With its soaring skyscrapers, epic architecture and a vibrant cultural scene, downtown Chicago is not necessarily the first thought that comes to mind when seeking out a boating destination. It’s actually Chicago’s bustling waterfront and maritime history, not to mention the urban beaches of Lake Michigan, that have made the city what it is today. Why not give the Windy City a second look with a few of the following boating activities?
Fun Water Activities in Chicago:
Paddle across the Chicago River in a kayak, canoe or stand-up paddleboard (SUP).
Zip around Lake Michigan on a jet ski.
Watch the sunset illuminate the downtown Chicago skyline from the deck of a sailboat.
Enjoy a brunch, lunch or dinner cruise aboard the Odyssey luxury yacht.
Take a water taxi across the lake.
Spend family time exploring the entertainment venues and cruise docks of Navy Pier, which is one of Chicago’s most popular attractions.
Rent a kayak or take a guided tour with Urban Kayaks. Enjoy the scenery as you paddle through the Chicago River. Along the way, your guide will point out interesting sites and give commentary on historical facts. You can also book a sunset tour.
Rent a Privately-owned Boat
Rent a boat
from a boat sharing company like Boatsetter
- with or without a captain and have a private boating experience for the day.
Chicago Sailboat Charters
Whether you want to view the Chicago skyline from the water, watch fireworks, take a romantic nighttime sail or spend the day swimming and sunning, Chicago Sailboat Charters is the place to go. Sailboats hold anywhere from two to 10 people. Book a private charter and plan your own personalized itinerary for the day.
Booking a cruise with Seadog Cruises is a great way to get a unique perspective of Buckingham Fountain, the Chicago Harbor, Grant Park and the Museum Campus. Your well-informed captains will share interesting facts about the Tribune Building, the John Hancock Center, the Willis Tower and many other visually appealing buildings along Chicago’s shoreline. Located at Navy Pier, Seadog also offers nighttime haunted cruises where you can take in the darkened skyline while hearing tales of Chicago’s various spirits and scandals. During the summer months, you’ll have the best seat in town on a fireworks cruise.
Chicago has been named one of the Top 10 Cities in the United States by Conde Nast Traveler readers because of its restaurants, museums, skyscrapers and active waterfront. We think the waterfront played a big part in that title. Why not rent a boat in Chicago
and judge for yourself?
Chicago Lakefront Night Skyline
By Tony Webster
(Own work) [CC BY-SA 3.0 (], via Wikimedia Commons