Chicagoland, Illinois hikes & adventures: Dog-friendly guide

Chicago doesn’t pop to mind when thinking of classic hiking destinations, but we’re here to show you that there is SO much nature to explore with your dog in/around the windy city! In this post, you’ll find our favorite hiking and nature areas in the Chicagoland area.

This site contains affiliate links, which means when you click, we may receive a small commission from your purchase at no additional cost to you. This helps us run this page and offer great content free of charge, and we only recommend products that we use and love. We appreciate you!

A Quick Little Love Letter to Chicago

A region that takes itself incredibly seriously, while embracing its quirkiest blemishes…

The place where Paris on the Prairie simultaneously birthed a serial killer and an architectural revolution…

The land where every John Huges character lost & found love…

A locus where any building not made of brick is viewed with suspicion, and silver shovels are required to unearth mountains of corruption… 

The town that loves to love their own denial of their sports teams’ losing ways…

A place where LSD is beloved for all the reasons you wouldn’t expect, but the condiment most Americans adore can’t be caught dead on a hot dog…

The crossroads where the stinking water meets big shoulders…

A metropolis where the Sears Tower will always reign supreme…

The headquarters from which gangsters kept prohibition from being dry…

The site where Jake & Elwood Blues faced down Illinois nazis in the name of helping the penguins…

A place where wind has both literal and figurative significance…

A landscape where jails masquerade as skyscrapers, and skyscrapers masquerade as the state’s most robust agricultural crop…

A community that helped birth the US labor movement…

The scene where Ferris, Sloan, and Cameron took their iconic day off…

The spot where a bean draws a crowd, but the Picasso sculpture bamboozles passers-by to this day…

A place where midwestern friendliness meets metropolitan hustle and bustle, meets old world hospitality…

Meet Chicago!

To me, Chicago feels like home. I grew up in the cornfields outside Dekalb, sandwiched between Chief Shabbona Forest Preserve and Shabbona Lake State Park. My childhood was one of walking our family sheltie through the woods, picking blackberries from the thickets down the road, and getting muddy in the creek behind our house. So it’s safe to say that this area had a huge impact on my love for nature, and my inclination to play outside as much as possible. 

Chicago was my “home city” growing up, and my roots run deep. My mom’s dad’s family lived and worked in Pullman, while my mom’s mom emigrated from the Netherlands to South Holland. My dad’s parents both hail from Aurora. As a child, we ventured into the city often to visit grandparents, indulge at Gino’s East or Carson’s Ribs, see the dinosaurs and mummies at the Field, see the holiday windows at Marshall Fields, bask in the Art Institute’s impressionism collection during the biting cold winters, or see a musical at the Auditorium Theater. As a young adult, I could be found vintage shopping around Belmont & Clark, attending parties in abandoned buildings, or catching shows at the Vic or Buddy Guy’s.

Seeking bigger, more western adventures, I moved to Colorado to attend college and explore the Rocky Mountains. While I’ve considered myself a fully cooked Coloradan for a while now, my Chicagoland roots have never failed to shine through. Most of my family stayed in the Chicagoland area, which means that our little Rocky Mountain pack visits often. North side, south side, burbs, or cornfields – We galavant around the area, and are always on the lookout for places where we can explore with our pupper gals. 

Land Acknowledgement

Chicago, Illinois is located on the ancestral homelands of the Bodwéwadmi (Potawatomi), Myaamia, Kaskaskia, Kiikaapoi (Kickapoo), Peoria peoples

To show respect to the native peoples who cared for these lands long before white settlers, we do several things: 

  • Research and speak the names of the traditional guardians of the land. We use Nativeland.net 
  • Ask permission from the land itself before we enter. It might seem silly, but the more this becomes a habit, the more you become attuned to the ways in which the land speaks.
  • Make donations to native-led organizations that support the communities whose ancestral lands were stolen. 

Favorite Places to Hike & Adventure in Chicagoland

Over the years, we’ve built this little list of our favorite spots to hike, roam, explore, and adventure, and we hope you enjoy them as much as we do. Some are wilderness, some are urban jaunts, many are filled with historical stories to discover, and all are captivating.

Related Post: Hiking with your Dog: 12 Tips to Always be Pup-Pared

Starved Rock State Park

Ogelsby, Illinois

Starved Rock State Park, located southwest of the city, along the banks of the Illinois River, is a breathtaking oasis. Famous for its dramatic sandstone cliffs, lush forests, and cascading waterfalls, this park offers a stunning backdrop for hiking, birdwatching, and photography. With over 13 miles of trails winding through diverse landscapes, visitors can explore canyons carved by glaciers and marvel at scenic vistas from high overlooks. Each season transforms the park’s beauty, from vibrant fall foliage to winter ice formations.

The best part? This park, and ALL Illinois State Parks are FREE.

