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Best Places to Boat in Chicago

Updated: May 9, 2023

Taking in the sights on a Chicago boat rental is truly an exhilarating experience. And with so many different things to do you may find that renting a boat in Chicago will become your new summer tradition! Chicago Yachting has been providing boat rentals to satisfied clients for over 10 years, and during that time we’ve had the chance to explore so many different itineraries. Here are some of our favorites!

#1 The Chicago Playpen!

We have to start with the most popular place for boats on the Chicago waterfront. The Playpen is where Chicago boat rental customers cruise to most often! So what is the Chicago Playpen and what makes it so popular? Well, the Playpen is a safe place to drop anchor downtown and combines great views of the skyline with calm, protected waters and a party vibe perfect for your special event! When I came here the scene was pretty calm. But on the weekends, boats from all over Chicago come to the Playpen to drop anchor and enjoy the scene. You’ll catch views of bronzed bodies dancing around on boats with sound systems that seem like they came from a nightclub! You might even meet the famous Chicago Flyboard Guy! Don’t forget to take that perfect Playpen photo of you and your friends and tag #chicagoyachting in your post. Swimming is a popular activity in the playpen, so if getting wet is part of your plan be sure to ask our staff about inflatable rafts available with our boat rentals! So pack our boat’s cooler full of your White Claws and let’s get this boat headed to the Playpen!

#2 The Chicago River Cruise

Chicago river cruise on a private yacht

The Chicago River isn’t always dyed green (only on St Patrick’s Day!) but it always makes for a great Chicago boat rental itinerary! Picture yourself on a yacht cruising through magnificent Chicago skyscrapers with your friends, family and food/drinks. If you have ever done the Chicago Architecture Boat Cruise, imagine doing that but with your own private Chicago yacht and captain. Highlights include the Chicago Riverwalk with numerous restaurants and bars you can dock up to! How about ordering Chicago pizza and picking it up by boat with a bottle of vino? It is possible with Chicago Yachting!

#3 Monroe Harbor (Chicago Playpen South!)

Monroe Harbor anchorage by downtown Chicago

If you prefer a more relaxing Chicago boat rental experience than the loud beats and high energy vibes of the Chicago Playpen, then the Monroe Harbor anchorage might be just what you need! Monroe Harbor is the most centrally located anchorage in Chicago and offers the best skyline views. This anchorage has become very popular over the last few summers and is even being called the Playpen South! You’ll be anchored in protected waters right next to Millennium Park, with the Buckingham fountain shooting up like a geyser every once in a while! Boaters at this anchorage tend to keep to themselves a little more, enjoying the company of their crew and the taste of their rose!

#4 Chicago Skyline Cruise

Cruising on a boat by the Chicago Skyline

Maybe you are doing a Chicago boat rental just to, well, be on a boat cruise! If you prefer to be in motion, feeling the warm summer breeze and hearing the sounds of the water blending with your beats then we would recommend the Chicago Skyline Cruise! The Chicago Skyline Cruise itinerary begins at 31st street harbor so you will get to experience the entirety of the Chicago skyline. You’ll cruise north, past McCormick place and Soldier Field to enter Chicago’s Museum Campus. What’s that big shiny dome? The planetarium! And that building with huge windows facing the lake - the Chicago Aquarium - wave to the dolphin show! Your Chicago Yacht rental will then take you through Monroe Harbor up to Chicago’s Navy Pier, where you can wave at the crowds of people on the Pier enjoying a summer day. You’ll get to tour out to the historic Chicago Harbor lighthouse on your way out into the open lake. A cruise up the coastline and back will take about two hours so you may still have time for a quick swim if you need to cool off!

#5 Chicago Fireworks Cruise

Chicago fireworks from a boat in Lake Michigan

Every Wednesday and Saturday night in Chicago is like the Fourth of July! Chicago puts on an incredible fireworks display off Navy Pier that is best viewed from the comfort of your Chicago boat rental. We usually recommend setting off around 7:30 or 8pm so you get the chance to have a nice Chicago Skyline Cruise up to Navy Pier, where you’ll drop anchor and grab your favorite snack and beverage to enjoy the show! Check with us about the current schedule, but typically the Chicago Navy Pier Fireworks show starts at 9pm on Wednesdays and 10pm on Saturdays.

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