Top Illinois City Tours

Luxury vehicles Professional chauffeurs Updated fleet Licensed chauffeurs Knowledge about navigating in the city

Luxury vehicles Professional chauffeurs Updated fleet Licensed chauffeurs Knowledge about navigating in the city

Luxury vehicles Professional chauffeurs Updated fleet Licensed chauffeurs Knowledge about navigating in the city

This Tour is the quickest, best way to explore a place that you are visiting for the first time, we take you to all the hot spots in the city in less than a day. We take care of everything for you, from picking you up at your hotel, to making reservations, parking, helping you with photos, all the way to dropping you off back where you started. zero worries and 100 percent enjoyment.

Make the best of your visit to Chicago and explore the interiors of the emblematic Loop of Chicago downtown with a private licensed guide. You will enjoy a private tour and discover the hidden architectural treasures of Chicago with a local expert

2 hours of being a kid again!!! Take a Segway tour with us and discover how beautiful Chicago truly is. Ride through some of Chicago's most popular destinations with an experienced guide. We will glide through scenic and historic downtown Chicago and explore the beautiful Grant Park, around the Buckingham Fountain, near the Museum Campus and near the lakefront. Or take our Riverwalk tour to explore the Chicago River to view Navy Pier and famous Chicago bridges, traveling up historic Michigan Avenue and passing by Millennium Park. No matter which tour you choose, it will be a memory lasting a lifetime!

Explore Chicago's buzzing food scene with a small group on this small group walking tour. Stroll around the 'Loop', stopping at hidden gems and hearing tales of the city from your guide. Taste classic Chicago foods, from deep-dish pizza to dipped Italian beef sandwiches.

We are Chi-Town foodies of the first order, and we're so excited to share with you all the culinary delights this historic Midwestern city has to offer. There is so much to share about Chicago: historic enclaves, stunning architecture, an extensive collection of publicly displayed civic artwork, and a culinary style steeped in history. We will discover each facet of this unique city as we eat and explore Chicago's Loop District. As a private tour, everything works around you! Our start times are much more easy going, dates can open up. It's a much more intimate and cozy experience. No need to shout over other tourists, you will have every question answered, and leave feeling like a native yourself!

Get a front row perspective on the exquisite buildings that line the Chicago River during a 45-minute architecture cruise. Hear live commentary about the history and architectural heritage of Chicago on this family-friendly tour, which highlights landmarks such as the Chicago Riverwalk, Michigan Avenue Bridge, Wrigley Building, and Willis Tower. Sit on the open-air top deck or the sheltered bottom deck for the ultimate view of Chicago.

Step aboard a boat for a comprehensive cruise that details the history of Chicago's architecture. Enjoy views of the Chicago skyline accompanied by architecture-focused commentary that points out each of the landmark buildings. As you cruise through Lake Michigan, snap photos of you and your party against the stretch of Chicago's 26-mile shoreline.

Discover the architectural gems of the Windy City from an ideal vantage point on a cruise down the Chicago River. Offered several times throughout the day, it’s easy to fit the leisurely excursion into your itinerary. Covering more than 130 years of architectural history, the tour is the perfect opportunity to see a huge area of the city without the hassle of taxis and public transit.

Get to know the River North district of Chicago through its food on a culinary walking tour that takes you to five local food venues. You'll enjoy tastings of Mexican fare, Chicago deep dish pizza, and other items while learning about the neighborhood's history and food culture.

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.

Experience a colorful side of Chicago history with this Gangsters and Ghosts Tour. With a historian as your guide, you’ll step back to the roaring 20’s, when the Chicago Loop was a hub for bootleggers, speakeasies, and gangsters like the infamous Al Capone. Visit onetime gangster hangouts and haunted sites like the Palmer House, Congress Hotel, and Death Alley.

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.

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 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.

An excellent choice for first-time visitors, this tour provides a comprehensive overview of the city and hits on both classic attractions and little-known sites. Beginning at the Chicago Theatre, work your way to the Chicago Pedway, an elaborate network of underground tunnels used by locals and commuters. Stroll the Chicago Riverwalk and the Magnificent Mile, then embark on a food tour to taste some of the city’s famous foods.

Get to know the food offerings in River North on this small-group walking tour. As you explore, listen to in-depth commentary from your guide on the culinary history of Chicago and the culture of the River North neighborhood. With a small group of just 12 fellow food-lovers, you'll enjoy personalized attention and the chance to chat about your favorite tastings. Samples include the classic Italian beef, a Chicago-style hot dog, and the famous deep dish pizza.

