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Find low faresSouthwest® flights from Chicago (Midway) to Hartford/Springfield from $148
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1 Passenger
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today
Low fares from Chicago (Midway) to Hartford/Springfield
$
Chicago (Midway) (MDW)to
Hartford/Springfield (BDL)
Depart: 05/02/2026
One-way
Choice
From
$148
Seen: 15 hrs ago
Chicago (Midway) (MDW)to
Hartford/Springfield (BDL)
Depart: 04/04/2026
One-way
Choice
From
$148
Seen: 20 hrs ago
Chicago (Midway) (MDW)to
Hartford/Springfield (BDL)
Depart: 04/04/2026
One-way
Basic
From
$158
Seen: 20 hrs ago
Chicago (Midway) (MDW)to
Hartford/Springfield (BDL)
Depart: 05/02/2026
One-way
Basic
From
$163
Seen: 15 hrs ago
Chicago (Midway) (MDW)to
Hartford/Springfield (BDL)
Depart: 03/14/2026
One-way
Choice
From
$169
Seen: 17 hrs ago
Chicago (Midway) (MDW)to
Hartford/Springfield (BDL)
Depart: 03/28/2026
One-way
Choice
From
$169
Seen: 15 hrs ago
Explore flights from Chicago (Midway) to Hartford/Springfield
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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.