There are so many exciting adventures and things to do in Chicago that truth be told, the options are pretty overwhelming. Fortunately, we’ve scouted out the perfect Chi-town adventure: sailing the lakefront on a yacht with On A Boat Sailing. Thanks to this unique Airbnb experience, you can enjoy some of the city’s most iconic views while surrounded by friends and loved ones. Curious to learn more? Keep reading about this epic Midwestern adventure!

Are you dreaming of the perfect Chicago adventure? Look no further; we've found it! Your epic lakeshore adventure awaits.
Greg / Airbnb
This stunning cruise, which many reviewers describe as bucket-list-worthy, begins at Monroe Harbor. There, guests will board a picture-perfect yacht and set sail for Lake Michigan.
Greg / Airbnb
From this unique vantage point, you'll be able to enjoy the city's most iconic buildings. Whether you're a resident or a visitor, you're sure to appreciate the views!
Greg / Airbnb
If you opt for this sailing tour in the summer, be sure to bring a bathing suit so you can take a dip in the water.

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Each ride can accommodate up to six guests, so you can reserve the whole boat ride for yourself and your friends. You're also invited to bring your own drinks and food to enjoy.
Greg / Airbnb
The captain, Greg, has a Greg holds a Master Captain’s license from the US Coast Guard, and his partner Cait has experience sailing the Great American Loop, Bahamas, and Caribbean. You will be in very capable hands!
Greg / Airbnb
No matter your reason for setting sail, you'll quickly discover it's a once-in-a-lifetime adventure.
Greg / Airbnb

What are your thoughts on this adventure? Do you agree that it’s one of the most unique things to do in Chicago? Share your thoughts with us in the comments below — we’d love to hear from you! Learn more about how you can enjoy this sailing adventure in Chicago.

For related content, be sure to take a look at our ultimate Illinois bucket list:

The Ultimate And Definitive Bucket List For Everyone In Illinois

 

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Lakefront Trail, Lakefront Trl, Chicago, IL, USA