Southwest® flights from Chicago (Midway) to Hartford/Springfield from $159

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Low fares from Chicago (Midway) to Hartford/Springfield

$

Chicago (Midway) (MDW)to

Hartford/Springfield (BDL)
Depart: 10/06/2026

One-way

Basic

From
$159
Seen: 15 hrs ago

Chicago (Midway) (MDW)to

Hartford/Springfield (BDL)
Depart: 09/15/2026

One-way

Basic

From
$159
Seen: 16 hrs ago

Chicago (Midway) (MDW)to

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

One-way

Basic

From
$159
Seen: 12 hrs ago

Chicago (Midway) (MDW)to

Hartford/Springfield (BDL)
Depart: 09/26/2026

One-way

Basic

From
$159
Seen: 22 hrs ago

Chicago (Midway) (MDW)to

Hartford/Springfield (BDL)
Depart: 09/23/2026

One-way

Basic

From
$159
Seen: 46 minutes ago

Chicago (Midway) (MDW)to

Hartford/Springfield (BDL)
Depart: 10/03/2026

One-way

Basic

From
$159
Seen: 15 hrs ago

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Explore flights from Chicago (Midway) to Hartford/Springfield

Aug 2026
From$244*
Seen: 14 hrs ago
One Way/Basic
Sep 2026
From$159*
Seen: 12 hrs ago
One Way/Basic
Oct 2026
From$159*
Seen: 3 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $159
cmp-daily-histogram-bars-legend-max-price-aria-label $316
Displaying fares for August-2026
  • MDW–BDL: cmp-view-offers-disclaimer. Find Offers
    22

    Sat

    AUG

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

    Sun

  • MDW–BDL, 08/24/2026: From $270
    24

    Mon

  • MDW–BDL, 08/25/2026: From $244
    25

    Tue

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

    Wed

  • MDW–BDL, 08/27/2026: From $270
    27

    Thu

  • MDW–BDL, 08/28/2026: From $270
    28

    Fri

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

    Sat

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

    Sun

  • MDW–BDL, 08/31/2026: From $270
    31

    Mon

  • MDW–BDL, 09/01/2026: From $244
    01

    Tue

    SEP

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

    Wed

  • MDW–BDL, 09/03/2026: From $280
    03

    Thu

  • MDW–BDL, 09/04/2026: From $270
    04

    Fri

  • MDW–BDL, 09/05/2026: From $186
    05

    Sat

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

    Sun

  • MDW–BDL, 09/07/2026: From $316
    07

    Mon

  • MDW–BDL, 09/08/2026: From $244
    08

    Tue

  • MDW–BDL, 09/09/2026: From $186
    09

    Wed

  • MDW–BDL, 09/10/2026: From $186
    10

    Thu

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

    Fri

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

    Sat

  • MDW–BDL: cmp-view-offers-disclaimer. Find Offers
    13

    Sun

  • MDW–BDL, 09/14/2026: From $159
    14

    Mon

  • MDW–BDL, 09/15/2026: From $159
    15

    Tue

  • MDW–BDL, 09/16/2026: From $159
    16

    Wed

  • MDW–BDL: cmp-view-offers-disclaimer. Find Offers
    17

    Thu

  • MDW–BDL: cmp-view-offers-disclaimer. Find Offers
    18

    Fri

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

    Sat

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

    Sun

  • MDW–BDL, 09/21/2026: From $159
    21

    Mon

    • Range$159-$316

    *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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