Take in iconic views of the beautiful Chicago lakefront and its many landmarks during this 40-minute Lake Michigan sightseeing boat cruise. Climb aboard your vessel for a laid-back ride, enjoying panoramic views of the Windy City's skyline from a unique perspective. Along the way, you'll listen to informative commentary and take in views of the John Hancock Center and Willis Tower, along with many other landmarks. Plus feel free to bring your own lunch or grab a drink at the onboard bar, during your ride.

Cruise down the Chicago River to see the city's famous architecture on this boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including more than 40 notable buildings like Navy Pier, the Wrigley Building, and the John Hancock Building. Cover all three branches of the Chicago River, passing the East Bank Club, the old Post Office Building and the Willis Tower (formerly known as the Sears Tower). From Memorial Day to Labor Day (May 29 - September 6,) each ticket includes a one-way water taxi ticket.

Downtown Chicago is filled with gems. Some famous, others known only by select locals. Many of these spots are best seen on foot as opposed to a moving vehicle. We'll take you inside several of these architectural masterpieces, to where much of Chicago's real beauty can be seen. We'll also give you time to check out famous public art by the likes of Picasso and Chagall and see the world's very first skyscrapers! All of our tours are led by experienced guide that have been giving quality tours of Chicago since 2005 and have accrued well over 500 five-star reviews. People mostly comment on how our tours are both informative and entertaining. The walk is a little under 2 miles and conducted at a comfortable pace.

Enjoy Chicago’s famous sights (now including Wrigley Field!) and fabulous views on this award-winning small-group sightseeing tour of the city. Travel through Chicago with an expert guide on a comfortable minibus, stopping at iconic locations like early skyscraper "The Rookery" (Frank Lloyd Wright architecture), Museum Campus (for the BEST skyline view in town), Millennium Park (The Bean), Buckingham Fountain, The Magnificent Mile, Lincoln Park, Chicago River, The Gold Coast, Lake Shore Drive and more! Along the way, your guide will provide historical and informational commentary about the area and its many attractions. The small-group atmosphere with maximum of 10 people ensures a more personal experience. 

Explore Chicago's iconic landmarks on this sightseeing tour led by an expert guide. Board a comfortable, large-windowed minibus and explore downtown and Northside neighborhoods. You have a chance to get out and visit several locations and hear about the historical and cultural factors that make Chicago unique. Upgrade your tour with a popular open-top boat tour on the Chicago River that focuses on the city's renowned architecture.

Experience Chicago like never before on this guided, 2-hour, small-group Segway tour. Visit popular Grant Park and see famous Buckingham Fountain’s breathtaking, evening light show, with an illuminated Windy City skyline as the perfect backdrop. Glide along the lakefront, taking in views of the Field Museum of Natural History, Shedd Aquarium, Soldier Field and Michigan Avenue. Guided Segway training plus the use of a helmet are included. Dress in weather-appropriate clothes with flat, closed-toed shoes.

Experience Chicago like never before on this small-group Segway tour. Visit Chicago’s ‘front yard,’ the beautiful lakefront and 57-acre Museum Campus. Glide along the fragrant floral paths to famous Buckingham Fountain. Then travel along the banks of Lake Michigan, past Monroe Harbor to the Museum Campus for a breathtaking view of the city’s iconic skyline. Guided Segway training plus the use of a helmet are included. Dress in weather-appropriate clothes with flat, closed-toed shoes.

Experience Chicago like never before on this guided, 2-hour, small-group Segway tour. Visit popular Grant Park and see Buckingham Fountain’s breathtaking, evening light show, with an illuminated Windy City skyline as the perfect backdrop. Glide along the lakefront, then witness Chicago's weekly summer fireworks display at Navy Pier from a secret location. Guided Segway training plus the use of a helmet are included. Dress in weather-appropriate clothes with flat, closed-toed shoes.

There's no better way to tour the world-class city of Chicago than on a Segway! On your very own private tour, we will cruise around the parks and along Michigan avenue and show you the best that Chicago has to offer. If you are passionate about history, architecture, hauntings, Al Capone, and gangster or more, just let us know! We will customize the tour to fit your interests!

Explore Chicago by Segway with the benefit of a scenic 7- or 8-mile tour led by your guide. Start with an orientation to operating the Segway and a few minutes to practice. Then roll through the paths of Grant Park to Buckingham Fountain and glide along the Chicago lakefront to view attractions such as Museum Campus, Shedd Aquarium, The Field Museum, and Soldier Field, homefield for the Chicago Bears.

