Live a Little Yachting

From corporate charters down the Chicago River to group parties for an afternoon in the Playpen, we have your boating needs covered. Our fleet can accommodate groups of all sizes. Live a Little Yachting offers a variety of different packages to make enjoying a day on the Lake fun and easy.

Don’t just take our word —

Read what our guests are saying:

  • We took the 36' Sea Ray out for the Chicago air show. Captain Lisa was great and the boat was spacious for 12 ppl. We sat in the water on the lily pad that was provided. Great day on the water.

    2024 Chicago Air & Water Show Booking

  • I couldn't recommend Captain Lisa and Live a Little Yachting higher. I rented a boat to surprise my fiance immediately after I proposed to her on the Chicago riverwalk. Lisa went above and beyond, from the moment I said "go," to curate a schedule and plan the boat ride to perfection. On the day of the celebration she was kind, courteous and professional toward myself and toward our families and guests. The day that we got engaged simply would not have been as perfect as it was without her help.

    Newly Engaged Couple

  • Captain Justin and his boat were great for my friend’s bachelorette party. He provided a good sound system, coolers, and was very accommodating to what we wanted even though the day we went had very choppy waters. 10/10 experience out on Lake Michigan!

    2022 Bachelorette Party Booking

  • Lived here for 7 years now rented many boats an this one by far has been the best experience!! The captain Justin is amazing, super nice and very accommodating - knows what he is doing!! The boat was nice and clean and had towels an waters all ready cups sunblock all the little things you might forget! Great price can’t beat it !! I’ll will be back for sure!!

    2024 Summer Charter Booking

Now Booking for Summer 2025

Choose your Boat

Book your preferred boat for your specific date here. You’ll be able to see available boats, including their size, photos, and capacity.

Book your Captain

After you book your boat, you’ll receive information on how to book a captain for your boat. We recommend budgeting $100-$125/hr for the captain.

Meet us at the Dock

After you book your boat and captain, prepare for your day of fun on the water! You can read FAQ here or contact us if you have any other questions.