Chicago, Illinois: 3 Adventures on the City’s Waterways

There are few better ways to take in Chicago’s world-class architecture than via a bike ride along Lake Michigan on the city’s Lakefront Trail. Start at bustling Navy Pier before rolling southbound through Maggie Daley Park and Millennium Park and past postcard-ready Buckingham Fountain in Grant Park. Wrap up at the Museum Campus to take in phenomenal Chicago skyline views. Navy Pier is also a prime starting point for on-the-water exploration, like a laid-back architecture cruise, a thrilling speedboat ride or a sailing trip on Lake Michigan.

For more fun, you can also wander Navy Pier. Start with a scenic spin on the Centennial Wheel, built in honor of the very first Ferris wheel that was invented for the Chicago World’s Fair. Attend live theater at Chicago Shakespeare Theater or treat young travelers to an action-packed visit to Chicago Children’s Museum. Every Wednesday and Saturday from Memorial Day to Labor Day, Navy Pier hosts fireworks that light up the night sky.

The blue stripes on Chicago’s flag represent the city’s waterfronts, including the Chicago River, which flows right through downtown. Rent a kayak or take a guided tour with an experienced outfitter like Urban Kayaks to paddle the Chicago River through the heart of the city. You’ll get an immersive look at the city’s natural beauty and architectural wonders. For a more leisurely experience, the Chicago Architecture Center hosts daily cruises down the Chicago River. Tour guides tell the city’s story through its famous buildings, from the curvilinear 82-story Aqua Tower to the showstopping Wrigley Building, known for its Spanish Colonial Revival details.

Chicago’s Riverwalk offers 2 kilometers of walkable waterfront, complete with restaurants, bars, art, museums and places to just relax and take in the view. Stroll this pathway along the river’s south bank for plenty of festive vibes and city views. Take a break at City Winery, a one-stop destination for sipping wine, people watching and live music right along the riverfront. For an educational detour, learn the story of Chicago’s bridges and waterways with a trip to the McCormick Bridgehouse and Chicago River Museum. Start your tour at river level where you’ll see the gears of the drawbridge at work. Then, continue through exhibits culminating with a sweeping view of the city from the top of the bridge house. The Chicago Riverwalk also makes plenty of room for nature. There’s an abundance of green spaces along the walkway, from the River Theater with trees sprouting from its steps, to the Centennial Fountain at the Water Plaza, as well as floating gardens.

Chicago O’Hare (ORD) and Chicago Midway (MDW) international airports both offer plenty of flights from destinations around the world. Rental cars are available, but Chicago has a convenient network of public transit options that makes it easy to get around.