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Find low faresSouthwest® flights from Chicago (Midway) starting at $40
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Book flights from Chicago (Midway) with Southwest Airlines
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$
Chicago (Midway) (MDW)to
Boston (BOS)Depart: 04/11/2026
From
$40
Seen: 3 hrs ago
One-way
Basic
Chicago (Midway) (MDW)to
St. Louis (STL)Depart: 04/04/2026
From
$40
Seen: 20 hrs ago
One-way
Basic
Chicago (Midway) (MDW)to
Memphis (MEM)Depart: 04/11/2026
From
$40
Seen: 1 hour ago
One-way
Basic
Chicago (Midway) (MDW)to
Columbus (CMH)Depart: 03/14/2026
From
$40
Seen: 1 hour ago
One-way
Basic
Chicago (Midway) (MDW)to
Cleveland (CLE)Depart: 04/18/2026
From
$40
Seen: 3 hrs ago
One-way
Basic
Chicago (Midway) (MDW)to
Baltimore/Washington (BWI)Depart: 04/11/2026
From
$50
Seen: 3 hrs ago
One-way
Basic
Chicago (Midway) (MDW)to
New York (LaGuardia) (LGA)Depart: 05/02/2026
From
$52
Seen: 3 hrs ago
One-way
Basic
Chicago (Midway) (MDW)to
Fort Myers/Naples (RSW)Depart: 03/07/2026
From
$56
Seen: 3 hrs ago
One-way
Basic
Chicago (Midway) (MDW)to
Dallas (Love Field) (DAL)Depart: 04/11/2026
From
$56
Seen: 1 hour ago
One-way
Basic
Chicago (Midway) (MDW)to
San Diego (SAN)Depart: 05/02/2026
From
$56
Seen: 3 hrs ago
One-way
Basic
Chicago (Midway) (MDW)to
Pittsburgh (PIT)Depart: 04/04/2026
From
$56
Seen: 2 hrs ago
One-way
Basic
Chicago (Midway) (MDW)to
Las Vegas (LAS)Depart: 04/25/2026
From
$57
Seen: 3 hrs ago
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.
Traveling from Chicago (Midway)
Southwest Airlines is proud to serve Chicago Midway International Airport.
Boarding a Southwest flight departing Midway is a snap—just hop on the “L” train! The Orange Line will take you directly to the airport, the first stop on your adventure beyond the Second City. Of course, long-term parking and calling a car are always options, too.
A world-class city like Chicago has something for everyone and pockets of cultures from around the globe, but it doesn’t have everything. Ocean views? Not one, though Lake Michigan is lovely. Mountain peaks? The only heights you’ll find among the flat terrain of this Midwestern hub are skyscrapers. Dry desert heat is of course unheard of—that lovely lake sure does make it plenty humid in the summertime. There’s so much world out there to explore beyond the Chicagoland area, and Southwest can take you there. And since Chicago Midway International Airport is a Southwest Airlines hub, many of those flights out of Chi-Town are direct!
Details about Chicago Midway International Airport
Airport code:
MDW
City:
Chicago (Midway)
State:
Illinois
Concourse:
Terminals A & B
Gates:
Gates A: 4a, 4b, 9, 11, 15-19, B: 1-3, 5, 7-12, 14-26
Airport-provided WiFi
Cities with weekly flights from MDW:
118†
Cities with daily nonstop flights Monday through Friday from MDW:
70‡
Cities with daily nonstop flights Saturday through Sunday from MDW:
140§
† Weekly flights based on DOT published scheduled average flights Monday through Sunday between 10/1/2025 and 10/31/2025. Note: route may not operate every day of the week.
‡ Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 10/1/2025 and 10/31/2025.
Popular Destinations from Chicago (Midway)
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$
From | To | Fare Type | Dates | Price | |
|---|---|---|---|---|---|
| Chicago (Midway) (MDW) | Boston (BOS) | One-way / Basic | Depart: 04/11/2026 | From $40 Seen: 3 hrs ago | |
| Chicago (Midway) (MDW) | St. Louis (STL) | One-way / Basic | Depart: 04/04/2026 | From $40 Seen: 20 hrs ago | |
| Chicago (Midway) (MDW) | Memphis (MEM) | One-way / Basic | Depart: 04/11/2026 | From $40 Seen: 1 hour ago | |
| Chicago (Midway) (MDW) | Columbus (CMH) | One-way / Basic | Depart: 02/28/2026 | From $40 Seen: 3 hrs ago | |
| Chicago (Midway) (MDW) | Cleveland (CLE) | One-way / Basic | Depart: 04/18/2026 | From $40 Seen: 3 hrs ago | |
| Chicago (Midway) (MDW) | Baltimore/Washington (BWI) | One-way / Basic | Depart: 04/11/2026 | From $50 Seen: 3 hrs ago | |
| Chicago (Midway) (MDW) | New York (LaGuardia) (LGA) | One-way / Basic | Depart: 05/02/2026 | From $52 Seen: 3 hrs ago | |
| Chicago (Midway) (MDW) | Fort Myers/Naples (RSW) | One-way / Basic | Depart: 03/07/2026 | From $56 Seen: 3 hrs ago |
*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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