Find low fares on Southwest Airlines® flights from or within the Midwest

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Flying from the Midwest.

Your wanderlust is calling—answer by winging away from your Midwest homestead on a Southwest flight toward your next adventure. We proudly serve several Midwestern metropolises, making it easy to choose your next bucket list destination. Whether you want to trade the Great Lakes for one of the coasts, the plains’ flats for mountains and valleys, or simply yearn to unplug from your day-to-day, explore everywhere you can escape to from your local airport.

Orlando

Featured destination.

Orlando

Experience otherworldly theme parks or enjoy the down-to-earth vibes in this Central Florida city that’s the perfect steppingstone for once-in-a-lifetime day trips.

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Low Fares from the Midwest

Detroit (DTW)to

Chicago (Midway) (MDW)
Depart: 01/29/2026
From
$46
One-way
Basic

Indianapolis (IND)to

Dallas (Love Field) (DAL)
Depart: 02/25/2026
From
$46
One-way
Basic

Chicago (Midway) (MDW)to

Atlanta (ATL)
Depart: 02/10/2026
From
$46
One-way
Basic

Chicago (Midway) (MDW)to

Houston (Hobby) (HOU)
Depart: 02/18/2026
From
$46
One-way
Basic

Chicago (Midway) (MDW)to

Miami (MIA)
Depart: 02/24/2026
From
$46
One-way
Basic

Minneapolis/St. Paul (MSP)to

Phoenix (PHX)
Depart: 02/24/2026
From
$46
One-way
Basic

Minneapolis/St. Paul (MSP)to

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

St. Louis (STL)to

Chicago (Midway) (MDW)
Depart: 01/31/2026
From
$46
One-way
Basic

Chicago (O'Hare) (ORD)to

Las Vegas (LAS)
Depart: 02/25/2026
From
$46
One-way
Basic

Chicago (O'Hare) (ORD)to

Orlando (MCO)
Depart: 01/13/2026
From
$46
One-way
Basic

Chicago (O'Hare) (ORD)to

Dallas (Love Field) (DAL)
Depart: 01/15/2026
From
$46
One-way
Basic

Chicago (O'Hare) (ORD)to

Nashville (BNA)
Depart: 01/07/2026
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 from the Midwest

  • Rent a car.

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  • Book a hotel.

    Find deals for any season.

    Book a hotel

  • Plan a vacation.

    Getaways by Southwest™ offers tons of vacation packages with amazing travel deals.

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Join Rapid Rewards, our award-winning frequent flyer program1.

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Free inflight WiFi thanks to T-Mobile®.2

Rapid Rewards members can go online to check email, snag a dinner reservation, or browse social media from takeoff to landing. Learn more ›

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