Chicago: Managing the Big City with Little Kids

A few months ago, my family planned a road trip to Chicago for over the 4th of July weekend. We’ve always wanted to go and decided now was the time. So, we packed up our 7 and 4 year olds and did our best to keep the 8 month old happy in his car seat (which he hates), and off we went! Road trips are no joke, but we did it like a boss (want some tips for successfully taking on a long road trip with kids? Check out my post on that here).

Chicago with kids can – and SHOULD – be done. Here’s how we made it happen successfully and filled it with tons of amazing memories for the little ones AND their parents. Don’t worry…there were plenty of meltdowns, time-outs and tantrums. We just didn’t capture those on camera.



Getting to Chicago will cost you a little extra in toll money, so fill a ziplock with quarters and dimes and stuff it in your glove box before you leave home. A couple other items to consider before leaving:

  • Consider buying the CityPass: Depending on where you’re staying, the length of your trip and the ages of your children, this is up to you. Could save you money, or could waste it. We didn’t purchase it (after much debate) because we knew how many museums and scheduled activities our littles could (not) handle, so we decided to just pay by activity.
  • Pack appropriately: You’re from the midwest. You know the drill on weather-appropriate clothes. Walking is big, so comfy shoes are key. We put on about 10 miles a day (and some of us have little legs). Also, a stroller will be key if you’re putting on tons of miles and public transportation isn’t your thing. Even our 7-year old took a fair share of turns in our stroller.
  • Check deals on places to stay: Depending on where you want to be, check rental websites for cheaper options. We had points for the Holiday Inn in Schaumburg so stayed there two nights. Then did the downtown Hyatt Magnificent Mile for another two nights to get the full experience. SO glad we did that! Staying in the city? Try sites like Groupon or LivingSocial. Staying in a suburb? Maybe find something cute on Airbnb or VRBO.
  • Save up: This city ain’t cheap. Don’t say I didn’t warn you.


The hike from Minneapolis to Chicago takes approximately 6-7 hours..with perfect traffic, no pitstops, and well-behaved children. Knowing our family as we do, my husband and I knew we had to build in some lengthy outings to get out and burn some energy along the way. Some of my favorite recommendations include:

  • Crystal Cave in Spring Valley: Not very far from the Twin Cities, but a fun stop for inquiring little minds who are into speleology and bats and stuff
  • Action City in Eau Claire: An arcade, go-karts, lazer maze, batting cages, mini bowling and mini golf, laser tag, a climbing wall and bumper cars
  • Mocha Mouse in Black River Falls: Ice cream and coffee and Wisconsin cheese and beer is sold at this cute little pit stop (there’s also a giant moose and mouse statue which make for cute photo opps)
  • Henry Vilas Zoo in Madison: One of my favorite FREE zoos in one of my favorite cities! This one is just awesome and it’s a little over halfway to Chicago, so a perfect place to break up the trip.
  • Ella’s Deli in Madison: One of the most bizarre little delis ever, with a working carousel and ice cream to boot

There’s plenty to see and do along the trek, so do your own research too if you know stops will be needed frequently with your crew. You know what they say…getting there is half the fun.

roadtrip to chicago


Our family tried to save a little money by staying in the outer suburb of Schaumburg the first two nights. I liked this because our kids are young and don’t know the difference yet, and it obviously cost far less than staying downtown. We filled our 1.5 days in Schaumburg with a lot of good memories, but my favorites was Medieval Times. Yup, I know it sounds cheesy (and it was a little bit), but to see my daughter meet a queen and my son cheer ferociously for his knight was just so worth it. I had been to a Medieval Times before, so knew to expect a gadzillion tchotchkes and overpriced crap that my kids would beg for. And I got them. Because, memories. The shows are as early as 4:30pm and the food is actually decent, but the price? Wooo doggies, it was expensive! We found a half-price “4th of July” package off their website, where you can find some other decent bargains too, or check Groupon.

Sidenote: Schaumburg also hosts a LEGOLAND Discovery Center if that’s more your cup of tea.

medieval times

Another of our “suburb days” was spent exploring. We drove to the Lake Michigan coastline and found some killer beaches! I was actually shocked and how nice and non-Midwestern they felt. We had to pay to access the two we went to, but we spent hours there, splashing in the waves, building sand castles, playing frisbee and relaxing on the blanket to care about the cost. If you’re curious, the two beaches we visited were Gillson Beach in Wilmette and Paulus Beach in Lake Zurich (which also has a playground and splash pad).

