Southwest® flights from Chicago (Midway) to Hartford/Springfield from $139

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Low fares from Chicago (Midway) to Hartford/Springfield

$

Chicago (Midway) (MDW)to

Hartford/Springfield (BDL)
Depart: 09/11/2026

One-way

Basic

From
$139
Seen: 1 hour ago

Chicago (Midway) (MDW)to

Hartford/Springfield (BDL)
Depart: 11/05/2026

One-way

Basic

From
$158
Seen: 23 hrs ago

Chicago (Midway) (MDW)to

Hartford/Springfield (BDL)
Depart: 10/14/2026

One-way

Basic

From
$158
Seen: 11 hrs ago

Chicago (Midway) (MDW)to

Hartford/Springfield (BDL)
Depart: 08/29/2026

One-way

Basic

From
$158
Seen: 17 hrs ago

Chicago (Midway) (MDW)to

Hartford/Springfield (BDL)
Depart: 10/15/2026

One-way

Basic

From
$158
Seen: 7 hrs ago

Chicago (Midway) (MDW)to

Hartford/Springfield (BDL)
Depart: 09/28/2026

One-way

Basic

From
$158
Seen: 5 minutes ago

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Explore flights from Chicago (Midway) to Hartford/Springfield

Aug 2026
From$158*
Seen: 17 hrs ago
One Way/Basic
Sep 2026
From$139*
Seen: 1 hour ago
One Way/Basic
Oct 2026
From$158*
Seen: 16 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $158
cmp-daily-histogram-bars-legend-max-price-aria-label $270
Displaying fares for August-2026
  • MDW–BDL, 08/02/2026: From $270
    02

    Sun

    AUG

  • MDW–BDL, 08/03/2026: From $270
    03

    Mon

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

    Tue

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    05

    Wed

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

    Thu

  • MDW–BDL, 08/07/2026: From $270
    07

    Fri

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

    Sat

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

    Sun

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

    Mon

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

    Tue

  • MDW–BDL: cmp-view-offers-disclaimer. Find Offers
    12

    Wed

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

    Thu

  • MDW–BDL: cmp-view-offers-disclaimer. Find Offers
    14

    Fri

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

    Sat

  • MDW–BDL, 08/16/2026: From $270
    16

    Sun

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

    Mon

  • MDW–BDL, 08/18/2026: From $244
    18

    Tue

  • MDW–BDL, 08/19/2026: From $244
    19

    Wed

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    20

    Thu

  • MDW–BDL: cmp-view-offers-disclaimer. Find Offers
    21

    Fri

  • MDW–BDL, 08/22/2026: From $240
    22

    Sat

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

    Sun

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

    Mon

  • MDW–BDL, 08/25/2026: From $158
    25

    Tue

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

    Wed

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

    Thu

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

    Fri

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

    Sat

  • MDW–BDL: cmp-view-offers-disclaimer. Find Offers
    30

    Sun

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

    Mon

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    01

    Tue

    SEP

    • Range$158-$270

    *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

    Route Information

    127† Weekly flights
    • 2‡ Nonstop flights per day Monday through Friday
    • 1‡ Nonstop flight on Saturday
    • 2‡ Nonstop flights on Sunday

    † 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

    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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