Make the most of warm summer weather by getting groups out on the waterfront. Whether your groups want to experience Chicago architecture boat tours or Chicago River tours — or even sunset dinner cruises — there are a number of options to choose from when crafting that perfect day on the water. Afterward, head to one of Chicago’s lively waterfront restaurants for an unforgettable dining experience.
Chicago architecture boat tours
Chicago First Lady Cruises
As the official cruise line of the Chicago Architecture Foundation, expect an informative and professional experience as groups are introduced to the architecture and design of more than 50 buildings, with the guidance of a CAF-certified volunteer. Open-air and air-conditioned seating is available. Tours depart from Chicago Riverwalk, 112 E. Upper Wacker Drive
Chicago Line Cruises
Book Chicago Line Cruise‘s tour, presented by Chicago’s oldest museum: the Chicago History Museum River Cruise. This 90-minute cruise will present fascinating facts and insight into Chicago’s history and architecture. Tours depart from 465 N. McClurg Ct.
Groups on Shoreline Sightseeing cruises will get a new appreciation for Chicago’s dramatic skyline with a Night Architecture Tour, showcasing buildings by world-famous architects all along the three branches of the Chicago River. Tours depart from Navy Pier’s Polk Bros Park and Michigan Ave. Bridge
Wendella Tours & Cruises
Book Wendella‘s Chicago’s Original Architecture Tour, a 75-minute architecture and history tour that takes groups through all three branches of the Chicago River. Tours depart from the Wendella Dock, 400 N. Michigan Ave.
Kayaking in Chicago
Chicago Water Sport Rentals at 31st Street Harbor
For active groups looking to enjoy the waterfront, rent kayaks and explore Lake Michigan with a morning of paddling. 3155 S. Lake Shore Drive
Rent kayaks or take a guided tours of the Chicago River or Lake Michigan with Urban Kayaks. They offer various guided tours, including sunset and historical paddles, plus paddleboard rentals. 435 E. Chicago Riverwalk and 111 N. Lake Shore Drive.
Specialty cruises in Chicago
Book the tour company‘s most popular cruise, The Urban Adventure Cruise, giving groups a glimpse at the skyline and historic buildings while traveling along the Chicago River and Lakefront Harbor. Discounts are offered for groups of 20 or more. Tours depart from Riverside Gardens, 112 E. Upper Wacker Drive
On Mystic Blue, groups can enjoy breathtaking views from the largest picture windows of any ship on Navy Pier, and the three enclosed climate-controlled decks and modern rooftop lounge ensure a comfortable, upscale environment while enjoying a lunch, brunch or dinner cruise. Tours depart from Navy Pier, 600 E. Grand Ave.
Odyssey Lake Michigan
Lakefront dining and exciting sightseeing are seamlessly combined during an upscale cruise, featuring brunch, lunch, or dinner options. Guests will enjoy a gourmet meal while sailing along Lake Michigan, and a live DJ will keep the vibe fun yet relaxed. Tours depart from Navy Pier, 600 E. Grand Ave.
This high-speed thrill ride is an adrenaline-pumping way to experience Lake Michigan. Seadog Cruises offers exciting speedboat rides, architecture and river tours, and extreme thrill rides. They also have lakefront fireworks tours during the summer. Be prepared to get wet. Tours depart from Navy Pier, 600 E. Grand Ave.
Spirit of Chicago
For lively groups, book the Spirit of Chicago‘s Eat, Drink & B. Mary Brunch Cruise, available on Sundays. This buffet-style brunch on Lake Michigan features a build-your-own Bloody Mary bar with fun options such as bacon-infused vodka and antipasto skewers. Tours depart from Navy Pier, 600 E. Grand Ave.
Navy Pier is a lakefront favorite, and one of Chicago’s top attractions. Navy Pier offers groups of 20 or more discounted tickets to Navy Pier-produced events and attractions, plus Food Court Certificates that provide a selection of meal options at various Navy Pier eateries. Reach for the sky on the Centennial Wheel, riding in temperature-controlled gondolas that soar 200 feet up in the air. Catch a cool 3-D flick at the AMC Navy Pier IMAX theater. Or see a show at the Chicago Shakespeare Theater. The Yard at Chicago Shakespeare Theater is a unique year-round theater venue, made up of mobile towers that can be configured into a variety of shapes and sizes, accommodating audiences ranging from 150 – 850 people.
Explore the pedestrian-friendly Chicago Riverwalk, which stretches from Lake Shore Drive to Lake Street. This all-seasons hot spot is where you’ll find public art, boat tours, kayak rentals, and more. Stop for a bite to eat at one of the waterside restaurants, including City Winery Chicago Riverwalk, with its signature wines, Mediterranean paninis, and beautiful waterside garden; steak sandwiches and vodka lemonade at O’Brien’s Riverwalk Café; and Tiny Tapp Riverwalk, known for its gourmet sliders and craft cocktails.
Chicago Lakefront Trail
The scenic Chicago Lakefront Trail stretches for 18 miles along Lake Michigan and is lined with beautiful parks, boat harbors, and beaches (Oak Street and North Avenue are great for people watching). Take time to sun on the sand at 31st Street Beach or gather the group for stand-up paddle boarding in the harbor with Chicago Water Sport Rentals. Don’t miss Northerly Island, a manmade peninsula that juts into Lake Michigan and features nature paths for strolling, as well as the outdoor Huntington Bank Pavilion that hosts big-name summertime concerts.
Rent some wheels and join the Lakefront Neighborhoods Bike Tour hosted by Bobby’s Bike Hike Chicago, with private group tours available. Or glide along the waterfront with Absolutely Chicago Segway Tours. Choose the Chicago Lakefront Museum Campus Tour or opt to have a private tour specially customized for your group.
Waterfront restaurants in Chicago
Castaways Bar & Grill
Bring groups to the rooftop at this North Avenue Beach bar and grill, where diners can look out onto the bustling beachfront while noshing on sandwiches and fresh salads. Or, head down to the first level to grab a scoop at the ice cream café. 1603 N. Lake Shore Drive
The Dock at Montrose Beach
Paninis, wraps, and tacos are served at this casual beachfront eatery, where a lineup of live music rocks the beach all summer long. 200 W. Montrose Harbor Drive
Groups will love the lively vibe at this beachfront restaurant at Ohio Street Beach, where lakefront views are paired with casual fare such as salads, burgers, and flatbreads. 550 E. Grand Ave.