Top Chicago How to Get Around in 2026

See Chicago your way with flexible hop-on hop-off tickets designed to suit every sightseeing style. Explore the Windy City at your own pace, hopping off to visit top attractions such as Millennium Park, Navy Pier, the Magnificent Mile, and the Chicago Riverwalk while enjoying onboard commentary that adds context to what you see. Perfect for first-time visitors or those short on time, this tour offers flexibility and ensures you don’t miss any of Chicago’s highlights. You can also upgrade your experience to enjoy extra sightseeing time and a panoramic sunset tour for unforgettable skyline views.

Explore a new side of Chicago and the city'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, John Dillinger, and more famous figures hung out. There are ample chances to get out of the bus and pose for pictures in front of a historic courthouse, among other infamous sites.

Maximize your limited sightseeing time in Chicago on this two-in-one tour, which covers the city’s notorious gangster history as well as its most famous dishes. Choose between private and shared tour options, and meet your guide right in the downtown Loop. Then, set off on foot: Learn about Al Capone and the city’s Prohibition past in between sampling classic bites, from deep-dish pizza to the Chicago hot dog and more.

Discover the hidden gems of Chicago’s Loop area on a walking tour that showcases the best of the neighborhood’s stunning interiors and architectural must-sees. Step behind the facades to explore beautifully designed interiors—from art deco spaces to stained glass mosaics—as you follow a carefully curated route led by a guide. Along the way, learn about the city’s architecture, art, and history, and experience a side of Chicago often missed by travelers, all from a local’s perspective.

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.

Discover the architectural gems of the Windy City from an ideal vantage point—and learn insider facts and stories about the city's top attractions—on this Chicago River cruise. Travel in comfort aboard a boat equipped with both indoor and outdoor seating areas. Covering more than 130 years of architectural history, this tour is the perfect opportunity to see a huge area of the city without the hassle of taxis and public transit.

Chicago is famous for its architecture, and the best way to see it is on a cruise down the Chicago River. Glide by historic and modern marvels like the Civic Opera House, Wrigley Building, and Willis Tower from the comfort of an open-deck boat. Live narration reveals each building’s fascinating history, so you'll learn more than you would just observing on your own.

Immerse yourself in one of Chicago's most vibrant neighborhoods—and head off the tourist trail to discover sights and bites many visitors miss—on this small-group Chinatown food and walking tour. With your guide in the lead, learn about the cuisine of different regions of China, and discover the history of Chicago's Chinatown. Along the way, enjoy a generous array of tastings, from dim sum to Sichuan cuisine and beyond.

There are lots of ways to take in Chicago’s architectural sights, but most tours don’t mix things up by teaching you about the city’s dark criminal past. On this combination architecture and true crime walking tour, explore with a local guide and listen to intriguing stories as you explore downtown landmarks such as Chase Tower, Palmer House, and much more.

Many Chicago architecture tours focus on the city’s famous buildings—but few actually venture inside the landmarks. On this shared or private tour, step right inside many of the city’s top architectural icons, discovering sights and details that few other travelers get to see. Visit the legendary Rookery, explore the Chicago Cultural Center, view Tiffany glass ceilings and art deco highlights, and much more.

Eat your way through downtown Chicago on a walking food tour. Visit Millennium Park, the Palmer House Hotel, and other city landmarks and taste quintessential Chicago foods such as deep-dish pizza, hot dogs, and chocolate brownies. All food tastings are included, and the tour covers an easy 1.5 miles (2.4 km) suitable for most fitness levels. A bike or kayak rental is also included in the tour cost.

Swap the standard Chicago itinerary for the chance to experience a whole different side to the city. Walk in the footsteps of Al Capone and John Dillinger while hearing tales of Chicago's haunted past. This walking tour takes you to prohibition-era speakeasies, sites of real life mob shootouts, and provides special access to places tied to historical events that have shaped Chicago.

