About
Chicago's Most Dependable Black Car Service
We don't just drive people around Chicago — we make sure they arrive on time, every time.
Built on a Simple Premise
Second City Livery was built on a simple premise: Chicago professionals, executives, and travelers deserve ground transportation that actually works. No surprises. No excuses. No chasing down a driver who's still five minutes away when your flight boards.
We started with a small fleet and a straightforward commitment — show up on time, know the city, and treat every client like their schedule matters. That reputation spread. Corporate accounts grew. The fleet expanded. But the standard never changed.
Today we serve business travelers, executives, convention attendees, and families across Chicago and Chicagoland — with the same reliability we built this company on. From the first booking to the ten thousandth, every client's schedule is treated as if it is the only schedule that matters today.
The Second City Difference
Five things separate a chauffeur service from a car service. We built Second City Livery around all five — and measure ourselves against them on every run.
On-Time, Every Time
We monitor traffic, track flights in real time, and plan routes around rush hour before you even think to ask. Punctuality isn't a feature — it's the baseline.
Drivers Who Know Chicago
Our chauffeurs know the shortcuts, the bottlenecks, and which route to O'Hare or Midway gets you there fastest depending on the hour. That knowledge saves time when it counts.
Professional Fleet for Every Occasion
From executive sedans to Sprinters, minibuses, and coaches — our fleet seats 2 to 54 passengers. Every vehicle is late-model, immaculately maintained, and ready when you are.
Discretion as Standard
Whether you're a C-suite executive, a VIP guest, or a family heading to the airport — your ride is private, professional, and handled without drama.
Corporate Accounts Welcome
One account, one point of contact, consistent service across every booking.
Every Ride, Handled
Whether you need a private chauffeur for corporate travel, a wedding, or a special event — or airport transfers to O'Hare or Midway — or a long distance ride to Milwaukee, Indianapolis, or anywhere across the Midwest — we handle it all with the same standard of service. Our fleet seats 2 to 54 passengers and we serve Chicago and all of Chicagoland.
- Private Chauffeur: Corporate travel, weddings, special events, and executive ground transportation.
- Airport Transfers: O'Hare, Midway, PWK, DPA, and UGN with real-time flight tracking.
- Long Distance: Milwaukee, Indianapolis, Detroit, Madison, and Midwest destinations flat-rate.
- Fleet Options: Executive sedans, luxury SUVs, Sprinter vans, and coaches — 2 to 54 passengers.
- Service Area: Chicago and all of Chicagoland including the North Shore, DuPage County, and western suburbs.
Verified by the Clients We Serve
Our reputation is documented across every major independent review platform and verified by national industry organizations that hold commercial ground transportation to a professional standard.
- Perfect 5.0 rating across 115+ verified Google reviews
- 5.0 rating on Yelp from independent customer feedback
- A+ rating with the Better Business Bureau
- Recognized as Top 10 Best Livery Service Near Chicago, Illinois
- Active member of the National Limousine Association (NLA)
Ready when you are — driver and vehicle locked in.
Book online in minutes or call to confirm availability for airport, corporate, wedding, event, and long-distance transportation.