Southwest Airlines has grown significantly over the past 50 years, evolving from a small regional airline to a major carrier with an extensive network across North America. Originally launched in June 1971 with routes between Dallas, Houston, and San Antonio, Southwest has since expanded its presence, particularly at Chicago Midway International Airport, one of its busiest hubs.
While Southwest primarily operates as a point-to-point carrier, some of its key bases—like Denver, Baltimore, and Chicago Midway—function as rolling hubs, offering high-frequency connections without traditional “banked” schedules. This strategy enables quick turnarounds, improves aircraft utilization, and keeps costs low.
Among all its destinations, Chicago Midway stands out as a crucial city in Southwest’s network. The airline dominates Midway’s market, carrying over 90% of its passengers, operating up to 250 daily departures to 79 cities, and employing more than 6,000 workers.
Let’s take a closer look at Southwest’s 15 busiest routes from Chicago Midway in January 2025, highlighting key connections for business, leisure, and hub connectivity.
1. New York LaGuardia Airport – 201 Monthly Flights
✅ Distance: 725 miles
✅ Available Seat Miles: 23,831,475
Southwest’s busiest route from Midway is to New York LaGuardia (LGA). While New York has three major airports, Southwest exclusively serves LaGuardia, having previously operated flights to Newark until 2019. Despite competition from airlines operating at Chicago O’Hare, Southwest holds a strong position on this route.
2. Phoenix Sky Harbor International Airport – 198 Monthly Flights
✅ Distance: 1,444 miles
✅ Available Seat Miles: 45,783,464
A key base for Southwest, Phoenix Sky Harbor serves as both a major market and a connecting hub. The airline competes with American Airlines, which inherited Phoenix as a hub after merging with US Airways.
3. Orlando International Airport – 180 Monthly Flights
✅ Distance: 989 miles
✅ Available Seat Miles: 32,074,259
As a major vacation destination, Orlando is one of Southwest’s most important airports. The airline is the market leader at Orlando, offering connections to Caribbean destinations.
4. Denver International Airport – 170 Monthly Flights
✅ Distance: 888 miles
✅ Available Seat Miles: 26,923,390
Southwest has invested heavily in Denver, including:
- Sponsoring three major sports teams (Avalanche, Rockies, Nuggets)
- Leasing 16 new gates
- Opening a $100 million maintenance hangar
Denver is Southwest’s busiest city and a major connecting point for passengers traveling to Western U.S. destinations.
5. Washington, D.C. (Reagan National & Dulles) – 165 Monthly Flights
✅ Distance: 612 miles
✅ Available Seat Miles: 17,133,909
Southwest serves Washington, D.C., primarily through Reagan National Airport (DCA), though it also operates limited flights from Dulles (IAD). Southwest entered the market in 2012 after acquiring AirTran Airways, securing valuable slots at Reagan.
6. Las Vegas McCarran International Airport – 160 Monthly Flights
✅ Distance: 1,514 miles
✅ Available Seat Miles: 43,033,653
As the second-busiest destination in Southwest’s network, Las Vegas has been a key city for the airline since it became Southwest’s 15th destination. The airline operates 276 daily departures to 70 cities from its Las Vegas base.
7. Dallas Love Field – 150 Monthly Flights
✅ Distance: 793 miles
✅ Available Seat Miles: 20,782,944
Southwest’s headquarters are in Dallas, and Love Field is the airline’s home airport. Despite legal battles over its right to use Love Field, Southwest remains dominant. The airline has also hinted at potentially expanding to Dallas/Fort Worth International Airport (DFW) in the future.
8. Kansas City International Airport – 145 Monthly Flights
✅ Distance: 403 miles
✅ Available Seat Miles: 9,076,860
Kansas City is a significant market for Southwest, serving as an important connection to the Midwest. Southwest was also the first airline to depart from the airport’s brand-new terminal, operating from Concourse B.
9. Nashville International Airport – 140 Monthly Flights
✅ Distance: 395 miles
✅ Available Seat Miles: 8,516,990
Nashville is Southwest’s newest crew base, making it a vital part of the airline’s Southeastern U.S. network. With 174 daily flights, the airline continues to expand its presence here.
10. Houston Hobby Airport – 135 Monthly Flights
✅ Distance: 937 miles
✅ Available Seat Miles: 19,323,751
Houston Hobby (HOU) serves as an international gateway for Southwest, offering flights beyond the U.S., including Mexico, the Caribbean, and Central America.
11. Tampa International Airport – 130 Monthly Flights
✅ Distance: 1,012 miles
✅ Available Seat Miles: 21,901,099
Tampa is a major leisure travel destination, connecting Midwest travelers to Florida’s beaches and warm weather. Southwest also operates international flights from Tampa to destinations like Havana, Cuba, and San Juan, Puerto Rico.
12. Baltimore/Washington International Airport – 125 Monthly Flights
✅ Distance: 621 miles
✅ Available Seat Miles: 12,630,592
Baltimore (BWI) is Southwest’s fourth-busiest city, serving as its primary gateway to the Northeast. Southwest operates 235 daily flights to 79 destinations from Baltimore.
13. Minneapolis/St. Paul International Airport – 120 Monthly Flights
✅ Distance: 349 miles
✅ Available Seat Miles: 7,521,997
Southwest competes directly with Delta on this route, as Minneapolis is a major Delta hub. Southwest holds the second-largest market share at MSP but only accounts for 5% of total airport traffic.
14. St. Louis Lambert International Airport – 115 Monthly Flights
✅ Distance: 251 miles
✅ Available Seat Miles: 5,056,395
Southwest’s first route from Midway was to St. Louis, and the route remains popular. The short 251-mile flight is critical for business travel between the two Midwestern cities.
15. Atlanta Hartsfield-Jackson International Airport – 110 Monthly Flights
✅ Distance: 606 miles
✅ Available Seat Miles: 11,775,810
Southwest entered Atlanta after acquiring AirTran Airways, but its presence has since declined. The airline is shifting flights to Nashville, reducing its Atlanta operations.
Southwest Airlines has built an extensive network from Chicago Midway, with high-frequency flights to key cities. Whether for business, leisure, or connections, these 15 busiest routes highlight the airline’s strategic growth and dominance at Midway Airport.
With continued expansion and network adjustments, Southwest remains a leader in affordable, high-frequency travel across North America.
