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Glancer Magazine

MOM'S LITTLE BLACK BOOK | Chi-Town Boat Charters

MOM'S LITTLE BLACK BOOK | Chi-Town Boat Charters

Lake Life

Chicago, famously known as the Windy City, offers a myriad of experiences for locals and tourists alike. One of the most exhilarating ways to soak in the city's skyline and vibrant atmosphere is by embarking on a journey with Chi-Town Boat Charters on Lake Michigan.


Imagine the thrill of cruising on crystal-clear waters, surrounded by skyscrapers and the refreshing breeze of the lake.

Seeking adventure and unforgettable memories, Chi-Town Boat Charters provided the ideal setting for our group of girlfriends.  As we stepped aboard our private chartered vessel, we were greeted by friendly staff, who also happen to be husband and wife, Kevin and Becca Molitor, a City of Aurora FireFighter and a Rush Copley Hospital ER Nurse.

MOM'S LITTLE BLACK BOOK | Chi-Town Boat Charters

Their beautiful yacht is located just steps away from parking at the 31st Street Harbor, and is equipped with refrigerators, Yeti Coolers, a dining and lounge area, a bathroom, and bedroom.  We brought along a bag of ice, refreshments, and a vast array of food for the sunny afternoon!


With beverages in hand and excitement in the air, we set sail, ready to explore Chicago from a unique perspective.  Our aquatic adventure included views of the Shedd Aquarium, Northerly Island Park, Buckingham Fountain, and Navy Pier.  From the comfort of our boat, we admired the iconic Ferris wheel and the bustling surrounding cultural atmosphere.  Captain Kevin shared fascinating tidbits about the Skyline’s history, adding depth to our experience. 

Eager to capture the beauty of our surroundings, we couldn’t resist snapping countless photos, and our captain was the perfect photographer!


Next, it was time to cruise the famous Chicago Playpen, where we had full access to the giant lily pad on board for our personal swimming entertainment!

MOM'S LITTLE BLACK BOOK | Chi-Town Boat Charters

As the afternoon winded down, we hit full speed ahead, providing an unexpected thrill to our relaxing day.  Laughter filled the air against the stunning backdrop of the city horizon. We raised our glasses in a toast to friendship and adventure; grateful for this indelible experience with Chi-Town Boat Charters!




A family owned business working together to make unforgettable memories for you and 12 of your closest friends to see and experience the Chicago Skyline from the water.  Chi-Town Boat Charter’s 39’ Sea Ray Sundancer is the perfect yacht for living and loving lake life in Chicago!


Chi-Town Boat Charters

3155 S. Lake Shore Drive, Dock F

Chicago, IL 60616

(708) 606-7440


Hours:  See Website

Price $:  Starting at $250/Hour



Kristen Kucharski’s days are never dull, her kids are never bored! Over the years #MomsLittleBlackBook has explored hundreds of kid friendly things to do in our surrounding community and on the road.  As her girls have grown and gone away to college, she continues to enjoy unique activities, excursions, day trips, weekend get-a-aways, and road trips while rediscovering my own passion for adventure with friends, girls nights outs, and date nights. In her words: “Life is a journey–might as well have fun along the way. Go, fly, roam, travel, voyage, explore, discover!”