Southwest® flights from Chicago-Midway to Hartford/Springfield from $149

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Low fares from Chicago-Midway to Hartford/Springfield

$

Chicago-Midway (MDW)to

Hartford/Springfield (BDL)
Depart: 11/14/2026

One-way

Basic

From
$149
Seen: 14 hrs ago

Chicago-Midway (MDW)to

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

One-way

Basic

From
$149
Seen: 10 hrs ago

Chicago-Midway (MDW)to

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

One-way

Basic

From
$149
Seen: 11 hrs ago

Chicago-Midway (MDW)to

Hartford/Springfield (BDL)
Depart: 10/20/2026

One-way

Basic

From
$149
Seen: 19 hrs ago

Chicago-Midway (MDW)to

Hartford/Springfield (BDL)
Depart: 11/12/2026

One-way

Basic

From
$149
Seen: 18 hrs ago

Chicago-Midway (MDW)to

Hartford/Springfield (BDL)
Depart: 11/23/2026

One-way

Basic

From
$149
Seen: 12 hrs ago

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Explore flights from Chicago-Midway to Hartford/Springfield

Sep 2026
From$254*
Seen: 13 hrs ago
One Way/Basic
Oct 2026
From$149*
Seen: 19 hrs ago
One Way/Basic
Nov 2026
From$149*
Seen: 18 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $200
cmp-daily-histogram-bars-legend-max-price-aria-label $349
Displaying fares for September-2026
  • MDW–BDL, 09/12/2026: From $264
    12

    Sat

    SEP

  • MDW–BDL, 09/13/2026: From $276
    13

    Sun

  • MDW–BDL, 09/14/2026: From $286
    14

    Mon

  • MDW–BDL, 09/15/2026: From $264
    15

    Tue

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

    Wed

  • MDW–BDL, 09/17/2026: From $290
    17

    Thu

  • MDW–BDL, 09/18/2026: From $286
    18

    Fri

  • MDW–BDL, 09/19/2026: From $254
    19

    Sat

  • MDW–BDL, 09/20/2026: From $280
    20

    Sun

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

    Mon

  • MDW–BDL, 09/22/2026: From $254
    22

    Tue

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

    Wed

  • MDW–BDL, 09/24/2026: From $349
    24

    Thu

  • MDW–BDL, 09/25/2026: From $286
    25

    Fri

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

    Sat

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

    Sun

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

    Mon

  • MDW–BDL, 09/29/2026: From $254
    29

    Tue

  • MDW–BDL, 09/30/2026: From $254
    30

    Wed

  • MDW–BDL: cmp-view-offers-disclaimer. Find Offers
    01

    Thu

    OCT

  • MDW–BDL, 10/02/2026: From $200
    02

    Fri

  • MDW–BDL, 10/03/2026: From $200
    03

    Sat

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

    Sun

  • MDW–BDL, 10/05/2026: From $200
    05

    Mon

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

    Tue

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

    Wed

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

    Thu

  • MDW–BDL, 10/09/2026: From $200
    09

    Fri

  • MDW–BDL, 10/10/2026: From $200
    10

    Sat

  • MDW–BDL, 10/11/2026: From $228
    11

    Sun

    • Range$200-$349

    *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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