I've taken quite a few boat rides over the years. Small boats, large boats, and a few in between…read more So when a friend invited me to join a few people for a ride with this charter service, I was happy to go. I really didn't have any expectations beyond what I already understood a boat trip to be. I figured we'd cruise up and down the waterfront, enjoy the scenery, and eventually make our way back to the pier, just like I've done plenty of times before. Well, I'm not above admitting when I'm wrong. This was an amazing experience. It wasn't because we stopped at an amazing restaurant. It wasn't because we traveled up and down the Chicago River. Those things certainly made the day special, but what really made the experience memorable was the captain and his wife. Before we even stepped onto the boat, we had to change our reservation a few times because of Chicago's bipolar summer weather. The captain was extremely responsive throughout the entire process. He explained why we needed to reschedule, stayed in communication with us, and made sure he personally took care of us when we were finally able to get out on the water. Once aboard, he and his wife were simply wonderful. They made the entire experience feel personal, comfortable, and genuinely enjoyable. All in all, this wasn't just an amazing boat rental. It was an amazing experience because of the people behind it. I would happily take another trip with this team again and again.

If you're looking to charter a boat in Chicago, this is the place. They have a variety of options…read moreavailable and Captain Russell is fantastic. We did a 5 hour charter for 7 and part of me wishes it was longer. Pack your cooler, get your tunes ready to Bluetooth into the boats sound system and enjoy a nice relaxing day on Lake Michigan.

As boating season starts in Chicago, I just wanted to let you know that Russell took me, my…read morechildren and their significant others out for my "birthday celebration" and it was thee BEST boating experience this Chicago gal has ever had. Russell took us on the most beautiful route and his boat is beautiful and comfortable for viewing, eating, drinking and laying out if you like. My favorite moment was when we anchored and me and my kiddos did a celebratory jump into the lake as Russell videotaped us. Big Thanks to Russell for the BEST Boating experience in CHI. He is so knowledgable and experienced that I highly recommend 1st Class Charters Chicago!!

SO MUCH FUN!! How it…read moreworks: You charter a boat along with the captain and crew. The boats are owned by the company. We chartered a boat on Labor Day, with Bill and Nancy. We departed from Montrose Beach. We were able to bring our own drinks and snacks for the sail. There were 7 of us total at ~$100/person. We specifically selected this company because they had a money back guarantee in the event of inclement weather - most other boating companies do not offer this! HUGE PLUS. Fun Fact: All of their boats mean "Lost" in different language, but not to be confused with lost at sea!

We had an excellent charter experience with Captain Bill on a speedboat. Booking the boat was quite…read moreeasy through the website, then you can contact the captain yourself to see who is available (company gives names/contact info). I would definitely rent from CSC again. Prices were also pretty average compared to other companies! Definitely recommend.

We rented a 8 person electric boat this weekend with the chicago boat company and had a very…read morepleasant experience! The staff was friendly, the boat was clean, and the online booking process was smooth. I even emailed them the morning of our trip because of possible weather issues and the acknowledged my email in a timely manner which was nice they took the time to check it and respond. Highly recommend!

The boat was a lovely slow ride. The staff was very helpful and accommodating. They allowed us to…read morewait out the rain a bit and then go out. The boat was clean and easy to manage.

We used Adeline's Sea Moose for a private corporate event (approximately 30 people), and it was an…read moreexcellent experience from planning through execution. The team was extremely responsive and accommodating, helping us build an event with a variety of food. On the day of the eventt, everyone was extremely hospitable, and we found it to be an unexpected nice touch that they regularly checked if we needed beverages, collected our garbage frequently, and passed out the apps to ensure people received food. Would absolutely recommend, and definitely plan to use this crew again. Thanks for a great time!

Responsive | Personable | Flexible |…read more Responsive - The crew at ASM was very flexible. Their website is well laid out with a chat service that answers most of your questions. Chelsea, the administrative assistant and scheduler answers emails in 24 hour or less and is very helpful with answering questions and providing examples to help customize the perfect charter for your group. Personable - the entire crew Flexible - The crew at ASM was very flexible throughout the process of securing the charter and the day of. There was a thunderstorm in chicago 30 minutes prior to Pro Tip: The Captain smokes, so if you have a sensitivity to smoking, just make sure you let Chelsea know that your group is sensitive to smoking. Pro Tip: Call the crew 5 minutes before you show, because they have to come out to a gate to get you. We were in the middle of a rain storm and had to wait 5 minutes at the gate before getting on the boat. Therefore, our group was soaked on our way on. It really affected our group because it set a bad tone. But, once everyone was warm we had a great time.

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!

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.

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.

Great company. It was a great experience from the beginning of the charter to the end. Safety was a…read morebig priority with this company, The captain was a licensed captain with years of experience. The boat was clean and we left on time. I would highly recommend this company if you are looking to have a great experience,