Southwest Airlines’ Busiest Routes from Chicago Midway in 2025
Southwest Airlines has grown significantly over the past 50 years, expanding its network across North America. While the airline primarily operates on a point-to-point model, some airports, like Chicago Midway International Airport (MDW), have evolved into crucial bases for the airline. As a result, Midway has become one of Southwest’s busiest cities, offering flights to 79 destinations with up to 250 daily departures.
In this article, we’ll explore Southwest’s 15 busiest routes from Chicago Midway in January 2025, ranked by the number of monthly flights.
Understanding Southwest’s Network Strategy
Unlike traditional banked hub systems used by airlines like Delta and American Airlines, Southwest operates on a rolling hub model. This means flights arrive and depart continuously rather than in structured waves, allowing for faster turnarounds and better aircraft utilization.
Chicago Midway plays a key role in this strategy, offering nonstop connections to major business and leisure destinations.
Southwest’s 15 Busiest Routes from Chicago Midway (January 2025)
Below are the top 15 busiest Southwest Airlines routes from Chicago Midway based on outbound flight frequencies in January 2025:
| Rank | Destination | Airport Code | Monthly Flights | Distance (Miles) | Available Seat Miles |
|---|---|---|---|---|---|
| 1 | New York LaGuardia | LGA | 201 | 725 | 23,831,475 |
| 2 | Phoenix Sky Harbor | PHX | 198 | 1,444 | 45,783,464 |
| 3 | Orlando International | MCO | 193 | 989 | 32,074,259 |
| 4 | Denver International | DEN | 190 | 888 | 26,923,390 |
| 5 | Washington Reagan National | DCA | 179 | 612 | 17,133,909 |
| 6 | Las Vegas Harry Reid | LAS | 171 | 1,524 | 43,033,653 |
| 7 | Dallas Love Field | DAL | 160 | 798 | 20,782,944 |
| 8 | Kansas City International | MCI | 148 | 403 | 9,076,860 |
| 9 | Nashville International | BNA | 134 | 395 | 8,516,990 |
| 10 | Houston Hobby | HOU | 129 | 939 | 19,323,751 |
| 11 | Tampa International | TPA | 129 | 1,013 | 21,901,099 |
| 12 | Baltimore/Washington | BWI | 128 | 621 | 12,630,592 |
| 13 | Minneapolis/St. Paul | MSP | 127 | 334 | 7,521,997 |
| 14 | St. Louis Lambert | STL | 127 | 251 | 5,056,395 |
| 15 | Atlanta Hartsfield-Jackson | ATL | 121 | 606 | 11,775,810 |
Key Highlights of Southwest’s Top Routes from Chicago Midway
1. Chicago Midway to New York LaGuardia (LGA) – 201 Monthly Flights
- Most frequent route from MDW.
- Southwest operates exclusively to LaGuardia (LGA) (not JFK or Newark).
- A key business route, competing with airlines flying from Chicago O’Hare (ORD).
2. Chicago Midway to Phoenix Sky Harbor (PHX) – 198 Monthly Flights
- A major base for Southwest and a key connecting hub.
- Competes with American Airlines, which operates from Phoenix as a legacy hub.
3. Chicago Midway to Orlando (MCO) – 193 Monthly Flights
- A high-demand leisure route due to Disney World and other attractions.
- Orlando serves as a gateway to the Caribbean for Southwest.
4. Chicago Midway to Denver (DEN) – 190 Monthly Flights
- Denver is Southwest’s busiest city in terms of overall operations.
- Southwest has heavily invested in Denver with new gates, sponsorships, and a $100M maintenance hangar.
5. Chicago Midway to Washington Reagan National (DCA) – 179 Monthly Flights
- A key government and business travel route.
- Southwest gained slots at DCA after acquiring AirTran Airways in 2012.
6. Chicago Midway to Las Vegas (LAS) – 171 Monthly Flights
- Las Vegas is Southwest’s second-busiest destination overall.
- Southwest operates 276 daily flights from Las Vegas.
7. Chicago Midway to Dallas Love Field (DAL) – 160 Monthly Flights
- Southwest’s headquarters is in Dallas Love Field.
- The airline may expand to Dallas-Fort Worth (DFW) in the future.
8. Chicago Midway to Kansas City (MCI) – 148 Monthly Flights
- Kansas City was Southwest’s first departure from Midway in 1985.
- The city recently opened a brand-new terminal with Southwest as its top airline.
9. Chicago Midway to Nashville (BNA) – 134 Monthly Flights
- Nashville recently became a crew base for Southwest.
- With the closure of Southwest’s Atlanta crew base, Nashville’s importance is increasing.
10. Chicago Midway to Houston Hobby (HOU) – 129 Monthly Flights
- Houston Hobby is a key base and an international gateway for Southwest.
- Southwest dominates HOU but has a limited presence at Houston Bush Intercontinental (IAH).
11. Chicago Midway to Tampa (TPA) – 129 Monthly Flights
- Tampa is a major tourist destination, especially for Midwestern travelers.
- Southwest flies internationally to Cuba and Puerto Rico from Tampa.
12. Chicago Midway to Baltimore/Washington (BWI) – 128 Monthly Flights
- Baltimore is Southwest’s fourth-busiest city overall.
- It serves as a gateway to both Washington, DC, and the Northeast US.
13. Chicago Midway to Minneapolis/St. Paul (MSP) – 127 Monthly Flights
- Southwest competes with Delta, which dominates the Minneapolis market.
- Minneapolis is a smaller Southwest market but still ranks among the top 15.
14. Chicago Midway to St. Louis (STL) – 127 Monthly Flights
- One of Southwest’s oldest routes, dating back to 1985.
- A short 251-mile hop that’s crucial for business travelers.
15. Chicago Midway to Atlanta (ATL) – 121 Monthly Flights
- Southwest entered Atlanta after acquiring AirTran Airways.
- Southwest has since reduced its Atlanta presence, shifting focus to Nashville.
Southwest Airlines’ Chicago Midway hub plays a crucial role in its network, connecting passengers to business hubs, leisure destinations, and major bases. With over 10 million passengers annually, Midway remains Southwest’s second-busiest airport after Denver.
As Southwest continues to refine its rolling hub strategy, Midway will likely remain a key player in the airline’s expansion plans. Whether you’re traveling for business or leisure, Southwest’s high-frequency flights from Midway ensure convenient connections across the US.
