Southwest® flights from Hartford/Springfield to Chicago-Midway from $165

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Low fares from Hartford/Springfield to Chicago-Midway

$

Hartford/Springfield (BDL)to

Chicago-Midway (MDW)
Depart: 12/08/2026

One-way

Basic

From
$165
Seen: 23 hrs ago

Hartford/Springfield (BDL)to

Chicago-Midway (MDW)
Depart: 02/13/2027

One-way

Basic

From
$165
Seen: 16 hrs ago

Hartford/Springfield (BDL)to

Chicago-Midway (MDW)
Depart: 01/23/2027

One-way

Basic

From
$165
Seen: 11 hrs ago

Hartford/Springfield (BDL)to

Chicago-Midway (MDW)
Depart: 12/16/2026

One-way

Basic

From
$165
Seen: 10 hrs ago

Hartford/Springfield (BDL)to

Chicago-Midway (MDW)
Depart: 01/06/2027

One-way

Basic

From
$165
Seen: 16 hrs ago

Hartford/Springfield (BDL)to

Chicago-Midway (MDW)
Depart: 12/09/2026

One-way

Basic

From
$165
Seen: 23 hrs ago

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Explore flights from Hartford/Springfield to Chicago-Midway

Nov 2026
From$235*
Seen: 3 hrs ago
One Way/Basic
Dec 2026
From$165*
Seen: 10 hrs ago
One Way/Basic
Jan 2027
From$165*
Seen: 18 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $165
cmp-daily-histogram-bars-legend-max-price-aria-label $350
Displaying fares for November-2026
  • BDL–MDW, 11/12/2026: From $235
    12

    Thu

    NOV

  • BDL–MDW, 11/13/2026: From $235
    13

    Fri

  • BDL–MDW, 11/14/2026: From $235
    14

    Sat

  • BDL–MDW: cmp-view-offers-disclaimer. Find Offers
    15

    Sun

  • BDL–MDW: cmp-view-offers-disclaimer. Find Offers
    16

    Mon

  • BDL–MDW, 11/17/2026: From $235
    17

    Tue

  • BDL–MDW, 11/18/2026: From $235
    18

    Wed

  • BDL–MDW, 11/19/2026: From $235
    19

    Thu

  • BDL–MDW, 11/20/2026: From $250
    20

    Fri

  • BDL–MDW, 11/21/2026: From $235
    21

    Sat

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

    Sun

  • BDL–MDW, 11/23/2026: From $235
    23

    Mon

  • BDL–MDW, 11/24/2026: From $235
    24

    Tue

  • BDL–MDW, 11/25/2026: From $235
    25

    Wed

  • BDL–MDW, 11/26/2026: From $235
    26

    Thu

  • BDL–MDW, 11/27/2026: From $235
    27

    Fri

  • BDL–MDW, 11/28/2026: From $344
    28

    Sat

  • BDL–MDW, 11/29/2026: From $350
    29

    Sun

  • BDL–MDW, 11/30/2026: From $315
    30

    Mon

  • BDL–MDW, 12/01/2026: From $235
    01

    Tue

    DEC

  • BDL–MDW: cmp-view-offers-disclaimer. Find Offers
    02

    Wed

  • BDL–MDW, 12/03/2026: From $185
    03

    Thu

  • BDL–MDW, 12/04/2026: From $200
    04

    Fri

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

    Sat

  • BDL–MDW, 12/06/2026: From $235
    06

    Sun

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

    Mon

  • BDL–MDW, 12/08/2026: From $165
    08

    Tue

  • BDL–MDW, 12/09/2026: From $165
    09

    Wed

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

    Thu

  • BDL–MDW, 12/11/2026: From $200
    11

    Fri

    • Range$165-$350

    *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:
    Chicago Midway International Airport
    Average flight time:
    2 hours 25 minutes
    Distance:
    776 miles

    Questions we hear the most

    The average flight time from Hartford/Springfield to Chicago (Midway) is 2 hours 25 minutes.
    There are 136 weekly flights from Hartford/Springfield to Chicago (Midway) on Southwest Airlines.
    Yes, Southwest flies nonstop from Hartford/Springfield to Chicago (Midway) 2 times per day from Monday through Friday.
    Yes, Southwest flies nonstop from Hartford/Springfield to Chicago (Midway) once per day on Saturdays and 2 times per day on Sundays.
    To find the lowest fares by day and time to fly Hartford/Springfield to Chicago (Midway) with Southwest, check out our Low Fare Calendar.
    You can rent a car at Chicago Midway International Airport book yours with your flight.
    Yes! Flights from Hartford/Springfield to Chicago (Midway)—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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