Road Trips for Chicagoans


As wonderful as Chicago is, there are some times when you need to just get out of town and a trip to the tropics simply isn’t in the budget. What to do? Pack up the car and head to some of these family friendly Road Trip Destinations for Chicagoans. Here are some of our favorite local options that are short on travel time but big on FUN.


I have written previous posts about one of our favorite vacation destinations, The Wisconsin Dells, but that isn’t the only great water based vacation in the state of the “cheese heads.” Sorry, Packer fans, I can’t help it.

Two summers ago we traveled to Sheboygan, Wisconsin and had an amazing time at the Blue Harbor Resort. Not only was the hotel beautiful with kid friendly rooms and restaurants, but they also have amazing pool facilities.

We spent hours upon hours in the indoor waterpark, outdoor pool, miniature golf course, and our absolute favorite—the beach! Although it was a little chilly when we visited (in July, isn’t it supposed to be hot then?!?) we had a great time walking on the pier, exploring the sand dunes, and just enjoying the beautiful view.

Since the American Club in Kohler isn’t too far away, it was a great place to visit for spa treatments for mom and dad, as well as a great family dinner at the Horse and Plow. The boys got a thrill from checking out the beautiful scenery outside the famous golf courses, including their grandpa’s favorite Whistling Straights.

Lastly, don’t overlook another fun Midwestern city–Milwaukee! Just about everything there is family friendly, from their hands on museums to their beautiful market and even the secret spy restaurant! You can check out my tips on visiting Milwaukee here.


Tim Allen sure isn’t lying in his “Pure Michigan” commercials. It is such a beautiful state with so many quaint and fun family friendly towns to visit. Last summer we booked a house for a long weekend in Coloma, Michigan, and had an amazing time enjoying the local beaches, parks, and forest preserves. Next time we will be bringing some babysitters so we can enjoy the wineries as well!

Since Coloma is nestled between Benton Harbor and South Haven, we had tons of options for family friendly activities when we wanted to take a break from cooking and hanging out at the rental home.

In South Haven, there are a ton of delicious and family friendly restaurants, as well as a giant pier and lighthouse (and a beach too) to enjoy. We liked going to South Haven for dinners, ending our day with some fresh ice cream and watching the sail boats while listening to local musicians play in the local park.

While Benton Harbor is another beautiful town on the beach, we spent more of our time in the beach in St. Joseph. We had a great time climbing on the water-inspired sculptures, the kids’ parks nestled on the beach, the ENORMOUS and interactive water fountain, as well as the whimsical carousel. We could have spent our entire trip at this one beach, rain or shine.


Don’t think that we Chicagoans need to escape the Land of Lincoln in order to have fun. I went to college for my undergraduate degree at Augustana College, one of the best parts of the Quad Cities. But trust me, that isn’t all that the Quad Cities have to offer.

John Deere started his company in Moline, Illinois, and there is a huge museum set up for visitors to learn all about the famous American company, as well as enthrall truck loving toddlers like my boys. The fact that you can touch tractors and combines, as well as climb up into them is worth the drive from Chicago.

Speaking of Augie, our campus is the perfect place to enjoy the beautiful weather and help your kids expend some energy. The rolling hills, especially the ones located along our iconic slough path, provide tons of entertainment and relaxation for nature lovers of all ages.

Finally, there is the fantastic Family Museum, which is on par with children’s museums in more Metropolitan areas, such as the Kohl Children’s Museum, DuPage Children’s Museum, and Chicago Children’s Museum. Located in Bettendorf, Iowa, it is a great way to learn and play with your little ones. You can read all about why your family should visit the Quad Cities here.

