Southwest® flights from Chicago-Midway to Hartford/Springfield from $160

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Low fares from Chicago-Midway to Hartford/Springfield

$

Chicago-Midway (MDW)to

Hartford/Springfield (BDL)
Depart: 12/09/2026

One-way

Basic

From
$160
Seen: 23 hrs ago

Chicago-Midway (MDW)to

Hartford/Springfield (BDL)
Depart: 12/16/2026

One-way

Basic

From
$160
Seen: 8 hrs ago

Chicago-Midway (MDW)to

Hartford/Springfield (BDL)
Depart: 01/05/2027

One-way

Basic

From
$160
Seen: 1 hour ago

Chicago-Midway (MDW)to

Hartford/Springfield (BDL)
Depart: 12/02/2026

One-way

Basic

From
$160
Seen: 22 hrs ago

Chicago-Midway (MDW)to

Hartford/Springfield (BDL)
Depart: 02/02/2027

One-way

Basic

From
$160
Seen: 16 hrs ago

Chicago-Midway (MDW)to

Hartford/Springfield (BDL)
Depart: 12/01/2026

One-way

Basic

From
$160
Seen: 16 hrs ago

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Explore flights from Chicago-Midway to Hartford/Springfield

Nov 2026
From$196*
Seen: 53 minutes ago
One Way/Basic
Dec 2026
From$160*
Seen: 22 hrs ago
One Way/Basic
Jan 2027
From$160*
Seen: 4 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $160
cmp-daily-histogram-bars-legend-max-price-aria-label $386
Displaying fares for November-2026
  • MDW–BDL, 11/11/2026: From $251
    11

    Wed

    NOV

  • MDW–BDL, 11/12/2026: From $241
    12

    Thu

  • MDW–BDL, 11/13/2026: From $241
    13

    Fri

  • MDW–BDL, 11/14/2026: From $241
    14

    Sat

  • MDW–BDL, 11/15/2026: From $241
    15

    Sun

  • MDW–BDL, 11/16/2026: From $251
    16

    Mon

  • MDW–BDL, 11/17/2026: From $241
    17

    Tue

  • MDW–BDL, 11/18/2026: From $241
    18

    Wed

  • MDW–BDL, 11/19/2026: From $251
    19

    Thu

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

    Fri

  • MDW–BDL, 11/21/2026: From $251
    21

    Sat

  • MDW–BDL, 11/22/2026: From $241
    22

    Sun

  • MDW–BDL, 11/23/2026: From $196
    23

    Mon

  • MDW–BDL, 11/24/2026: From $241
    24

    Tue

  • MDW–BDL, 11/25/2026: From $241
    25

    Wed

  • MDW–BDL, 11/26/2026: From $241
    26

    Thu

  • MDW–BDL: cmp-view-offers-disclaimer. Find Offers
    27

    Fri

  • MDW–BDL: cmp-view-offers-disclaimer. Find Offers
    28

    Sat

  • MDW–BDL, 11/29/2026: From $386
    29

    Sun

  • MDW–BDL, 11/30/2026: From $304
    30

    Mon

  • MDW–BDL, 12/01/2026: From $160
    01

    Tue

    DEC

  • MDW–BDL, 12/02/2026: From $160
    02

    Wed

  • MDW–BDL: cmp-view-offers-disclaimer. Find Offers
    03

    Thu

  • MDW–BDL, 12/04/2026: From $185
    04

    Fri

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

    Sat

  • MDW–BDL, 12/06/2026: From $241
    06

    Sun

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

    Mon

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

    Tue

  • MDW–BDL, 12/09/2026: From $160
    09

    Wed

  • MDW–BDL, 12/10/2026: From $175
    10

    Thu

    • Range$160-$386

    *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:
    Chicago Midway International Airport
    Arriving at:
    Bradley International Airport
    Average flight time:
    2 hours 1 minutes
    Distance:
    776 miles

    Questions we hear the most

    The average flight time from Chicago (Midway) to Hartford/Springfield is 2 hours 1 minutes.
    There are 127 weekly flights from Chicago (Midway) to Hartford/Springfield on Southwest Airlines.
    Yes, Southwest flies nonstop from Chicago (Midway) to Hartford/Springfield 2 times per day from Monday through Friday.
    Yes, Southwest flies nonstop from Chicago (Midway) to Hartford/Springfield once per day on Saturdays and 2 times per day on Sundays.
    To find the lowest fares by day and time to fly Chicago (Midway) to Hartford/Springfield with Southwest, check out our Low Fare Calendar.
    You can rent a car at Bradley International Airport book yours with your flight.
    Yes! Flights from Chicago (Midway) to Hartford/Springfield—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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