Southwest® flights from Hartford/Springfield to Chicago (O'Hare)

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Low fares from Hartford/Springfield to Chicago (O'Hare)

$

Hartford/Springfield (BDL)to

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

One-way

Basic

From
$159
Seen: 10 hrs ago

Hartford/Springfield (BDL)to

Chicago (Midway) (MDW)
Depart: 09/24/2026

One-way

Basic

From
$159
Seen: 16 hrs ago

Hartford/Springfield (BDL)to

Chicago (Midway) (MDW)
Depart: 11/16/2026

One-way

Basic

From
$159
Seen: 6 hrs ago

Hartford/Springfield (BDL)to

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

One-way

Basic

From
$159
Seen: 5 hrs ago

Hartford/Springfield (BDL)to

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

One-way

Basic

From
$159
Seen: 3 hrs ago

Hartford/Springfield (BDL)to

Chicago (Midway) (MDW)
Depart: 12/02/2026

One-way

Basic

From
$159
Seen: 1 hour ago

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Explore flights from Hartford/Springfield to Chicago (O'Hare)

Aug 2026
From$244*
Seen: 22 hrs ago
One Way/Basic
Sep 2026
From$159*
Seen: 23 hrs ago
One Way/Basic
Oct 2026
From$159*
Seen: 20 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $159
cmp-daily-histogram-bars-legend-max-price-aria-label $270
Displaying fares for August-2026
  • BDL–MDW, 08/25/2026: From $244
    25

    Tue

    AUG

  • BDL–MDW, 08/26/2026: From $244
    26

    Wed

  • BDL–MDW, 08/27/2026: From $270
    27

    Thu

  • BDL–MDW, 08/28/2026: From $270
    28

    Fri

  • BDL–MDW, 08/29/2026: From $244
    29

    Sat

  • BDL–MDW, 08/30/2026: From $270
    30

    Sun

  • BDL–MDW, 08/31/2026: From $270
    31

    Mon

  • BDL–MDW, 09/01/2026: From $244
    01

    Tue

    SEP

  • BDL–MDW, 09/02/2026: From $244
    02

    Wed

  • BDL–MDW, 09/03/2026: From $270
    03

    Thu

  • BDL–MDW, 09/04/2026: From $270
    04

    Fri

  • BDL–MDW, 09/05/2026: From $186
    05

    Sat

  • BDL–MDW, 09/06/2026: From $186
    06

    Sun

  • BDL–MDW, 09/07/2026: From $270
    07

    Mon

  • BDL–MDW, 09/08/2026: From $244
    08

    Tue

  • BDL–MDW, 09/09/2026: From $186
    09

    Wed

  • BDL–MDW: cmp-view-offers-disclaimer. Find Offers
    10

    Thu

  • BDL–MDW, 09/11/2026: From $186
    11

    Fri

  • BDL–MDW, 09/12/2026: From $186
    12

    Sat

  • BDL–MDW, 09/13/2026: From $270
    13

    Sun

  • BDL–MDW, 09/14/2026: From $159
    14

    Mon

  • BDL–MDW, 09/15/2026: From $159
    15

    Tue

  • BDL–MDW, 09/16/2026: From $159
    16

    Wed

  • BDL–MDW, 09/17/2026: From $173
    17

    Thu

  • BDL–MDW, 09/18/2026: From $173
    18

    Fri

  • BDL–MDW: cmp-view-offers-disclaimer. Find Offers
    19

    Sat

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

    Sun

  • BDL–MDW, 09/21/2026: From $159
    21

    Mon

  • BDL–MDW, 09/22/2026: From $159
    22

    Tue

  • BDL–MDW: cmp-view-offers-disclaimer. Find Offers
    23

    Wed

  • BDL–MDW, 09/24/2026: From $159
    24

    Thu

    • Range$159-$270

    *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:
    Bradley International Airport
    Arriving at:
    O'Hare International Airport
    Distance:
    783 miles

    Route Information

    29† 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 29 weekly flights from Hartford/Springfield to Chicago (O'Hare) on Southwest Airlines.
    To find the lowest fares by day and time to fly Hartford/Springfield 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 Hartford/Springfield 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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