On to Illinois with stops in Waukegan and Chicago and seeing lots of family!
Tuesday, August 25 through Monday, August 31, 2026
8/27/20265 min read


On Tuesday, August 25, we left Milwaukee at 7:45 and had a calm ride to Waukegan, Illinois. We passed Wind Point Lighthouse, Racine and Kenosha before arriving at about 1:00. We rested and cleaned and walked around a little bit near the marina and waterfront. On Wednesday, August 26 we walked around downtown and looked for some groceries. I took a photo of the Jack Benny statue. I didn't realize he was from Waukegan! We came back to the boat and I did laundry and ordered groceries from Walmart Delivery since we didn't find much within walking distance. Later, another serendipity happened since our nephew, Joe, moved back from Oregon to take a job in Waukegan of all places! He has been staying at his Aunt Julie's(Tim's sister) and taking the train and his bike to Waukegan by train and biking to nearby Gurnee for his job. We had a great time catching up and went downtown to Green Town Tavern, known for their Italian Beef sandwiches. We came back to the boat and enjoyed the evening and moonlight. Tomorrow his commute will be shorter since it is just the 5 mile bike ride.
























Thursday, August 27, Tim's sister Julie arrived about noon to Waukegan by train from Chicago. We walked around the marina and park area and later met Joe after work at the outdoor bar called Green Town on the Rocks and had dinner from the food truck called La Chuparosa Mexican Urban Kitchen. The burritos were as big a your head, quite filling. Later we watched the partial eclipse from the boat. It was tough to get a decent photo of that but I tried.



















On Friday, August 28 we left about 8:30 from Waukegan with Tim's sister Julie and arrived at Belmont Harbor in Chicago about noon. Julie took the helm a few times and did a great job. It was a nice ride and we enjoyed seeing Gross Point Lighthouse and Northwestern University in Evanston, passing Loyola and seeing the Chicago skyline come into view. We were welcomed by the Chicago Yacht Club at Belmont Harbor where we docked. Julie added the pin to our map! This was a great stop because we could walk to Julie's condo which was only about a mile from the harbor in Lincoln Park. We walked there and had a Chicago hot dog on Clark Street at The Wiener's Circle. After that we toured the Shrine of Saint Frances Xavier Cabrini since that was near her condo. Sister Cabrini was an Italian immigrant who opened schools, hospitals, and orphanages in Chicago and elsewhere in the early 1900s. Later we had margaritas at Las Fuentes on Halsted. After this our nephew Jake made pizzas for us all!




































































On Saturday, August 29 we walked to nearby Belmont Market to get a few groceries. Then we walked over to Wrigley Field for the 1:20 game. We chose to watch a few innings from the popular bars around the stadium because it was just the Cubs, not the White Sox, and we had other things we wanted to do that afternoon. Cubs had a good win that day over Cincinnati, hmm. We went back to the boat to get some rest before daughter Caitlin and family's arrival later that night. We also had a delicious dinner with Julie at the Chicago Yacht Club at Belmont Harbor. Caitlin, Henry, Connor and Claire arrived late in the evening after a family birthday party on Henry's side in the suburbs. It was great to welcome them to the boat and the kids went to sleep soon after arrival and the rest of us followed soon after.
























On Sunday, August 30 we had rain and some high winds predicted but we found a window of time and made a quick decision to leave sooner than expected but it was just a short 4 mile ride to Navy Pier. It was cloudy so not the best ride for visitors but we made it work! Connor had fun with binoculars before we left and walking around the gunnels when we arrived. The Navy Pier transient marina is only a couple years old and is on the north side of Navy Pier. The staff and dockhands were excellent and the cleats are actually movable which we had not seen before. They have a very nice boater lounge above the office and restrooms and laundry area. We went exploring and found a Build-a-Bear store and Caitlin and Henry decided this would be a good time to get Connor's birthday bear which only costs as much as child's age in their birthday month and he just turned 2 on August 15. After that we had ice cream from the famous Rainbow Cone kiosk. We were joined by Julie and two of our nephews so we all had lunch at Harry Caray's on Navy Pier. After lunch both Connor and Claire fell asleep in the stroller on the way back to the boat so they decided to head back to Iowa during nap time. After they left, the rest of us rode the ferris wheel and took in the amazing views of the city from there (including our own boat). For dinner, Tim and I ate at Bar Sol and watched the charter boats on the south side of Navy Pier. We walked to the end and enjoyed the nighttime views of the pier and city from the pier and then from back on our boat.




























































Monday, August 31 was our last day in Chicago. It started out with a lot of rain so we didn't venture out for a walk until around 10:30 and still dodged some raindrops a first. We walked along the lake shore trail and crossed over the bridge at the entrance to the Chicago River. We walked past Dusable Marina, Columbia Yacht club, which is located an old ship, and the Chicago Yacht Club at Monroe Station. We had planned to move to the Chicago Yacht Club today but due to the rain and the fact that the clubhouse is closed on Monday, we just stayed at Navy Pier. We then walked by Buckingham Fountain in Grant Park and to Millennium Park. We ran an errand at Target on State and Madison Street, located in the historic Sullivan Center building. We walked back to the water on the BP pedestrian bridge. Later we met Tim's sister Julie back at Navy Pier for Happy Hour at Chef Art Smith's Reunion restaurant and dinner at the Offshore Rooftop Bar. It poured rain while at the rooftop bar but it has a glass barrel shaped roof so we stayed dry and then enjoyed a beautiful rainbow crowning Navy Pier afterward! After the rain we walked around the pier and saw the iconic Bob Newhart statue based on the 1970s Bob Newhart show where he plays a psychologist living and working in downtown Chicago. Being in Chicago on our own boat and seeing family there will definitely be one of the highlights of our Great Loop adventure! Our next stops will be working our way down the Illinois Waterway to Grafton, Illinois near St. Louis.































































