Had a great evening out on a pontoon boat. It was so easy to drive, and we enjoyed seeing beautiful…read moreviews of the city skyline. Such a fun experience for summer in Chicago and it's one of the most affordable ways to rent a boat in the city. Would recommend!

My friends and I booked a private pontoon ride with Chicago Boat Rentals for a Monday night at…read more7:30, and it was the perfect way to soak up a Chicago summer evening on the water! The crew made everything easy -- they showed us how to drive the boat ourselves, and we got to bring our own food and drinks onboard. Such a fun, laid-back way to see the skyline. Highly recommend!

Captain Brian, Russell, and Ulysses were amazing! We rented both the Catamaran and the Monohull…read moreboats for 3 hours on a sunny Saturday in June and filled the boats with a bachelorette and her friends. I cannot say enough about the experience! So much fun! The Catamaran boat is nicer than I was expecting. There is a bathroom and indoor cabin area to relax if you get too hot in the sun and don't want to cool off with a swim. The captain and crew took care of us the whole time. They have a giant cooler filled with ice and packed the cooler with our goodies so we could relax. They then waited on us, putting on our music, bringing us our drink requests and snacks. That part was so luxurious and absolutely unexpected! We had too many people to fit on one boat so we rented the Monohull as well and the experience was seamless. They made sure the group was together as much as possible. We boarded the boats while the boats were parked next to each other, then both sailed to the playpen and tied up together. We were allowed to hop between the boats so that the whole crew could mingle. It was perfect! The Monohull is also a very nice boat with room for 6 people to sit comfortably in the back or on the front to sunbath. I highly recommend! The only thing I regret is not booking this for a longer time slot.

My friends and I chartered the catamaran in August 2021 and it was the highlight of our summer! It…read morewas such a great way to enjoy the Chicago skyline and swim in the lake. The boat was spacious and comfortable. Can't wait to go again this year!

Sophisticated lady is a gorgeous boat, I really like the myriad of spaces where you can sit down…read moreand talk or dance or just take in the view. The food on the boat is excellent and the crew is very attentive. Overall, highly recommended.

We got married on the Sophisticated Lady at the end of September 2025 with just our respective kids…read more(his 4, my 2) and siblings/spouses on board...a total of 17 people...most from out of state. I contacted Taylor for all the arrangements early summer and my fiance and I went to the city overnight to see the boat. (We live in Western Suburbs) My kids have always loved our overnights in Chicago and a sunset cruise the second time around seemed like the perfect wedding. We prayed the weather would cooperate! Booking was easy, selecting food options and drink packages was not necessarily cheap but they had a great selection with the premium beverage package that was good for all. The 3 person crew were great...they went with the flow. We got married on Lake Michigan (bartender said it was the first wedding they'd ever had ON the boat.) We are bikers so most of our kids dressed accordingly (as did we). The Captain stopped the boat in a protected harbor for the 20 minute ceremony so no one would get pitched over. Everyone had a fantastic cruise and the sunset did NOT disappoint! We absolutely LOVED this unique wedding experience!

Highly recommend to celebrate a birthday with tailgate the lake for an evening firework cruise!…read more The dock is easy to find, definitely recommend to Uber to the recommended location shown on their website, it's a short walk to the boat after the drop off. There is a bathroom on board which is great! There is a Bluetooth speaker, so you can jam to whatever you like. There is also a cooler for drinks, table for food and games. You can also swim before sundown. The crew was great, shout out to Steve and Captain Jerry! They were a lot of fun, took us super close to the firework show and out to the lighthouse. It was a blast!! We will definitely be back!

I can't speak to the experience on the boat but the captain intentionally drove by my canoe and…read morepartner on a SUP causing a huge wake in the harbor. When I later confronted the captain he said he was "running late," perhaps a sign he doesn't have safety as a top priority.

Captain Kirk Kessler, a United States Coast Guard - Certified Master Captain, goes all out to give…read morehis passengers a wonderful experience. His boat, the Peony, is equipped in a manner to meet the needs of his guests. His first mate, Woody, a chipper mini Golden Doodle, adds a fun touch to each outing. Kirk is extremely professional, going over his shipboard rules with all his charges before they embark. His rule #1 - "Stay on the boat!" Captain Kirk gets a sense of each of his sets of guests, and how comfortable (or apprehensive) they are on the water. Passengers preferring a sedate, "gentle" excursion will get one (to the extent weather and lake conditions permit); those guests up for a more adventurous outing with 15-30 degrees of heeling will have their wishes fulfilled. As a USCG-certified Master Captain, Kirk knows what he needs to do to trim the sails and change his headings to make his cruises pleasant ones for his passengers and their predilections. A charming host/skipper, Captain Kirk will make your sail/cruise an unforgettable one - withe the beautiful Chicago skyline as your sunset backdrop. You can't do better than Salty Dog Sailing Co.!

I highly recommend chartering with Salty Dog. Captain Kirk () was very professional. I was a…read morelittle nervous, but he set everyone in our party at ease. The boat comfortably fits 4 people, and you can just sit back and relax. Woody is extremely friendly, greeting us on the dock when we arrive, and sleeping next to us the entire trip, except when we turned and he had to flip to the other side! And it's true sailing, we went about 3.5 miles from shore, getting some incredible views of the city. It was a great day, great conversation and an overall awesome time!

I wanted to find an affordable private boat tour for a bachelorette party, and this fit the bill…read more Dan was very accommodating and made sure everything went smoothly for the day. When we decided to bring food onto the water, he met us by the harbor and provided a cart for us to place all the bags of food onto it. He let us choose if we wanted to spend more time at The Playpen or sailing on the open waters. Floaties were also available. Communication was great, the weather was great, the music was great, and the people were great. Thank you for an authentic and fun boating experience!

One of the best things I did while visiting Chicago! I booked the 8:30 p.m. Tall Ship Windy sail,…read moreand it was worth every penny. We left around 8:30 to 8:45, and by the time the 9:00 p.m. fireworks started, we had a front row view from the water. It was absolutely incredible. The captain and crew were friendly, welcoming, and did an amazing job. The ship wasn't overcrowded, so there was plenty of room to walk around and take in the views. Watching the fireworks with the Chicago skyline in the background was unforgettable. After the fireworks, we sailed under the night sky with the sails up and great music playing. It honestly felt like I was in the Caribbean, except with an amazing city skyline all around us. I'm from New York and was in Chicago for work, and I have to say this was even more impressive than seeing the New York skyline from the water. I also own a sailboat, so I really appreciated how well the crew handled the ship. One of my favorite parts was that guests could even help hoist the sails. There was a full bar with a really good rum punch, and so many great spots to take pictures of the sunset and the skyline. The crew was also happy to take photos for people. If you're going, get to Navy Pier early and enjoy the restaurants and drinks before your sail. This is great for families, couples, or even if you're traveling by yourself like I was. It's a unique experience that you won't get on one of the regular tour boats. I would absolutely do this again the next time I'm in Chicago.

Staff was so amazing and kind, relaxing way to see the city on a calm and quiet sailboat so much funread more

We've rented here twice last summer and plan on it again. The boat is awesome, the guys are super…read morefriendly and flexible and set us up with everything we needed. We will definitely do it again!

I wanted to rent a boat with my colleagues and I checked the website, called a week before, and…read moreSofia was great! She was very responsive and accommodating. Nothing like other rentals. Everything is quick and efficient like you would want it to be! Getaway Chartering exceeded my expectations and I will definitely return, one of those places where you receive value for the price and all thanks to Sofia for making it such a relaxing day.