Things To Do In Chicago Illinois For Adults – The Outwardlab Guide
Think a trip to a massive city like Chicago means leaving your hiking boots and sense of adventure behind? Many outdoor enthusiasts feel a little out of place navigating a concrete jungle, missing the call of the trail and the quiet of the wild.
We promise you can find incredible adventures right in the heart of the Windy City. You just need to know where to look. Chicago is an urban basecamp teeming with unique outdoor opportunities, from paddling through skyscraper canyons to exploring miles of shoreline trails.
This guide on things to do in chicago illinois for adults is built specifically for you—the camper, the hiker, the self-reliant explorer. We’ll show you how to paddle the river, find the best urban trails, practice sustainability, and even plan the perfect nature-filled day trip just beyond the city limits.
Beyond the Bean: Urban Paddling on the Chicago River
One of the most breathtaking ways to experience Chicago is from the water. Paddling the Chicago River offers a perspective you simply can’t get from the sidewalk, turning the city’s famous architecture into a stunning, modern canyon.
How to Paddle the River Safely
The Chicago River is a busy waterway. For a safe and enjoyable trip, following a few best practices is essential. If you’re a beginner, we strongly recommend a guided tour.
- Choose Your Craft: Kayaks are the most popular option. Companies like Urban Kayaks or Wateriders offer rentals and guided tours, which are perfect for learning the rules of the river.
- Check the Conditions: The river’s current and boat traffic can change. Always check the weather and be aware of tour boats and water taxis. A good guide service will handle this for you.
- Gear Up: Wear your Personal Flotation Device (PFD) at all times. Bring water in a reusable bottle, sunscreen, and a hat. Store your phone in a dry bag, like those from Sea to Summit.
What You’ll See
As you paddle, you’ll glide past iconic structures like the Willis Tower, the Wrigley Building, and the art deco Merchandise Mart. Architectural tours by kayak are one of the most popular things to do in chicago illinois for adults, combining a good workout with a fascinating history lesson.
The benefits of this activity go beyond sightseeing. It’s a chance to connect with an urban environment in a totally new way, finding a moment of peace and flow amidst the city’s hustle.
Finding Your Trail: Hiking and Biking in the Concrete Jungle
You don’t have to leave the city to stretch your legs. Chicago is home to an impressive network of parks and multi-use trails perfect for a day of exploration on foot or by bike.
The Lakefront Trail: 18 Miles of Shoreline
The 18.5-mile Lakefront Trail is the crown jewel of Chicago’s park system. It runs along the coast of Lake Michigan, offering stunning views of the skyline and the water. This is a multi-use path, so be prepared to share it with cyclists, runners, and skaters.
Pro-Tip: For a less crowded experience, try exploring the southern sections of the trail near Jackson Park and the Museum of Science and Industry.
The 606: An Elevated Urban Trail
The 606, also known as the Bloomingdale Trail, is a 2.7-mile elevated park built on a former industrial rail line. It’s a fantastic example of urban green space reclamation, weaving through neighborhoods like Wicker Park and Logan Square. It’s perfect for a walk, run, or a casual bike ride away from street-level traffic.
Northerly Island: A Nature Sanctuary with a View
For a wilder feel, head to Northerly Island. This 91-acre peninsula offers walking paths that wind through prairie grasses and provide sanctuary for migratory birds. It’s one of the best spots in the city to watch a sunset over the skyline, feeling miles away from it all.
Sustainable & Eco-Friendly Things to Do in Chicago Illinois for Adults
Exploring responsibly is a core value for any outdoor adventurer. Practicing sustainability in a city is just as important as following Leave No Trace principles in the backcountry. This is your care guide for exploring Chicago with a light footprint.
Embrace Public Transportation
One of the most eco-friendly things to do in chicago illinois for adults is to leave the car behind. Chicago’s ‘L’ train and bus system is extensive and can get you almost anywhere you need to go, including trailheads for the Lakefront Trail and The 606. A Ventra card is your key to easy, low-impact travel.
Visit a Local Farmers Market
Connect with the local food scene and reduce your food miles by visiting a neighborhood farmers market. The Green City Market in Lincoln Park is one of the most famous, offering sustainably grown produce from regional farms. It’s a great way to stock your cooler or grab a healthy, trail-ready snack.
Urban Leave No Trace Principles
- Pack It In, Pack It Out: Just like on the trail, carry out everything you bring with you. Use designated recycling and trash bins.
