The views, the waves, the shimmering lights – it’s no secret that the best way to see Chicago is from the water. And with two gorgeous waterways, there’s tons of fun activities to choose from! Whether it’s floating across Lake Michigan at sunset or kayaking beneath towering skyscrapers on the Chicago River, the possibilities are truly endless.
If you’re wondering where to start, you’ve come to the right place. We’ve rounded up all of our favorite boat rides, sailing experiences, river cruises, and more. So, you can spend less time planning and more time playing in the Windy City!
Lake Michigan and the Chicago River
Chicago’s waterways offer two fantastic ways to experience the city. But where exactly are they located and what makes them unique?
Lake Michigan stretches along the eastern edge of Chicago, providing a vast and open playground with stunning views. It’s perfect for leisurely sunset cruises, exhilarating sailboat rides, and sun-filled adventures on the water.
On the other hand, the Chicago River winds through the heart of downtown. Whether you’re enjoying a river cruise or paddling a kayak, you’ll admire one-of-a-kind views of the city’s architecture and vibrant urban scenes.
Activities on Lake Michigan
Whether you’re seeking a private getaway, a sunset escape, or a delicious meal on the water, there’s a Lake Michigan adventure calling your name.
Sailing on the Lake
1. Private Charters
Grab your crew and set sail on a private charter! With a certified captain at the helm, you’ll relax and take in the stunning views. Your captain will guide the sailboat out of the harbor, then unfurl the sails and shut off the engine for a wind-fueled adventure.
Private charters are perfect for celebrating special occasions, enjoying a romantic date, or simply escaping the city’s hustle and bustle.
2. Sunset Sails
Simply put, Chicago at sunset is magical. And now, you can experience it from the deck of a sailboat! You won’t believe your eyes as the setting sun paints the city in golden hues before slipping beneath the horizon. Then, watch as the skyline begins to twinkle, casting a mesmerizing glow on the water.
3. Firework Experiences
A summertime must-do! Every Saturday and Wednesday between May and October, the Chicago night sky comes alive with a stunning firework display. Enjoy a front-row seat to this dazzling show as you sail across Lake Michigan.
With the city skyline as your backdrop and the fireworks reflecting off the water, it’s the most enchanting way to experience a summer evening in Chicago.
4. Sailing Lessons
Be your own captain! During a guided sailing lesson, you’ll learn basic sailing terminology, operations, navigation rules, and boating safety. You’ll help unfurl and hoist the sails, tie key knots, and steer along the sparkling lake.
Of course, you’ll also be treated to breathtaking views of the city – a true win-win!
Lake Cruises
1. Dining Cruises
These experiences are the perfect blend of good food and epic views. Plus, you can cruise at your favorite meal time (think, lunch, dinner, or even brunch). No matter what, you’ll be treated to a relaxing and gourmet dining experience as you glide past Downtown.
2. Speedboat Rides
Add a little adrenaline to your sightseeing! Feel the rush as you zip across the water, taking in the exhilarating speed and panoramic views of the city. But that’s not all. You’ll also learn interesting facts about Chicago’s history and architecture, all while enjoying a lively soundtrack.
3. Historic Fireboat Tours
Who knew you could cruise Lake Michigan from a vintage fireboat? You’ll feel like you’ve stepped back in time as you board this floating museum filled with photos and artifacts.
Explore Chicago’s maritime history, complete with stories and insights into the city’s fire-fighting past while enjoying unique views of the lake and skyline!
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Activities on the Chicago River
Glide through the heart of the city with these unforgettable boat rides and tours on the Chicago River.
Downtown Boat Rides
Explore the architectural wonders of Chicago! These tours offer informative commentary and unparalleled views of the city’s iconic skyscrapers and historic landmarks. Plus, you can choose from multiple departure points including Navy Pier and Michigan Avenue.
Kayaking on the Chicago River
For a more hands-on adventure, grab a paddle and experience the river up close. Kayaking allows you to navigate past the city’s stunning architecture and bustling urban scenes at a slower pace. Choose from a variety of options including daytime, sunset, nighttime, and even summer firework tours.
Find More Activities in Chicago
There’s so much more to see and do in the Windy City. Discover some of our all-time favorites (no boat or paddles necessary)!
1. Pie in the Sky: Dine on delicious, Chicago-style pizza from a table that’s 1,353 feet above the city!
2. 360 Chicago Observation Deck: Enjoy dazzling panoramic views from 1,000 feet above the Magnificent Mile.
3. Barrel Bus Tour: Experience the best of Chicago’s craft beer scene, all while riding on a unique barrel-shaped bus.
4. Chicago Food Tours: Dig into all the Chicago classics. We’re talking about deep-dish pizza, hot dogs, Italian beef, Jibarito sandwiches, and more.
5. Chicago Driving Experiences: Get behind the wheel of your favorite sports car at the Autobahn Country Club.
6. Helicopter Rides: Enjoy a bird’s eye view of the Windy City.
Summary
So, there you have it: the best activities and trips on Chicago’s iconic waterways. Whether you’re sailing, cruising, or paddling, the Chicago River and Lake Michigan are full of unforgettable ways to explore and enjoy the city. What are you waiting for? Grab a paddle or hop aboard a luxurious sailboat today!
Looking for even more fun things to do in the Windy City? Check out our full range of Chicago Experience Gifts & Things To Do.
