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Find low faresSouthwest® flights from Eugene to Chicago (Midway) from $165
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Low fares from Eugene to Chicago (Midway)
$
Eugene (EUG)to
Chicago (Midway) (MDW)
Depart: 05/02/2026
One-way
Basic
From
$145
Seen: 21 hrs ago
Eugene (EUG)to
Chicago (Midway) (MDW)
Depart: 02/13/2026
One-way
Basic
From
$165
Seen: 16 hrs ago
Eugene (EUG)to
Chicago (Midway) (MDW)
Depart: 04/30/2026
One-way
Basic
From
$165
Seen: 16 hrs ago
Eugene (EUG)to
Chicago (Midway) (MDW)
Depart: 05/07/2026
One-way
Basic
From
$165
Seen: 18 hrs ago
Eugene (EUG)to
Chicago (Midway) (MDW)
Depart: 05/06/2026
One-way
Basic
From
$165
Seen: 23 hrs ago
Eugene (EUG)to
Chicago (Midway) (MDW)
Depart: 05/10/2026
One-way
Basic
From
$170
Seen: 23 hrs ago
Explore flights from Eugene to Chicago (Midway)
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Flight Details
Departing from:
Eugene Airport
Arriving at:
Chicago Midway International Airport
Distance:
1791 miles
Route Information
69† 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 69 weekly flights from Eugene to Chicago (Midway) on Southwest Airlines.
To find the lowest fares by day and time to fly Eugene 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 Eugene 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.