Southwest® flights to destinations in the Midwest

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Visit the Midwest.

See how nice the Midwest can be—explore everywhere Southwest® flies in the region and start planning to check off some of your bucket list trips. Whether you crave the hustle and bustle of a world-class city with a skyscraper-packed skyline or a sleepy town tucked away in the middle of nowhere, there’s something for every kind of traveler to find in the Midwest.

Chicago

Now serving.

Chicago (O'Hare)

See why the Second City is second to none when you start your adventure in Chicago with service to Chicago O'Hare International Airport or Chicago Midway International Airport.

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Low Fares for the Midwest and beyond

Chicago (Midway) (MDW)to

Detroit (DTW)
Depart: 02/05/2026
From
$46
One-way
Basic

Dallas (Love Field) (DAL)to

Indianapolis (IND)
Depart: 01/07/2026
From
$46
One-way
Basic

Houston (Hobby) (HOU)to

Chicago (Midway) (MDW)
Depart: 02/14/2026
From
$46
One-way
Basic

Orlando (MCO)to

Chicago (Midway) (MDW)
Depart: 02/11/2026
From
$46
One-way
Basic

Las Vegas (LAS)to

Chicago (Midway) (MDW)
Depart: 01/27/2026
From
$46
One-way
Basic

Baltimore/Washington (BWI)to

Chicago (Midway) (MDW)
Depart: 02/04/2026
From
$46
One-way
Basic

Nashville (BNA)to

Chicago (Midway) (MDW)
Depart: 01/08/2026
From
$46
One-way
Basic

Chicago (Midway) (MDW)to

Minneapolis/St. Paul (MSP)
Depart: 01/08/2026
From
$46
One-way
Basic

Chicago (Midway) (MDW)to

St. Louis (STL)
Depart: 02/05/2026
From
$46
One-way
Basic

Dallas (Love Field) (DAL)to

Chicago (O'Hare) (ORD)
Depart: 01/27/2026
From
$46
One-way
Basic

Nashville (BNA)to

Chicago (O'Hare) (ORD)
Depart: 01/14/2026
From
$46
One-way
Basic

Orlando (MCO)to

Chicago (O'Hare) (ORD)
Depart: 01/13/2026
From
$46
One-way
Basic

*Fares displayed have been collected within the last 24 hours and may no longer be available at time of booking. Additional fees and charges for optional products and services may apply. Modifying this information may result in a different fare. To find the most updated fare, please visit Southwest.com. Fares listed are Basic, which are subject to additional terms and conditions.

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Plan your trip to the Midwest

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12022–2023 Freddie Awards. 2Where available. Available only on WiFi-enabled designated aircraft. Free WiFi is only for Rapid Rewards® Members.