Oak Street Beach and North Avenue Beach were also supposed to be solid choices. We just didn’t get to them.


If you are near the coast and have a soft spot in your heart for the iconic Kevin McAllister (like I do), take a detour to visit the well-groomed and well-secured Home Alone house. It’s located at 671 Lincoln Ave. in Winnetka, IL and has a pretty decent gate blocking tourists like ourselves, but whatever. We got our pictures. We were tourists. We probably angered the lady who owns the joint. And we went on our merry little way. It was the highlight of my trip (nerd alert!).

Along the same level of excitement as the Home Alone house for us parents was devouring the best of the best deep dish pizza and Chicago-style hot dogs. My husband is an absolute pizza whore (can I say that here? I just did) and we really wanted him to find something that blew his mind. We asked around and received a lot of the same names: Lou Malnati’s, Giordano’s and Gino’s East were the top three by a landslide. We (sadly) only tried Lou Malnati’s from that list, but also gave Pizzaria Due a shot downtown and…mmmm…that one should’ve made more lists! Of course, I’m no food blogger, so take it or leave it, but we liked them both very much.

home alone house

Also in the suburbs, we tried the highly-recommended Portillo’s, known for their hot dogs and shakes. Not gonna lie, you guys – this one hit the spot! It quickly became my son’s favorite restaurant and even the baby gobbled up their tasty french fries. There are a number of Portillo’s in the Chicago area so just make a point to have one of their dogs while you’re there. Nom nom nom.

And as you venture closer to the city, just north of downtown, you’ll find Lincoln Park Zoo. We didn’t visit the zoo simply because we stopped at Henry Vilas Zoo on the ride down, but it’s supposed to be AMAZING! And…FREE! The only downside I could see from their website was parking – pricey and hard to find. But once you’re there, it’s incredible. I can’t comment on it firsthand, but I CAN tell you that it will definitely be one of our must-sees on our next trip to Chicago.



Before we settled in to our hotel, we drove on the western outskirts to the United Center to show our basketball-obsessed son the statue of Michael Jordan. I don’t know who enjoyed it more…him or my husband.


Our hotel was in a fabulous location – right between the water and the Magnificent Mile! I recommend the Hyatt Magnificent Mile for families with kids who want to get everywhere without having to trek 10 miles. Navy Pier was only one mile away and the Magnificent Mile shops were only two blocks away. Plus, it had a small swimming pool and hot tub, a Starbucks in the lobby, and it’s right next to some great little bakeries and donut shops (and if you know the Brunner’s at all, you know our obsession with donuts).

The kicker to staying downtown is parking. Valet parking is sometimes just as cheap as driving and walking a mile from a nearby parking ramp. Otherwise, feel free to just ask the valets where the closest ramp is with the best rate. They are happy to tell you and you can make the decision on the spot. Sometimes they will even give you a discount code to the ramps to save you money. If you’re feeling techy and smart, use an App on your phone to find parking spots anywhere in Chicago for specific times or locations. Download SpotHero or ParkWhiz to make this job a lot easier during your vacation.

Speaking of the Magnificent Mile, there are some fun shops the whole family can enjoy, including a Disney Store, Jordan Store, Nike Store, and Bye Bye Chicago (great souvenirs). Also, you MUST buy a bag or two of popped goodness at Garrett’s Popcorn Shop and – when you’re feeling risky – take your kids to Dylan’s Candy Bar and let them enjoy two levels of sugar-coma-inducing consumerism. It’s a diabetic’s nightmare, but a child’s dream!

dylans candy bar

Just walking the street is an adventure in and of itself – street performers, magicians, and food vendors make it a sight to see. If you are pushing a stroller, do note that you will want to always try to go OVER (not under) bridges to cross streets. Safer, cleaner, faster and smarter. Oh, and little people will LOVE that every single building has a rotating door (thanks to the “wind” in the “windy city”). Rotating doors are fun, but heads and hands can get smucked if you don’t watch kiddos carefully, so just be aware.

If walking sounds overwhelming (no judgment – I get it x3), or you need to get from one end of the city to the other, do not be afraid to utilize their public transportation – namely, their bus system. There are bus stops all over the place, and the schedules are listed right online. We just asked our concierge at the hotel. It’s a really good deal with kids since it only costs $.75 for kids ages 7-11 (and free for under 7). Ages 11+ are only $2.25 to ride. This was worth it for us to get to the Shedd Aquarium and other sites that were a lot further south than our hotel.

