Premium chauffeured car and limo service in Old Town, Chicago's historic and bohemian Near North neighborhood. Flat-rate airport transfers, nights out on Wells Street, Second City and comedy shows, dinner reservations, and hotel transfers. Professional chauffeurs who know every block of the Triangle's winding streets, available 24/7.
Old Town is one of Chicago's oldest and most charming neighborhoods, a historic Near North enclave between downtown and Lincoln Park. Founded by German settlers in the 1850s, it is famous for The Second City comedy theater, the buzzing Wells Street corridor of restaurants and bars, and the Old Town Triangle, a district of preserved Victorian cottages and winding streets that predate the Chicago grid and survived the Great Chicago Fire. Add St. Michael's Church, the long-running Old Town Art Fair, and the Chicago History Museum, and you have a neighborhood rich in art, architecture, and entertainment. We provide flat-rate, chauffeur-driven car and limo service throughout Old Town, for the comedy crowds, diners, visitors, and residents who fill it. Whether you are catching a flight, heading to a show, going to dinner, or out for the night, we know every block of the Triangle's winding streets.
One trusted chauffeur service for every reason you move through downtown, all at transparent flat rates.
Flat-rate rides to and from O'Hare and Midway, with flight tracking and meet-and-greet, so arriving in or leaving the Loop is effortless.
The Second City, Zanies, and UP Comedy Club make Old Town the comedy capital of the city. We get you to the show on time and are ready the moment the laughs are done.
Smooth arrivals and departures at the hotels around Old Town and the nearby Gold Coast, with help for your luggage every time.
The Wells Street corridor is packed with restaurants and bars. We handle dinner drop-offs and pickups so your table runs on time and nobody has to drive or park.
The Old Town Art Fair, the farmers market, and neighborhood festivals draw crowds all summer. We handle event-day transfers so you skip the parking and the crowds.
A comedy show, dinner on Wells, drinks at a historic tavern, or a special celebration, with a chauffeur so your whole group can relax and skip the parking.
Old Town is full of landmarks, Second City, Wells Street, St. Michael's, and the historic Triangle, packed into a compact Near North neighborhood. We know the best drop-off points and the quickest routes between them.
The world-famous comedy theater that opened in 1959 and launched Belushi, Murray, Tina Fey, Amy Poehler, Stephen Colbert, Steve Carell, and countless more. The heart of Old Town's entertainment scene, and a constant stop for us.
Built by German settlers in 1869, St. Michael's is one of the few buildings to survive the Great Chicago Fire of 1871, its red-brick walls still standing and its bells ringing over the Triangle since 1852.
The lively main strip of Old Town, lined with restaurants, bars, and independent shops, marked by the iconic Old Town gate at Wells and North Avenue. Home to the first Crate and Barrel, opened in 1962.
A historic district of preserved Victorian cottages, brownstones, and winding streets that predate the Chicago grid, including Crilly Court and the Carl Street Studios. A Chicago Landmark and a walker's delight.
Held every June in the Triangle for more than 70 years, the Old Town Art Fair is one of the city's premier outdoor art festivals, drawing artists and crowds from across the country.
At the neighborhood's north edge by Clark and North Avenue, the Chicago History Museum tells the city's story from the Fire to today, steps from Lincoln Park and the Triangle.
The Second City, Zanies, and UP Comedy Club make Old Town a top comedy destination in the country. We serve showgoers every night of the week, on time for the curtain.
The Wells Street corridor is packed with restaurants, bars, and independent shops, a lively scene day and night. We handle dinner drop-offs and late-night pickups.
The Old Town Triangle's Victorian cottages, brownstones, and pre-Fire streets make it one of the city's most beautiful historic districts. We serve tours, events, and visits.
St. Michael's Church, a survivor of the Great Chicago Fire, anchors the neighborhood's deep history going back to its 1850s German settlers. We serve services, weddings, and events.
The Old Town Art Fair, the farmers market, and summer festivals fill the neighborhood with crowds and energy. We handle event-day transfers so you skip the parking.
Professional chauffeurs, immaculate vehicles, and on-time service that showgoers, diners, and residents count on, on every trip, day or night.
Old Town and the adjacent Gold Coast and Lincoln Park hold a range of hotels close to the comedy theaters and Wells Street. We provide smooth airport transfers and around-town car service for guests at every property.
The hotels and inns near Wells Street put guests steps from Second City, the restaurants, and the historic Triangle, in the heart of the neighborhood.
Just east of Old Town, the Gold Coast's landmark and boutique hotels are a short ride from the comedy theaters and Wells Street dining.
To the north, the hotels around Lincoln Park and the zoo are minutes from Old Town, an easy ride for guests exploring both neighborhoods.
Many visitors stay downtown and head to Old Town for a show or dinner. We handle the round trip with ease, dropping you at the door and picking you up when you are ready.
Many visitors stay in the neighborhood's historic walk-ups, condos, and short-term rentals. We provide airport transfers and around-town service straight to the door.
For weddings, galas, and group visits with rooms across multiple properties, we coordinate transfers and multi-vehicle dispatch for the whole party.
