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Find low faresSouthwest® flights from Midland/Odessa to Chicago (Midway) from $168
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1 Passenger
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Low fares from Midland/Odessa to Chicago (Midway)
$
Midland/Odessa (MAF)to
Chicago (Midway) (MDW)
Depart: 03/11/2026
One-way
Basic
From
$168
Seen: 18 hrs ago
Midland/Odessa (MAF)to
Chicago (Midway) (MDW)
Depart: 04/09/2026
One-way
Basic
From
$180
Seen: 18 hrs ago
Midland/Odessa (MAF)to
Chicago (Midway) (MDW)
Depart: 04/18/2026
One-way
Basic
From
$180
Seen: 14 hrs ago
Midland/Odessa (MAF)to
Chicago (Midway) (MDW)
Depart: 05/07/2026
One-way
Basic
From
$185
Seen: 23 hrs ago
Midland/Odessa (MAF)to
Chicago (Midway) (MDW)
Depart: 04/17/2026
One-way
Basic
From
$204
Seen: 14 hrs ago
Midland/Odessa (MAF)to
Chicago (Midway) (MDW)
Depart: 03/14/2026
One-way
Basic
From
$204
Seen: 15 hrs ago
Explore flights from Midland/Odessa to Chicago (Midway)
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Flight Details
Departing from:
Midland International Airport
Arriving at:
Chicago Midway International Airport
Distance:
1047 miles
Route Information
142† Weekly flights
† 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
There are 142 weekly flights from Midland/Odessa to Chicago (Midway) on Southwest Airlines.
To find the lowest fares by day and time to fly Midland/Odessa 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 Midland/Odessa 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.