Our Favorite Starved Rock Trails

Personal Perspectives

We love all the trails we’ve tried here! We especially like to venture here in the winter, when crowds are smaller, and the waterfalls are frozen.

Indiana Dunes National Park

Porter, Indiana

Indiana Dunes National Park, nestled along the southern shore of Lake Michigan, is a stunning natural gem where towering sand dunes meet lush forests and vibrant wetlands. Spanning over 15 miles of scenic coastline, this park offers a diverse landscape rich in biodiversity, featuring over 1,500 species of plants and animals. Visitors can hike the many trails that wind through the dunes, enjoy breathtaking views of the lake, or relax on the sandy beaches. 

The Money Stuff

Park Admission Fees

  • Day Admission: $25/vehicle
  • Annual National Parks Pass: $80 (Covers 1 vehicle or 4 walk-ins per park entrance)

National Park Entrances get pricey if you pay park by park, but we cannot purchasing an annual pass highly enough! An America the Beautiful Pass covers national park entrance fees, but SO MUCH MORE Covers entrance fees and standard amenity (day-use) fees at lands managed by: US Army of Corps of Engineers, National Park Service, US Fish & Wildlife Service, US Forest Service, Bureau of Land Management, & Bureau of Reclamation. You will be shocked how often this pass saves you a few bucks on parking if you are at all a regular hiker!

Purchase or Renew your America The Beautiful Pass

Our Favorite Indiana Dunes Trails

Personal Perspectives

This area is a downright smorgasbord of landscapes, and we like to visit in any season. Winter hikes are nice, because you can have the place to yourself, but the park is especially beautiful in the early summer when the weather is mild and the dunes bloom with so many wildflowers.

Jackson Park

Chicago, Illinois (Hyde Park, Woodlawn, South Shore)

Jackson Park, located on Chicago’s South Side, is a picturesque urban oasis that combines natural beauty with rich history. Spanning over 500 acres along the shores of Lake Michigan, this park features stunning landscapes, serene lagoons, and winding paths that invite visitors to explore and unwind. Originally designed for the 1893 World’s Columbian Exposition, Jackson Park is home to notable attractions, including the Japanese Garden and the historic Wooded Island. Note: Dogs are not allowed on the Wooded Island. 

Our Favorite Route

While there are trails listed in this area on AllTrails, none of them perfectly capture the route we prefer. Since Wooded Island is closed to dogs, we like to pair a large loop around the lagoon in Jackson Park, with a long loop down Midway Plaisance to see the iconic Fountain of Time sculpture by Laredo Taft. Our favorite time to visit is in the late spring, when the cherry blossoms are in bloom. Additionally, we like to pair a walk here with a stroll up the Midway Plaisance, to Laredo Taft’s stunning sculpture “Fountain of Time”. An example of the route we like to walk is pictured below.

Orland Grasslands

Orland Park, Illinois

Orland Grasslands, located in the heart of the Chicago metropolitan area, is a hidden gem for nature enthusiasts and wildlife lovers. Spanning over 1,000 acres, this expansive landscape features rolling prairies, wetlands, and vibrant wildflower fields that burst with color in spring and summer. The grasslands are home to a diverse array of flora and fauna, making it an ideal spot for birdwatching and hiking. With miles of trails winding through this serene setting, visitors can immerse themselves in the sights and sounds of nature, spotting everything from migratory birds to playful deer. 

Orland Grasslands is FREE to park and use.

Our Favorite Orland Grassland Trails

Personal Perspectives

We love to hike this area around sunset, because the wide open prairie provides a picturesque view of the sky.

Pullman National Historical Park

Chicago, Illinois (Pullman)

Pullman National Historical Park, located on the south side of Chicago, is a captivating destination that brings to life the rich industrial and social history of America. Established in the late 19th century as a model company town for the Pullman Company, it showcases the vision of George Pullman and the lives of the workers who built and maintained the famous Pullman cars. Visitors can stroll through beautifully restored streets, explore historic buildings, and learn about the labor movements and civil rights struggles that unfolded here. With its blend of architectural charm and significant historical narratives, Pullman National Historical Park offers a unique glimpse into the complexities of American industry and community, making it a must-visit for history buffs and curious travelers alike.

Pullman National Historical Park is FREE to park and use.

Our Preferred Pullman Route

Pullman is an urban neighborhood, rather than a nature preserve or wilderness. Thus, there are no designated “trails”, and you can simply walk around and make your journey your own. Below is one example of a route we might walk, equalling about 2 miles. An example of a route we might walk is pictured below.

No matter your route, be sure to check out the following:

  • Visitor Center (Be sure to ask a ranger to initiate your dog as a BARK Ranger!)
  • Murals at E. 111th St & S. Cottage Grove Ave.
  • Hotel Florence exterior
  • Pullman Park & mural
  • Circle Park
  • Historic row homes
  • Market Hall
  • Pullman Club Coffee Shop (Dogs welcome!)

