Downtown Chicago Limo Service & The Loop

Why Us?

Legacy Executive Limousine is the preferred private transportation provider for Downtown Chicago, The Loop, and the Gold Coast. Whether you are a C-level executive attending meetings at the Old Post Office, a couple enjoying a weekend at The Langham, or heading to a game at the United Center, we deliver a travel experience defined by sophistication and punctuality.

Navigating downtown traffic requires a professional. Our chauffeurs know the city grid intimately—from Lower Wacker Drive shortcuts to the specific VIP entrances at Wrigley Field and Soldier Field—ensuring you arrive relaxed and on time.

Airport Transfers (ORD & MDW)

For downtown residents and hotel guests, reliable airport connectivity is essential. We manage the I-90/I-94 congestion so you don't have to.

• O'Hare (ORD) to Downtown: The trip to O'Hare typically takes 35 to 60 minutes, depending on the time of day. We monitor the Kennedy Expressway constantly to time your departure perfectly. We provide curbside service for quick departures and Meet & Greet service for guests arriving at the International Terminal.

• Midway (MDW) to Downtown: We offer the most efficient route to Midway via I-55. It is the preferred option for many private aviation clients and business travelers flying Southwest.

• FBO Services: We provide discreet black car service to Gary Jet Center in Gary Indiana, Atlantic Aviation and Signature Flight Support at both major airports for private jet arrivals.

Corporate & Hotel Transport

We serve the financial district and the city's premier hospitality venues.

• Corporate Roadshows: We specialize in hourly charters for executives moving between meetings in the Loop, West Loop, and Fulton Market. Your chauffeur remains on standby, creating a mobile office where you can leave your belongings securely.

• Luxury Hotel Transfers: We are the trusted partner for guests staying at The Peninsula, Four Seasons, The Langham, and Waldorf Astoria. We coordinate with concierges to ensure a seamless arrival and departure experience.

• McCormick Place Conventions: We provide executive transfers for convention attendees who prefer the privacy of a sedan over crowded shuttle buses.

Dining, Sports & Nightlife

Experience Chicago's world-class entertainment without the hassle of parking or finding a rideshare.

• Sports Venues: We offer VIP drop-offs for the United Center (Bulls/Blackhawks), Wrigley Field (Cubs), and Soldier Field (Bears). Avoid the chaos of post-game traffic with a pre-arranged pickup location.

• Michelin Dining: Arrive in style at Alinea, Oriole, or Maple & Ash. We provide door-to-door service, allowing you to enjoy your evening responsibly.

• Theater District: Whether it’s a show at the Cadillac Palace or the Chicago Theatre, we ensure you arrive with plenty of time before the curtain rises.