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Find low faresSouthwest® flights from Omaha to Chicago (Midway) from $101
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1 Passenger
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Low fares from Omaha to Chicago (Midway)
$
Omaha (OMA)to
Chicago (Midway) (MDW)
Depart: 03/21/2026
One-way
Basic
From
$101
Seen: 18 hrs ago
Omaha (OMA)to
Chicago (Midway) (MDW)
Depart: 03/28/2026
One-way
Basic
From
$101
Seen: 17 hrs ago
Omaha (OMA)to
Chicago (Midway) (MDW)
Depart: 02/28/2026
One-way
Choice
From
$105
Seen: 18 hrs ago
Omaha (OMA)to
Chicago (Midway) (MDW)
Depart: 02/21/2026
One-way
Basic
From
$105
Seen: 14 hrs ago
Omaha (OMA)to
Chicago (Midway) (MDW)
Depart: 04/18/2026
One-way
Basic
From
$109
Seen: 18 hrs ago
Omaha (OMA)to
Chicago (Midway) (MDW)
Depart: 05/07/2026
One-way
Basic
From
$115
Seen: 15 hrs ago
Explore flights from Omaha to Chicago (Midway)
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Flight Details
Departing from:
Eppley Airfield
Arriving at:
Chicago Midway International Airport
Average flight time:
1 hour 26 minutes
Distance:
423 miles
Route Information
150† Weekly flights
- 4‡ Nonstop flights per day Monday through Friday
- 3‡ Nonstop flights on Saturday
- 5‡ 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 Omaha to Chicago (Midway) is 1 hour 26 minutes.
There are 150 weekly flights from Omaha to Chicago (Midway) on Southwest Airlines.
Yes, Southwest flies nonstop from Omaha to Chicago (Midway) 4 times per day from Monday through Friday.
Yes, Southwest flies nonstop from Omaha to Chicago (Midway) 3 times per day on Saturdays and 5 times per day on Sundays.
To find the lowest fares by day and time to fly Omaha 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 Omaha 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.