Southwest® flights from Chicago-Midway to Hartford/Springfield from $135

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Low fares from Chicago-Midway to Hartford/Springfield

$

Chicago-Midway (MDW)to

Hartford/Springfield (BDL)
Depart: 01/26/2027

One-way

Basic

From
$135
Seen: 15 hrs ago

Chicago-Midway (MDW)to

Hartford/Springfield (BDL)
Depart: 12/05/2026

One-way

Basic

From
$135
Seen: 16 hrs ago

Chicago-Midway (MDW)to

Hartford/Springfield (BDL)
Depart: 11/25/2026

One-way

Basic

From
$135
Seen: 8 hrs ago

Chicago-Midway (MDW)to

Hartford/Springfield (BDL)
Depart: 01/28/2027

One-way

Basic

From
$135
Seen: 9 hrs ago

Chicago-Midway (MDW)to

Hartford/Springfield (BDL)
Depart: 11/26/2026

One-way

Basic

From
$135
Seen: 3 hrs ago

Chicago-Midway (MDW)to

Hartford/Springfield (BDL)
Depart: 01/15/2027

One-way

Basic

From
$135
Seen: 20 hrs ago

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Explore flights from Chicago-Midway to Hartford/Springfield

Oct 2026
From$238*
Seen: 21 hrs ago
One Way/Basic
Nov 2026
From$135*
Seen: 5 hrs ago
One Way/Basic
Dec 2026
From$135*
Seen: 4 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $135
cmp-daily-histogram-bars-legend-max-price-aria-label $296
Displaying fares for October-2026
  • MDW–BDL, 10/21/2026: From $238
    21

    Wed

    OCT

  • MDW–BDL, 10/22/2026: From $296
    22

    Thu

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

    Fri

  • MDW–BDL: cmp-view-offers-disclaimer. Find Offers
    24

    Sat

  • MDW–BDL: cmp-view-offers-disclaimer. Find Offers
    25

    Sun

  • MDW–BDL, 10/26/2026: From $296
    26

    Mon

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

    Tue

  • MDW–BDL, 10/28/2026: From $238
    28

    Wed

  • MDW–BDL, 10/29/2026: From $296
    29

    Thu

  • MDW–BDL, 10/30/2026: From $296
    30

    Fri

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

    Sat

  • MDW–BDL, 11/01/2026: From $296
    01

    Sun

    NOV

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

    Mon

  • MDW–BDL, 11/03/2026: From $238
    03

    Tue

  • MDW–BDL: cmp-view-offers-disclaimer. Find Offers
    04

    Wed

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

    Thu

  • MDW–BDL: cmp-view-offers-disclaimer. Find Offers
    06

    Fri

  • MDW–BDL, 11/07/2026: From $238
    07

    Sat

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

    Sun

  • MDW–BDL, 11/09/2026: From $150
    09

    Mon

  • MDW–BDL, 11/10/2026: From $135
    10

    Tue

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

    Wed

  • MDW–BDL, 11/12/2026: From $135
    12

    Thu

  • MDW–BDL, 11/13/2026: From $135
    13

    Fri

  • MDW–BDL, 11/14/2026: From $191
    14

    Sat

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

    Sun

  • MDW–BDL, 11/16/2026: From $270
    16

    Mon

  • MDW–BDL, 11/17/2026: From $145
    17

    Tue

  • MDW–BDL, 11/18/2026: From $145
    18

    Wed

  • MDW–BDL, 11/19/2026: From $145
    19

    Thu

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

    Fri

    • Range$135-$296

    *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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