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  1. Becky says

    Have you ever been to Galena? Fun restaurants and cute downtown with some great trails for families! You might want to put that on your summer list 🙂

    • amandasimkin says

      Yes, I was just there last summer for my cousin’s bachelorette party. It is such a cute little town…definitely somewhere to take my boys (along with my cousin and her new hubby!). Thanks for the recommendation! Hope all is well with you and your girls! 🙂

  2. Jody @ Because I'm Me says

    Sheboygan is one of our favorite towns. We stayed at Blue Harbor when it first opened and fell in love with the place, especially that water park (hotels don’t have indoor water parks in south Florida). A great stop when in Sheboygan is the free John Michael Kohler Arts Center, especially the bathrooms, one of which was rated as one of the top 10 restrooms in the United States.

    • amandasimkin says

      When I was a little girl I spent HOURS in that bathroom. I was enamored with the fact that their soap was in little sheets.

  3. Terri Ramsey Beavers says

    What a great place to vacate at. The kids would go super nuts over a place that has an indoor waterpark and mini golf. It would sure help curb some of their energy to get out and have a great time doing things they love.

  4. Giveaways 4 Mom says

    It sounds like you were able to see some great places. When my boys are older I hope to be able to travel more. There are so many places in and out of the states that I want to see.

  5. Stacie @ Divine Lifestyle says

    The Midwest may have some crazy bad winters, but it certainly makes up for it in attractions. It seems like there’s something to do all over the place there. I think the American Club would be a great destination for me and my family.

  6. Chubskulit Rose says

    We love going on a road trip during summer time but you guys are amazing, you have been through so many already and it’s not even Spring, great jpb! Thanks a lot for these tips and the links you’ve included. I hope that we could visit Wisconsin someday.

  7. Mindi says

    We were in Chicago last year and had such a great time. We want to go back for a return visit sooner than later. When we do, hopefully we’ll be able to add some time to do a road trip. Great suggestions!

    • amandasimkin says

      There are so many great new restaurants…and a ton of hidden gems that are simply amazing. Do your research before you come back (and ask me for tips, too!).

  8. Nancy says

    Is it bad to say that I’m on “spring break” year round? I’m kind of one of the lucky one’s who doesn’t have to work just yet. We recently moved from Canada to California. But speaking of Chicago, I think I said this before – but I am having a 9hr layover in Chicago airport next month and having never been in the city before, I’d love to check it out.

    • amandasimkin says

      Depending on which airport you will be at (OHare or Midway) there are some fun things that you can do. No one wants to stay in an airport for 9 hours, that’s for sure!

  9. Tammilee Tips says

    There are so many great places to travel to in the Midewest! I cannot believe that it is almost time for spring break. Doing a local type of staycation is a great way to spend spring break.

  10. Amy Kelsch @ItsAMindfulLife says

    I live in Minnesota so this post has a ton of helpful information for me. I was really drawn to the Blue Harbor Resort. It looks like a wonderful place to visit- both for adults and children. I am putting it on my to-do list!

    • amandasimkin says

      It is really a nice resort and the area is gorgeous. I would think that it wouldn’t be too far of a drive for you, depending on where in Minnesota you live. Midwest is best, right?!?

  11. Geanine says

    We have taken a Spring Break road trip to the South with two little ones, and it was awesome! We stopped in just about every other state and made an adventure of it all. Of course there were a few tantrums etc, but in the end memories were made. Glad you had as much fun!

    • amandasimkin says

      That sounds like fun. I have such good memories of road trips in my grandma’s huge Lincoln town car as a girl…it was so sad when she got rid of it!

  12. Amanda @ Adorkablii says

    Looks like there are some awesome places to go on Spring Break! I don’t even know when my son’s spring break starts. Today is the first day of spring and we are in the middle of a snow storm… lets talk about how happy I am not! hahaha I want to go on a road trip with my son. There are so many places to explore and I know he would love it! =) Thank you so much for sharing!!

    • amandasimkin says

      Ugh–no more snow!!! We are supposed to get some on Monday. Typical Spring Break in Chicagoland….

  13. jared's mum says

    even when we do not have spring where i am, it is my favorite season next to summer! the riotous colors of different flowers, in my opinion, is simply lovely + breathtaking!

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