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: 09/11/2026

One-way

Basic

From
$139
Seen: 12 hrs ago

Hartford/Springfield (BDL)to

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

One-way

Basic

From
$158
Seen: 11 hrs ago

Hartford/Springfield (BDL)to

Chicago (Midway) (MDW)
Depart: 10/24/2026

One-way

Basic

From
$158
Seen: 1 hour ago

Hartford/Springfield (BDL)to

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

One-way

Basic

From
$158
Seen: 5 hrs ago

Hartford/Springfield (BDL)to

Chicago (Midway) (MDW)
Depart: 08/27/2026

One-way

Basic

From
$158
Seen: 2 hrs ago

Hartford/Springfield (BDL)to

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

One-way

Basic

From
$158
Seen: 3 hrs ago

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

Aug 2026
From$158*
Seen: 2 hrs ago
One Way/Basic
Sep 2026
From$139*
Seen: 12 hrs ago
One Way/Basic
Oct 2026
From$158*
Seen: 22 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $158
cmp-daily-histogram-bars-legend-max-price-aria-label $328
Displaying fares for August-2026
  • BDL–MDW, 08/05/2026: From $244
    05

    Wed

    AUG

  • BDL–MDW, 08/06/2026: From $270
    06

    Thu

  • BDL–MDW: cmp-view-offers-disclaimer. Find Offers
    07

    Fri

  • BDL–MDW: cmp-view-offers-disclaimer. Find Offers
    08

    Sat

  • BDL–MDW, 08/09/2026: From $270
    09

    Sun

  • BDL–MDW, 08/10/2026: From $270
    10

    Mon

  • BDL–MDW: cmp-view-offers-disclaimer. Find Offers
    11

    Tue

  • BDL–MDW, 08/12/2026: From $244
    12

    Wed

  • BDL–MDW, 08/13/2026: From $270
    13

    Thu

  • BDL–MDW, 08/14/2026: From $280
    14

    Fri

  • BDL–MDW, 08/15/2026: From $244
    15

    Sat

  • BDL–MDW, 08/16/2026: From $328
    16

    Sun

  • BDL–MDW, 08/17/2026: From $270
    17

    Mon

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    18

    Tue

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    19

    Wed

  • BDL–MDW, 08/20/2026: From $285
    20

    Thu

  • BDL–MDW, 08/21/2026: From $270
    21

    Fri

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    22

    Sat

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    23

    Sun

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    24

    Mon

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    25

    Tue

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    26

    Wed

  • BDL–MDW, 08/27/2026: From $158
    27

    Thu

  • BDL–MDW, 08/28/2026: From $190
    28

    Fri

  • BDL–MDW, 08/29/2026: From $158
    29

    Sat

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    30

    Sun

  • BDL–MDW: cmp-view-offers-disclaimer. Find Offers
    31

    Mon

  • BDL–MDW: cmp-view-offers-disclaimer. Find Offers
    01

    Tue

    SEP

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    02

    Wed

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    03

    Thu

  • BDL–MDW, 09/04/2026: From $190
    04

    Fri

    • Range$158-$328

    *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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