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

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Low fares from Hartford/Springfield to Chicago (Midway)

$

Hartford/Springfield (BDL)to

Chicago (Midway) (MDW)
Depart: 09/05/2026

One-way

Basic

From
$139
Seen: 23 hrs ago

Hartford/Springfield (BDL)to

Chicago (Midway) (MDW)
Depart: 09/15/2026

One-way

Basic

From
$158
Seen: 15 hrs ago

Hartford/Springfield (BDL)to

Chicago (Midway) (MDW)
Depart: 10/05/2026

One-way

Basic

From
$158
Seen: 11 hrs ago

Hartford/Springfield (BDL)to

Chicago (Midway) (MDW)
Depart: 10/24/2026

One-way

Basic

From
$158
Seen: 1 hour ago

Hartford/Springfield (BDL)to

Chicago (Midway) (MDW)
Depart: 09/24/2026

One-way

Basic

From
$158
Seen: 5 hrs ago

Hartford/Springfield (BDL)to

Chicago (Midway) (MDW)
Depart: 10/03/2026

One-way

Basic

From
$158
Seen: 11 hrs ago

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Explore flights from Hartford/Springfield to Chicago (Midway)

Aug 2026
From$158*
Seen: 21 hrs ago
One Way/Basic
Sep 2026
From$139*
Seen: 23 hrs ago
One Way/Basic
Oct 2026
From$158*
Seen: 1 hour ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $158
cmp-daily-histogram-bars-legend-max-price-aria-label $310
Displaying fares for August-2026
  • BDL–MDW, 08/01/2026: From $244
    01

    Sat

    AUG

  • BDL–MDW, 08/02/2026: From $310
    02

    Sun

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

    Mon

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

    Tue

  • BDL–MDW, 08/05/2026: From $277
    05

    Wed

  • BDL–MDW, 08/06/2026: From $270
    06

    Thu

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

    Fri

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

    Sat

  • BDL–MDW: cmp-view-offers-disclaimer. Find Offers
    09

    Sun

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

    Mon

  • BDL–MDW, 08/11/2026: From $244
    11

    Tue

  • BDL–MDW, 08/12/2026: From $244
    12

    Wed

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

    Thu

  • BDL–MDW, 08/14/2026: From $270
    14

    Fri

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

    Sat

  • BDL–MDW, 08/16/2026: From $301
    16

    Sun

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

    Mon

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

    Tue

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

    Wed

  • BDL–MDW, 08/20/2026: From $270
    20

    Thu

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

    Fri

  • BDL–MDW, 08/22/2026: From $158
    22

    Sat

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

    Sun

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

    Mon

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

    Tue

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

    Wed

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

    Thu

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

    Fri

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

    Sat

  • BDL–MDW, 08/30/2026: From $208
    30

    Sun

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

    Mon

    • Range$158-$310

    *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

    Route Information

    136† 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 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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