Service Area
Chauffeur Service in Kenilworth, IL
The North Shore's smallest and most private village — discreet, consistent chauffeur service.
Service area
A Village That Values Privacy — Served Accordingly
Kenilworth occupies barely half a square mile between Wilmette and Winnetka, and that scale is the point. It is a village of established families, quiet streets laid out by Joseph Sears, and residents who would rather not have a different driver in the driveway every week.
Second City Livery serves Kenilworth households with airport transfers, standing weekly runs, downtown evenings, and wedding and event transportation — handled by a small, consistent roster of licensed chauffeurs who learn your preferences and keep them on file. Low-profile vehicles, no logos, no fuss.
O'Hare and Midway Connections
~30–40 min to ORD via the Edens · PWK close by for private aviation
From Kenilworth, O'Hare is typically 30–40 minutes down the Edens (I-94), though the Lake Cook and Dempster stretches can slow considerably at peak. Chicago Executive (PWK) is a short run for private aviation, and we cover Midway for south-side and Southwest itineraries.
- O'Hare (ORD): Typically 30–40 minutes via I-94 Edens
- Chicago Executive (PWK): A short run for FBO and private aviation
- Midway (MDW): Full coverage for south-side and Southwest travel
- Flight tracking: We monitor your flight and adjust staging automatically
- Meet-and-greet available: Baggage claim or curbside, your preference
Corporate Travel Accounts
Preferences on file · Consistent chauffeurs · One-touch rebooking
Most Kenilworth clients aren't booking one trip — they're booking a pattern. A household or executive account keeps your addresses, vehicle preference, child-seat requirements, and standing schedule on file so rebooking is a single message.
- Consistent chauffeur roster: The same vetted professionals, not a rotating pool
- Preferences on file: Addresses, vehicle choice, and special requests remembered
- Standing schedules: Weekly airport runs and recurring trips rebook in seconds
- Discretion by default: Low-profile vehicles and a chauffeur who does not chat unless invited
- Direct operations contact: A real line, not a general dispatch queue
In a village this small, reputation is the whole business — which is precisely why we protect ours on every trip.
What to Expect
Confirmed booking · BACP-licensed chauffeur · Owned and maintained fleet. Every Second City Livery booking in Kenilworth is confirmed in advance, every chauffeur holds a valid City of Chicago Public Chauffeur License, and every vehicle is owned and maintained to our fleet standard.
- Every booking is confirmed: Reservation locked in advance — no last-minute reassignments
- BACP-licensed chauffeurs: Valid City of Chicago Public Chauffeur License on every driver
- Owned and maintained fleet: Professional vehicles held to our standard between every trip
- Transparent, all-inclusive quotes: No surge pricing and no surprise add-ons
- Accountable, every trip: A real operations team you can reach directly
Why Kenilworth Clients Rely on Second City Livery
Clients booking ground transportation look for verified licensing, documented reliability, and the operational infrastructure to support recurring travel.
- 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)
Serving Kenilworth, IL and All of Chicagoland
Second City Livery serves Kenilworth households and executives across the village and the adjoining North Shore — Wilmette, Winnetka, Glencoe, and Northfield — with airport transfers, downtown evenings, club and school events, and wedding transportation.
We also handle long-distance regional travel to Milwaukee, Madison, Michigan lakefront destinations, and beyond, with the same chauffeur for the full trip.
Service Area Coverage
- Kenilworth, Wilmette, Winnetka, Glencoe, and Northfield across the North Shore
- O'Hare International (ORD) via the Edens for domestic and international flights
- Chicago Executive Airport (PWK) for FBO and private aviation
- Midway (MDW) for south-side and Southwest travel
- Downtown Chicago for business, dining, theatre, and events, plus Midwest long-distance routes
Also Serving Nearby
Based in Chicago
Chauffeur service reaching Kenilworth, IL from downtown Chicago.
Second City Livery Service dispatches from 332 S Michigan Avenue in the Loop, with pre-assigned chauffeurs staged across the metro for residence, hotel, office, and venue pickups.
332 S Michigan Ave, Suite 900
Chicago, IL 60604
312.448.8787 · View on Google Maps
Frequently Asked Questions
How far is Kenilworth from O'Hare?
Typically 30–40 minutes via the Edens (I-94), depending on the hour. We schedule around your flight and track it for changes.
Will I get the same chauffeur each time?
Wherever scheduling allows, yes — Kenilworth clients are served by a small, consistent roster, and your preferences stay on file.
Is the service discreet?
Yes. Unmarked, low-profile vehicles, vetted licensed chauffeurs, and a quiet, professional approach.
Can you handle a standing weekly airport run?
Yes — recurring trips are kept on file so rebooking takes a single message.
Do you provide wedding and event transportation?
Yes — weddings, club and school events, galas, and nights in the city, with the chauffeur on standby throughout.
Are your chauffeurs licensed and insured?
Every chauffeur holds a valid City of Chicago Public Chauffeur License, is fully insured and vetted, and drives a vehicle we own and maintain.