Southwest® flights to Chicago (Midway) starting at $64

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Popular flights to Chicago (Midway) on Southwest Airlines

$

Phoenix (PHX)to

Chicago (Midway) (MDW)
Depart: 12/30/2025
From
$130
Seen: 10 hrs ago
One-way
Basic

Dallas (Love Field) (DAL)to

Chicago (Midway) (MDW)
Depart: 01/04/2026
From
$133
Seen: 2 hrs ago
One-way
Basic

Houston (Hobby) (HOU)to

Chicago (Midway) (MDW)
Depart: 12/16/2025
From
$164
Seen: 13 hrs ago
One-way
Basic

Atlanta (ATL)to

Chicago (Midway) (MDW)
Depart: 12/30/2025
From
$125
Seen: 8 hrs ago
One-way
Basic

Orlando (MCO)to

Chicago (Midway) (MDW)
Depart: 12/16/2025
From
$164
Seen: 13 hrs ago
One-way
Basic

Denver (DEN)to

Chicago (Midway) (MDW)
Depart: 01/01/2026
From
$153
Seen: 12 hrs ago
One-way
Basic

Los Angeles (LAX)to

Chicago (Midway) (MDW)
Depart: 12/17/2025
From
$204
Seen: 13 hrs ago
One-way
Basic

Tampa (TPA)to

Chicago (Midway) (MDW)
Depart: 12/16/2025
From
$164
Seen: 13 hrs ago
One-way
Basic

Las Vegas (LAS)to

Chicago (Midway) (MDW)
Depart: 12/26/2025
From
$90
Seen: 12 hrs ago
One-way
Basic

New York (LaGuardia) (LGA)to

Chicago (Midway) (MDW)
Depart: 12/12/2025
From
$95
Seen: 4 hrs ago
One-way
Basic

Baltimore/Washington (BWI)to

Chicago (Midway) (MDW)
Depart: 12/12/2025
From
$174
Seen: 4 hrs ago
One-way
Basic

Nashville (BNA)to

Chicago (Midway) (MDW)
Depart: 01/03/2026
From
$150
Seen: 6 minutes ago
One-way
Basic

Kansas City (MCI)to

Chicago (Midway) (MDW)
Depart: 12/31/2025
From
$175
Seen: 5 hrs ago
One-way
Basic

Fort Lauderdale (FLL)to

Chicago (Midway) (MDW)
Depart: 12/16/2025
From
$164
Seen: 9 hrs ago
One-way
Basic

Washington, D.C. (Reagan National) (DCA)to

Chicago (Midway) (MDW)
Depart: 01/03/2026
From
$155
Seen: 7 hrs ago
One-way
Basic

Fort Myers/Naples (RSW)to

Chicago (Midway) (MDW)
Depart: 12/16/2025
From
$164
Seen: 13 hrs ago
One-way
Basic

Austin (AUS)to

Chicago (Midway) (MDW)
Depart: 01/03/2026
From
$169
Seen: 18 hrs ago
One-way
Basic

St. Louis (STL)to

Chicago (Midway) (MDW)
Depart: 12/29/2025
From
$170
Seen: 9 hrs ago
One-way
Basic

New Orleans (MSY)to

Chicago (Midway) (MDW)
Depart: 12/31/2025
From
$225
Seen: 4 hrs ago
One-way
Basic

Oakland (OAK)to

Chicago (Midway) (MDW)
Depart: 01/02/2026
From
$140
Seen: 1 hour 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.

Explore Chicago with Southwest Airlines

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.


Flying into Chicago Midway with Southwest

  • Midway offers an easy, convenient entry point to Chicago that is distinct from O’Hare.
  • Get downtown fast via the CTA Orange Line, or enjoy quick access to neighborhoods like Bridgeport, Pilsen, and Chinatown.
  • With frequent nonstop flights to Chicago Midway, you can plan your trip with maximum flexibility.

Top Things to Do in Chicago

  • Admire world-class art at the Art Institute of Chicago and public installations at Millennium Park.
  • Savor Chicago classics, from deep-dish pizza at Lou Malnati’s to Italian beef sandwiches and iconic hot dogs.
  • Cheer on Chicago's legendary sports teams, including the Cubs, White Sox, Bears, Bulls, and Blackhawks.
  • Enjoy live music at summer festivals like Lollapalooza or year-round in one of the many historic blues and jazz clubs.
  • Get out on the water with architectural river tours or scenic dinner cruises on Lake Michigan.
  • Make the most of every season with film festivals, street fests, and scenic fall walks.

Got flexible travel plans?

Use our Low Fare Calendar to find the lowest fares available inside your travel window.

Find flights

Details about Chicago Midway International Airport

Chicago airport
Airport code:
MDW
City:
Chicago
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:
114†
Cities with daily nonstop flights Monday through Friday from MDW:
74‡
Cities with daily nonstop flights Saturday through Sunday from MDW:
147§

† 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.

Find cheap flights to Chicago (Midway)

$

Boston (BOS)to

Chicago (Midway) (MDW)
Depart: 12/13/2025

One-way

Basic

From
$64
Seen: 13 hrs ago

Baltimore/Washington (BWI)to

Chicago (Midway) (MDW)
Depart: 01/22/2026

One-way

Basic

From
$70
Seen: 10 hrs ago

Charlotte (CLT)to

Chicago (Midway) (MDW)
Depart: 01/13/2026

One-way

Basic

From
$70
Seen: 5 hrs ago

San Diego (SAN)to

Chicago (Midway) (MDW)
Depart: 01/21/2026

One-way

Basic

From
$76
Seen: 9 hrs ago

Houston (Hobby) (HOU)to

Chicago (Midway) (MDW)
Depart: 02/14/2026

One-way

Basic

From
$76
Seen: 22 hrs ago

Orlando (MCO)to

Chicago (Midway) (MDW)
Depart: 02/11/2026

One-way

Basic

From
$76
Seen: 20 minutes ago

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