Service Area
Private Car Service in Winnetka, Illinois
Quiet, refined North Shore village along Sheridan Road and Lake Michigan.
Service area
Winnetka: Discreet North Shore Chauffeur Service, Done Right
Winnetka has a rhythm of its own — quiet, refined, and residential — from the lakefront estates along Sheridan Road to the tree-lined streets of Indian Hill and the shops of Hubbard Woods. Ground transportation here isn't a corporate-fleet exercise; it's about a dependable, discreet chauffeur who knows the village and treats every ride like a standing arrangement.
Second City Livery serves Winnetka households, New Trier families, and North Shore professionals with airport transfers, event transportation, and recurring travel handled by the same team every time — punctual, private, and consistent.
O'Hare and Midway Connections
O'Hare ~30-45 min via I-94 Edens · Midway & Chicago Executive (PWK) also served
From the lakefront, O'Hare is typically 30-45 minutes via the Edens (I-94) depending on the hour; we also handle Midway and Chicago Executive (PWK) for private aviation. Early-morning departures and late-night arrivals are where a confirmed chauffeur matters most.
- O'Hare (ORD): Typically 30-45 minutes via I-94 Edens, timed around your flight, not a guess
- Midway (MDW): Full coverage for south-side and Southwest departures
- Chicago Executive (PWK): Convenient North Shore FBO / private-aviation option
- Flight tracking: Staging window adjusts automatically when arrivals shift early or late
- Luggage & door-to-door: Curb-to-curb assistance, ready before you are
Corporate Travel Accounts
One trusted team · Standing airport runs · Discreet, recurring travel
Many Winnetka clients don't need a one-off ride — they need a standing arrangement: the same reliable chauffeur for weekly airport runs, school and activity logistics, and evenings in the city. Our residential program keeps your preferences, addresses, and recurring trips on file so booking takes seconds.
- One trusted team: Consistent chauffeurs who know your household's routine and preferences
- Standing airport runs: Recurring O'Hare/Midway trips scheduled once, repeated reliably
- Privacy & discretion: Professional, low-profile service for residents who value both
- Events on standby: Weddings, New Trier and club functions, nights downtown — chauffeur waits, ready when you are
On the North Shore, dependable and discreet aren't extras — they're the whole point.
What to Expect
Ground transportation should be something you never think about twice. Every Second City Livery booking in Winnetka 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. The result is simple: your car is there, on time, every time, with a professional you can count on for the early-morning departure and the late-night arrival alike.
- Every booking is confirmed: Your reservation is locked in advance — no last-minute reassignments or cancellations on departure day
- BACP-licensed chauffeurs: Every driver holds a valid City of Chicago Public Chauffeur License and is fully insured and vetted
- Owned and maintained fleet: Professional vehicles held to our standard — cleaned, inspected, and ready between every trip
- Accountable, every trip: A real operations team you can reach directly — your chauffeur is dispatched, flight-tracked, and positioned early
Why Winnetka Clients Rely on Second City Livery
Clients booking ground transportation look for verified licensing, documented reliability, and the operational infrastructure to support recurring travel. Second City Livery maintains top-tier ratings, national association membership, and consistent recognition across independent review platforms.
- 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 Winnetka, IL and All of Chicagoland
Second City Livery serves Winnetka households, professionals, and event hosts across the North Shore, with pickups from lakefront residences, Hubbard Woods, downtown Winnetka, and New Trier-area addresses. We provide airport transfers, wedding and event transportation, city trips, and recurring household travel.
Chauffeurs respond quickly with flexible scheduling around school runs, flight times, dinner reservations, and multi-stop North Shore evenings.
Service Area Coverage
- Winnetka, Kenilworth, Wilmette, Glencoe, and Northfield across the North Shore
- O'Hare International (ORD) via I-94 Edens; Midway (MDW) for south-side travel
- Chicago Executive Airport (PWK) for FBO and private aviation
- Downtown Chicago for business, dining, theatre, and events
- Full Chicagoland including the northwest corridor and western suburbs
Also Serving Nearby
Based in Chicago
Chauffeur service reaching Winnetka, 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 Winnetka from O'Hare?
Typically 30-45 minutes via the Edens (I-94) depending on time of day; we schedule pickups around your flight and track it for changes.
Do you cover Midway and private aviation too?
Yes — Midway (MDW) and Chicago Executive (PWK) for FBO/private flights, in addition to O'Hare.
Can you handle a standing weekly airport run?
Yes — our residential accounts keep recurring trips and preferences on file so rebooking takes seconds.
Do you provide wedding and event transportation?
Yes — weddings, galas, New Trier and club events, and nights in the city, with the chauffeur on standby.
Is the service private and discreet?
Yes — consistent, vetted, licensed chauffeurs and a low-profile approach.
Are your chauffeurs licensed?
Every chauffeur holds a valid City of Chicago Public Chauffeur License, is fully insured and vetted, and drives a vehicle we own and maintain.