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Find low faresSouthwest® flights from Rochester to Chicago (Midway) from $129
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1 Passenger
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Low fares from Rochester to Chicago (Midway)
$
Rochester (ROC)to
Chicago (Midway) (MDW)
Depart: 02/21/2026
One-way
Basic
From
$129
Seen: 15 hrs ago
Rochester (ROC)to
Chicago (Midway) (MDW)
Depart: 02/25/2026
One-way
Basic
From
$139
Seen: 22 hrs ago
Rochester (ROC)to
Chicago (Midway) (MDW)
Depart: 02/24/2026
One-way
Basic
From
$139
Seen: 23 hrs ago
Rochester (ROC)to
Chicago (Midway) (MDW)
Depart: 03/11/2026
One-way
Basic
From
$139
Seen: 20 hrs ago
Rochester (ROC)to
Chicago (Midway) (MDW)
Depart: 03/04/2026
One-way
Basic
From
$139
Seen: 12 hrs ago
Rochester (ROC)to
Chicago (Midway) (MDW)
Depart: 02/21/2026
One-way
Choice
From
$157
Seen: 15 hrs ago
Explore flights from Rochester to Chicago (Midway)
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Flight Details
Departing from:
Greater Rochester International Airport
Arriving at:
Chicago Midway International Airport
Average flight time:
1 hour 51 minutes
Distance:
523 miles
Route Information
79† Weekly flights
- 1‡ Nonstop flight per day Monday through Friday
- 1‡ Nonstop flight on Saturday
- 1‡ Nonstop flight 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 Rochester to Chicago (Midway) is 1 hour 51 minutes.
There are 79 weekly flights from Rochester to Chicago (Midway) on Southwest Airlines.
Yes, Southwest flies nonstop from Rochester to Chicago (Midway) once per day from Monday through Friday.
Yes, Southwest flies nonstop from Rochester to Chicago (Midway) once per day on Saturdays and Sundays.
To find the lowest fares by day and time to fly Rochester 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 Rochester 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.