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Visiting Chicago: Your travel guide for kid-friendly destinations

Tips for taking on the Windy City from a mama who calls it home.

Visiting Chicago: Your travel guide for kid-friendly destinations
Leyla Tran for Motherly

When a baby is born, for many families, the vacations stop. And while it can be intimidating to get out and just go with a little one in tow, with the right preparation, family vacations can be a rewarding, memorable experience for everyone.

All it takes to make your next adventure a success is a little planning―and a great, grab-and-go carrier like a BABYBJÖRN Baby Carrier One Air. Simply pop your little one into the breathable mesh carrier, secure the straps, and you're ready to take on your destination like a pro―all while providing a fresh perspective for your baby or toddler (it's suitable for children up to age three!).

Next, pick your destination. Thanks to easy-to-access beaches, a host of incredible museums, and a variety of outdoor and indoor activities, Chicago is a popular vacation hot spot for families year-round.

Not sure where to start? Leyla Tran, Chicago native and blogger behind Second City Mom, filled us in on her favorite kid-friendly spots around the Windy City.


DO

Leyla Tran, with her husband and twins at Chicago's Garfield Park Conservatory in front of one of her favorite features.

Chicago Children's Museum
Sure, you'll have to battle a throng of tourists to get through Navy Pier most times of year, but it's worth it to reach this gem. From a dinosaur dig to arts and crafts areas, there's something to satisfy every interest at the Children's Museum. Plus, you can face baby out in the BABYBJÖRN Baby Carrier One Air so there will be plenty to hold their attention while they ride along! Check the museum's calendar to find out what special events and exhibits are open during your visit.

Garfield Park Conservatory
If you're visiting during the colder months, the Garfield Park Conservatory is the city's largest botanical conservatory. It's a great place to explore, play, and learn indoors during the Midwestern winter months. To get around hassle-free, check the stroller and take in the sights hands-free with the Baby Carrier One Air. You can carry bigger babies on your back starting at 12 months old. "My favorite thing at the conservatory may not be all the plants but the mosaic fountain in the Horticulture Hall, which was gifted to the city of Chicago from sister city, Casablanca," Tran says.

The Sod Room
Speaking of indoor activities, The Sod Room is another great indoor playspace located in the South Loop neighborhood where the design, toys, and activities are all put together with the Earth in mind. "The play space teaches kids to be creative to reuse things and the importance of being eco-friendly," Tran says. "There are so many different events for parents, caregivers, and kids to enjoy throughout the week such as baby yoga and music concert."

Galt Baby

While you probably won't get to do as much shopping on the Miracle Mile as you might without littles in tow, you should try to squeeze in a visit to Galt Baby for any must-haves. From travel gear (like the Carrier One!) to replacement sippy cups should yours get lost (the horror!), Galt Baby has you covered on the go.

SEE

Leyla Tran with her family in front of the iconic Cloudgate at Millennium Park.

Millennium Park

A trip to Chicago isn't really complete until you've taken a family selfie at the Bean. And while you're there, take advantage of the cultural events, exhibitions, and landscape design (hello, wide open spaces for toddlers to run!). Many events are free, so be sure to visit the park's website to find out what's on the calendar. "Although it is a tourist destination, we love it as locals because there is so much to do here from summer concerts to fun kids events," Tran says. "From the iconic Cloudgate (AKA, the Bean) to Crown Fountain to the Lurie Garden, there's something for everyone in our family. Our six-year-old son loves Crown Fountain, with the changing faces on the LED screens waiting for the water to spray out."

Harold Washington Library

The Harold Washington Library is a book worm's dream, no matter your age. Explore the Children's Library, which is broken up into "neighborhoods" based on age with an interactive puppet stage, STEAM-based activities, a digital media center, and more. Parents will love the indoor Winter Garden (with free wifi!) and taking in the local art throughout the library. Let your little one fall asleep in the Baby Carrier One Air while you enjoy the interior architecture—quietly.

Seasonal festivals

From holiday markets to beerfests to parades, there are seasonal activities to take advantage of year-round in Chicago―and many are free! Check the city's calendar during your trip to find out what's available. With so many wearing options on the Baby Carrier One, little ones from newborn to 3 years can stay close while you stroll, sip, or shop. Partner it with the Cover for Baby Carrier and baby will stay warm in all seasons.

EAT

Little Beans Cafe

All the best family vacations start off with a little caffeination. We love Little Beans Cafe because it doubles as an indoor playground for kids, meaning parents get to enjoy a good cup of coffee while kids get to play and learn. "We've had so many fun playdates here with our first child that we're looking forward to more playdates with the twins," Tran says. "It's a great place for new moms to meet during the week."

Giordano's
If you go to Chicago and don't eat deep dish pizza, did you ever really go? Don't take the chance. Book a table at Giordano's and indulge in a slice of Chicago's finest slice. Besides, how often is the local delicacy something you don't have to beg your kids to eat?


Making the time for travel is one of the greatest gifts you can give your family―and yourself. And thanks to BabyBjörn, now everyone can come along for the ride.

This article is sponsored by BabyBjörn. Thank you for supporting the brands that support Motherly and mamas.

In This Article

Why right now is the best time for a drivable getaway

Flexible schedules mean more vacation options. 🙌

Looking back now, last winter feels like a lifetime ago. At the time, my husband and I were eagerly planning our summer vacation just as we've done in years past. You know how the next part goes: COVID-19 came into the picture and changed our plans not only for vacationing, but for so much else in life.

In the time since then, we've gained a truly valuable new perspective on what matters—and realized we don't have to look so far to make beautiful memories with our kids. By exploring getaways within driving distance of our home, we've developed a new appreciation for the ability to "pack up the car and go."

