Jake & Bryan
Things To Do
Take a Boat Tour!
-Chicago Architecture Foundation Center River Cruise aboard Chicago’s First Lady -Lakefront Speedboat Tours from Seadog Cruises -Classic Skyline Lake Tour with Shoreline Sightseeing -Dinner Cruise on the Chicago River with City Cruises
Go to the Beach!
Chicago has more than two dozen free public beaches, and they officially open for the summer season on Memorial Day weekend — we actually don't recommend going for a swim though, because the average water temperature in May is below 50 degrees.
Explore the Lakefront Trail!
The 18-mile Lakefront Trail hugs Lake Michigan and is a popular place for walkers, bikers, and hikers all year long. The scenic path connects to boat harbors, nature sanctuaries, waterfront restaurants, boardwalks, and cultural gems like the South Shore Cultural Center, the Museum of Science and Industry, and the Nature Museum. It’s also a great way to access Chicago’s beaches, which open Memorial Day weekend.
Check out Cloud Gate (a.k.a. The Bean)
If you're visiting Chicago, be sure to check out The Bean (officially called Cloud Gate) in Millennium Park. It's a striking, reflective sculpture that offers great photo opportunities and a fun way to experience the city’s skyline. The polished surface reflects both the city and the sky, making it a must-see landmark for any visitor.
Visit the Museum of Science and Industry
At the Museum of Science and Industry, expect interactive exhibits on science, technology, and history. Highlights include a real WWII U-boat, a coal mine replica, space exploration displays, and hands-on activities for all ages. It’s a fun and engaging experience that’s perfect for exploring science in a unique way.
Experience the Skydeck @ Willis Tower (f.k.a. — but always known as — the Sears Tower)
The Skydeck at Willis Tower offers stunning, 360-degree views of Chicago from 1,353 feet above ground. As a visitor, you can enjoy breathtaking panoramas of the city, Lake Michigan, and beyond. For an extra thrill, step out onto The Ledge, a glass-enclosed balcony that lets you look straight down. It's an unforgettable experience that provides a unique perspective of the Windy City. (Jake loved the Skydeck; Bryan, not so much.)
5/24/25: AC/DC at Solider Field
For the first time in nine years, legendary rock band AC/DC will tour in North America beginning in 2025, including a stop in Chicago the night before our wedding.
5/26/25: Memorial Day Fireworks at Navy Pier
One of the city’s top attractions is Navy Pier, a waterfront stretch of rides, restaurants, entertainment, and more. The Pier is known for its spectacular summer fireworks displays, which kick off with the Memorial Day fireworks show. While you’re there, take a spin on the iconic Centennial Wheel, grab a drink at Offshore (the largest rooftop bar in the world), and check out more things to do at Navy Pier.