    09

    Wed

  • BOS–MDW, 09/10/2026: From $128
    10

    Thu

  • BOS–MDW, 09/11/2026: From $128
    11

    Fri

  • BOS–MDW, 09/12/2026: From $128
    12

    Sat

  • BOS–MDW, 09/13/2026: From $168
    13

    Sun

  • BOS–MDW, 09/14/2026: From $109
    14

    Mon

  • BOS–MDW, 09/15/2026: From $109
    15

    Tue

  • BOS–MDW, 09/16/2026: From $109
    16

    Wed

  • BOS–MDW: cmp-view-offers-disclaimer. Find Offers
    17

    Thu

  • BOS–MDW: cmp-view-offers-disclaimer. Find Offers
    18

    Fri

  • BOS–MDW, 09/19/2026: From $109
    19

    Sat

  • BOS–MDW: cmp-view-offers-disclaimer. Find Offers
    20

    Sun

  • BOS–MDW: cmp-view-offers-disclaimer. Find Offers
    21

    Mon

  • BOS–MDW: cmp-view-offers-disclaimer. Find Offers
    22

    Tue

  • BOS–MDW, 09/23/2026: From $109
    23

    Wed

  • BOS–MDW, 09/24/2026: From $109
    24

    Thu

    • Range$109-$169

    *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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