Unique Things To Do In Chicago With Kids – Your Adventure-Ready Guide
Planning a family trip to a major city like Chicago can feel like plotting a course through an unknown wilderness. You know your family thrives in wide-open spaces, not crowded sidewalks, and the thought of trading hiking trails for high-rises can be daunting.
But what if you could explore the Windy City with the same spirit of adventure you bring to the backcountry? I promise, Chicago is packed with incredible opportunities that will challenge, engage, and inspire your young explorers, connecting their love for the outdoors with unforgettable urban experiences.
This guide will show you how. We’re skipping the obvious and diving into a curated list of unique things to do in Chicago with kids, from paddling through skyscraper canyons to discovering hidden nature sanctuaries. Get ready to see the city not as a tourist, but as a true adventurer.
Beyond the Pavement: Urban Adventures on Water and Wheels
The best way to get the lay of the land—any land—is to see it from a new perspective. In Chicago, that means getting on the water or hitting a dedicated trail. This is a fantastic way to introduce kids to urban navigation while burning off some serious energy.
Paddle Through Skyscraper Canyons
Imagine gliding on the water, looking up at some of the world’s most famous architecture. Kayaking the Chicago River offers just that. It’s an accessible adventure that feels worlds away from the bustling streets just a few feet above you.
- The Gear: Reputable outfitters like Urban Kayaks or Wateriders provide everything you need: stable tandem kayaks (perfect for a parent and child), personal flotation devices (PFDs), and paddles. Your only job is to bring water, sunscreen, and a waterproof pouch for your phone.
- The Route: Opt for a guided tour. A good guide not only ensures safety but also points out landmarks and shares stories, turning a simple paddle into a history and engineering lesson. The tours are paced for beginners, making it a low-stress activity.
- Pro-Tip: Book a morning tour to avoid the afternoon boat traffic and sun. This is one of the best eco-friendly unique things to do in Chicago with kids, as you’re using people-power to explore.
Bike the Lakefront Trail
Chicago’s 18-mile Lakefront Trail is a paved paradise for families. It’s a completely car-free path that hugs the shore of Lake Michigan, offering stunning views of both the water and the skyline. You can tackle a small section or make a day of it.
Start near Navy Pier and head south toward the Museum Campus. You’ll pass beaches, parks, and harbors. Pack a lunch in your daypack—we love the Osprey Daylite Plus for its versatility—and find a grassy spot for a picnic with a world-class view.
Explore the 606 Bloomingdale Trail
For a different vibe, check out the 606. This is a 2.7-mile elevated park built on a former industrial rail line, connecting several vibrant neighborhoods. It’s less crowded than the Lakefront Trail and offers a unique, above-the-streets perspective of the city’s residential side.
It’s a fantastic spot for a walk, bike ride, or scooter session. The trail is lined with art installations and native plants, providing plenty of interesting stops for curious kids.
Urban Oases: Finding Wilderness Within the City
Even in a metropolis of millions, nature finds a way. Chicago has deliberately carved out stunning green spaces that feel like genuine escapes. Teaching kids to find and appreciate these pockets of wilderness is a core survival skill, whether you’re in the mountains or the city.
Discover the Alfred Caldwell Lily Pool
Tucked away inside Lincoln Park, this National Historic Landmark is a hidden gem. Designed to look like a river meandering through a prairie, its winding stone paths, gentle waterfall, and secluded benches feel like a secret garden. It’s a perfect spot for a quiet moment, a quick lesson in landscape architecture, or some urban birdwatching.
Hike the Trails at Northerly Island
What was once a small airport is now a 120-acre nature preserve jutting into Lake Michigan. Northerly Island features walking paths that wind through prairie grasses and offer unparalleled views of the city skyline. It’s a prime location for birding, especially during migration seasons. This is one of the top sustainable unique things to do in Chicago with kids, showcasing how urban spaces can be reclaimed for nature.
Explore the Lincoln Park Conservatory
When the weather turns, head inside to this stunning Victorian glass house. The Conservatory is a lush, tropical world filled with ancient ferns, towering palms, and exotic flowers. The humid air and vibrant green are an instant mood-lifter on a gray day. It’s a great, low-key way to teach kids about different ecosystems from around the world.
Indoor Expeditions: Skill-Building Fun for Any Weather
A rainy day doesn’t mean the adventure stops; it just moves indoors. Chicago’s museums offer more than just exhibits—they offer hands-on experiences that can teach valuable lessons in science, nature, and engineering that connect directly to an outdoor lifestyle.