This is a tour like no other! Our newest Segway adventure is completely unique and will cover the good, the bad, the ugly and the totally weird stories of Chicago. We will travel back through the ages as you discover the city through the lens of the Chicago Syndicate, hear the whispers of the city’s elite (or politicians), and be entertained by stories that are rarely told. You’ll think “No, really I never would have known!” Glide around Millennium Park, through the new neighborhood of Lakeshore East, and along the Lakefront as we unveil Chicago’s forgotten past in two hours! Your imagination will come alive as you hear stories of the Chicago Mob, the truth behind the 1968 Democratic National Convention, innovations that changed history, and so much more!

Glide through the city of Chicago by moonlight on this haunted Segway tour. Follow your costumed local guide as they show you the sites of some of the most gruesome murders and disasters in Chicago's colorful history. See Chicago's iconic landmarks lit up during the spookiest time of year and hear about the mysterious, haunted history of this storied city.

Explore the art and architectural highlights of Chicago on a Segway during this guided tour. This family-friendly tour takes visitors by the outdoor sculptures, landmark buildings, and iconic skyline of the city. Accompanied by educational and informative commentary, this city tour saves you from hours of walking and lets you see all of Chicago's top art and architectural attractions in one tour.

Our tours are not only personable (due to small group sizes), but also create an immersive experience with our knowledge and expertise in street art. What better way to explore a new neighborhood but with a local artist in tow to give expert commentary on the vibrant history and culture of the Chicago Art Scene. Pilsen owes its' name to the Czech population that emigrated here in the late 19th century, but is now home to one of Chicago's biggest Mexican populations and a hot bed for new & exciting art. The rich Mexican heritage can be seen throughout the neighborhood; everywhere from the Mexican Heritage Museum to the numerous murals found all throughout. Explore this neighborhood and it's rich culture new & historic with us.

See Chicago's dazzling skyscrapers lit up for the night during this 75-minute Big Bus tour. The entire loop takes passengers from the Magnificent Mile to Michigan Avenue, through the Museum Campus and around the architectural gems on the Loop skyline. Live commentary in English.

Don’t spend time figuring out what to see in Chicago and how to get there—this hop-on hop-off tour provides a mapped-out itinerary of the city's top sights. With several strategically located stops, the tour allows you to explore the Windy City at your own pace. See the world-class Art Institute and landmark skyscrapers, while live commentary onboard gives you insight into the city's colorful history.

If you’ve ever dreamed of sailing away on your own private sailboat, this is the perfect excursion for you. You and up to five other invited guests will have the exclusive use of a sailboat, complete with captain and crew for the duration of your tour. Sail on Lake Michigan and enjoy the sights of Chicago’s striking skyline. If you want, you could even take a turn at the helm.

The Chicago Architecture Center River Cruise aboard Chicago's First Lady has long been the gold standard among all Chicago tour experiences, and is the only Chicago architecture boat tour led by highly trained expert docents. On this 90-minute cruise, you will enjoy an overview of historic and modern architectural styles including stories about the people who designed and built Chicago. No visit to Chicago is complete without experiencing this award winning tour, so accept no substitutes.

The easiest and most affordable way to explore some of Chicago's top attractions at your own pace, the Go Chicago Explorer Pass saves you up to 45 percent on regular ticket prices. Create your own sightseeing itinerary by choosing 2, 3, 4, or 5 attractions, tours, and activities from among more than 30 top sites, including SkyDeck, 360 Chicago, the Field Museum, a shoreline sightseeing cruise, a hop-on hop-off Big Bus tour, Lincoln Park Zoo, Navy Pier, and LEGOLAND® Discovery Center. Please note: Enjoy the extra flexibility in case your travel plans need to change: All passes are valid for two year from purchase date and only become activated with your first attraction visit. After activation your pass will be valid for 60 days and/or the remaining number of attraction choices purchased.

Whether you’re short on time or want to orient yourself to Chicago, a 3.5-hour land and river tour is the perfect option. The comprehensive itinerary takes you through both the North and South sides. Listen as your guide tells insider stories about the people who shaped the city. After the land tour, rest your feet and see the city from a unique vantage point during a 90-minute river cruise.

Explore Chicago’s most iconic sites on a bike tour that explores Museum Campus, parks, and monuments. Follow your guide along the waterfront as you soak up the city skyline and enjoy the breeze along the easy-going route. Circle the Buckingham Fountain while you learn the history of the city’s public art, parks and museums, and capture unforgettable images of the Windy City.