Service Area
Chauffeur & Car Service in Highland Park, Illinois
Affluent North Shore community and home of the Ravinia Festival.
Service area
Highland Park: North Shore Living, Ravinia Nights, Reliable Chauffeurs
Highland Park pairs affluent North Shore residential life with one of the region’s marquee draws, the Ravinia Festival, where parking and post-show traffic are exactly the kind of headache a chauffeur erases. From lakefront neighborhoods to the downtown district, this Lake County community values dependable, discreet transportation for events, airports, and everyday household travel.
Second City Livery serves Highland Park residents and event-goers with Ravinia drop-offs and pickups, airport transfers, and recurring household travel — consistent chauffeurs, timed around real conditions.
O'Hare and Midway Connections
O’Hare ~35–45 min via I-94 · Midway & Chicago Executive (PWK) served
From Highland Park, O’Hare is typically 35–45 minutes via the Edens/Tri-State depending on the hour; we also cover Midway and Chicago Executive (PWK) for private aviation. Early departures and late arrivals are where a confirmed chauffeur earns its keep.
- O’Hare (ORD): Typically 35–45 minutes via I-94 / I-294
- Chicago Executive (PWK): Convenient North Shore FBO / private-aviation option
- Midway (MDW): Full coverage for south-side and Southwest travel
- Flight tracking: Staging window adjusts automatically for early/late arrivals
- Door-to-door: Luggage assistance and curb-to-curb service, ready before you are
Corporate Travel Accounts
No parking, no post-show traffic · Drop-off & scheduled pickup · Groups welcome
Ravinia is the reason many Highland Park nights need a chauffeur: skip the parking hunt, enjoy the show, and step into your car at a scheduled pickup instead of crawling out of a lot. We handle Ravinia drop-offs and pickups, plus weddings, galas, and nights in the city, for couples or full groups.
- Ravinia made easy: Curbside drop-off and a scheduled post-show pickup — no parking, no traffic crawl
- Groups welcome: Sedans through larger vehicles for parties heading to the same show
- Events on standby: Weddings, galas, and North Shore celebrations with the chauffeur ready
- Household accounts: Recurring family and airport travel kept on file for fast rebooking
The best seat at Ravinia is the one waiting for you at the curb when the show ends.
What to Expect
Confirmed booking · BACP-licensed chauffeur · Owned and maintained fleet. Ground transportation should be something you never think about twice. Every Second City Livery booking in Highland Park 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: Your reservation is locked in advance — no last-minute reassignments
- BACP-licensed chauffeurs: Every driver holds a valid City of Chicago Public Chauffeur License
- Owned and maintained fleet: Professional vehicles held to our standard between every trip
- Accountable, every trip: A real operations team you can reach directly
Why Highland Park 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 Highland Park, IL and All of Chicagoland
Second City Livery serves Highland Park residents, event-goers, and households — from lakefront neighborhoods and the downtown district to Ravinia and beyond. We provide Ravinia and event transportation, airport transfers, city trips, and recurring household travel.
Chauffeurs respond quickly with flexible scheduling around show times, flight times, and multi-stop North Shore evenings.
Service Area Coverage
- Highland Park, Highwood, Deerfield, Lake Forest, and Glencoe across the North Shore
- Ravinia Festival drop-offs and scheduled pickups throughout the season
- O’Hare (ORD) via I-94 / I-294; Midway (MDW) for south-side travel
- Chicago Executive Airport (PWK) for FBO and private aviation
- Downtown Chicago and full Chicagoland including the northwest and western suburbs
Also Serving Nearby
Based in Chicago
Chauffeur service reaching Highland Park, 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