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Find low faresSouthwest® flights from Hartford/Springfield to Chicago (Midway) from $145
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1 Passenger
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Low fares from Hartford/Springfield to Chicago (Midway)
$
Hartford/Springfield (BDL)to
Chicago (Midway) (MDW)
Depart: 02/24/2026
One-way
Basic
From
$145
Seen: 10 hrs ago
Hartford/Springfield (BDL)to
Chicago (Midway) (MDW)
Depart: 03/04/2026
One-way
Choice
From
$145
Seen: 17 hrs ago
Hartford/Springfield (BDL)to
Chicago (Midway) (MDW)
Depart: 02/28/2026
One-way
Choice
From
$145
Seen: 17 hrs ago
Hartford/Springfield (BDL)to
Chicago (Midway) (MDW)
Depart: 02/21/2026
One-way
Choice
From
$145
Seen: 10 hrs ago
Hartford/Springfield (BDL)to
Chicago (Midway) (MDW)
Depart: 05/09/2026
One-way
Choice
From
$148
Seen: 10 hrs ago
Hartford/Springfield (BDL)to
Chicago (Midway) (MDW)
Depart: 03/04/2026
One-way
Basic
From
$155
Seen: 17 hrs ago
Explore flights from Hartford/Springfield to Chicago (Midway)
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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.