Exploring the Windy City: A Local’s Guide to Chicago with Kids

Welcome, fellow explorers and travel-savvy parents, to the vibrant city of Chicago—a place where family fun takes center stage against the backdrop of bustling neighborhoods and iconic attractions. As a former resident and devoted Chicago enthusiast, I am thrilled to be your guide on an extraordinary journey through the Windy City, tailored especially for families with young adventurers in tow.

In this guide, we’ll go beyond the ordinary tourist path, uncovering the hidden treasures that make Chicago a truly wonderful destination for families. While most Chicago tourists don’t leave the downtown area, there’s a better way to experience the city – from charming neighborhoods, to family-friendly eateries, to off-the-beaten-path activities – your journey promises to be as unforgettable as the city itself.

Let’s get started! Here’s your ultimate guide to a non-touristy family-friendly vacation in Chicago.

Psst… if you’d rather experience Chicago like a tourist, no judgment! I’ve got you covered!

Please note: I do not earn commission off any of the links in this blog post. All opinions are my own based off of personal experiences.

Navigating Beyond Michigan Avenue: Exploring Chicago’s Neighborhoods

While the infamous Michigan Avenue might be how most people envision Chicago, that actually isn’t the heart of the city – not even close! Chicago is a city of neighborhoods and if you venture a bit further you’ll get more charm, more authenticity, and more fun. For quirky boutiques, local eateries, and charming parks, you’ll get a true taste of the city. Here are the best Chicago neighborhoods to visit for young families:

Andersonville, Lincoln Square, and Surrounding Areas

Starting with a favorite of ours, the Andersonville and Lincoln Square areas offer a quieter and more neighborly feel than downtown. Bursting with charm and family-friendly options, it’s a perfect base for your Windy City escape.

• Where to stay:
  • The Guesthouse Hotel – Our go-to choice due to its family-friendly atmosphere. With studios and one-to-three-bedroom apartments equipped with full kitchens, this pet-friendly hotel is perfect for traveling with kids.
• What to eat:
  • Bad Apple – known for burgers, great with kids.
  • Spacca Napoli – delish pizza (my mouth is watering thinking about it).
  • Luella’s Southern Kitchen – great food with lots of kid-friendly options.
  • Hopleaf – for craft beer enthusiasts.

Nearby, Malt Row (known as ‘Chicago’s most diverse beer destination’) beckons beer lovers. While seemingly unconventional for families, these breweries, like Begyle Brewing, Half Acre, Dryhop, and Dovetail, are surprisingly kid-friendly and fun – definitely worth checking out.

Wrigleyville & the Southport Corridor

For the baseball fans, Wrigleyville is a must-visit (and be sure to catch a game in the atmospheric bleachers if you’re visiting in season). While the nearby trendy Southport Corridor promises a great shopping and restaurants.

• Where to Stay:
  • Hotel Zachary – a Marriott hotel in the heart of Wrigleyville. Request an east-facing room for mesmerizing views of Wrigley Field.
• Where to Eat:
  • Crosby’s Kitchen – a go-to spot for families, priding itself on being family-friendly.
  • Uncommon Ground – enjoy a cozy atmosphere and delicious food.
  • Jeni’s Ice Cream – because no trip is complete without ice cream!

Family-Friendly Chicago Activities that Are Off the Beaten Path

While downtown may beckon you (I see you, American Girl Store!) once you start exploring the neighborhoods, you won’t want to stop. Get out of the downtown area and the real magic happens. Here are our favorite things to do in Chicago that are not downtown:

• Lincoln Park Zoo: A free and thrilling zoo experience, not to be missed.
  • In summer months, check out the Green City Market, an awesome farmer’s market across the street
  • In the winter months, don’t miss Zoo lights – but plan ahead and buy your tickets, they sell out!
• Chicago Botanic Gardens: Discover the epic Model Railroad Garden (train lovers will not want to leave!) and the captivating Butterflies & Blooms exhibit.
  • In the winter months, Lightscape is second to none. It sells out early (I’m talking August), so get your tickets – you won’t regret it.
• Playgrounds: One of our favorite family activities on vacation is to find nearby playgrounds, and Chicago has some amazing playgrounds.
• Gallagher Way: A year-round family fun plaza next to Wrigley Field, offering ice skating, movie screenings, and more.
• The 606: An abandoned rail line turned walking path and public park.
• Ride the El: Chicago’s public transportation (the ‘El’evated train) is easy to navigate and our kids love it.
  • Don’t miss the Holiday Train during the holidays!
• Ravinia Music Festival: An outdoor venue with epic concerts, including kid’s shows. Take the train and have a picnic while you listen to the music.

As you embrace Chicago like a local, you’ll uncover a city that defies expectations. From traversing the El to discovering local gems, you’ll create memories beyond the ordinary. Chicago’s energy, culture, and family-friendly attractions await—embark on your Windy City adventure!

PS – there’s so much more to Chicago! Check out the downtown guide, too!