Discover the beauty of Chicago at night during a 1.5-hour cruise on the Chicago River and Lake Michigan. Watch the city sparkle as you pass landmarks such as Museum Campus, Willis Tower, Aon Center and the John Hancock Building, and the illuminated waters of Buckingham Fountain. You'll learn about the history of the city from live commentary by your knowledgeable guide as you glide along the waterfront of Chicago.

Most Chicago sightseeing tours focus on the city’s key landmarks. But on this unique excursion, you cam dig deeper than surface level, and discover some of the city’s spookiest stories. Pick between private or shared options, and set off to explore the South Loop with your guide. Along the way, see where notorious gangsters like Al Capone operated, hear about their bloody backstories, and even visit several of the state’s most haunted addresses.

Discover the dark side of the Windy City on this nighttime crime history bus tour of Chicago. Through your expert guide's rich storytelling, immerse yourself in tales of notorious mobsters like Al Capone, Frank Nitti, and Bugs Moran as you explore infamous crime scenes including the site of the St. Valentine’s Day Massacre.

Get to know the Windy City the easy and comfortable way on a small-group minibus tour. Instead of long walks and navigating public transit, see major landmarks like Museum Campus, Buckingham Fountain, the Magnificent Mile, and Millennium Park from an uncrowded minibus with large picture windows. Your driver and guide knows where to find all the best views, and there are plenty of photo stops along the way.

Chicago dogs, deep-dish pizza, brownies, and craft beer are all sampled on this half-day bike tour through the Windy City. Cover about 13 miles (21 km), following your guide at a moderate pace through Chicago neighborhoods. On the day tour, ride through Wrigleyville, Old Town, Lincoln Park, and Gold Coast. On the night tour, visit Chicago’s Riverwalk, Millennium Park, Buckingham Fountain and the Lakefront Trail. As you go, stop for generous food and beer tasters.

This walking tour is a feast for the eyes, combining art, architecture, and history as you navigate through bustling downtown Chicago. In a small group, you’ll marvel at skyscrapers and mosaic murals as you discover stories and secrets about the city’s past. See the stunning interiors and exteriors of noteworthy buildings and leave with a comprehensive understanding of the city’s downtown.

Experience Chicago like a true insider on this top-rated walking tour that blends the city’s most iconic food, awe-inspiring architecture, and rich history — all in one unforgettable day. From deep-dish pizza to legendary skyscrapers, you’ll taste, see, and learn what makes the Windy City a world-class destination. Led by expert local guides and limited to just 12 guests, this immersive, small-group tour is the perfect way to discover the real Chicago — not just the tourist spots.

Explore Chicago's buzzing food scene—and see some of its best-known landmarks on the way—on this two-in-one walking tour. The small group size offers are more intimate experience as you stroll around the vibrant Loop area, spotting highlights from the Willis Tower to the Rookery building. Indulge in a variety of famous Chicago foods, from deep-dish pizza to the world-famous dipped Italian beef sandwiches.

Skip navigating around the city with a map and guidebook and explore Chicago's iconic landmarks in just a few hours on this sightseeing tour led by an expert guide. Board a comfortable, large-windowed minibus and explore Downtown and North Side neighborhoods, stopping to 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.

Explore the hidden side of Downtown Chicago—and see sights that even many locals miss—on a small-group walking tour of the Pedway (an underground network of tunnels that connects Chicago buildings) and the vibrant Loop. Ideal for architecture fans, this tour includes insider stories and landmarks you wouldn't spot on your own—plus a chance to see Windy City icons like the Picasso Statue and Millennium Park.

Enjoy a quintessential Chicago experience—and see more of the city's highlights in less time—on an architecture-themed boat tour of the Chicago River. Pick from multiple convenient start times, and board your vessel directly from the Chicago Riverwalk. Thanks to your trained docent guide, receive a rich introduction to the Windy City’s history, key landmarks, and architectural highlights—and spy landmarks like the Marina City towers and Navy Pier from the water’s edge.