Sailing on Lake Michigan
Option 1: Charter a boat and captain
Everyone should experience seeing the Chicago Skyline from the water! A sailboat is a relaxing way to do this. If you don’t know someone that sails, you can easily find experiences online where you charter a captain and invite a certain number of people on board!
I was lucky to be invited on one of these can be such a special experience. A sunset cruise is perfect for any summer night, even for a weeknight if you are able to get downtown on time. Bring some wine and snacks, and enjoy the skyline with friends!
Option 2: Rent a sailboat
If someone in your group knows how to sail, head to Glencoe Beach. You can rent a small sailboat by the hour at the boathouse on the beach. You just need to know how to sail yourself! We did this for my dad for Father’s Day a few years ago since he sails!
Renting boats on the rivers in Chicago or Milwaukee
Kayak
There are a few great spots to rent private boats on the Chicago river. If you’re seeking a more active adventure, rent kayaks. I love kayaking the quieter, South Branch of the river from China town. There is a kayak rental right by REI.
Motorized Boats
If someone in your group can rent a motorized boat, rent a pontoon boat for the afternoon in Downtown Chicago! Bring snacks and cruise up and down the river.
Chicago Electric Boat Company at Rockwell on the River rent kayaks and fun electric boats. This would be awesome for a group of friends. Book early because they fill up!
Take a trip up to Milwaukee!
Milwaukee also has plenty of motorized boat options on the river. Last year I rented a boat at Boat MKE for Mo’s birthday for 4 people. It was small but so fun! Whatever boat you’re taking on the river, definitely pass by the bridge – it’s beautiful, especially around sunset. You also have to stop at the bars! There are 2 bars that you can easily park your boat at.
