A Complete Guide to Chauffeured Transfers at Midway
What Makes Midway Different From O'Hare
Midway International sits twelve miles southwest of the Loop, split between the Clearing and Garfield Ridge community areas, and it was Chicago's primary airport from 1927 until O'Hare eclipsed it. That history is why it is compact: one terminal, three concourses, and an urban footprint hemmed in by residential streets on all sides.
Compactness is its advantage. Baggage claim empties quickly, the arrivals curb is a short walk from the carousel, and there is no inter-terminal train to ride. Roughly twenty-two million passengers a year move through it, most of them on Southwest Airlines, which runs its largest base here. For the south and southwest suburbs, Midway is not just closer than O'Hare, it is materially faster.
The Stevenson, Cicero Avenue and the Route Question
Most Midway transfers use I-55, the Stevenson, out to Cicero Avenue. It is a short run and usually an easy one, which is precisely why people underestimate it. The Stevenson backs up in ways that have very little to do with the airport, and Cicero Avenue at rush hour is an entirely different proposition from Cicero Avenue at 4 AM.
There is also the CTA Orange Line, which runs directly into the Midway terminal and, per an announcement made in late 2025, will move to twenty-four-hour service in the second half of 2026 under the Northern Illinois Transit Authority Act. That is genuinely useful for a solo traveler with a carry-on. It is not useful for a family of four at 11 PM with checked bags, which is where a chauffeur earns the fare.
Why the Southwest Suburbs Should Default to Midway
Oak Lawn is about seven miles from Midway and our transfers start there at $85. Orland Park is seventeen miles and starts at $95. Tinley Park, Burbank, Palos Heights, Evergreen Park and Bridgeview all sit inside a comfortable half-hour of the airport in ordinary traffic.
The same trips to O'Hare mean crossing the entire metropolitan area, usually via I-294 and the Tri-State, and add thirty to fifty minutes each way. Unless the flight schedule demands O'Hare, or the itinerary is international and needs Terminal 5 customs, Midway is the correct answer for anybody living south or southwest of the city, and the chauffeured transfer costs the same or less.
Private Aviation at Midway
Midway carries two fixed base operators, Atlantic Aviation and Signature Flight Support, and dedicates two of its runways to general aviation traffic. It is open around the clock, has customs and immigration on the field, and offers passenger lounges, conference rooms and heated hangars.
For a chauffeured pickup, that means the reservation is built around a tail number rather than a flight number. We coordinate directly with FBO line staff so the vehicle is positioned as the aircraft comes off the runway, and the passenger walks from the aircraft door to the vehicle door. It is the same protocol we run at Chicago Executive Airport in Wheeling and DuPage Airport in West Chicago.
