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

Promo Code

Low fares from Chicago-Midway to Hartford/Springfield

$

Chicago-Midway (MDW)to

Hartford/Springfield (BDL)
Depart: 11/18/2026

One-way

Basic

From
$149
Seen: 13 hrs ago

Chicago-Midway (MDW)to

Hartford/Springfield (BDL)
Depart: 12/23/2026

One-way

Basic

From
$149
Seen: 17 hrs ago

Chicago-Midway (MDW)to

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

One-way

Basic

From
$149
Seen: 17 hrs ago

Chicago-Midway (MDW)to

Hartford/Springfield (BDL)
Depart: 12/08/2026

One-way

Basic

From
$149
Seen: 12 hrs ago

Chicago-Midway (MDW)to

Hartford/Springfield (BDL)
Depart: 11/04/2026

One-way

Basic

From
$149
Seen: 7 hrs ago

Chicago-Midway (MDW)to

Hartford/Springfield (BDL)
Depart: 12/14/2026

One-way

Basic

From
$149
Seen: 2 hrs ago

Looking for more low-fare flights?

Check out the Low Fare Calendar to find a fare that works for you. Just choose the month you want to depart and return, and we’ll show you the best fares available.

Find low fares

Explore flights from Chicago-Midway to Hartford/Springfield

Oct 2026
From$149*
Seen: 23 hrs ago
One Way/Basic
Nov 2026
From$149*
Seen: 12 hrs ago
One Way/Basic
Dec 2026
From$149*
Seen: 22 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $149
cmp-daily-histogram-bars-legend-max-price-aria-label $383
Displaying fares for October-2026
  • MDW–BDL, 10/01/2026: From $296
    01

    Thu

    OCT

  • MDW–BDL, 10/02/2026: From $286
    02

    Fri

  • MDW–BDL, 10/03/2026: From $264
    03

    Sat

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

    Sun

  • MDW–BDL: cmp-view-offers-disclaimer. Find Offers
    05

    Mon

  • MDW–BDL, 10/06/2026: From $264
    06

    Tue

  • MDW–BDL, 10/07/2026: From $264
    07

    Wed

  • MDW–BDL, 10/08/2026: From $286
    08

    Thu

  • MDW–BDL, 10/09/2026: From $301
    09

    Fri

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

    Sat

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

    Sun

  • MDW–BDL, 10/12/2026: From $383
    12

    Mon

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

    Tue

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

    Wed

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

    Thu

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

    Fri

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

    Sat

  • MDW–BDL, 10/18/2026: From $286
    18

    Sun

  • MDW–BDL, 10/19/2026: From $286
    19

    Mon

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

    Tue

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

    Wed

  • MDW–BDL: cmp-view-offers-disclaimer. Find Offers
    22

    Thu

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

    Fri

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

    Sat

  • MDW–BDL, 10/25/2026: From $260
    25

    Sun

  • MDW–BDL, 10/26/2026: From $149
    26

    Mon

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

    Tue

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

    Wed

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

    Thu

  • MDW–BDL, 10/30/2026: From $165
    30

    Fri

  • MDW–BDL, 10/31/2026: From $149
    31

    Sat

    • Range$149-$383

    *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.

    Explore Flights from Other Popular Origins

    Popular Flights from Chicago-Midway