The Best Boat Rentals Near Portage

Sail & Swim from a Luxury Sailing Yacht

This is an iconic trip in Chicago. I have always been on the river walk or on a kayak looking at people boats and thought "Those lucky kids." So this time I rented a sailboat to go out on the lake- even luckier! The operators are very organized and helpful. Everything was as expected from the site. Communication throughout was excellent. Thanks for lovely and memorable sail. I'm coming back to jump in the lake when the water temperature is a bit warmer :)

20' Lund Bass Boat for 3 in Chicago, Illinois

I honestly didn’t expect to walk away from this trip with a whole new hobby, but here I am—hooked for life. Guy has this way of making the entire experience feel effortless and exciting, whether you’re a total beginner or someone who’s been at it for years. From teaching the basics with real patience to creating an atmosphere that’s both laid-back and full of energy, he made it easy to fall in love with fishing. The way he explained the gear, read the water, and shared his stories made every moment out there on the water feel like something special. You can tell he truly loves what he does, and that kind of passion is contagious. I went in thinking this was just a one-time adventure, but now I’m already planning my next trip—and buying my own gear. Can’t thank Guy enough for turning what was supposed to be a relaxing weekend into the start of a lifelong obsession. If you’ve ever been on the fence about trying fishing, let Guy be the reason you dive in—you won’t regret it.

20' Lund Bass Boat for 3 in Chicago, Illinois

Thanks for a great day on the water, Capt. Guy! We had a phenomenal morning, and we hope to fish with you again soon! Great variety of salmon & steelhead. 10/10 recommend

Super Fun Like New 2022 Tahoe T-18 Sport Boat (2 Tubes / Ski's Onboard).

Jim's communication was great. We had an amazing day on the lake. His boat was clean and he had tubes and ski's for us to use. We spent the whole day tubing. Would rent from him again.

Sail & Swim from a Luxury Sailing Yacht

We had a great experience with Captain Greg. The boat was very nice and clean, and we had a great sunset sail! Our kids loved their first sailing experience. Captain Greg even taught my 9 year old how to steer and let all 3 kiddos help with hoisting the sails. Couldn’t have asked for a better night in Chicago!

SeaRay 310 Sundancer for Rent on Chicago's Lake Michigan

Captain at his passionate, but mellow and totally shows everybody a great time all day out in Lake Michigan, and through the river of Chicago