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

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Low fares from Hartford/Springfield to Chicago-Midway

$

Hartford/Springfield (BDL)to

Chicago-Midway (MDW)
Depart: 01/20/2027

One-way

Basic

From
$135
Seen: 17 hrs ago

Hartford/Springfield (BDL)to

Chicago-Midway (MDW)
Depart: 11/15/2026

One-way

Basic

From
$135
Seen: 13 hrs ago

Hartford/Springfield (BDL)to

Chicago-Midway (MDW)
Depart: 12/05/2026

One-way

Basic

From
$135
Seen: 13 hrs ago

Hartford/Springfield (BDL)to

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

One-way

Basic

From
$135
Seen: 15 hrs ago

Hartford/Springfield (BDL)to

Chicago-Midway (MDW)
Depart: 11/17/2026

One-way

Basic

From
$135
Seen: 8 hrs ago

Hartford/Springfield (BDL)to

Chicago-Midway (MDW)
Depart: 11/14/2026

One-way

Basic

From
$135
Seen: 52 minutes ago

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Explore flights from Hartford/Springfield to Chicago-Midway

Oct 2026
From$237*
Seen: 16 hrs ago
One Way/Basic
Nov 2026
From$135*
Seen: 17 hrs ago
One Way/Basic
Dec 2026
From$135*
Seen: 15 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
  • BDL–MDW, 10/23/2026: From $296
    23

    Fri

    OCT

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

    Sat

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

    Sun

  • BDL–MDW: cmp-view-offers-disclaimer. Find Offers
    26

    Mon

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

    Tue

  • BDL–MDW, 10/28/2026: From $237
    28

    Wed

  • BDL–MDW: cmp-view-offers-disclaimer. Find Offers
    29

    Thu

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

    Fri

  • BDL–MDW, 10/31/2026: From $237
    31

    Sat

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

    Sun

    NOV

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

    Mon

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

    Tue

  • BDL–MDW, 11/04/2026: From $237
    04

    Wed

  • BDL–MDW, 11/05/2026: From $296
    05

    Thu

  • BDL–MDW, 11/06/2026: From $296
    06

    Fri

  • BDL–MDW, 11/07/2026: From $237
    07

    Sat

  • BDL–MDW, 11/08/2026: From $296
    08

    Sun

  • BDL–MDW, 11/09/2026: From $135
    09

    Mon

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

    Tue

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

    Wed

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

    Thu

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

    Fri

  • BDL–MDW, 11/14/2026: From $135
    14

    Sat

  • BDL–MDW, 11/15/2026: From $135
    15

    Sun

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

    Mon

  • BDL–MDW, 11/17/2026: From $135
    17

    Tue

  • BDL–MDW, 11/18/2026: From $135
    18

    Wed

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

    Thu

  • BDL–MDW, 11/20/2026: From $270
    20

    Fri

  • BDL–MDW, 11/21/2026: From $135
    21

    Sat

  • BDL–MDW, 11/22/2026: From $135
    22

    Sun

    • 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:
    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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