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Find low faresSouthwest® flights from Richmond to Chicago (Midway) from $125
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Low fares from Richmond to Chicago (Midway)
$
Richmond (RIC)to
Chicago (Midway) (MDW)
Depart: 03/21/2026
One-way
Basic
From
$125
Seen: 7 hrs ago
Richmond (RIC)to
Chicago (Midway) (MDW)
Depart: 04/04/2026
One-way
Basic
From
$125
Seen: 12 hrs ago
Richmond (RIC)to
Chicago (Midway) (MDW)
Depart: 03/07/2026
One-way
Basic
From
$133
Seen: 14 hrs ago
Richmond (RIC)to
Chicago (Midway) (MDW)
Depart: 02/25/2026
One-way
Basic
From
$143
Seen: 22 hrs ago
Richmond (RIC)to
Chicago (Midway) (MDW)
Depart: 04/25/2026
One-way
Basic
From
$143
Seen: 23 hrs ago
Richmond (RIC)to
Chicago (Midway) (MDW)
Depart: 03/17/2026
One-way
Basic
From
$143
Seen: 20 hrs ago
Explore flights from Richmond to Chicago (Midway)
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Flight Details
Departing from:
Richmond International Airport
Arriving at:
Chicago Midway International Airport
Average flight time:
1 hour 59 minutes
Distance:
629 miles
Route Information
84† Weekly flights
- 1‡ Nonstop flight 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 Richmond to Chicago (Midway) is 1 hour 59 minutes.
There are 84 weekly flights from Richmond to Chicago (Midway) on Southwest Airlines.
Yes, Southwest flies nonstop from Richmond to Chicago (Midway) once per day from Monday through Friday.
Yes, Southwest flies nonstop from Richmond 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 Richmond 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 Richmond 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.