Five Reasons Why All Chicago Families Should Take a Road Trip to Milwaukee

As wonderful as Chicago and its suburbs are, sometimes it’s great to just get away for a bit. But when you have small kids who don’t do well in the car, your options are pretty limited. That’s why I am reminding you that there is a gem of a city located right over the border…Milwaukee! It has amazing museums, delicious restaurants, beautiful sites…and all at a fraction of the cost of typical Chicago activities. Don’t believe me? Here are five reasons why every Chicago family should take a road trip to Milwaukee.

Reason #1: The short and scenic drive. SO many people complain about how their baby or toddler WAILS every time he or she is buckled into the car. It’s enough to make you home bound until they reach school age, but don’t give in! Milwaukee is a straight shot from Chicago and there are tons of spots to stop off (hello, outlet malls!) if you are desperate to get out of the car for a bit.

Reason #2: The big city feel on a small scale. Small boutiques? Delicious farm to table restaurants? Busy public market? Gorgeous lakeshore? A vast zoo? Checkity check, check, check.  And did I mention that parking is readily available and so affordable that you will still have money left over to splurge on an ice cream flight at the Purple Door (psst…the Banana Pudding Ice Cream is out of this world)? Cha ching.

Reason #3: The museums. We are old pros when it comes to Chicago’s museums, and I have to admit that the Milwaukee ones are just as impressive. The Milwaukee Art Museum is a stunning piece of architecture that actually MOVES twice a day (seriously…it’s amazing) and Discovery World is so packed with family fun activities that you could spend the entire weekend there. Our personal favorite? The Kohl’s Design it Lab, where creativity abounds. For the littlest tourists, the Betty Brinn Children’s Museum is the perfect fit with its interactive exhibits that encourage learning and curiosity. And don’t miss the Milwaukee Public Museum and its wide array of exhibits, from the world’s largest dinosaur skull to interactive displays that allow you to swim under water or climb Mt. Everest.

Reason #4: Everything is kid friendly. EVERYTHING. The Third Ward is the trendiest spot in all of Milwaukee with cute shops, restaurants and café’s…and the children’s menus were just as drool worthy as the adult menus. You can even bring your kids to Sprecher Brewery so they can learn all about soda flavors while you learn about beer. Kids are also welcomed and encouraged at the Harley Davidson Museum and Safe House—if you know the password!

Reason #5: There are comfy hotels with nice indoor pools, plush beds that you don’t have to make yourself, and room service! My family prefers to stay the Marriott because of its location and low price point, and other options include the Hampton Inn and Suits in Downtown Milwaukee and fancy Pfister Hotel. But seriously, sometimes just a change of scenery is exactly what you need to clear your head and relax…especially when you don’t have to clean up after yourself.

Looking for other fun road trip options? Check out my family’s tried and true favorites, including our family travel checklist and other things that make traveling a breeze!

Bon Voyage!
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  1. Robin Rue says

    I have never been to that part of the country at all, so I would love to see Chicago AND Milwaukee someday.

  2. Jeanette says

    I have been in the lock if you times but I’ve never seen any of the stuff. Obviously I need to go back and check these places out because they look awesome.

  3. candy says

    Milwaukee sounds like fun place to visit. I have never been there and would enjoy visiting and seeing all the different things the city has to offer.

  4. Christy Maurer says

    I had no idea there was so much to do in Milwaukee! It sounds like a great city to visit. I’ll have to add this city to my travel list. I’m in Ohio, so it’s not all that far!

  5. Mars says

    Oh wow it seems that you had a great trip to Milwaukee. Never been to that place but I love to go someday. I want to see those museums.

  6. Pam Wattenbarger says

    I have actually been hearing a lot about Milwaukee lately. It seems to really be on the up and up when it comes to being a destination spot.

  7. Claudia Krusch says

    I would love to go to The Milwaukee Art Museum. I had no idea there was so much to do in Milwaukee.

  8. Destany says

    You had me at “children’s museum.” I’m a HUGE fan of children’s museums. Now that my son’s older, he doesn’t really care for them, but I love visiting the one in Indianapolis

  9. Annemarie LeBlanc says

    I have been through that “wailing child in the car” phase of life. I am glad I’ve survived that! Short road trips with small children would be best because the little ones cannot sit still for a long time. Milwaukee looks like a fun-packed place to take the family. I only wish I lived closer so I can take the grandkids there to have a great time too.

  10. My Teen Guide says

    Me and my family love visiting museums. Everytime we are in a new place, we ask around for the location of the museums. It is an awesome experience to view artifacts of times that have passed. I did not know Milwaukee has a lot of museums to visit. Hope to do so soon!

  11. Rebecca Swenor says

    These are all great reasons that every Chicago family should visit Milwaukee or any near by family for that matter. The Sprecher Brewery sounds interesting for the whole family including the children. Thanks for sharing your experiences.

  12. Katie says

    We’re a Chicago family (both my husband and I were born and raised in Chicagoland) who visited Milwaukee several times and loved it. When we outgrew our lakeview condo and started looking at more-house-for-the-money suburban options we actually ended up moving here! We love that we have a city life at suburban prices, we’re still close to Chicago, and that we’re in such a vibrant but approachable city (although we do have to make our own beds here 😉 ). My husband commutes to Chicago 1-2 times per week (so easy on the train!) and otherwise works from home. And, we’re in good company – many families do the same. Once Chicagoan’s realize just how close Milwaukee is they often return again and again… and I’ve now learned that many of us end up here permanently!

    • Amanda says

      I can totally see how Chicago families feel at home in Milwaukee. So many great similarities…except for football rivalries every Sunday! 😉

      • Katie says

        Ha, yes… that’s true! This is for sure Packer’s country but we’ve been surprised how many Bears (and Cubs) fans we meet up here!

  13. Katie says

    Already posted but just thought of a Milwaukee attraction that we LOVE with our family and readers should check out – beer gardens! They’re part of the culture here and on summer nights you’ll find families sitting around listening to live music (often polka) adults drinking a beer, kids playing on the lawn or munching on a giant soft pretzel. It’s amazing! Our favorite is Estabrook Park (in part because it has a huge playground adjacent!) but there are beer gardens throughout the city.

  14. Eileen Collins says

    Hi Amanda! #6. You can find cool cousins there! Charlie lives there, sheila is going to school there next year, and I’m there weekly!
    Like Chicago it’s even better in the summer! Summer fest and Irishfest rock even for the wee ones!

  15. David Elliott says

    Ah! Happy Days and the Fonz! It has been such a long time. I wouldn’t have thought about going to Milwaukee, but this makes it look like a lot of fun. If I plan a road trip up that direction I will have to make a stopover there.

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