Top Chicago How to Get Around

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.

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.

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!

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.

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.

Explore Chicago's gangster past on this mafia tour in a coach vehicle. Drive around the Windy City to see where Al Capone, The Untouchables, Hymie Weiss, and John Dillinger, among other thugs hung out. A history-savvy guide introduces you to some of the most storied locations of Chicago’s criminal past, including Holy Name Cathedral, Biography Theatre, and the site of the bloody St. Valentine’s Day Massacre. You'll be able to get out and pose for pictures in front of a historic courthouse, among other infamous sites.

See Chicago light up with a 4-hour bicycle tour of the Windy City’s most iconic sights and neighborhoods. Follow your guide along a leisurely route, watch the Buckingham Fountain light show and take in daytime or evening views of Millennium Park and the Museum Campus. Sample culinary classics of Chicago, like deep-dish pizza, a true Chicago hot dog, Italian beef, and a tasty dessert for good measure. Upgrade your experience to enjoy a locally crafted beer pairing at three of the food stops. As you pedal through downtown streets, capture unforgettable images of Chicago’s magnificent skyline then finish your tour in the heart of the city.

Chicago dogs, deep-dish pizza, cupcakes and craft beer are all sampled on this half-day bike tour through the Windy City. Cover about 13 miles (21 km), following an informative guide at a moderate pace through the Chicago neighborhoods of Wrigleyville, the Gold Coast, Old Town, Lakeview and Lincoln Park. Stop along the way at a popular downtown bakery, pizza shop, hot dog stand and two breweries for a taste of local flavors.

Pedal past the lakefront neighborhoods of Chicago's North Side on this bike tour of the Windy City. Follow a local guide along quiet streets, city parks and scenic beaches, starting at Lake Shore Drive and continuing along Rush Street and the Magnificent Mile. Catch a glimpse of the Playboy Mansion, Oprah’s penthouse and the Victorian houses of Old Town. Select from several departure times in the morning or afternoon.

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.

Step into the heart of Chicago with this 2-hour walking tour of the Loop. You’ll meet your local guide at the Chicago Cultural Center and make your way through the city’s downtown. Stop to check out the elevated “L” train, buildings by Burnham and Sullivan, busy commercial centers and lesser-known quiet corners of this vibrant area. You’ll come away with a deeper sense of Chicago’s rich history and architecture.

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.

Taste food from around the world on this half-day cycling and tasting tour of Chicago. Follow your biking guide through the Chicago streets, stopping for views of Chicago’s famous architecture as well as bites like Polish pierogis, locally made chocolates, and Mexican tacos.

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.

Rather than taking selfies everywhere you go or trusting a stranger to take a picture for you, leave capturing the special moments to us. You will be escorted by a local professional photographer who will guide you through your chosen route and will take pictures of your experience so you can return home with the ultimate souvenir. Your photo tour includes: -1 or 2-hour private session with a professional, local photographer -High-resolution edited images delivered via a private online gallery within 24-48 hours

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.

Rather than taking selfies everywhere you go or trusting a stranger to take a picture for you, leave capturing the special moments to us. You will be escorted by a local professional photographer who will guide you through your chosen route and will take pictures of your experience so you can return home with the ultimate souvenir. Your photo tour includes: -Your choice of a 30 minute or 1-hour private tour with a professional photographer -High-resolution edited images delivered via a private online gallery within 1-2 days -Enjoy unlimited access to your photos and download as many as you would like with no expiration date *not all stops may be included depending on the length of time you select.

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.

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.

Discover the ‘dark side’ of the Windy City thanks to this 2.5-hour, bus-based, nighttime crime history tour of Chicago. Explore the lives of notorious mobsters like Al Capone, Frank Nitti, Bugs Moran, and more as you explore infamous crime scenes like the St. Valentine’s Day Massacre, learn about ‘The Enforcer’s Safe,’ and stop by local watering holes.

