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Illinois • United States

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Let the spirit of adventure guide you as you uncover the hidden gems and unforgettable experiences that make Chicago a destination like no other. Uncover awe-inspiring locations and exciting attractions across Chicago, chosen by our community and tailored to you.

Pizzeria Uno in Chicago, Illinois
Food & Dining

Pizzeria Uno

Chicago, Illinois
Chicago Botanic Garden in Chicago, Illinois
Nature, Parks, & Gardens

Chicago Botanic Garden

Chicago, Illinois
Lincoln Monument in Chicago, Illinois
Sights & Landmarks

Lincoln Monument

Chicago, Illinois
Medieval Times Chicago in Chicago, Illinois
Entertainment

Medieval Times Chicago

Chicago, Illinois
Lookingglass Theatre Company in Chicago, Illinois
Entertainment

Lookingglass Theatre Company

Chicago, Illinois
Chinese American Museum of Chicago in Chicago, Illinois
Museum

Chinese American Museum of Chicago

Chicago, Illinois
Chicago River in Chicago, Illinois
Nature, Parks, & Gardens

Chicago River

Chicago, Illinois
Navy Pier in Chicago, Illinois
Amusement Parks & Rides

Navy Pier

Chicago, Illinois
Chicago Riverwalk in Chicago, Illinois
Nature, Parks, & Gardens

Chicago Riverwalk

Chicago, Illinois
Wrigley Building in Chicago, Illinois
Sights & Landmarks

Wrigley Building

Chicago, Illinois
Skydeck Chicago at Willis Tower (Sears Tower) in Chicago, Illinois
Museum

Skydeck Chicago at Willis Tower (Sears Tower)

Chicago, Illinois
Tribune Tower in Chicago, Illinois
Sights & Landmarks

Tribune Tower

Chicago, Illinois

Epic travel experiences

Explore new destinations throughout with ease and expert guidance with tour packages and experiences from Viator. With knowledgeable guides to enrich your journey with local insights and cultural experiences, you can fully immerse yourself in the destination without the stress of planning logistics. Whether you're seeking adventure, relaxation, or cultural exploration, a tour ensures a seamless and enriching travel experience.

$89 Tour Provided by Viator
5.00 (97 reviews)

Small-Group Sightseeing Boat Tour in Chicago

The ultimate custom sightseeing experience in Chicago! Enjoy the City from great vantage points and photograph the world-famous skyline. We zip you to many sights around the local waterways including the Navy Pier, Soldier Field, Fort Dearborn, Vietnam Memorial, Wolf Point, Shedd Aquarium, and many others. Come aboard our safe and seaworthy US NAVY built Rigid Inflatable Boat (RIB), and experience a unique & personal tour of the City!

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 $508 Tour Provided by Viator
5.00 (70 reviews)

Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline. Make the experience your own. The flexibility of a private charter allows customization of virtually any aspect of the sailing adventure from guest list to music selection to sailing route. Three departure times offered daily. This experience is not meant to be an in-depth guided tour; however, our captain is always happy to point out interesting sights with anecdotes and historical information. Just ask you captain. Looking for a sunset sail, see our other product listing "Come Sailing with us at Navy Pier - Sunset Sail on Lake Michigan". Looking to watch the Navy Pier Fireworks from a private sailing charter, see our other product listing "Come Sailing with us at Navy Pier - Saturday Fireworks Sail". All charters are NON-SMOKING experiences.

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 $35 Tour Provided by Viator
5.00 (43 reviews)

Chicago Walking Tour: Connecting Past and Present

This lively overview of Chicago architecture explores iconic buildings from the 1890s to present. We'll compare and contrast a wide range of buildings with varying architectural styles and see how older structures connect to new skyline additions. On this tour, we'll make seven stops in downtown Chicago where we can compare the histories and styles of buildings located within sight of each other. The tour features 19th-Century Commercial, Beaux-Arts, Mid-Century Modern and Postmodern buildings, as well as the latest in architecture from Frank Gehry, Renzo Piano and Adrian Smith. At each stop, we’ll look at the connections between the past and present and discover what inspires design today. The tour culminates with a visit to Millennium Park, where world-class art and architecture combine, creating a unique urban fabric. As a certified nonprofit, all CAC ticket purchases directly support our education efforts and community engagement projects.

