Chicago’s Architecture & Sightseeing Tours

Explore Chicago’s exciting attractions, historic landmarks, museums, magnificent architecture, shopping districts, theaters, art galleries, neighborhoods and majestic waterfront on the many exciting sightseeing tours on land and lake. From free trolley and walking tours to double-decker bus trips, boat cruises, and guided architecture tours, the beauty and history of Chicago comes to life before your eyes. Chicago’s amazing architecture tours and boat cruises illuminate the city’s architectural and industrial heritage, showcasing the city’s modern architectural marvels, historic landmarks and the world’s tallest skyscrapers.

Chicago Architecture & Sightseeing Tours Packages. Our Hotel Indigo Chicago Concierge can arrange your sightseeing tour, boat cruise or private charter and offer you a special discount rate. Let us help you design Chicago sightseeing and tour packages that fit your curiosity and craving. 

Please Call the Hotel at 866-521-6950 to inquire about Packages

Chicago’s top sightseeing and architectural tours

• Loop the Loop. Discover downtown Chicago through free audio walking tours of “The Loop” - Art Loop, Theater Loop and Landmark Loop. The Loop is a dynamic district of theaters, shops, museums, landmarks, and Chicago’s symbolic architecture. The tour stops at Millennium Park, Chicago Art Institute, State Street Shopping District, Field Museum and Navy Pier.
• Chicago Trolley Co. Enjoy Chicago's hop-on, hop-off city sightseeing tours in classic trolleys and double-decker buses. Take an entertaining 2-hour tour of the Chicago’s attractions, shopping, and dining venues. With your Hop On Hop Off ticket, you’ll enjoy a narrated tour that covers 13 miles of Chicago's downtown and The Loop. Call 773-648-5000 or visit www.chicagotrolley.com.
• Spirit of Chicago. Departing from Navy Pier, Spirit of Chicago features a Lake Michigan skyline cruise with dining, dancing and entertainment. Enjoy a lunch buffet cruise, plated dinner cruise, midday celebration cruise, or midnight moonlight cruise. See famous sites such as Sears Tower, Buckingham Fountain, McCormick Place, and Shedd Aquarium, while enjoying live entertainment and dining.
• Wendella Boat Tours. Capture the essence of Chicago and learn about the city’s architecture and history on narrated sightseeing boat tours on Lake Michigan, Chicago River, and Chicago Lock. Experience Chicago's architectural heritage, including the Wrigley Building, Chicago's architectural treasure, on the Chicago River Architectural Tour. Call 312-337-1446 or visit www.wendellaboats.com.
• Shoreline Sightseeing Tours. Shoreline Sightseeing offers exciting boat cruises, water taxis and charter tours of Chicago, departing from Navy Pier, Shedd Aquarium and Buckingham Fountain. The ½-hour Skyline Boat Tour on Lake Michigan showcases Chicago's skyline and landmarks. The Architecture Cruise travels on the historic Chicago River past celebrated buildings. Visit Chicago's popular destinations by water taxi, private charter boat or on a dinner cruise with music and dancing. Call 312-222-9328 or visit www.shorelinesightseeing.com.
• Chicago Architectural Cruise. Enjoy a one-hour boat cruise on the historic Chicago River that highlights city’s most famous architectural landmarks. Guides recount the dramatic story of Chicago's rise from the Great Fire of 1871 to become the home of the skyscraper and the cradle of modern American architecture. Visit www.chicagotours.us.
• Chicago Architecture Foundation Tours. Experience Chicago’s incredible architecture on boat, bus, walking and bike tours by the Chicago Architecture Foundation. Discover the diversity of Chicago’s finest buildings on this fascinating odyssey, which covers miles of Chicago architecture, historic districts, university campuses, parks, neighborhoods, and modern art deco skyscrapers. Call 312-922-3432 or visit www.architecture.org.
• American Sightseeing Tours. Hop on board one of the many exciting bus tours that wind through Chicago. These tours explore Chicago’s interesting landmarks and neighborhoods, such as North Side, South Shore, The Loop, Sears Tower, State Street, Grant Park, Soldier Field, Orchestra Hall, Grant Park, the Lake Michigan shoreline, Chinatown, Lincoln Park Conservatory, Adler Planetarium, and the Chicago River. Call 312-251-3100.
• Tall Ship Windy. Tall Ship Windy is Navy Pier's 148-foot, four-masted schooner. Embark on 90-minute cruises, charter and educational trips offered each day. The traditional American schooner ship pays tribute to the Great Lakes' rich maritime heritage and holds up to 150 passengers who are encouraged to help raise and trim her 11 sails and take turns at the ship's wheel. Cruises are available daytime and evenings from May to October. Call 312-595-5555 or visit www.tallshipwindy.com.
• Seadog I, II, III and IV. Cruise Lake Michigan on the 70-foot-long Seadog vessels - four of the fastest speedboats in the country. Departing from Navy Pier's Dock Street, you’ll enjoy fun 30-minute cruising adventures along the lakefront with 15 feet of cool spray shooting from the sterns. They also offer 75-minute architectural tours Call 312-822-7200 or visit www.seadogcruises.com.