Chauffeur’s guide
A local chauffeur's guide to arriving in Chicago — airports, business districts, conference venues and the landmarks our clients ask for, with discreet black car and executive transfers.
In Chicago, trips are driven by a vetted local affiliate chauffeur and coordinated by our 24/7 desk.
Where to eat
Avant-garde · $$$$ · Lincoln Park
Grant Achatz's temple of avant-garde cuisine — theatrical, playful and profound.
Contemporary American · $$$$ · West Loop
A West Loop kitchen sourcing from its own farm — precise, ingredient-led cooking.
Contemporary · $$$$ · West Loop
A hidden tasting-menu jewel down a freight-elevator hallway in the West Loop.
New American · $$$ · West Loop
Stephanie Izard's boisterous, wildly popular Randolph Street sharing-plates flagship.
Deep-dish pizza · $$ · River North
A Chicago deep-dish — buttery crust, chunky sauce and layers of cheese.
Chicago classics · $ · River North
The fast-casual home of the Italian beef and the dragged-through-the-garden hot dog.
Places to go
The Loop
The lakefront park home to Anish Kapoor's mirror-polished 'Bean' sculpture.
The Loop
Art Institute of Chicago, The Loop.
The Loop
Step onto glass ledges 1,353 feet above the Loop at the top of the Willis Tower.
Streeterville
The lakefront pier of rides, gardens and cruises jutting into Lake Michigan.
The Loop
A landscaped promenade along the river beneath the city's landmark architecture.
Museum Campus
A vast natural-history museum home to SUE, the largest T. rex ever found.
The perfect chauffeured day
Where business happens
Meetings & events
Worth seeing
Chicago · Local intel
Add River North for galleries and dining, and West Loop or Fulton Market for a polished dinner scene. For a more residential, upscale feel, Lincoln Park and the Gold Coast are strong chauffeured stops.
Chicago’s core is compact, but traffic, one-way streets, and limited curb space can make short trips slow. Parking is costly and inconvenient in downtown and near major attractions, so a private chauffeur removes the hassle and keeps schedules tight. It is the easiest way to move between meetings, dinner reservations, and neighborhoods without time lost to cabs or parking.
Chicago · Chauffyr operating model
A comparable vehicle class to our standard: Business Sedan for one or two passengers, Executive SUV for three to five with luggage, and Executive Sprinter or Jet Sprinter equivalents for groups. Vehicle class is chosen from your headcount and luggage count, and the price is confirmed in writing before you book. The chauffeur’s name, mobile and plate are confirmed by SMS and email the night before departure (or on dispatch for same-day rides).
Our 24/7 reservations desk watches the flight (commercial) or tail number (private aviation) from before block-out. Commercial arrivals carry 60 minutes of complimentary wait after wheels-down to clear immigration and baggage; private aviation includes 15 minutes of complimentary wait after actual landing time, and is met plane-side where the FBO permits, lobby-side otherwise. Non-airport pickups carry 15 minutes of complimentary wait at the quoted pickup time.
Every quote is in USD; your confirmed quote is locked when you book — no distance surcharge, no fuel surcharge. The 20% gratuity is added when you book; any wait time beyond the complimentary windows above are the only post-ride line items on the receipt. Written confirmation of chauffeur, vehicle and pickup follows by email. Our 24/7 desk responds right away.
The desk takes same-day and overnight requests by phone when the quote widget on this page isn’t enough — for multi-stop itineraries, late-night private arrivals, event-week movements or corporate billing changes. Call +1-833-457-5466.
Service · at a glance
Our 24/7 reservations desk watches the flight (commercial) or tail number (private aviation) from before block-out. Commercial airport arrivals get up to 60 minutes of complimentary wait after wheels-down to clear immigration and baggage, then extra wait is billed at the vehicle's hourly rate in 15-minute increments; private-aviation (FBO) arrivals get 15 minutes of complimentary wait after actual landing time, then extra wait is billed at the vehicle’s hourly rate in 15-minute increments; they are met plane-side where the FBO permits, lobby-side otherwise. Non-airport pickups carry 15 minutes of complimentary wait at the quoted pickup time.
You are dispatched a late-model Mercedes-Benz E-Class, Lincoln Aviator or similar executive sedan, a Cadillac Escalade / Chevrolet Suburban or similar SUV, or an Executive Sprinter van depending on headcount and luggage. The chauffeur’s name, mobile and vehicle plate are confirmed by SMS and email the night before departure (or on dispatch for same-day rides). Every chauffeur holds a current commercial licence, is background-checked, drug-tested, and carries the state-required commercial livery insurance.
Chauffyr quotes are in USD; your confirmed quote is locked when you book — no distance surcharge, no fuel surcharge. The only post-ride adjustments are the 20% gratuity added when you book any wait time beyond the policy windows above, both of which appear as explicit line items on your receipt. Billing to a corporate account is available on request; our desk invoices against a single credit card or ACH relationship.
Most rides can be booked up to a few hours before pickup through the live quote widget on this page; our 24/7 US-based desk handles same-day and overnight requests by phone. Every booking returns a written confirmation to your email, with the dispatcher’s direct line should anything on the day of travel change. Cancellation and no-show policy vary by vehicle class and are listed on our cancellation policy page.
Our own fleet serves Napa and the Bay Area; elsewhere, trips are run by vetted affiliate partners.
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