Arrivals meet-and-greet
Your chauffeur tracks the flight and meets the group at Midway's central terminal with a name sign, then loads the bags. No hunting a pickup lot after you land.
CHICAGOExecutive Charters
CHICAGOExecutive Charters
Private group transfers to and from Chicago Midway in black Mercedes-Benz Sprinters seating up to 12–14. One central terminal, one flat quote, one coach for the whole party. We track your flight, meet the group, and get everyone there together — no surge, no separate fares.
Executive Sprinter
Chicago Executive Charters runs private, chauffeured group transfers between Chicago Midway International Airport (MDW) and any address across the city and the suburbs. Our black Mercedes-Benz Sprinters seat up to 12–14 with room for luggage. Midway has one terminal, so pickups are easy: we track your flight, meet the group, and quote one flat rate up front.
We're based in Elmwood Park, about 14 miles from Midway by way of I-55 and Cicero Avenue. Southwest Airlines runs most of the traffic through MDW, and its compact, single-terminal layout makes a group pickup far tidier than the sprawl of a bigger airport. Sports teams, families, and corporate groups all get the same thing: one coach, one chauffeur, one number to call.
Your chauffeur tracks the flight and meets the group at Midway's central terminal with a name sign, then loads the bags. No hunting a pickup lot after you land.
Pre-dawn pickups for the first Southwest flight out. The coach arrives early and drops the group curbside with time to check bags and clear security.
Rosters, coaches and gear ride together from Midway to the hotel, the venue or the field, on one schedule — not scattered across a caravan of cars.
Families flying in for a holiday, a reunion or a wedding land at MDW and ride into the city together, with room for every suitcase and the kids' gear.
Client teams and crews landing at Midway get a chauffeur in a jacket, direct billing and clean documentation, ready to run downtown or out to the suburbs.
Suitcases for the whole party, plus team bags, instruments or equipment cases. Everything rides with the group in one coach, not split across three cars.
Flying in with a mix of needs — a car seat, oversized bags, an accessibility request? Tell us when you book and we'll plan the right coach and the right buffers so the Midway pickup runs clean.
Split a group of ten across rideshares at Midway and you get several cars, several routes and several arrival times, plus surge pricing at peak hours and the odd cancellation while everyone is standing at the curb with their bags.
One Sprinter keeps it together. The whole group rides in a single coach, tracks one pickup, and pays one flat rate that was quoted before anyone flew. Nobody is fronting fares and chasing a reimbursement, nobody is squinting at license plates on the arrivals level, and the cabin earns the trip — captain's chairs or lounge seating, climate control, USB power and room for the luggage. For a smaller party, a shuttle van does the same job in a tighter package.
Mercedes-Benz Sprinter
Midway's single-terminal layout is its advantage. There's no terminal-hopping — the whole group meets the coach in one place.
For arrivals, give us the flight number when you book. We watch it land, factor in taxi and baggage time, and time the chauffeur so nobody is waiting and the coach isn't circling. Midway is one central terminal with concourses A, B and C under one roof, so wherever your Southwest or other flight comes in, the meeting point is the same. Your driver greets the party with a name sign and walks everyone to the Sprinter with the luggage handled.
If a flight is early, we're already there. If it runs late, nobody is stranded and there's no charge for the wait on a normal delay. One point of contact at dispatch owns the booking from start to finish, so if the plan shifts you reach a person, not a menu.
For departures, the coach arrives early at the hotel, office or home, loads the group and the bags, and runs the route to Midway with buffer built in for I-55 and Cicero Avenue. We drop curbside at the terminal so everyone walks straight to the airline counter. Early-morning and late-night flights are routine; dispatch runs 24/7, so a pre-dawn call time is confirmed the same as any other.
Round trips are handled on a single booking. We hold the return, track the inbound flight for the ride home, and keep the same standards on both legs. When a party is bigger than one Sprinter, we send more than one coach on the same schedule so everyone stays together and arrives at the same time.
Fourteen miles separate our base from MDW, and a local chauffeur knows every way to cover them without cutting a flight close.
From Elmwood Park, Midway is a straight shot south down Cicero Avenue, or a quick hop onto I-290 and then I-55, the Stevenson, into the airport. Our drivers run these roads daily, so they know when Cicero backs up around the shopping strips, how the Stevenson behaves at rush hour, and which approach to the terminal is quickest for a departure. That local read is the difference between a coach that's curbside when you land and one still stuck on the expressway. Groups coming from Oak Park, Berwyn and the near-west suburbs are on the way, which keeps the routing tight.
Elmwood Park base
No fine print, no surge, no surprises at the curb. Here's exactly what your group gets on a Chicago Executive Charters airport transfer. If a detail matters to your trip, ask, and we'll put it on the quote.
We monitor your flight number, so pickups shift with the real landing time. Early or delayed, the coach is timed to the plane, not the schedule.
A name sign at Midway's central terminal and a chauffeur who handles the luggage — no terminal-hopping, no guessing where to meet.
Commercial livery vehicles with active commercial insurance and professional, background-checked chauffeurs. Documentation on request.
One all-in rate confirmed before the trip. No surge, no meter, no per-head math for the group after a flight.
A real person answers around the clock, so a late flight, a delay or a same-day change reaches us, not a voicemail box.
Up to 12–14 per Sprinter with a dedicated luggage area, or multiple coaches in convoy for a larger party on one schedule.
Big companies treat a group airport run like an afterthought and an app treats it like ten separate fares. We don't.
Based in Elmwood Park, a straight run down Cicero and I-55 to Midway — fast dispatch, drivers who know the route, and quick response when a flight moves.
We watch your flight number, so an early landing or a long delay doesn't leave your group waiting or your car circling the terminal.
Flat, agreed pricing confirmed before the trip — easy for a team, a company or a family to plan around, with no surge on arrival.
Midway has one central terminal, so the pickup is simple. Your chauffeur tracks the flight and meets the group at the terminal with a name sign, then walks everyone to the Sprinter and loads the luggage. For departures the coach arrives early at your door and drops the group curbside at the terminal with time to check bags.
Midway is about 14 miles from our Elmwood Park base, a straight run south on Cicero Avenue or by I-290 to I-55. Because we know the route, a chauffeur builds in the right buffer for the Stevenson and for Cicero at rush hour, so the group isn't cutting it close for a flight.
Yes. Southwest runs most of Midway's traffic, and we handle Southwest arrivals and departures every day, along with every other airline flying out of MDW. With one terminal and concourses A, B and C under one roof, there's no guessing which building your group lands in.
Our black Mercedes-Benz Sprinters seat up to 12–14 passengers with a dedicated luggage area for suitcases, sports gear or equipment cases. For a larger party we send more than one coach on the same schedule so the whole group travels together and arrives at the same time.
Yes. We monitor your flight number, so arrivals shift with the real landing time and there's no charge for a normal delay. Early-morning departures are routine — dispatch runs 24/7, so a pre-dawn pickup for the first flight out of Midway is confirmed the same as a midday run. Ask about our 10% first-time offer when you call.
Yes. Sports teams, family groups and corporate parties are our regular Midway work. Everyone rides together in one coach with room for luggage and gear, on one flat quoted rate, instead of splitting the party across several rideshares with separate fares and arrival times.
Tell us the flight, the group size, the date and the address — we'll send back the right Sprinter, a vetted chauffeur, and a flat quote. Teams, families and corporate groups all welcome.
Choose your date, route and vehicle, see your live price, and book in a couple of minutes — or call (773) 923-0220, 24/7.