Southwest Moves to Midway
Southwest Airlines is consolidating all Chicago operations at Midway effective June 4, 2026. New airport, new route — book your car service now. Midway transfers from $130.
Reserve Your Chicago Limo
Instant availability, flat fares locked at booking, no peak-hour upcharges. Confirmed by text in under 15 minutes.
Midway Car Service Options
Midway Airport Transfers
Downtown, suburbs, or McCormick Place to/from Midway. Sedan from $130, SUV from $165. Flight tracking and curbside pickup.
O'Hare to Midway Transfer
Connecting flights across airports? We handle inter-airport transfers starting at $130. Plenty of time built in for traffic.
Corporate Accounts
Frequent Southwest flyers get a corporate account with monthly billing, dedicated drivers, and priority scheduling. No per-trip booking.
What Southwest's Move Means for Your Travel
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.
Drive Times & Flat Fares to MDW
From downtown — the Loop or the Magnificent Mile — Midway is about 11 miles, typically 20 to 35 minutes via I-55 or Lake Shore Drive to Cicero Avenue. The flat sedan rate from downtown is $130, with a six-passenger SUV at $165 for families or groups traveling with luggage. From the North Side and the North Shore the run is longer, since Midway sits opposite O'Hare on the map, so if your old Southwest routine had you 20 minutes from O'Hare, plan for more time now and book the pickup a little earlier.
Every rate is flat and locked at booking — no peak pricing during rush hour or holidays, and tolls and gratuity are included. For a typical domestic Southwest departure we suggest arriving at Midway about two hours ahead; your chauffeur knows the terminal's drop-off pattern and gets you to the right door.
O'Hare-to-Midway & Split Itineraries
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 $130 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.
Corporate Accounts for Regular Midway Travel
If you fly Southwest weekly for work, the move to Midway is a chance to drop the per-trip booking entirely. We set up corporate accounts with monthly invoicing, a dedicated driver who learns your routine, and priority scheduling so a 5 AM Monday departure is handled without a scramble. The same account covers the occasional O'Hare-to-Midway connection and any downtown or suburban transfers your team needs.
Whether it is a single trip during the June transition or a standing weekly ride, the booking is the same: flat fare, assigned chauffeur, flight tracked, confirmed in advance. New airport, same service.
Southwest Midway Questions
New Airport, Same Great Service
Southwest at Midway starting June 4. Book your car service before the rush.
Questions? Contact us — corporate accounts available.
What Our Customers Say
“MDW pickup at 4:15 AM, Cadillac CT6, driver had a bottle of water and the heat already cranked because it was 14°. That kind of thinking-ahead is what you're paying for.”
— Karen S. · Midway weekly traveler
“Royal Carriage tracks my Thursday return flight automatically. When it delays — which happens often — the driver is there when I actually land, not when the original gate said. Two years of weekly O'Hare runs, never once stranded.”
— Dr. M. Reyes · Hinsdale
Lock Your Chicago Airport Transfer
ORD + MDW flat-fare from $130 · No peak pricing · Flight-tracked · 24/7