Of course, that isn't to say that travel is the carefree adventure it once was. With COVID-19 still a very big part of the equation, we've become much more diligent about planning trips that allow for social distancing and exceed cleanliness standards. That's why we've exclusively turned to Vrbo, which helps us find nearby accommodations that meet our new criteria. Better yet?

Thanks to the money we've saved by skipping air travel and our remote-friendly work schedules, we're able to continue with the trips throughout the fall.

Here are a few more reasons we believe it's a great time for drivable getaways.

Flexible schedules allow us to mix work + play.

After months of lockdown, my family was definitely itching for a change of scenery as the summer began. By looking at drivable destinations with a fresh set of eyes—and some helpful accommodation-finding filters on Vrbo—we were able to find private houses that meet our needs. (Like comfortably fitting our family of five without anyone having to sleep on a pull-out couch!)

With space to spread out and feel like a home away from home, we quickly realized that we didn't need to limit our getaways to the weekends—instead we could take a "Flexcation," a trip that allows us to mix work and play. Thanks to the ability to work remotely and our kids' distance-learning schedule for the fall, we're planning a mid-week trip next month that will allow us to explore a new destination after clocking out for the day.

We’re embracing off-season deals.

With Labor Day no longer marking the end of our vacationing season, we're able to take advantage of nearby getaways that mark down their rates during the off season. For us in the Mountain West, that means visiting ski-town destinations when the leaves are falling rather than the snow. By saving money on that front, we're able to splurge a bit with our accommodations—so you can bet I search for houses that include a private hot tub for soaking in while enjoying the mountain views!

Vacationing is a way to give back.

If we've learned one thing this year, it's that life can change pretty quickly. That's given us a new appreciation for generous cancellation policies and transparent cleaning guidelines when booking trips. By seeing both of these things front and center in Vrbo listings along with reviews from fellow travelers, I feel confident when I hit the "book now" button.

Beyond that, I know that booking a trip through Vrbo isn't only a gift to my family. On the other side of the transaction, there are vacation home owners and property managers who appreciate the income during these uncertain times. What's more, taking getaways allows us to support our local economy—even if it's just by ordering new takeout food to enjoy from our home away from home.

While "looking ahead" doesn't feel as easy as it once did, I am confident that there will be a lot of drivable getaways in our future.

This article was sponsored by Vrbo. Thank you for supporting the brands that support Motherly and mamas.

Our Partners

This post is brought to you by Staples. While this was a sponsored opportunity, all content and opinions expressed here are my own.

One of the biggest changes in my household once my daughter started homeschooling was that, suddenly, everything and everyone in our home had to start pulling double duty. While I was used to wearing a lot of hats (mom, wife and WFH employee, to name a few), suddenly our dining room was also pulling shifts as a classroom. My laptop was also a virtual teacher. Our living room hutch was also a school supply closet.

If I didn't want my home to be overrun with an abundance of clutter, I had to find products that could multitask. Here are 10 products that are saving this WFH + homeschooling mama right now.

Stylish storage cabinet

Whether I need a place to keep the printer or just want to keep crayons and colored pencils organized, this pretty cabinet provides a mixture of exposed and hidden storage without clashing with my living room decor.

White board calendar + bulletin board

With so much on our plates these days, I need a visual reminder of our daily schedule or I'll forget everything. This dry erase version makes it easy to keep track of Zoom meetings and virtual classes—and I also love using the corkboard to display my daughter's latest work from art class.

Natural Recycled 3-Ring Binder

From tracking our curriculum progress to organizing my family's paperwork, I can never have enough binders. Even better, this neutral version is pretty enough that I can display them on the bookshelf.

Bamboo storage drawers

The instant you start homeschooling, it can feel like you're suddenly drowning in papers, craft supplies and more. Fortunately, these simple bamboo drawers can be tucked into the cabinet or even displayed on top (seriously, they're that cute!) to keep what we need organized and close at hand.

Laminated world map

I love this dry-erase map for our geography lessons, but the real secret? It also makes a cute piece of wall decor for my work space.

Rolling 7-drawer cabinet

When you're doing it all from home, you sometimes have to roll with the punches—I strongly recommend getting an organizational system that rolls with you. On days when both my husband and I are working from home and I need to move my daughter's classes to another room, this 7-drawer cabinet makes it easy to bring the classroom with us.

Letterboard

From our first day of school photo to displaying favorite quotes to keep myself motivated, this 12"x18" letterboard is my favorite thing to display in our home.

Expandable tablet stand

Word to the wise: Get a pretty tablet stand you won't mind seeing out every day. (Because between virtual playdates, my daughter's screen time and my own personal use, this thing never gets put away.)

Neutral pocket chart

Between organizing my daughter's chore chart, displaying our weekly sight words and providing a fits-anywhere place to keep supplies on hand, this handy little pocket chart is a must-have for homeschooling families.

Totable fabric bins

My ultimate hack for getting my family to clean up after themselves? These fabric bins. I can use them to organize my desk, store my oldest's books and even keep a bin of toys on hand for the baby to play with while we do school. And when playtime is over, it's easy for everyone to simply put everything back in the bin and pop it in the cabinet.

Looking for study solutions for older children? Hop over to Grown & Flown for their top picks for Back to School.

Work + Money

Mama, all I see is you

A love letter from your baby.

Mama,

I can't see past you right now, I'm so small and everything's a little blurry.

All I see is you.

When you feel alone, like the walls are closing in, remember I'm here too. I know your world has changed and the days feel a little lonely. But they aren't lonely for me.

You are my everything.

When you feel like you don't know what you're doing, you're making it look easy to me. Even though we're still getting to know each other, you know me better than anyone.

I trust you.

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