- Respect the Space: Stick to designated paths and trails, even in city parks, to protect vegetation and wildlife habitats.
- Be Considerate of Others: Share the trail and keep noise to a reasonable level. You’re sharing these green spaces with both people and urban wildlife.
Your Urban Basecamp: Smart Lodging for Adventurers
Where you stay can make or break your adventure. For those with an RV, campervan, or a tent, finding a good basecamp near a major city can be one of the most common problems with things to do in chicago illinois for adults.
Camping Near the City
For a true camping experience, Illinois Beach State Park is your best bet. Located about an hour north of the city along the shores of Lake Michigan, it offers reservable campsites and is the only remaining beach ridge shoreline left in Illinois. You can take the Metra train from the city for a car-free trip.
RV and Van Life Options
Several RV parks are located in the suburbs, like the McCormick Place Marshalling Yard (for a no-frills, in-city option) or Camp Bullfrog Lake in the Forest Preserves of Cook County for a more natural setting. Always book in advance, especially during peak season.
Essential Gear & Best Practices for Urban Exploration
Exploring a city requires a slightly different kit than a backcountry trek, but the principles of preparedness are the same. This things to do in chicago illinois for adults guide wouldn’t be complete without a gear check.
Your Urban Daypack Essentials
Treat a day in the city like a day hike. Your pack, like an Osprey Daylite Plus, should always contain a few key items:
- Water Filtration Bottle: A bottle with a built-in filter, like a GRAYL GeoPress or Lifestraw Go, allows you to safely refill from any public fountain, saving money and plastic.
- Portable Power Bank: Navigating with your phone drains the battery. Carry a reliable power bank like an Anker PowerCore to stay charged.
- Lightweight Rain Shell: Chicago weather is famously unpredictable. A packable rain jacket, such as the Marmot PreCip Eco, is a must-have.
- Comfortable Footwear: You’ll be doing a lot of walking. A sturdy pair of walking shoes or trail runners like the HOKA Speedgoat are essential.
- Small First-Aid Kit: A compact kit with blister care, bandages, and pain relievers is always a smart idea.
Day Trip Adventures: Escaping the City Limits
When you’re ready for a full day immersed in nature, Chicago’s location provides excellent access to some of the Midwest’s most beautiful state parks.
Starved Rock and Matthiessen State Parks
About a 90-minute drive from Chicago, these neighboring parks feel like another world. They are famous for their stunning sandstone canyons, seasonal waterfalls, and miles of hiking trails. Starved Rock is more popular, so consider visiting Matthiessen for fewer crowds and a more rugged experience.
Indiana Dunes National Park
Located just across the state line in Indiana, this national park boasts massive sand dunes towering over the southern shore of Lake Michigan. Hike the challenging 3 Dune Challenge, relax on the beach, or go for a bike ride. It’s an easy and rewarding day trip for any nature lover.
Frequently Asked Questions About Things to Do in Chicago Illinois for Adults
What is the best way to get around Chicago with outdoor gear?
The ‘L’ train system is highly effective. For bulkier gear like bikes, the Metra commuter rail (which services outlying areas and state parks) has bike-friendly cars on weekends. If you’re kayaking, it’s easiest to rent from an outfitter located directly on the river to avoid transport issues.
Is Chicago safe for solo outdoor adventurers?
Like any major city, awareness is key. Stick to well-populated trails like the Lakefront Trail and The 606 during daylight hours. Let someone know your plans and itinerary. The main parks and public areas are generally very safe for solo explorers exercising standard precautions.
Can you camp directly in Chicago?
No, there are no public campgrounds within the Chicago city limits. The closest options are in the surrounding suburbs and state parks, like Illinois Beach State Park or the Forest Preserves of Cook County, which are accessible via public transit or a short drive.
What is the best season for outdoor activities in Chicago?
Late spring (May-June) and early fall (September-October) offer the most pleasant weather for hiking, biking, and paddling. Summer is also fantastic but can be hot and humid, with more crowds. Winter offers unique opportunities like cross-country skiing on the trails, but requires proper cold-weather gear.
Chicago is so much more than deep-dish pizza and skyscrapers. For the adventurous adult, it’s a dynamic urban landscape filled with green spaces, waterways, and trails waiting to be explored. By looking at the city through an outdoor lens, you can craft a trip that satisfies both your wanderlust and your need to connect with nature.
Pack your daypack, grab your water bottle, and get ready to discover the wilder side of the Windy City. Adventure is out there—even in the middle of a metropolis.
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