Top Illinois On the Water - page 3

Set sail on a private fireworks cruise along the Chicago Lakefront aboard a meticulously maintained sailing yacht. Enjoy complimentary drinks or BYO. Perfect for summer birthdays, romantic proposals, anniversaries, and any reason to celebrate Summertime Chi!

Soak up unbeatable views of Lake Michigan and the Chicago skyline—and stay on the water long enough to watch the lights come on in the city—on this private, sunset sailing tour. This charter is completely customizable, giving you the chance to choose your music, route, and up to five additional guests. Sail into the sunset with your own drinks and snacks (refrigerator and ice on board) and your family or friends by your side, all led by US Coast Guard–certified captain.

Chase away your Monday blues with Chicago’s coolest concert at sea! Hop aboard the historic Tall Ship Windy for a 2-hour live blues music cruise on Lake Michigan, featuring city skyline views and a rotating roster of top local and international artists. With a full-service bar and plenty of space to move, relax, and dance, this floating music event blends unbeatable atmosphere with legendary sounds—perfect for date nights, group outings, or music lovers looking for a summer highlight. VIP boarding upgrades and kid discounts available. Book early; these shows sell out fast!

Arrange for a stress-free ride to O'Hare International Airport (ORD) or Midway Airport (MDW) with this private transfer service. Meet your professional chauffeur at your hotel in downtown Chicago (or other Chicagoland destinations), and relax on the journey to the airport in a private sedan or minivan. You can leave the navigation to someone else, and reach the airport relaxed and in time for your flight.

Get ready for the most complete adventure the city has to offer—an immersive Full Day Chicago Food Tour and Walking Tour that blends Chicago’s legendary flavors with its most iconic landmarks. Savor Chicago Pizza, Hot Dogs, Italian Beef, Garrett’s Chicago Mix Popcorn, and the original Palmer House Brownie, or elevate your day with our VIP craft beer upgrade. This unforgettable Chicago in a Day Tour explores Millennium Park, the Chicago Riverwalk, Michigan Avenue, Cloud Gate, Chicago Theater, and more, guided by true local experts. Enjoy a 5-hour journey through culture and cuisine, plus a FREE 2-hour bike or kayak rental to continue the adventure along Lake Michigan. Recently honored among the “Top 10 Food Tours in America” (USA Today) and “Top 20 Food Tours in the World” (TripAdvisor), this award-winning Culinary Tour is one of the top Things to do in Chicago. Don’t miss the most delicious, scenic Full Day Food Tour in Chicago—all in one extraordinary day.

Our tours have varying difficulty levels to accommodate different skill levels. We take every safety precaution available to prioritize your well-being. Our routes that take you to must-see attractions and beautiful destinations. The Bahāʾī temple that we will pass is listed on the National Register of Historic Places and the only Bahāʾī place of worship in North America. This weekend vacation to Milwaukee is a vibrant mix of urban excitement and nature. Notable spots that riders can visit are the Milwaukee Art Museum, the National Bobblehead Hall of Fame Museum, and the Black Holocaust Museum. The city is also home to over 40 breweries, with iconic names like Schlitz and Pabst leading the way. On the ride you'll traverse mostly flat terrain that shifts between suburban areas and secluded bike paths. Expect southward winds along the lake, be prepared to experience some headwinds during your ride. Roads: 79% paved, 21% trails Distance: 74.6 miles Elevation: +963 ft/ - 1,058 ft

Admire a side of Chicago that few other visitors get to experience—and enjoy a relaxing trip out on the water, tailored to your party—with this private sailboat charter and sailing tour. You and up to five other guests will have the exclusive use of a sailboat, complete with a captain for the duration of your tour. Sail on Lake Michigan and enjoy the sights of Chicago’s striking skyline. If you want, you can even take a turn at the helm.

See Chicago’s legendary Air & Water Show from the best seat in the city! Secure a VIP spot on a Lake Michigan cruise (or Skydeck viewing party) and watch the U.S. Air Force Thunderbirds, Golden Knights, and dazzling stunt pilots soar overhead. Enjoy premium amenities, from fast-track boarding to reserved seating, up-close views, and included food or drinks (per package). With unmatched photo ops and the sound of jets flying overhead, this is a must-see experience for locals and visitors alike—just in time for summer’s biggest Chicago festival. Book early; these shows always sell out fast.

JT and the team ensures a seamless, guided experience, whether you're a seasoned angler or a first-timer. Enjoy satellite entertainment and hi speed wifi for those last minute video conference calls. Our commitment to comfort, elegance, and excellence sets us apart in every detail. From sunrise departures to golden hour returns, every moment is tailored for exclusivity. Whether you're celebrating a milestone or escaping the ordinary, we make every trip unforgettable. Discover what it means to fish luxuriously—reserve your elite charter today.

Looking for something truly local, active, & unforgettable for your kids while you explore Chicago? Bobby’s Chicago Kids Camp is a one-of-a-kind day camp Chicago experience designed with both visiting families and locals in mind. While you enjoy adult time—deep dish at Lou Malnati’s, a stroll through the Art Institute, or an adult-oriented bike tour up to Wrigley—your child is biking the lakefront, kayaking calm waters, & making new friends at the best summer camp in Chicago. Our camp blends active outdoor fun with real Chicago stories. Campers visit landmarks like Millennium Park, the Lincoln Park Zoo, & Buckingham Fountain—learning fun facts & building confidence along the way. We offer flexible booking by the day or week, with half-day & full-day options—perfect for travelers building an itinerary. It’s not just a Chicago kids camp—it’s a chance for your child to experience the city like a local, while you enjoy some grown-up adventure of your own. Book your kids adventure today