Tailgate The Lake Boat Charters — Local services in Chicago

WOW, what a fun day on the water. From start to finish the experience was great. Troy was amazing to work with in booking a charter for my family and some friends. He was quick to respond and made everything seamless, as a day on the water should be. When we arrived at the dock, Captain Jerry and crew were waiting and quick to help us with getting our food and drinks in the coolers. Captain Jerry was funny and very accommodating asking what we would like to do from cruising the harbors for some great city photos or going to the play to anchor and swim, to getting us set up with the blue tooth to play the music of our choice. We did it all. When we did anchor, the crew set up a table for us to play some drinking games and put out food while setting up a swim pad and providing noodles for us to float around with in the water. From start to finish the 3 hours was well worth it for my family and friends. I had 17 people this time but they have bigger boats that can accommodate more and I will definitely make sure I invite more people on my next charter I...

My group visited from Cali and wanted a fun activity to celebrate a combined bachelor/bachelorette. This was the perfect idea! You get what you want out of the experience whether you want to party, relax, or both! We cruised through Chicago, napped, relaxed, swam, & danced. 3 hours was a good amount of time. We got a beautiful view of the city without the touristy lecture haha. It was my favorite activity all weekend. Troy was very helpful and responsive. Many of us were hungover lol but Captain Mike’s vibe, driving skills, and beautiful route brought us back to life.

They provided speakers, ice, cooler, & swimming supplies. There’s a bathroom on board. The boat was clean. The water was cold but not too cold to swim. I compared prices with other boat companies and I definitely...

🗣 You guys - there's a bathroom on the pontoon boat! 🥳

Excellent way to spend an afternoon viewing the Chicago skyline with 15 of your closest friends and family! This pontoon boat has an awesome Bluetooth connection to play whatever music we wanted. Believe, Thunderstruck was blasted! There's a table that we used to set up snacks and later used that same table to play Stack Cup, Flip Cup, Quarters, and Beer Pong. There's coolers with ice that kept our drinks very cold. We anchored in the Playpen South because of the amazing views and warmer water. There was a swim mat that was rolled out, foam noodles, and life jackets to swim with. Booking was a breeze and the Captain and Crew were amazingly...