Rather than taking selfies everywhere you go or trusting a stranger to take a picture for you, leave capturing the special moments to us. You will be escorted by a local professional photographer who will guide you through your chosen route and will take pictures of your experience so you can return home with the ultimate souvenir. Your photo tour includes: -Your choice of a 30 minute, 1-hour, or 2-hour private tour with a professional photographer -High-resolution edited images delivered via a private online gallery within 1-2 days -Enjoy unlimited access to your photos and download as many as you would like with no expiration date *not all stops may be included depending on the length of time you select.

Sample some of the Windy City’s tastiest donuts on this Underground Donut Tour, celebrating the magic of Chicago’s tastiest sugar-filled concoctions. Donut-lovers are sure to enjoy this visit to some of Chicago’s tastiest donut purveyors, offering a chance to savor all of your favorite varieties, on the city's only donut-themed excursion. All tastings are included, and vegan, gluten-, and nut-free options are also available.

Discover the sights and sounds of Chicago’s various cultural scenes on a 2-hour walking tour. The 1.5-mile route covers music, literature, art, and architecture within the Windy City. Hear insider stories about Chicago's cultural movements and visit little-known locations linked to iconic artists.  Be sure to have your camera ready for the pièce de résistance, the Tiffany stained glass dome at the Chicago Cultural Center.

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.

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.

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.

See the overlooked highlights of Chicago’s Loop district with a 2-hour walking tour that takes in the best of the bustling, vibrant neighborhood’s inside spaces. Get behind the façades to explore stunningly designed interiors as you follow a specially-designed route with an experienced guide. Learn about the city’s architecture, art and history while visitng a side of Chicago that’s beyond the tourist trail, and experience the Windy City with a local perspective.

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.

Step off the tourists’ path to visit Lincoln Park, a neighborhood beloved by Chicagoans for its stately homes, historic zoo, and stunning green areas. Your tour begins at the charming Children’s Fountain and continues to unexpected sites like the shrine of the first American saint. As your local guide leads you through the city’s largest park, you’ll marvel at the wild feel of this neighborhood just north of downtown Chicago.

On this two-in-one tour, you won’t just discover Chicago’s highlight public park: you’ll also do so in the company of a professional photographer, who will capture portrait shots as you explore. Pick from multiple daily tour times, and meet your private guide at Millennium Park. You can look forward to seeing park highlights like Anish Kapoor’s "Cloud Gate" sculpture (better known as “The Bean”), Lurie Garden, Maggie Daley Park, Buckingham Fountain, and more. Following the tour, receive high-quality digital photos of your experience.

Experience Chicago like never before on this guided, 3-hour bicycle tour. Ride the walking- and cycling-only Chicago Lakefront Trail to and through the city’s beautiful beaches, parks and lagoons. See the coast of Lake Michigan and the breathtaking Chicago skyline, plus bustling Navy Pier, popular North Avenue Beach, the 35-acre Lincoln Park Zoo and Conservatory and much more. The use of a bike and helmet is included.

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.

Stroll through downtown Chicago on this walking food tour. Visit Millennium Park, the Palmer House Hotel and other city landmarks. Taste quintessential Chicago foods such as deep-dish pizza, hot dogs, plus chocolates and pastry. All food tastings are included, and the tour covers an easy 1.5 miles (2.4 km) suitable for most fitness levels.

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.

Enjoy a walking tour of Chicago’s Magnificent Mile. Located in the heart of downtown, this scenic stretch is beloved by locals and tourists alike for its great shopping and rich history. Visit a Water Tower that survived the Chicago Fire and gave its name to one of the city’s most elegant shopping centers. See a church frequented by Abraham Lincoln and other historic highlights dating back over 344 years.

Book in advance to take this popular tour that details the mob history of Chicago during the Prohibition Era (1920s-1930s). Learn about the exploits of gangsters like Capone, Dillinger, Moran, and others as you travel by minibus to sites like the Biograph Theater, Holy Name Cathedral, and St. Valentine's Day Massacre. Your guide adopts gangster attire and characteristics that add dramatic flair to the historical commentary.

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.

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.

A river runs through it: the Chicago River passes right through the heart of downtown and is a major part of city identity. You’ll begin this walking tour at Navy Pier and follow your local guide along the scenic river walk. You’ll learn the role of the river in Chicago’s history, and stop to admire iconic architecture and bridges celebrated as feats of engineering.

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.