Top Chicago Private & Custom Tours

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.

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.

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.

Get to know the city through the eyes of a passionate local. With no set itinerary, you can customize the tour or leave it up to the local for an insightful introduction to the city. Make travel about the people you meet not just the places you see.

No more selfies or pestering strangers for photos of yourself and loved ones, enjoy the services of a professional vacation photographer in Chicago to capture your travels in a contemporary and candid style. Specialising in delivering quality photography with photographers all over the world, we guarantee you amazing photos to remember your travels. All images shown were taken by our photographers.

Soak up the views of Lake Michigan and the Chicago skyline with a 2-hour sailing tour. This private charter is completely customizable, giving you the chance to choose your music, route, and up to 5 additional guests. Sail into the sunset with your own drinks and snacks (refrigerator and ice on board) and your family or friends by your side.

Treat yourself to an unforgettable Chicago experience with this private sailboat cruise under the Navy Pier fireworks. Over the course of two hours, you’ll sail along Chicago’s beautiful lakefront with a view of the city skyline. You’ll have the perfect vantage point to enjoy the incredible fireworks from Navy Pier. This customizable experience allows you to choose your own, route, music, and guest list.

Explore stunning, trend-setting Chicago at your own pace—and in your own language. Choose from Arabic, French, Mandarin, Russian, and more, and get personalized attention from your own multilingual guide. Build your own itinerary using a tailor-made list of stops—from Lake Shore Drive and Millennium Park to under-the-radar local neighborhoods—and customize your own sightseeing trip just as you like it.

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.

Experience Chicago in style on a half-day tour in a luxury mini-bus with a private chauffeur. Choose from a themed itinerary—from the Loop to local sports—or ask your driver to customize the experience to match your group’s interests. Cruise the city’s streets with a group of up to 12 passengers and a professional guide who narrates the outing in the language of your choosing.

See Chicago your way on this private guided tour. Up to 12 passengers can take part in this tour that features the parts of Chicago that you are most interested in. Your driver will take you to select points of interest, while your guide fills you in on the history and insider information of the sights--all at your speed, according to your preferences.

Experience Chicago with a private guide and seperate driver in a luxury SUV. The tour is fully customizable with different itineraries to suit your tastes and interests. Visit Wrigley Field, peruse Fulton Market, and bring your camera for famous skyline views. Then get of the beaten path and venture into local neighborhoods. This tour is ideal for visitors who value privacy and who are looking for a personalized experience.

Designer boutiques, home decor, or gourmet food, chocolate and wine! Your guide will curate a day just for you and your crew! Visit upscale Lincoln Park or trendy Bucktown and Wicker Park. Discover why Chicago's design and food scene is hot! You'll travel in complete comfort in a luxury mini-coach stopping where you desire. Choose from a 5 or 7 hour day to immerse yourself in the best of the city! With a 7 hour day, your guide can make advance lunch reservations for the group to dine on their own. One small cooler of champagne is permitted per group. Other alcohol consumption on the coach is prohibited.   Great for: BirthdaysCelebrationsIcebreakersConvention ActivitiesTeam Building

Fly high over Chicago on a private helicopter tour just for you and your group of up to five people. Look down on Soldier Field, the Magnificent Mile, Millennium Park, the former Sears Tower (Willis Tower), and more as you learn a bit about the history of the city's landmarks. This VIP-style experience starts and ends at the dedicated lounge area of the heliport.

Discover Chicago's bold character through its beautiful landmarks and fascinating backstories on this thoughtfully designed tour of history, contemporary life and world-famous architecture.

Basic, intermediate, and advanced interpretation services offered.  GMD Linguistics is a linguistic agency which offers certified translation, interpretation, transcription, voice-over/dubbing, subtitling, editing/proofreading, configuration, localization, web design and foreign language learning services. Price listed is all inclusive, no hidden fees.

You and a guest will soar above Chicago’s skyscapers, shoreline and iconic sights on a private, 15-minute helicopter tour of the city. Communicate with your personal pilot through a two-way headset, and personalize your flight to your interests. Capture extraordinary aerial images of the city scape as you fly past Lincoln Park and Lake Michigan, then spot Willis Tower, the John Hancock Building and the gleaming Trump Tower. Bank high above Millennium Park and enjoy views of the Windy City from the comfort of a climate-controlled private helicopter. Tour route is subject to change.