Flat-rate transfers to Chicago Midway with flight tracking on every ride. We plan around the heavier south-side traffic so you reach MDW on schedule, every time.
Chicago Midway sits roughly 93 miles south of Milwaukee, a drive of about an hour and 50 minutes. Because Midway is deeper into the city than O'Hare, the last stretch runs through heavier traffic. That is exactly why a professional chauffeur earns their keep on this route: we know when to leave, which way to go, and how to keep your schedule intact.
Every Milwaukee to Midway ride is a flat rate, fixed at booking, with real-time flight tracking included. Southwest Airlines runs the bulk of Midway's schedule, so early departures are common. Our 24/7 dispatch handles pre-dawn pickups without drama.
Pick a sedan for solo and couple travel, an SUV for extra luggage or up to six riders, a Sprinter for groups, or a stretch limo for a special arrival. Whatever you choose, you get the same promise: on time, every trip.
Starting rates by vehicle for one-way and round-trip service. Midway runs a little higher than O'Hare because of the longer city drive. Every fare is fixed at booking.
| Vehicle | Capacity | One way | Round trip |
|---|---|---|---|
| Mercedes S-ClassEXECUTIVE SEDAN | 3 passengers | from $215 | from $410 |
| Cadillac EscaladeLUXURY SUV | 6 passengers | from $245 | from $465 |
| Chevrolet SuburbanFULL-SIZE SUV | 7 passengers | from $255 | from $485 |
| Mercedes SprinterEXECUTIVE VAN | 12 passengers | from $345 | from $655 |
| Stretch LimoSPECIAL OCCASION | 10 passengers | from $390 | from $740 |
Rates are starting estimates from downtown Milwaukee and vary by exact pickup address. Suburban and outlying pickups are quoted on booking.
Get your exact quoteWe watch your Midway flight and adjust pickup for early or late arrivals automatically.
Add a name-sign greeting at baggage claim so your chauffeur is waiting inside.
We plan around the busier south-side approach so a slow stretch does not cost you the gate.
Built-in grace time at the airport so a slow bag carousel never costs you extra.
Infant and booster seats available when you ask at booking, fitted and ready.
Every vehicle is detailed before each trip and driven by a licensed chauffeur.
From booking to drop-off, the whole trip is handled. No phone tag, no curbside guessing.
Start a bookingPick your vehicle and get a flat quote. Confirm online or by phone in under two minutes.
Dispatch monitors your Southwest or other carrier flight and adjusts pickup to match.
Your driver is at the pickup point ahead of time, ready to load bags and get moving.
A smooth drive planned around traffic and a drop-off right at the Midway terminal door.
Midway is a single-terminal airport, which keeps arrivals and departures straightforward. Here is how we handle each.
Direct to the departures level so you walk straight to security.
Curbside pickup, or a meet-and-greet inside at baggage claim on request.
The bulk of Midway flights. We track your gate and time the pickup.
We stage nearby and pull up the moment you have your bags.
Quiet sedans, on-time pickups, and corporate billing for client and team trips.
Room for luggage and child seats, so the whole family starts the trip relaxed.
One Sprinter, one price, everyone arrives together with bags and gear.
Pre-dawn pickups handled by a 24/7 dispatch that does this every day.
Land at any hour and find your chauffeur waiting, flight already tracked.
Arrive for the trip in a stretch limo when the moment calls for more.
The number you see is the number you pay. No surge, no meter, no surprises.
Early arrivals are standard. We plan for the south-side traffic so you do not have to.
Licensed, insured, and background-checked drivers who know the route and the airport.
A late-model fleet, detailed before every trip, so each ride feels first class.
Lock both legs to Midway at one fixed price. We track your return flight and have a chauffeur ready the moment you land, no second booking required.
Caught an early Southwest flight out of Midway without a hint of stress. Driver knew exactly which way to go through the city.
They tracked my late return and were waiting at baggage claim. After a long travel day that meant everything.
Booked a Suburban for the family and all our bags fit easily. On time both directions.
The questions Midway riders ask most. Still unsure? Call (414) 916-7648 any hour.
About an hour and 50 minutes for the roughly 93-mile drive in normal traffic. Because Midway is deeper into the city than O'Hare, we plan extra buffer for the south-side approach.
One-way service starts at $215 for a sedan and $245 for an SUV. Larger vehicles and round trips are priced accordingly, and every rate is flat and quoted before you book.
Midway sits farther south, so the drive is longer and runs through heavier Chicago traffic. The flat rate reflects the extra distance and time.
Yes. Southwest runs most of Midway's schedule and early departures are common. Pre-dawn pickups are routine for our 24/7 dispatch.
Standard pickup is curbside once you have your bags. Add a meet-and-greet at booking and your chauffeur will wait inside at baggage claim.
We track arrivals in real time and shift your pickup to the new landing time at no extra charge.
Yes. Book both legs at one fixed price and we track your return flight so the pickup is ready when you land.
We serve the full metro, including Brookfield, Waukesha, Racine, and Kenosha. Rates start from downtown Milwaukee and adjust for your exact pickup address.
From one rider in a sedan up to twelve in a Sprinter van. SUVs seat six to seven with luggage, and the stretch limo holds up to ten.
Tolls and gratuity are added at checkout and shown clearly before you confirm, so the total you approve is the total you pay.
Earlier is better for early-morning and peak-day departures, but our 24/7 dispatch handles same-day and last-minute Midway rides whenever a vehicle is available.
Yes. We run flat-rate transfers to O'Hare and downtown Chicago destinations as well, with the same flight tracking and professional chauffeurs.
Our most-booked route. Limo and car service to every O'Hare terminal.
View route → MKE → CHIDowntown hotels, McCormick Place, meetings, and events across the city.
View route → ROUND TRIPBoth legs at one fixed price with return-flight tracking built in.
View route → CORPORATEExecutive accounts, priority dispatch, and consolidated billing.
View route →Every vehicle is late-model, detailed before each trip, and driven by a licensed, insured chauffeur who tracks your flight.
First-class quiet for solo and couple travel.
Room, presence, and a smooth highway ride.
Spacious cabin with a refined, steady drive.
Extra luggage space for full schedules.
Stand-up cabin for groups and teams.
For events, nights out, and arrivals in style.
Flat rates, flight tracking, and a chauffeur waiting when you land. Reserve in under two minutes.