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Find low faresSouthwest® flights from Manchester, NH to Chicago (Midway) from $139
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Low fares from Manchester, NH to Chicago (Midway)
$
Manchester, NH (MHT)to
Chicago (Midway) (MDW)
Depart: 05/02/2026
One-way
Basic
From
$137
Seen: 13 hrs ago
Manchester, NH (MHT)to
Chicago (Midway) (MDW)
Depart: 04/01/2026
One-way
Basic
From
$139
Seen: 19 hrs ago
Manchester, NH (MHT)to
Chicago (Midway) (MDW)
Depart: 03/04/2026
One-way
Basic
From
$139
Seen: 14 hrs ago
Manchester, NH (MHT)to
Chicago (Midway) (MDW)
Depart: 03/31/2026
One-way
Basic
From
$139
Seen: 23 hrs ago
Manchester, NH (MHT)to
Chicago (Midway) (MDW)
Depart: 03/10/2026
One-way
Basic
From
$149
Seen: 21 hrs ago
Manchester, NH (MHT)to
Chicago (Midway) (MDW)
Depart: 05/02/2026
One-way
Choice
From
$165
Seen: 13 hrs ago
Explore flights from Manchester, NH to Chicago (Midway)
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Flight Details
Departing from:
Manchester-Boston Regional Airport
Arriving at:
Chicago Midway International Airport
Average flight time:
2 hours 33 minutes
Distance:
838 miles
Route Information
113† 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 Manchester, NH to Chicago (Midway) is 2 hours 33 minutes.
There are 113 weekly flights from Manchester, NH to Chicago (Midway) on Southwest Airlines.
Yes, Southwest flies nonstop from Manchester, NH to Chicago (Midway) 2 times per day from Monday through Friday.
Yes, Southwest flies nonstop from Manchester, NH 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 Manchester, NH 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 Manchester, NH 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.