Approximate distances and drive times from Old Town. Every transfer is a flat rate, confirmed at booking with no surge. Times vary with traffic on the Kennedy and Lake Shore Drive.
| Destination | Distance | Est. drive time | Price |
|---|---|---|---|
| O'Hare (ORD) | ~16 mi | 30 to 55 min | Quote |
| Midway (MDW) | ~12 mi | 25 to 45 min | Quote |
| The Loop / downtown | ~2 mi | 8 to 18 min | Quote |
| Magnificent Mile | ~1.5 mi | 8 to 15 min | Quote |
| Navy Pier | ~2 mi | 10 to 18 min | Quote |
| United Center | ~3 mi | 10 to 20 min | Quote |
Heading somewhere else? We serve all of Chicagoland from Old Town. Call (708) 289-0488 for a flat-rate quote.
From executive sedans to party buses, every vehicle is modern, spotless, and driven by a vetted chauffeur.
EXECUTIVEThe default for solo travelers and couples. Quiet, discreet, and ideal for airport runs and corporate trips.
MOST POPULARThe most-requested luxury SUV. Room for up to six with luggage, perfect for families and small groups.
QUIET LUXURYA refined, understated full-size SUV for travelers who prefer an elegant, low-profile ride.
XL SPACEMaximum space for passengers and luggage, perfect for crews, families, and groups with extra gear.
BEST VALUEA spacious, comfortable full-size SUV that balances room and value for groups and family arrivals.
GROUPSFor larger groups and crews, including the Jet Style executive lounge variant for VIP travel.
CLASSICClassic, elegant stretch limousine for weddings, proms, and milestone celebrations.
SHOW-STOPPERA bold statement vehicle seating up to sixteen, for groups making a memorable entrance.
BIG GROUPA celebration on wheels for up to sixteen, ideal for group nights out and events.
Old Town is the home of Chicago comedy. The Second City has launched legends since 1959, Zanies brings in top stand-up, and UP Comedy Club rounds out a night of laughs, all within a few blocks of the Wells Street restaurants and bars. It is one of the best nights out in the city.
We make the evening effortless. Your chauffeur drops you at the theater door, circles back after the show, and has you home without the late-night rideshare surge. For dinner before or drinks after, we know the best spots on Wells and the quickest routes between them.
Wells, North Avenue, Clark, Division, Sedgwick, Eugenie, and the Triangle's winding diagonal streets that predate the grid. Our chauffeurs navigate it all.
For O'Hare and Midway runs we track your flight in real time and adjust for delays at no extra charge, so your ride is always there.
Your price is confirmed up front with no surge and no meter, even during conventions, rush hour, and major events downtown.
Every chauffeur is licensed, insured, background-checked, and trained in courteous, discreet, professional service.
Parking near Wells Street and the theaters is scarce and pricey, and rideshare surges after shows. A pre-booked flat-rate chauffeur drops you at the door and is there when you finish.
Every vehicle in our fleet is a current-generation model, detailed before each ride and maintained to the highest standard.
Old Town is compact, historic, and famously tricky to drive, with narrow one-way streets and diagonal blocks in the Triangle that predate the Chicago grid. Wells Street fills with showgoers and diners at night, parking is scarce, and the winding layout confuses anyone who does not know it. Our chauffeurs know the gate, the theaters, and the shortcuts through the Triangle.
On show nights, art-fair weekends, and summer festivals, the neighborhood packs out and rideshare prices spike. A pre-booked flat-rate chauffeur sidesteps all of it: no surge, no parking, no circling the block. You are dropped at the door and picked up on your schedule, whether that is Second City, dinner on Wells, or a 5 a.m. flight.
Old Town blends comedy, history, and Wells Street nightlife in one of Chicago's oldest and most charming neighborhoods. Our chauffeured car and limo service is built for it, with flat-rate pricing, professional chauffeurs, immaculate vehicles, and deep familiarity with every block of the Triangle's winding streets.
Old Town is the home of Chicago comedy, and we serve it every night. The Second City, Zanies, and UP Comedy Club draw crowds for shows, and the Wells Street restaurants and bars keep the night going. Your chauffeur handles the driving, the parking, and the late-night pickup, so your whole group can relax with no rideshare surge.
The Old Town Triangle's pre-Fire cottages and winding streets, St. Michael's Church, and the long-running Old Town Art Fair make this a neighborhood for history and architecture lovers. We handle tours, weddings, services, and event-day transfers, with the route knowledge to navigate the diagonal streets the grid never reached.
The airport run is what we do best. O'Hare is about 16 miles northwest and Midway about 12 miles south, both handled with flight tracking, meet-and-greet, and a flat rate confirmed at booking. With sedans, SUVs, stretch limos, and party buses, we have the right vehicle for any occasion. Reserve online or call (708) 289-0488 to book your Old Town car service today.
Flat-rate pricing, professional chauffeurs, and reliable airport, comedy, dining, and around-town travel across Old Town and all of Chicagoland. Available 24/7.