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

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Low fares from Hartford/Springfield to Chicago-Midway

$

Hartford/Springfield (BDL)to

Chicago-Midway (MDW)
Depart: 11/07/2026

One-way

Basic

From
$149
Seen: 22 hrs ago

Hartford/Springfield (BDL)to

Chicago-Midway (MDW)
Depart: 12/08/2026

One-way

Basic

From
$149
Seen: 19 hrs ago

Hartford/Springfield (BDL)to

Chicago-Midway (MDW)
Depart: 12/15/2026

One-way

Basic

From
$149
Seen: 23 hrs ago

Hartford/Springfield (BDL)to

Chicago-Midway (MDW)
Depart: 10/23/2026

One-way

Basic

From
$165
Seen: 16 hrs ago

Hartford/Springfield (BDL)to

Chicago-Midway (MDW)
Depart: 01/04/2027

One-way

Basic

From
$165
Seen: 8 hrs ago

Hartford/Springfield (BDL)to

Chicago-Midway (MDW)
Depart: 12/21/2026

One-way

Basic

From
$165
Seen: 11 hrs ago

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Explore flights from Hartford/Springfield to Chicago-Midway

Oct 2026
From$165*
Seen: 16 hrs ago
One Way/Basic
Nov 2026
From$149*
Seen: 22 hrs ago
One Way/Basic
Dec 2026
From$149*
Seen: 23 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $165
cmp-daily-histogram-bars-legend-max-price-aria-label $368
Displaying fares for October-2026
  • BDL–MDW: cmp-view-offers-disclaimer. Find Offers
    03

    Sat

    OCT

  • BDL–MDW, 10/04/2026: From $296
    04

    Sun

  • BDL–MDW, 10/05/2026: From $286
    05

    Mon

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

    Tue

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

    Wed

  • BDL–MDW, 10/08/2026: From $296
    08

    Thu

  • BDL–MDW, 10/09/2026: From $368
    09

    Fri

  • BDL–MDW, 10/10/2026: From $264
    10

    Sat

  • BDL–MDW, 10/11/2026: From $286
    11

    Sun

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

    Mon

  • BDL–MDW, 10/13/2026: From $264
    13

    Tue

  • BDL–MDW, 10/14/2026: From $264
    14

    Wed

  • BDL–MDW, 10/15/2026: From $296
    15

    Thu

  • BDL–MDW, 10/16/2026: From $286
    16

    Fri

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

    Sat

  • BDL–MDW, 10/18/2026: From $331
    18

    Sun

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

    Mon

  • BDL–MDW, 10/20/2026: From $264
    20

    Tue

  • BDL–MDW, 10/21/2026: From $264
    21

    Wed

  • BDL–MDW, 10/22/2026: From $286
    22

    Thu

  • BDL–MDW, 10/23/2026: From $165
    23

    Fri

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

    Sat

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

    Sun

  • BDL–MDW, 10/26/2026: From $204
    26

    Mon

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

    Tue

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

    Wed

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

    Thu

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

    Fri

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

    Sat

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

    Sun

    NOV

  • BDL–MDW, 11/02/2026: From $204
    02

    Mon

    • Range$165-$368

    *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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