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TripSavvy's editorial guidelines Updated on 05/17/19 Share Pin Email We independently research, test, review, and recommend the best products—learn more about our process. If you buy something through our links, we may earn a commission. The Rundown Best Bus Tour: Chicago Crime and Mob Tour – Buy Tickets at Viator "Gain in-depth knowledge of Chicago’s notorious gangster history." Best Dinner Cruise: Chicago Sunset Dinner Cruise – Buy Tickets at Viator "The luxury boat sails past Soldier Field and Buckingham Fountain and offers stunning views of the city skyline." Best Night Tour: Chicago Segway Night Tour – Buy Tickets at Viator "The small group tour is limited to just eight people and is a great way to mingle with other travelers." Best Aerial Tour: Chicago Helicopter Tour – Buy Tickets at Viator "You’ll get to see the famous buildings and landmarks such as the Willis Tower, the Navy Pier, Wrigley Field, Lincoln Park and more." Best Walking Tour: Historic Skyscrapers Chicago Walking Tour – Buy Tickets at Viator "The tour is led by an expert guide from the Chicago Architecture Foundation and will provide in-depth information about the cityscape." Best Food Tour: Famous Tastes of Chicago Food Tour – Buy Tickets at Viator "Sample some of the best dishes Chicago has to offer." Best Architecture Cruise: Lake Michigan & Chicago River Architecture Cruise – Buy Tickets at Viator "Combine a leisurely architecture voyage with a thrilling speedboat adventure." Best Bar Crawl: Chicago Prohibition Tour – Buy Tickets at Viator "Board an air-conditioned bus as it transports you to watering holes in Old Town, Wicker Park and the Chicago Loop." Best Bike Tour: Chicago Lakefront Neighborhoods Bicycle Tour – Buy Tickets at Viator "The three-hour tour explores city parks, hidden streets and beaches beginning with Lakefront Drive." Best Bus Tour: Chicago Crime and Mob Tour Getty Images Buy on Viator.com The stories of Chicago’s underworld have fascinated visitors and has been the subject of many films, books and other media. On the 90-minute Crime and Mob Tour, you can gain in-depth knowledge of Chicago’s notorious gangster history. Travelers will cruise around the city in a comfortable, air-conditioned bus to the old stomping grounds of Al Capone, the Untouchables, Hymie Weiss and John Dillinger, as well as many other outlaws while the guide provides narrative to the locations. The tour stops at famous places, including the site of the St. Valentine’s Day Massacre, Holy Name Cathedral, Biography Theatre, the Clark Street Bridge and more, with a chance to hop out and take some photos. Best Dinner Cruise: Chicago Sunset Dinner Cruise Viator Buy on Viator.com If you’re looking for a fun and relaxing way to see Chicago from a different point of view, the Chicago Sunset Dinner Cruise is the tour to book. The three-hour-long tour blends a fabulous buffet dinner, sightseeing and dancing as you coast through the waters of Lake Michigan. The luxury boat sails past Soldier Field and Buckingham Fountain and offers stunning views of the city skyline. The buffet dinner includes starters such as mixed greens, kale, beets, shrimp, or couscous salad, followed by main choices like north Atlantic sole filet, sesame chicken, pork loin or short ribs. It's all finished off with desserts such as apple cobbler, chocolate cake or cheesecake. After dinner, a live DJs performs as everyone heads to the dance floor. Best Night Tour: Chicago Segway Night Tour Viator Buy on Viator.com For a way to get outdoors and see the city of Chicago at night without having to walk or ride a bike, consider the Chicago Segway Night Tour. The city becomes illuminated in the evening with beautiful lights, and the two-hour tour lets travelers experience some of the most stunning sites and landmarks after dark. The small group tour is limited to just eight people and is a great way to mingle with other travelers. Some stops include the Navy Pier, Buckingham Fountain in Grant Park, the sprawling Museum Campus and Lincoln Park, with informative narration from the guide. Viator members felt that the Segways were very easy to use after the initial lesson. Best Aerial Tour: Chicago Helicopter Tour Viator Buy on Viator.com For a birds’ eye view of the city and to get a lay of the land, the Chicago Helicopter Tour is a great brief introduction to the city. The tour includes 15 minutes of flight time where you’ll get to see the famous