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.

Captain Rob and Jill were great. Everything ran like clockwork and they were accommodating on the…read moreboat. Great conversationalists as well. I appreciated the simplicity of booking and acquiring their services. It felt a little too easy to be true but it was. They just have an efficient and fun operation. Thanks captain Rob and Jill!

I recently rented a yacht from this company for my birthday, and the experience exceeded all…read moreexpectations :) From the moment we boarded, the captain was professional, welcoming and very attentive to all of our requests. The yacht itself was super clean, beautifully maintained, and equipped with everything we needed --plenty of space, float rafts to hang out on, great sound system, and perfect views from the top of the yacht. The captain was amazing--knowledgeable, friendly, and made us feel safe and relaxed. He has DECADES of experience and knows the lake Michigan and the Chicago river like the back of his hand. We cruised along stunning views of the Chicago skyline, and we saw the sunset on the way back. It was pure magic and oh so romantic. Perfect for a cancer horoscope sign such as myself;) I highly recommend this yacht rental company for anyone looking to celebrate, relax, or just enjoy an amazing Chicago experience on the water. I will be booking again!!

Chicagoland Yacht Rentals completely ruined what should have been one of the happiest days of our…read morelives. We rented a yacht for a gender reveal celebration, and what we experienced was traumatizing, unsafe, and felt like a complete setup. The captain, Joe, seemed fine at first he even helped us open our biodegradable powder cannons and posed for pictures. But seconds after the reveal, he started yelling that he needed to "settle everyone down" and demanded I Zelle him $400 on the spot for him to start while claiming the boat was damaged. He blamed his "friend," who then came aboard and aggressively insulted our entire family yelling in front of all our guests and young children. Two children were so traumatized!! This celebration turned into fear and panic. It didn't end there. The captain was drinking alcohol, slurring his words, smoking, and taking unauthorized photos of minors. His behavior was reckless and disturbing. We have video proof of his conduct. When I contacted Chicagoland Yacht Rentals, they did absolutely nothing. No call, no check-in, no apology just silence and a ridiculous claim that I had "spray painted the boat." I'm eight months pregnant, and they want to blame me for something I physically couldn't have done. We're now out thousands, and I've had to file a police report and begin legal proceedings. This company is dangerous, dishonest, and completely unprofessional. The dozens of 5-star reviews seem fake they don't match what we went through. Please do not trust them with your money, your event, or your family's safety.

Captain Tim is the best and so is his beautiful, clean boat! He can help create the perfect vibes…read morefor your party with all the accommodations needed to have a great time. This is the only charter I recommend to people!

if you are looking for a wonderful experience on the water in Chicago, this is the boat tour to…read moretake! Captain Tim is very accommodating and his boat tours are always a blast! I highly recommend if you are looking for someone on time, fun and entertaining and most importantly a great tour! Dor Sea Tours should be your top pick!

Included everything to make sure everything was perfect and easy going. All the girls from the…read morebachelorette party wish to go back! Thank you for making everything enjoyable for everyone!

Booked Captain Tom's Penalty Box for my boyfriend's Birthday! Sent out information on Tom's website…read moreand Tom got back at me the next day. Whenever I have questions I'll just text Tom and he usually replies pretty quick. We scheduled the cruise at 3 but we didn't get to the harbor until almost 4 due to traffic. Tom is very understanding. We brought some food and drinks and Tom has a cooler with ice ready on the boat. Started off with a Chicago river cruise. My boyfriend got a bit sea sick when we were cruising on the lake... what can I say, freaking Chicago wind, but the river cruise is calm and nice. Caption Tom is patient to explain all the functions of the boat (wow two engines) and other interesting facts about Michigan Lake and Chicago river. We got caught in the rain for a bit but lucky the boat has a roof and we brought cards. When we got back on the lake the sun came out again so we stayed a while for a little lake front swim party... kinda funny since my boyfriend can't swim. Tom eventually find a rope to tie to his life vest so he had fun. Finished off the cruise at around 8 as we planed. Great day! Highly recommended!

Went here for a sunset sail with my boyfriend. Really…read moreEnjoyed being able to go on a sail boat. They let volunteers from the crowd pull open the sails. Staff is friendly and funny.

Windy City Sailing always exceeds expectations. My family and I look forward to our annual sailing…read moretrip w/ Captain Joe and his crew. Even just unplugging on a three hour tour beats some week long vacations we've taken in terms of the chill factor. Our family and friends pretty much compete every year to be the lucky ones who get invited to join us. Our favorite one is the Air & Water Show. Can't wait for this year's trip.

Had the most incredible experience on seabird sailing! Eric is an amazing captain and makes…read moreeveryone comfortable, the boat was stunning, and the views were immaculate. We came for an engagement shoot but will be back every summer!

I could not recommend Seabord Sailing enough. I chartered a private trip with them to propose to my…read morenow fiancé and it was a phenomenal experience - I would trust them to celebrate any event. They prioritize safety and are amazing hosts. If you're going to sail Lake Michigan, sail with this outfit, they're incredible.

They cancelled and won't give my money back. Lost $1000. They should be ashamed of themselves, how…read moreis this legal??

We had a blast! Gorgeous yacht and awesome crew. Spending memorial day on Stray Kat was amazing…read moreexperience. We absolutely loved everything.