Outdoor Adventures To Try This Summer In Chicago

If you’re looking for outdoor adventure activities in Chicago, look no further!

“City in a Garden” is one of Chicago’s most unique nicknames, and as the name implies, Chicago has one of the most unique and large arrays of green spaces in a modern city.  So, if you’re looking for ways to experience the great outdoors but don’t want to jump on a plane, you’re in luck.  Chicago has parks galore, artificial rock climbing, trails for hiking, and some incredible infrastructure for city biking.

Biking in Chicago

Nothing quite screams adventure like city biking!  Chicago has a long-standing history of being friendly towards cyclists since the infrastructure started being built into the cityscape in the 1960s.  Today Chicago boasts trails such as the 606 and the Lakefront Trail.  If you want a truly spectacular adventure, can I recommend booking a bike tour of Chicago?  Here at Bobby’s Bike Hike, we offer city tours and food tours.  Bike up to Wrigley Field on our Bikes, Bites and Brews Tour and sample Chicago’s favorite dishes while learning about the city’s history along the way.  Or take our Westside Foodie Tour and head out to the western neighborhoods and learn how immigrant culture has shaped Chicago from the beginning.  A bike tour is a great way to learn more about Chicago’s history and culture while also having a guide teach you the intricacies of city cycling.

If a tour isn’t your style but you would still like to adventure around Chicago via bike, we also offer bike rentals.  Cruise through the city in style with one of our comfort hybrid cruisers, or if it’s a special activity with your sweetheart, consider renting a tandem bicycle!  You can explore, adventure, and practice your communication skills while you’re at it.  E-bikes are also becoming more popular country-wide.  Rent an e-bike to cover more ground in less time, and never worry about biking into a headwind again!  You can cycle down the city streets on the designated bike lanes or ride along one of Chicago’s great pathways.

The Lakefront Trail

The Lakefront Trail was constructed in the 1960s as a space for Chicagoans to better appreciate our natural water systems.  It has conveniently become a commuter pathway for cyclists, roller skaters, and scooter riders to quickly traverse the city while also getting world-class views of Lake Michigan and Chicago’s Skyline.  You can find beaches, restaurants, art installations, picnic areas, and designated parks along the trail.

The Riverwalk

Water enthusiasts will also find an array of activities to enjoy here on the Third Coast.  Along the main branch of the Chicago River is the Riverwalk.  During the warm summer months, there’s an assortment of restaurants with outdoor seating so you can enjoy a cheeky beverage while also appreciating the views of our legendary architecture that only Chicago can offer.  Not only are there many great restaurants along the Riverwalk, this 1.5-mile-long path also has many public art displays for your viewing pleasure.  It is also a fan favorite for bird watchers city-wide.  You can stroll down the Riverwalk and come across the Vietnam Memorial and other public installations of note.  The Riverwalk offers one of the best places in Chicago to reflect on our species’ capabilities to expand and build, but also to reverse course and protect our natural spaces.

Paddling in Chicago

Maybe you want to get on the water itself; well I’ve got great news. One of our favorite summer activities is to rent a kayak and cruise along the river.  While kayaking down the Chicago river, you can almost imagine what once was before mankind came in and industrialized this ancient swamp.  Bobby’s Bike Hike offers kayak rentals on Ohio Street beach where you can enjoy seeing our mountain of Skyscrapers from Lake Michigan. Go tandem and share this unique experience with a friend, or go solo, giving yourself a chance to contemplate mankind’s growth over the past 150 years.

Rock Climbing in Chicago

Rock Climbing has become an international sensation and is one of the fastest-growing sports in the world.  Chicago may be notoriously flat, but you can’t count out rock climbing.  There are a few indoor gyms in the city, such as First Ascent, Movement, and Brooklyn Boulders, where you can learn the necessary skills to take to real rocks outdoors.  If you would like to take your skills outdoors in Chicago, you can find artificial walls at both Maggie Daley Park downtown in the Loop as well as at Steelworkers Park in South Chicago.  Currently, you can climb for free at Steelworkers, but you will have to pay an admission fee to climb the walls at Maggie Daley Park.  

If you’re looking for real rocks to hug your body to, consider taking a day trip out of Chicago up to Devil’s Lake.  These routes are more advanced, so I recommend booking a guiding service such as those offered through REI, especially for those new to outdoor climbing.  The best practice for those interested in climbing is safety first! Since Chicago is home to a vibrant climbing community, you will have no issue connecting to a gym and finding a community to adventure with you at either the artificial rock walls in the city, or taking a trip out of Chicago to climb natural rocks nearby.

Cook County Forest Preserve: Home to all types of  Outdoor Adventure Activities in Chicago

So far, most of the suggestions have kept you in the heart of the city, but for those who prefer Trees to Skyscrapers, Chicago is home to the Cook County Forest Preserve.  This natural paradise spans 70,000 acres and can cater to all sorts of outdoor adventure activities such as bird watching, cycling, cross-country skiing, kayaking, swimming, and even ziplining.  For hiking enthusiasts, this will be your best destination in Chicago.  The preserve has over 100 miles of paved walkways if you prefer staying on a paved trail.  If you would rather feel the dirt beneath your boot, then worry not because there are over 200 miles of unpaved trails to traverse.  If this sounds like your version of paradise and you wish you could escape the concrete jungle for a reprieve, then pack your camping gear and book a campsite for the night.  If you want to continue your outdoor adventuring while giving back to your community, consider volunteering at the preserve.  There are a plethora of activities to take part in at the Forest Preserve; however, some do require a permit so be sure to check out their website and plan your trip in advance.

BONUS: Winter Outdoor Adventure Activities in Chicago

So far, most of these activities are best enjoyed during the Summer months, but even though Chicago is famous for its rougher winters, there are still many activities to enjoy outdoors year-round.  The Cook County preserve has winter activities such as snowmobiling and cross-country skiing.  You can also find ice skating in Millennium Park and Maggie Daley Park during winter.  Ice skating at Millennium Park is free, but if you want to skate the Ribbon in Maggie Daley Park, you’ll need to make a reservation and pay an admission fee.  Chicago winter doesn’t have to mean skipping outdoor adventures; it simply means you will need a heavier coat.

Chicago may be famous for its architecture, vibrant theater community, and, of course, deep-dish pizza, but outdoor adventurers don’t have to compromise their love of nature to be city dwellers.  Chicago has parks in every corner of the city and the legacy of outdoor adventure and access to these green spaces are almost as old as the city itself.  Our love of city and nature makes Chicago, Chicago.  Whether you want to kayak on the river, take a bike tour of the city, enjoy a meal outdoors, go bird watching, or go camping at the Cook County Preserve, Chicago has an outdoor adventure to tickle almost every fancy.