buildings and landmarks such as the Willis Tower, the Navy Pier, Wrigley Field, Lincoln Park and more. The pilot offers informative and fun commentary through noise-canceling headsets during the flight, and after the adventure, you can “pilot an aircraft” in an interactive flight simulator at the guest center. Viator members stated that although short, the flight was a highlight of their trip to Chicago. Best Walking Tour: Historic Skyscrapers Chicago Walking Tour Getty Images Buy on Viator.com For an affordable way to learn about Chicago’s mesmerizing architecture, join the Chicago Historic Skyscrapers Walking Tour, – a budget-friendly, two-hour experience. The tour is led by an expert guide from the Chicago Architecture Foundation and will provide in-depth information about the beginning of the Chicago School of Architecture as you explore skyscrapers that were built between the 1870s and the 1930s. The tour also visits several buildings like The Rookery, a (National Historic Landmark), the Auditorium Building, a masterpiece from Louis Sullivan and the Art Deco-era Chicago Board of Trade Building. Viator members felt that the tour guides fit an incredible amount of information in a short time and that it was a terrific value. Best Food Tour: Famous Tastes of Chicago Food Tour Viator Buy on Viator.com Foodies will fall in love with the Windy City’s eclectic array of dining options, and on the Famous Tastes of Chicago Food Tour, you’ll sample some of the best dishes Chicago has to offer. On the three-hour, small-group walking tour, travelers will not only learn about the cuisine of Chicago but the history and architecture as well. Restaurant stops include Berghoff, the oldest family run-establishment in Chicago known for German cuisine, Pizano’s Pizza for a taste of the famous deep-dish pizza, Fannie May Chocolates, Sugar Bliss Cake Boutique for cupcakes, Al’s Beef for a famous beef sandwich and more. The tour explores the central business district, the Loop, and includes a stop at the Chicago Cultural Center. Best Architecture Cruise: Lake Michigan & Chicago River Architecture Cruise Viator Buy on Viator.com One fabulous way to view Chicago’s famous architecture is on the water and a number of boat cruises offer guided insight and front row seats to the stunning skyline. You can combine a leisurely architecture voyage with a thrilling speedboat adventure on the Architecture Cruise and Speedboat Tour. The 75-minute river and lake cruise begins with a relaxed trip up the river to view and learn about landmarks, including the Willis Tower and the Tribune Tower. After that, board a speedboat and cruise along the shoreline of Lake Michigan past Grant Park (home to Buckingham Fountain), the Chicago Harbor and the Museum Campus. The tour departs from the legendary Navy Pier. Best Bar Crawl: Chicago Prohibition Tour Viator Buy on Viator.com For a twist on the typical bar crawl, the Chicago Prohibition Tour incorporates the rebellious era of the 1920s when alcohol was banned and hidden speakeasies cropped up all over the city. Board an air-conditioned bus as it transports you to watering holes in Old Town, Wicker Park and the Chicago Loop to learn about gangsters, underground speakeasies and how Prohibition came to be, as well as what life was like during the 10-year period. The 3.5-hour tour includes stops to historic bars, including the Green Door Tavern (built in 1872) and Exchequer Pub for a total of four stops. Although a printed drink recommendation card is provided, the drinks are an additional charge. Best Bike Tour: Chicago Lakefront Neighborhoods Bicycle Tour Getty Images Buy on Viator.com Bike tours of Chicago are a great way to cover a lot of ground outside in a short time – without being confined to a bus, and the Chicago Lakefront Neighborhoods Bicycle Tour is a fantastic option for exploring Chicago’s north side. The three-hour tour explores city parks, hidden streets and beaches beginning with Lakefront Drive and passing through the Magnificent Mile and the Historic Old Town District. You’ll catch a glimpse of celebrity sites, including the Playboy Mansion, Oprah Winfrey’s house, St. Michael's Church and beautiful brick mansions. The guided tour covers around nine miles with interesting information and facts woven into the bike ride. One Day in Chicago: The Perfect Itinerary Was this page helpful? Thanks for letting us know! Share Pin Email Tell us why! Submit Continue to 5 of 9 below. Continue to 9 of 9 below.