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 $30 Tour Provided by Viator
5.00 (39 reviews)

Chicago Haunts and Hooligans Tour

Nightly Spirits’ Haunts and Hooligans Tour will illustrate Chicago’s haunted history of secret parlors, underground tunnels, murderous movie theaters and supernatural speakeasies. Whether you’re a recent transplant to Chicago or have lived among the Windy City’s ‘others’ for years, you’re about to get a haunted history that may leave you with more memories than you dare to retain.   Tours begin at the haunted Harry Caray’s Italian Steakhouse in downtown Chicago. A costumed guide will lead tour goers on a walking journey exploring the creepy past of one of Chicago’s most famous bootleggers, offering glimpses into the past and revealing the stories of long-dead phantoms and specters who still call Chicago home.

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 $90 Tour Provided by Viator
5.00 (38 reviews)

Chicago Shoreline Adventure Boat Tour

This tour is the perfect way to experience the shoreline of Chicago in a new and exciting way! Our tour vessel is a former military Williard Marine, which provides a unique and interesting touch to the normal tour experience. Being both sturdy in the water, and fast! Reaching up to speeds of 35 Knots! We work hard to provide historical context for our great city, as well as provide an exhilarating experience through the use of high speed runs and spins!

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 $169 Tour Provided by Viator
5.00 (31 reviews)

Chicago Photo Walk to Bean and Landmarks

We’ll begin our photo walk in Millennium Park with portraits at Cloud Gate (The Bean), one of Chicago’s most iconic landmarks. During our time together, we’ll visit a rooftop spot for skyline views, cross the scenic DuSable Bridge, and stop by the elegant Wrigley Building - all perfect for beautiful photos. Along the way, I’ll guide you with natural poses and creative ideas, helping you feel relaxed and confident. By the end of this walk, you’ll not only have a beautiful photo gallery - you’ll have also visited many of the MUST-SEE places in downtown Chicago.

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 $315 Tour Provided by Viator
5.00 (22 reviews)

Chicago Scenic Driving Tour

Chicago is a big city with a lot of activities & sightseeing. To tour the city quickly, it requires the help of a knowledgeable local driving guide and that's where we step in to assist. Your Private Chicago Scenic Driving Tour will start by meeting our knowledgeable Guide/Driver who will pick you up at your hotel or other location provided and then proceed with the exploration of the beautiful windy city.

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 $30 Tour Provided by Viator
5.00 (21 reviews)

History and Architecture of Chicago Loop Walking Tour

Discover the rich history and architecture of downtown Chicago with local expert Dave Lineal. Walking underneath the soaring buildings, we will learn how Chicago grew to become a global force in culture, commerce, and architecture. How did this roaring city come to be? We will hear the tales of Chicago history immersed in the places where it happened -- exploring historic building interiors like the world's oldest skyscrapers, City Hall, and the old library. This deep dive in city history and architecture aims to deepen our appreciation of what Chicago is today.

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 $160 Tour Provided by Viator
5.00 (20 reviews)

O'Hare Airport Transfer to Chicago, Curbside - Luxury SUV

Chicago’s top-rated limo and car service — with 16+ years of proven service, licensed drivers, and full commercial insurance. Enjoy a safe, private transfer between Midway Airport (MDW) and any destination within Chicago city limits. All chauffeurs are fully uniformed, background-checked, and trained for professionalism and safety. Vehicles are equipped with GPS tracking and dispatch monitors every trip. Upon arrival, you’ll receive a text with your driver’s details. At the airport, meet your driver curbside after exiting baggage claim. Skip the hassle of taxis, shuttles, or rideshares — and travel in a clean, comfortable, late-model private sedan. Ideal for business or leisure travelers, solo riders or families. 24/7 support. Chicago-based and proud to be a 5x Certificate of Excellence winner on TripAdvisor. Reliable. Professional. Local.

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 $163 Tour Provided by Viator
5.00 (20 reviews)

Private Chicago History Museum Tour

Our private walking tour of the Chicago History Museum offers a personalized, in-depth experience led by expert guides who bring Chicago’s vibrant past to life through captivating stories, insider insights, and exclusive information tailored to your interests.

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