10 Favorite Things to Do on the Water in Chicago This Summer

Nautical Miles Team
Jun 1
3 min read

Updated: Jun 7

Chicago is known for its stunning skyline, vibrant culture, and beautiful lakeside setting. As summer rolls in, the city’s waterfront offers an array of exciting activities for locals and visitors alike. Whether you’re looking to relax, explore, or embrace adventure, there’s no shortage of things to do on the water. Here are 10 of our favorite ways to enjoy Chicago’s aquatic beauty this season!

1. Architectural Boat Tour

Chicago is home to one of the world’s most iconic skylines. A guided boat tour along the Chicago River will offer a fresh perspective on the city’s stunning architecture, with knowledgeable guides sharing fascinating stories behind the buildings.

2. Yacht Charter with Nautical Miles Yacht Charters

For those looking to experience the lake in style, a private yacht charter with Nautical Miles Yacht Charters is the ultimate way to soak in the sights of Lake Michigan and the Chicago skyline.

Whether you’re hosting a social or corporate event, enjoying a sunset cruise, looking to experience a spectacular view of the Navy Pier Wednesday & Saturday fireworks, or simply getting away for a few hours of relaxation, a Nautical Miles charter experience offers luxury, privacy, and incredible views. With options ranging from intimate cruises to themed special events, you can customize your experience and create memories that will last a lifetime.

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3. Dinner Cruise

Combine dinner with a scenic cruise on Lake Michigan. Nautical Miles, in partnership with Lettuce Entertain You, Chicago's premier restaurant and hospitality group offers dinner cruises that allow you to enjoy a delicious meal while watching the sun set behind the city skyline.

4. Stand-Up Paddleboarding

Get your balance and core strength in check with stand-up paddleboarding (SUP). Lake Michigan’s calm waters make it an ideal spot for beginners, and the views of the skyline from the water are simply unbeatable.

5. Kayaking on the Chicago River

Explore the winding Chicago River with a kayak rental. Paddle past the towering skyscrapers and under the famous bridges while taking in the city's unique vibe from the water’s edge.

6. Sailing Lessons

If you've always wanted to learn how to sail, summer is the perfect time to take sailing lessons. Various schools offer courses for beginners and experienced sailors alike, teaching you how to navigate the lake and feel the thrill of the wind in the sails.

7. Chicago Water Taxi

Hop on a Chicago Water Taxi to zip across the river while enjoying picturesque views of the city’s waterfront. It’s a convenient and scenic way to get around, with stops at some of Chicago’s top destinations.

8. Jet Skiing

For a high-speed adventure, rent a jet ski and race across Lake Michigan’s waters. It’s the perfect way to feel the rush of summer while enjoying the expansive views of the lake and city skyline.

9. Lakefront Beach Day

Relaxing on one of Chicago’s many beautiful beaches, like Oak Street Beach or North Avenue Beach, is a summer tradition. Whether you're sunbathing, playing beach volleyball, or just taking a dip, the beaches are a great spot to unwind.

10. Fishing on the Lake

For a more laid-back activity, try your hand at fishing on Lake Michigan. Rent a boat or join a fishing charter to spend a relaxing day on the water, all while casting your line for some of the lake’s popular species, like perch and bass.

Whether you’re looking for a thrill or some serenity, the waters around Chicago have something for everyone. Make the most of the season and dive into these unforgettable experiences!

– The Nautical Miles Team