Top Chicago Luxury Car Tours

Take in sweeping views of Chicago from the air during a scenic helicopter flight that offers a premier experience of the Windy City. This private 45-minute flight provides an aerial look at landmarks such as Millennium Park, Navy Park, and Wrigley Field. Ideal for a special occasion, this helicopter tour accommodates up to three people and includes the use of noise-cancelling headsets to hear the pilot clearly.

Have only a short stay planned in Chicago? Make the most of your time in the Windy City, and see more of the city in less time, when you book a private driving tour of Chicago. Pick between several convenient tour times, and meet your guide and driver directly at your hotel. Over the course of your excursion, you’ll make stops at highlight attractions like the Lincoln Park Conservatory, Millennium Park, and Museum Campus. You’ll also learn about Chicago’s history and can spy other remarkable sights as you go.

Get an insider’s look at the Windy City’s most iconic monuments during this 3-hour private tour. Travel through Chicago aboard a private vehicle as you discover some of the city’s top neighborhoods, including the Loop, River North, the Magnificent Mile (along Michigan Avenue), Streeterville, the Gold Coast and much more. Your private driver-guide and vehicle, bottled water and round-trip hotel transport are all included.

Ever since Chicago became the birthplace of the modern skyscraper, the city has been renowned for its architectural creativity and ingenuity. Led by an expert guide, explore some of the city’s most iconic buildings such as Sears Tower, The John Hancock Building, historic brownstones, and the homes of Oak Park designed by beloved architect Frank Lloyd Wright. You will be able to explore the insides of some locations on this completely customizable tour.

Discover many of Frank Lloyd Wright’s best-known architectural creations, all in one excursion: this convenient, time-saving tour will whisk you from your Chicago hotel straight to nearby Oak Park. Aboard a private, luxury vehicle, you’ll drive by all 25 of the legendary architect’s local buildings, with time to stop and admire—and take photos—as you go (you are not accompanied by a tour guide). At tour’s end, return to your Chicago accommodation.

See Chicago the way you want to see it. This private tour is fully customizable to your specifications. Whether you are interested in the architecture and history, the art, the cool neighborhoods, or peaceful parks and happening beaches, this tour will cater to your tastes. Work with a guide to discover Chicago your way.

If it’s your first time in Chicago or you just have limited time, make the most of a day in the Windy City on a private driving tour. Instead of navigating public transit or waiting for ride shares, relax as a dedicated driver takes you to all the major attractions of downtown and beyond, including Navy Pier, Michigan Avenue, Wrigley Field, Millennium Park, and Museum Campus. Plus, get local insight into Chicago along the way.

Chicago’s mob history has long been immortalized in popular media. Embark on this Chicago Gangster Tour to learn the true story. With an expert historian as your guide, you’ll visit notorious hangouts of John Dillinger, The Untouchables, and the legendary Al Capone. You’ll stop at former speakeasies, historic hotels, and epic crime sites like that of the Saint Valentine’s Day Massacre.

Explore Chicago your way and on your own schedule on a private walking tour that's completely customized based on your interests. Whether you want to learn Windy City history or focus on architecture, street art, or Chicago's food scene, your local guide knows all the best places to see, shop, and dine. Plus, get plenty of personalized recommendations on where to go once the tour ends.

Ideal for travelers short on time, this day trip covers the best of the Monterey and Carmel region in one day of sightseeing from San Francisco. Highlights include spending two hours in both Monterey and Carmel, driving the scenic 17-Mile Drive through Pebble Beach and Pacific Grove, and stopping at a garlic shop in Gilroy, known as the “Garlic Capital of the world.”

Travel back in time to the 1920s, when Chicago was a prohibition era hub for lively speakeasies. Your guide, a local historian in period dress, will lead you through secret entrances to speakeasies once frequented by bank robbers and Chicago gangsters like Al Capone. Order prohibition era cocktails (additional cost) and listen to stories about bootlegging and racketeering in 1920s Chicago. Guests are welcome to come in period dress.

See the best of the Windy City—and have the freedom to stop at only the sights that interest you most—on this private tour. Meet your chauffeur at a time and place that work best for you, hop aboard your luxury sedan, and set off. Over the course of half a day (or 50 miles maximum), choose to visit landmarks like Navy Pier, Wrigley Field, Millennium Park, the Magnificent Mile, and more.

Discover spooky stories in the Windy City on a private haunted history tour. Visit places with names such as the Murder Castle and Death Alley, and hear about Al Capone and the Old Congress Hotel. See all three locations on one tour that reveals fascinating details about historical events, and rumors of murder and mayhem in Chicago.

Travel through the Windy City in style—and plan your own day out or sightseeing itinerary—with this private, fully customizable stretch limo charter. Meet your driver at a starting time and place that work best for you, hop aboard, and make yourself comfortable—with this itinerary, you’ll have 2 hours to explore Chicago’s highlights as you see fit.

Enjoy a one-of-a-kind way to get married—and make the most of Chicago’s romantic side—with this personalized elopement package. Upon booking, choose a start time that works best for you, and speak with the planners to pick your perfect location and backdrop. The officiant, photographer, and private transit are all included to make your big day seamless and stress-free—so you can focus on the magic.