St. Louis (STL)to
Chicago (Midway) (MDW)Washington, D.C. (Reagan National) (DCA)to
Chicago (Midway) (MDW)New York (LaGuardia) (LGA)to
Chicago (Midway) (MDW)Baltimore/Washington (BWI)to
Chicago (Midway) (MDW)Dallas (Love Field) (DAL)to
Chicago (Midway) (MDW)New Orleans (MSY)to
Chicago (Midway) (MDW)Las Vegas (LAS)to
Chicago (Midway) (MDW)Tampa (TPA)to
Chicago (Midway) (MDW)Atlanta (ATL)to
Chicago (Midway) (MDW)Denver (DEN)to
Chicago (Midway) (MDW)Austin (AUS)to
Chicago (Midway) (MDW)Phoenix (PHX)to
Chicago (Midway) (MDW)Kansas City (MCI)to
Chicago (Midway) (MDW)Houston (Hobby) (HOU)to
Chicago (Midway) (MDW)Orlando (MCO)to
Chicago (Midway) (MDW)Fort Lauderdale (FLL)to
Chicago (Midway) (MDW)Fort Myers/Naples (RSW)to
Chicago (Midway) (MDW)Oakland (OAK)to
Chicago (Midway) (MDW)Nashville (BNA)to
Chicago (Midway) (MDW)Los Angeles (LAX)to
Chicago (Midway) (MDW)*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.
Book your next flight to Chicago Midway with Southwest Airlines and experience seasonal events, cultural hotspots, and neighborhood charm. Learn more about the Southwest Experience and start planning your Chicago getaway today.
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† Weekly flights based on DOT published schedule average flights Monday through Sunday between 9/1/2025 and 9/30/2025. Note: route may not operate every day of the week.
‡ Weekday flights based on DOT published schedule average flights Monday through Friday between 9/1/2025 and 9/30/2025.
§ Nonstop flights based on DOT published schedule average flights Saturday through Sunday between 9/1/2025 and 9/30/2025.
St. Louis (STL)to
One-way
Basic
Boston (BOS)to
One-way
Basic
Minneapolis/St. Paul (MSP)to
One-way
Basic
Memphis (MEM)to
One-way
Choice
Cleveland (CLE)to
One-way
Choice
Washington, D.C. (Reagan National) (DCA)to
One-way
Basic
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