Chicago · Established 2017
Chicago Chauffeur Service. No Surprises. Ever.
Your driver and vehicle are locked in before pickup day — not assigned at the last minute. Airport · Corporate · Events · Long Distance.
5 Star Chauffeur
115+ Google Reviews
A+ BBB Rated
Better Business Bureau
NLA Member
National Limousine Association
ORD · MDW · FBO · PWK
All Chicago Airports
Why We're Different
Pre-assigned drivers. Late-model fleet. Zero last-minute chaos.
Most chauffeur service delays happen because the driver is assigned at dispatch time, not when you book — which means your pickup window competes with real-time demand. Second City Livery Service uses pre-assigned professional drivers and a late-model luxury fleet matched to your trip before the pickup day.
Reservations confirm the vehicle class and chauffeur assignment in advance — critical for airport transfers, corporate travel, weddings, and long-distance routes where timing and presentation are non-negotiable.
Our Services
Reliable chauffeur service, purpose-built for how Chicago moves.
Our Protocol
The Chicago chauffeur service protocol from booking to completion.
Pre-trip scoping, vehicle-to-need matching, licensed driver assignment, and flight-aware execution. Businesses that skip requirements assessment rebuild the same mismatch problems repeatedly.
01
Consultation & Trip Requirements
We confirm pickup, destination, passenger count, luggage volume, child seat needs, and billing before quoting — preventing the vehicle mismatch that causes most chauffeur service failures.
02
Route Optimization & Fleet Matching
Route planning accounts for Chicago traffic patterns, construction, event congestion, and seasonal restrictions. Vehicle class is assigned based on passenger and luggage needs.
03
Chauffeur Assignment with Local Expertise
Drivers hold Chicago Public Chauffeur Licenses, complete background checks, and carry commercial livery insurance. We match chauffeurs to trip type by route familiarity and vehicle certification.
04
Real-Time Execution & Post-Trip Confirmation
Flight tracking adjusts airport pickups automatically. Chauffeurs confirm arrival by text, handle luggage, and provide climate-controlled comfort. Post-trip notes are documented for billing or future reference.
Our Fleet
Meticulously maintained, late-model luxury vehicles.
Client Reviews
Rated 5.0 stars by our clients.
115+ verified reviews on Google & Facebook · Trusted by executives, wedding parties, and corporate travel managers.
Licensed & Insured
Chicago Public Chauffeur Licenses via BACP. Commercial livery insurance per Illinois requirements.
Top-Rated Locally
5.0 stars from 115+ verified Google reviews. Ranked among the top livery services near Chicago.
NLA Member · A+ BBB
National Limousine Association member. A+ rating with the Better Business Bureau.
Coverage
Chicago metro coverage from downtown to the suburbs.
Executives, families, and corporate clients throughout Chicago and surrounding communities — scheduled chauffeur transportation directly at residences, hotels, offices, and event venues.
- Chicago Loop
- River North
- Gold Coast
- Lincoln Park
- West Loop
- Oak Brook
- Naperville
- North Shore
- Evanston
- Schaumburg
- Rosemont
- Cook · DuPage · Lake Counties
Long Distance
Chicago to Milwaukee, Indianapolis, Detroit, and beyond.
Scheduled long-distance chauffeur service using confirmed pickup times, professional route planning, and vehicles matched to passenger and luggage volume.
Service Area
Chicago metro coverage from downtown to the suburbs.
Second City Livery Service serves executives, families, and corporate clients throughout Chicago and surrounding communities — scheduled chauffeur transportation delivered directly at residences, hotels, offices, and event venues. The service area covers Chicago's Loop, River North, Gold Coast, Lincoln Park, West Loop, Oak Brook, Naperville, and North Shore municipalities, serving residential and commercial customers across Cook, DuPage, and Lake counties.
Chauffeurs are pre-assigned throughout the metro area, with pickup scheduling coordinated in advance around flight arrivals, meeting times, and event schedules in Chicago and regional destinations.
- Serving Chicago Loop, River North, Gold Coast, Oak Brook, Naperville, and North Shore communities
- Accessible throughout the region via I-90/94, I-290, Lake Shore Drive, and local arterials
- Mobile chauffeur service reaching customers across Cook, DuPage, and Lake counties
- Scheduled transportation directly at your residence, hotel, office, or venue
Second City Livery Service
332 S Michigan Ave, Suite 900
Chicago, IL 60604
312.448.8787 · View on Google Maps
332 S Michigan Ave, Suite 900
Chicago, IL 60604
312.448.8787 · View on Google Maps
FAQ
Frequently asked questions.
What makes Second City Livery's private chauffeur approach different?
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We assign dedicated chauffeurs who learn client preferences and routes rather than rotating drivers randomly. Consistency improves when the same professional handles your transportation.
What should corporate clients expect for multi-stop business days?
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Multi-stop chauffeur service requires advance route planning, flexible scheduling windows, and clear communication. Efficiency depends on realistic time buffers between appointments and driver familiarity with downtown parking access.
How do I choose the right chauffeur service for my trip?
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Airport chauffeur service fits scheduled airport transportation. Private chauffeur service fits local rides, half or full-day hourly bookings, corporate travel, weddings, events, and family transportation. Long-distance service supports city-to-city travel from Chicago.
How does Second City Livery handle special requests?
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We accommodate custom routing, vehicle preferences, and client-specific protocols when communicated during booking. Feasibility depends on advance notice and whether modifications conflict with safety or licensing.
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.