Midwest 7 Day Road Trip Itinerary – Chicago, Wisconsin, Minnesota

In 2019 we embarked on a Midwest road trip from Omaha, Nebraska to Chicago, IL, to Sheboygan, WI to the North Shore of Minnesota. Today I’m sharing all the details with links to where we stayed, ate, and played.

Day 1-3: Chicago

Day 1: We hit the ground running and walked all over the city. We stayed at a Marriott and never moved our car. Walking or taking Uber everywhere was much easier.

We made our way to The Bean. We are suckers for the tourist pictures everyone takes.

For dinner we ate at Revival Food Hall where we met up with old friends. If you have followed my blog for a long, long time then you will recognize this face. Revival was so fun and perfect with food court type selections for everyone plus games and entertainment. A low cost meal option was nice too.

Day 2: Architecture Boat Tour River Cruise on Chicago’s First Lady. This was an absolute highlight of our trip. I have never taken so many pictures of buildings. The tour guide was fabulous and we learned things about these buildings and the history we wouldn’t have learned otherwise. I’m not one for group tours or anything guided. However, this was excellent, and I’m so glad we didn’t miss it!

Lunch was at Portillo’s. It was worth all the hype. Our boys loved eating hot dogs with all the unique toppings you don’t see often. Or ever.

The Field Museum was the next stop after lunch. If you love museums, you’d enjoy the Field Museum. We flew through it because none of us are big museum lovers. However, you could spend hours here, especially if you have younger children. I’m still glad we stopped in.

Navy Pier was next where we enjoyed a fun drink and snack at Bubba Gumps. It’s very touristy, but still a fun experience if you’ve never been. Both Navy Pier and Bubba Gumps! If you are a Forest Gump fan, you have to eat at Bubba Gumps at least once in your life. When you need service, you place a Stop Forest Stop sign on your table. If you are all good, keep the sign on Run Forest Run. The peel and eat shrimp soaked in garlic butter is our favorite.

You can’t visit Chicago without having pizza. Dinner was at Giordano’s South Loop.  It was everything you think a Chicago style pizza should be.

Day 3: Our final day in Chicago started with a walk to breakfast at Yolk. Breakfast might be our favorite meal so on each trip we try to find at least one or two great spots for a memorable meal. This picture would be the breakfast my middle son, Zachary, chose. Full of sugar.

We took in an afternoon Chicago Cubs game. I’ve never been more impressed by a stadium. Wrigley Field was so clean and had an old, classic look, yet felt so updated. I don’t even remember who they played, but I loved every second of being at that field.

We packed in everything we wanted with 3 days in Chicago. Next stop Sheboygan, WI.

Days 4-6: Sheboygan, WI

The drive from Chicago to Sheboygan is only a 3 hour drive. So we timed our drive in order to visit the Jelly Belly Factory on the way north. This was such a fun, quirky stop. I’ve recently learned this factory closed. So sad as it was so much fun!

Had we known how much we’d love the Airbnb and Sheboygan, we would’ve stayed more than 2 days. This was a nice change of pace from the city.

The house was spacious and spotless. The views of Lake Michigan were incredible. You walked right out the back door through the yard onto your own private beach. Lake Michigan is impressive. I describe it as a lake that behaves like the ocean.

The house was perfect for our family. My husband loved the record player and selection of vinyls. The boys loved the loft with binoculars and lots of board games, particularly Monopoly. I really dislike that game. They started a game that continued for the full 2 days we stayed here. My favorite part of the house was the backyard and beach. It was so nice to grill, sit around the fire, and watch the moon over the lake. This rental goes down as one of my favorites of all time.

Day 4 we simply enjoyed the home, grilled, and played at the beach.

Day 5 we explored Sheboygan. We walked the paths and enjoyed the views at Blue Harbor Resort. The South Pier District was so quaint! We played mini golf at Harbor Pointe, ate ice cream at South Pier Parlor, kayaked, and simply enjoyed the stroll along the pier.

Next we headed to Kohler State Park and raced up and down the dunes. It was an absolute blast.

Days 6-7: Lake Superior, Minnesota, and the North Shore

Day 6: We woke and began the 6 hour drive before dawn. We started our Minnesota portion exploring in Duluth, MN at the southern tip of Lake Superior. Our first stop was the Lake Superior Maritime Museum. This was informative and interactive. We all enjoyed it.

We stopped at pullouts along the drive enjoying the wildness of Lake Superior. We spent the night in Two Harbors. We wished we had not stopped here for the night. To do it over we would have driven straight up and stayed 2 nights at our final destination, Grand Marais.

Day 7: Gooseberry Falls State Park and Black Beach were both complete treats. We hiked through Gooseberry. It was beautiful. Black Beach was our favorite. We played in the sand and climbed rocks. We slowed down and took it all in.

We made it to Grand Marais, the most adorable harbor village. After checking into our hotel at The Best Western Plus Superior Inn (which we loved because the rooms came with incredible views of the lake), we hit the pavement once again to explore all the town had to offer. I quickly found an adorable bookstore, Drury Lane Books. I almost never travel without visiting a bookstore. Or several.

We ate dinner on the rooftop of one of the many restaurants and went back to the hotel for a good night’s sleep before driving home the next day.

This was a perfect 7 day road trip and I wouldn’t add or take away a single day. My only change to what we did is that I would skip staying in Two Harbor.

The fun is in the discovery and the exploration. The memories you make traveling with the people you love last a lifetime.