It’s a city known for its bold architecture, iconic skyline, rich history and beautiful lakefront.
With so much to see across Chicago, it’s no surprise that there are countless ways to get around and take in the sights. Whether it’s an educational tour through the city’s interior or a relaxing ride along Chicago’s famed Lake Michigan shoreline, these excursions offer can’t-miss insight and entertainment for an unforgettable Chicago vacation.
Dinner with a View on an Odyssey Cruise
Step just outside the city to take in the full, sweeping skyline from one of the best vantage points: Lake Michigan. Cruise aboard Odyssey at Navy Pier and venture out onto the water for an elegant dining experience where the city skyline is your backdrop. Enjoy a multi-course meal complemented by drinks, music and dancing. Toast champagne on the rooftop, or feast with friends in one of three dining decks. Odyssey’s varied themed cruises, such as “Prix Fixe Dinner” and “Sunday Brunch,” are available year round. In the summer, see the skyline illuminated under a show of fireworks on an Odyssey Fireworks Dinner Cruise. It’s a truly unique-to-Chicago experience.
Toasting with friends on an Odyssey Cruise
By Land with Big Bus Tours
Cruise through the city with ease on Big Bus Tours Chicago. This double-decker ride offers up-close views of Chicago’s skyscrapers, historic buildings and iconic institutions. Warm and welcoming local guides will talk you through your journey with memorable storytelling, adding a personal touch to your tour. Take a seat on the first floor to enjoy a climate-controlled ride, or head upstairs for the full wind-in-your-hair, panoramic experience. When something piques your interest, just hop off the bus and explore (and hop back on when you’re ready to continue the tour). Big Bus is one of the easiest ways to get to know Chicago.
View from the top deck on a Big Bus Tour
Skylines and Skyscrapers with Shoreline Sightseeing
So much to see, so little time. That’s why Shoreline Sightseeing, the largest tour boat fleet in Chicago, offers different tours at different departure times, all day long. Take your pick of tour themes, from “Architecture” to “Classic Lake,” or hop on one of their water taxis to get to Chicago’s popular sites, such as Museum Campus and Navy Pier. Shoreline Sightseeing really shines with their themed and special events cruises which feature wine tasting, stand-up comedy, craft brews and more.
Visiting Chicago attractions via Shoreline Sightseeing tours
All About the Details on the Chicago Architecture River Tour
Get a river-level perspective of the city’s spectacular buildings on a Chicago Architecture Foundation River Cruise aboard Chicago’s First Lady Cruises. Coasting on the Chicago River, the 90-minute tour cuts through downtown to give you an up-close view of the towering skyscrapers. Pass by historic buildings and new designs, while knowledgeable docents explain the changing architectural landscape of the city. This is the only tour to partner with the Chicago Architecture Foundation, and it was named one of the top 10 tours in the U.S. by TripAdvisor reviewers.
Listening to a docents on First Lady Cruises
More experiences nearby
7 Festivals to Boogie to the Blues
Chicago's Exciting Attractions
Chicago's Famous Magnificent Mile
City Tour - Chicago, Illinois
7 Spots for Family Fun Around the USA
Top Cycling Spots in the USA