If your destination is the Navy Pier, be sure to check out the free trolley. It really is easy to get around the city sans car. I highly recommend.

bus ride


There are SO many ways to play downtown, but here is a quick list of our favorite downtown adventures:

  • Visit the Bean in Millenium Park. It’s actually called “Cloud Gate” but us commoners just call it “The Bean.” A fun way to see yourselves and the city through a giant house-sized mirror.

the bean


  • Spend half a day playing at Maggie Daley Park. This place has the potential to overwhelm you. In fact, during busy Saturdays, an estimated 15-20 kids are reported lost per day! You better believe this made us nervous to visit the park, but it’s really a beautiful work of art, and when we split the kids in half it wasn’t that bad. This 20-acre play area sits in the middle of the city and is separated into different sections…from mini golf to water fountains to a giant ship to slides and climbing structures (and even a skate rink in the winter months)…it’s crazy fun! Bring your swimsuits on a hot day and enjoy the experience.


maggie daley

  • Visit the Shedd Aquarium. Our clan spent nearly four hours here, watching shows, checking out the creatures of the sea and touching sting rays. This place is huge and well laid out, it’s very easy to get from A to B without little legs getting tired. A couple notes about the aquarium: Buy your tickets online to skip the (very long) lines. Also, there is a door on the side for strollers/families that you should definitely utilize to avoid the crowds. And go early! You could quite literally be waiting down the outdoor steps if you get there at peak time. The admission rates aren’t cheap, but it really is a cool experience. It’s also part of the CityPass, if you go that route.


  • Get some education at the Field Museum. Similar to the Science Museum here, the Field Museum is a great place to fill your children’s minds with history, geography and dinosaur lessons. Mine? Far too young. We just didn’t go. Their attention span = a gnat’s attention span, so we knew better. But if your kids yearn to learn, this is supposed to be awesome! Also part of the CityPass.
  • Enjoy everything on Navy Pier. During our visit, we only got to the tip of the pier to watch 4th of July fireworks (incredible, btw), but I do regret not making the full walk. With food vendors, the Children’s Museum, and the new Polk Bros. Park (fountains in the summer, ice rink in the winter), this is a great place to visit to grab some souvenirs or take a ride on the freshly-updated ferris wheel overlooking Lake Michigan.

navy pier

  • Step into the sky at the Sky Deck. I’m not sure this is worth the mega bucks it costs to experience it, but it IS unique and incredibly frightening. The Ledge sits on the 103rd floor of the Willis Tower and is basically a glass box that allows you feel as though you’re standing in thin air. Kids think that part is sweet, but the rest of the “experience?” Meh. Take it or leave it. Also part of the CityPass.

There’s a Museum of Science and Industry, the Adler Planetarium, Water Taxis, double decker buses, Soldier Field and Wrigley Stadium as good tourist options as well. I know there’s an American Girl Cafe and a Rainforest Cafe that people say are very kid-friendly, but I loved just taking my kiddos to some unique restaurants along the streets of Chicago, like Broken English Taco Pub (mmmm, some of the best carnitas ever!) and sipping on orange pop and Goose Island Green Line IPA.


Mostly, our favorite memories took place strolling the streets and stopping in random shops or grabbing a spontaneous craft brew or a snow cone from a street vendor. While kids should be treated like kids and have plenty of kiddy experiences, Chicago is a city where both kids AND adults can have fun taking the same types of adventures. Everything is big, bold and beautiful and if there’s ever been a city where everything becomes an experience, Chicago is it.

Just as any trip with kids goes, do your best to go with the flow, set low expectations, say yes more than no (it’s a vacation!), prepare enough ahead of time, do your research and try new things.

Chicago is a city of wonderful adventure and, if you do it right, maybe your kids will fall in love with it like mine did. My daughter wants to move there and become a “pizza cooker” (maybe she’ll perfect the art of deep dish and offer to host Christmas dinners. Hey, a mom can dream).

You Might Also Like

  • Holly
    09/27/2016 at 10:31 am

    We took a family road trip to Chicago this year with our kids (ages 6 1/2, 4 and 2 1/2) and love your article for more ideas on what to do the next time we go! Our kids loved it. We were there in the very early Spring so missed out on the beaches and Navy Pier and stayed in a suburb all 4 nights. Your tips make me brave enough to stay downtown the next time. I totally agree with hitting the big tourist attractions early and buying tickets online. We spent a day at the Field Museum and a day at the Shedd Aquarium and when we were leaving mid to late afternoon, the lines to get in were literally blocks long. We also made the short trip to see Kevin’s house – SO fun and totally nerdy!