Navigate the U-505 Submarine at the Museum of Science and Industry
The MSI is an adventurer’s playground. The crown jewel for any explorer-in-training is the U-505 Submarine, a real German U-boat captured during WWII. Touring its cramped quarters is a lesson in self-reliance, teamwork, and how to operate in confined spaces. Elsewhere, the FarmTech exhibit connects directly to homesteading principles, while the Science Storms exhibit is a powerful lesson in respecting the forces of nature.
Get Hands-On at the Peggy Notebaert Nature Museum
This is a must-do. The museum is dedicated to the natural history of the Chicago region. Kids can get up close with native animal species, learn about local ecosystems, and, best of all, step inside the Judy Istock Butterfly Haven. Walking among 1,000 free-flying butterflies is a magical experience that fosters a deep appreciation for delicate ecosystems. It’s a perfect example of the benefits of unique things to do in Chicago with kids that are both educational and awe-inspiring.
Build and Create at the Chicago Children’s Museum
Located at Navy Pier, this museum is all about hands-on learning. The Tinkering Lab lets kids use real tools—saws, drills, and hammers (with supervision!)—to build whatever they can imagine. This is an incredible way to build confidence and practical skills. The Cloud Buster climbing structure is a 37-foot-tall vertical maze that challenges kids to problem-solve and push their physical limits in a safe environment.
A Practical Guide to Unique Things to Do in Chicago with Kids
Success in any environment, urban or wild, comes down to good planning. Navigating a big city with children presents its own set of challenges. Addressing these common problems with unique things to do in Chicago with kids head-on will ensure your trip is smooth and enjoyable.
Mastering the Urban Grid: Transportation Tips
Ditch the car. Driving and parking in Chicago are expensive and stressful. The city’s public transit system, the ‘L’ train, is an adventure in itself. Here’s how to tackle it:
- Get a Ventra Card: Purchase a Ventra card at any ‘L’ station kiosk. You can load money onto it as you go. Kids under 7 ride free with a paying adult.
- Use a Transit App: Apps like Google Maps or Citymapper provide real-time train and bus schedules. It’s like having a trail map for the entire city in your pocket.
- Embrace Walking: Chicago is a very walkable city, especially downtown and in the lakefront neighborhoods. Pack comfortable shoes—think trail runners like the Merrell Moab, not flimsy sneakers.
Packing Your Urban Daypack
Treat a day in the city like a day hike. You need to be prepared for changing conditions and long stretches between “base camp” (your hotel or RV). Here are some best practices:
- Water and Snacks: Always carry more than you think you’ll need. A reusable water bottle like a Hydro Flask is essential.
- Layers: Chicago weather is famously unpredictable. Pack a lightweight rain jacket (the Marmot PreCip Eco is a great choice) and a fleece or hoodie, even in summer.
- First-Aid Kit: A small kit with bandages, antiseptic wipes, and pain relievers is a must.
- Portable Power Bank: Navigating with your phone drains the battery quickly. A power bank ensures you’re never without your map.
Frequently Asked Questions About Unique Things to Do in Chicago with Kids
What’s the best time of year to visit Chicago with kids for these activities?
Late spring (May-June) and early fall (September-October) are ideal. The weather is pleasant for outdoor activities, and you’ll avoid the peak summer crowds and humidity. However, with the right gear and planning, Chicago is a year-round destination.
Are there any free, unique activities for families on a budget?
Absolutely! Many of the best experiences don’t cost a dime. Exploring the 606, hiking at Northerly Island, visiting the Lincoln Park Conservatory and Zoo, and spending a day at one of the many public beaches are all completely free.
How can we make our Chicago trip more eco-friendly and sustainable?
This is a great mindset to have. Prioritize using public transportation over rideshares or taxis. Carry reusable water bottles and coffee cups to minimize waste. When possible, support local farmers’ markets for picnic supplies and choose restaurants that source their ingredients locally.
What is one “must-do” unique experience you’d recommend above all others?
If I had to pick one, it would be the architecture river tour by kayak. It combines physical activity, incredible scenery, and a unique educational experience that you just can’t get anywhere else. It perfectly encapsulates how to turn a city visit into a genuine adventure.
Exploring Chicago with your family doesn’t have to be a departure from your love of the outdoors—it can be an extension of it. By seeking out these unique experiences, you’re not just seeing a city; you’re teaching your kids valuable skills in navigation, adaptability, and finding nature wherever you go.
So pack your daypack, grab your sense of adventure, and get ready to discover the wild side of the Windy City. The urban wilderness is waiting.
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