Southwest Moves to Midway

Effective June 4, 2026, Southwest Airlines is consolidating all of its Chicago operations at Midway International Airport. If you have been flying Southwest out of O'Hare, those flights now leave from Midway on the city's southwest side near Cicero and 55th: a different airport, a different drive, and for most North Side and suburban travelers, a different amount of time to budget. The change affects where your car drops you off, how early you should leave, and which side of the metro your return pickup comes from.

We have run Midway transfers since 2018, so the airport itself is familiar ground for our chauffeurs. What is new for a lot of Southwest loyalists is simply the destination. The fix is the same one that works for any flight: a flat fare set before you ride, a chauffeur who tracks the flight, and a pickup confirmed in advance so you are not standing curbside re-hailing a car.

The move creates a new kind of trip for travelers whose itineraries now straddle both airports, land at O'Hare on one carrier, depart Midway on Southwest, or the reverse. The two airports are roughly 25 miles apart on opposite sides of the city, generally 45 to 70 minutes by car depending on traffic, so a tight connection needs real margin. We run inter-airport transfers starting at $149 by sedan, with the time built in and your chauffeur tracking the inbound flight so the handoff actually works.

On returns into Midway, the car is timed to your actual landing rather than the schedule. Land early and the driver is already there; land late and the flat fare still holds, with free wait time and a curbside or baggage-claim meet, your choice at booking.