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Road Trip Recap (Plus Our Chicago Itinerary!)

  • June 28, 2021
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We returned from our annual family vacation last week, and we had such a blast. I know vacationing with kids is not all that relaxing, but I love thinking about all the memories we are giving to our kids with new people, new places, and new experiences.

For our family trip this year we traveled to Madison, Wisconsin to see some college friends, to Chicago, and finally to a small beach town along Lake Michigan.

If you’re traveling in the area, I included some family friendly activities and restaurants. Otherwise, please humor me with all the sappy family pictures. I couldn’t resist making this post as a scrapbook of our travels.

Day 1 through 3: Madison, Wisconsin

This portion of our trip was really just to visit some old friends so we didn’t sightsee much in the area, but we still had a great time. The weather was HOT so we did visit our friend’s neighborhood pool twice which the kids LOVED because they had a huge slide. We also grabbed donuts and breakfast sandwiches downtown at Bloom Bake Shop (so amazing, some of the best donuts I’ve ever eaten!) and sat out on the Memorial Union Terrace on the University of Wisconsin campus which is a popular spot for students and locals and gave us a beautiful view of the water.

The kids had a blast in Madison and said it was their favorite portion of the trip.

Day 4 through 6: Chicago, Illinois

This is where Danny and I planned a ton of activities to fill our days. We stayed in the downtown area at the Homewood Suites which is nothing special but was in a great location for all the tourist sites. I will say that although Danny and I are foodies and would have loved to try all the hip local cuisine in Chicago, we mostly stuck with family friendly, touristy spots that were within walking distance of our hotel. Parking is expensive in Chicago so we just parked our car for the entirety of our trip and walked or took public transportation to most places.

Day One In Chicago
a dad and two kids walking into the Field Museum in Chicago

We got into the city around noon and drove straight to the Field Museum. We stopped at a little hot dog stand outside the museum for a Chicago dog, which was delicious, but that pickle spear on top is a little awkward to eat (LOL).

The Field Museum was really amazing. The kids were fascinated with the collection of dinosaurs bones and were of course amazed (as was I) to see the only complete T. Rex ever to be discovered (named Sue after the paleontologist who first uncovered her).

After the Field Museum and checking into our hotel, we went to Doc B.’s Restaurant which was across the street from our hotel, very kid friendly and a had a great selection of semi-healthy options. I got the turkey burger!

We then went for a walk along the Chicago Riverwalk and stopped for donuts and ice cream at Firecakes.

Day Two in Chicago

The first stop of the morning took us to Intelligentsia Coffee for breakfast of coffee and pastries.

Then on to Millennium Park to see The Bean and then to Maggie Daley park for some play time.

If you have playground age kids, I would definitely plan a stop at this park in the middle of the city. It’s really a magical little park with all sorts of creative playgrounds and little places for kids to explore.

After the kids got some wiggles out, we trekked over to the Navy Pier with a stop at Cupitol for lunch. The Navy Pier had a bunch of things for the kids to do. We let the kids pick which rides they wanted to go on, and they chose the carousel and the tea cups.

After heading back to the hotel to rest up, we headed out for deep dish pizza at Lou Malnati’s by the Magnificent Mile. I was nervous that the pizza was going to be super greasy, but it wasn’t all all. It was really saucy with thick crust (loved it!).

Day Three in Chicago

Our last half day in Chicago, we took the subway to the Lincoln Park area and stopped at a French bakery called La Fournette for coffee and pastries (can you tell we like coffee and pastries?) The last stop was the Lincoln Park Zoo which was really good for being a free zoo (donations are accepted).

If you can believe it, even though I’ve lived in the Midwest most of my life, I’ve never been to Chicago, and I LOVED it. I’m hoping to get back soon with just Danny to try out some cool restaurants and see some shows.

Day 6 Through 7: St. Joseph, Michigan

Our last on our road trip was to St. Joseph, Michigan which is a little beach town along Lake Michigan. The big draw to the area is Silver Beach County Park which is a nice little beach area with a playground area, splash pad, and restaurant. We spent most of our last day here just enjoying the sand and water. We had lunch at Silver Beach Pizza which is right near the park.

After resting at the hotel for a little while, we grabbed dinner at Silver Harbor Brewery which had a decent beer selection and good food. It was also SUPER kid friendly.


We had so much fun on our little family trip. I love exploring new places with Danny and my two little sidekicks. I have such fond memories of the trips we would take as a family growing up, and I want my kids to have those same happy memories.

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