Personal Perspectives

This area has a special place in my heart, because several generations of my grandparents worked for Pullman, and lived in the famous row houses. There’s so much to see here, from signs explaining the history, to contemporary murals, to historic architecture. But one thing to absolutely do is stop by the visitor center and ask if your dog can become a BARK Ranger! They’ll gift you with a sweet tag, and an activity book for your pup. 

Waterfall Glen Forest Preserve

Lemont, Illinois

Waterfall Glen Forest Preserve, located just southwest of Chicago, is a serene escape that offers a perfect blend of natural beauty and recreational opportunities. Spanning over 2,400 acres, this preserve features picturesque woodlands, expansive prairies, and winding trails that beckon hikers, cyclists, and nature lovers alike. The highlight of the park is its enchanting waterfall, which flows through a rocky ravine, creating a tranquil atmosphere that invites visitors to relax and recharge. The waterfall itself has a fascinating history, because it is man-made, built to be part of an urban oasis by the Civilian Conservation Corps in the 1930’s. 

Waterfall Glen is FREE to park and use.

Our Favorite Waterfall Glen Trails

Personal Perspectives

This sprawling park is a lovely place to walk, and we love to sit by the waterfall on a sunny day. 

Pilcher Park Nature Center

Joliet, Illinois

Pilcher Park Nature Center, nestled in the heart of Joliet, Illinois, is a delightful sanctuary for nature enthusiasts and families alike. This charming park features a variety of habitats, including woodlands, prairies, and wetlands, providing ample opportunities for exploration and wildlife observation. With miles of scenic trails for hiking and a tranquil pond for fishing, Pilcher Park is perfect for a leisurely day outdoors.

Pilcher Park is FREE to park and use.

Our Favorite Pilcher Park Trail

If you’re after an escape to the woods, this place is a gem! It’s especially beautiful in the autumn when the leaves start to change color. 

Sag Valley Forest Preserve

Palos Park, Illinois

Sag Valley Forest Preserve, located in the southwestern suburbs of Chicago, is a picturesque natural retreat that invites visitors to immerse themselves in its tranquil landscapes. Spanning over 1,000 acres, this preserve features a diverse mix of woodlands, wetlands, and open fields, making it a haven for outdoor enthusiasts and wildlife watchers. With miles of well-maintained trails for hiking, biking, and horseback riding, guests can explore the serene beauty of the area while keeping an eye out for various bird species and other native wildlife. 

Sag Valley is FREE to park and use.

Our Favorite Sag Valley Trails

Personal Perspectives

This is one of our favorite wooded areas near the city, with so many trails to explore. This area is particularly stunning in the autumn, when you can bask in the changing colors. We also love to visit on snowy winter days when the woods are quiet and serene.

Cranberry Slough Nature Preserve

Willow Springs, Illinois

Cranberry Slough Nature Preserve, located in Cook County, Illinois, is a hidden gem. Spanning over 140 acres, this preserve features a rich mosaic of wetlands, including one of only a handful of peat bog ecosystems in Illinois. Wetlands, woodlands, and open grasslands make it a vital habitat for diverse wildlife, including migratory birds and native plants.

Cranberry Slough is FREE to park and use.

Our Favorite Cranberry Slough Trail

Personal Perspectives

These woods are tranquil, and we love to hike them in the winter after a fresh snow.

Midewin National Tallgrass Prairie

Wilmington, Illinois

Midewin National Tallgrass Prairie, located in northeastern Illinois, is a remarkable restoration project that brings to life the vast grasslands that once dominated the region. Spanning over 19,000 acres, this national prairie is a haven for biodiversity, showcasing native grasses, wildflowers, and a rich array of wildlife. A herd of bison even roams the restored landscapes (behind a fence, of course). Visitors can explore miles of trails that wind through rolling hills and open prairies, perfect for hiking, birdwatching, and photography. The preserve also offers educational programs and events that celebrate the natural and cultural history of the area. Midewin is not just a beautiful escape; it’s a vital conservation effort that reconnects people with the importance of preserving our natural heritage.

Midewin Prairie is FREE to park and use.

Our Favorite Midewin Prairie Trails

Personal Perspectives

This area is such a beautiful way to experience the prairie as it once was. We love to visit in the summer, when everything is in bloom and pollinators are buzzing around. Our favorite thing to do is to look for the bison. The grasses are so tall, that they can be hard to see as they free-roam in their gigantic enclosure, but it’s pure magic when you catch a glimpse.

Lake Katherine Nature Center

Palos Heights, Illinois

Lake Katherine Nature Center, located in Palos Heights, Illinois, is a serene oasis that invites visitors to connect with nature in a beautifully preserved setting. This 85-acre park features scenic walking trails that wind through lush woodlands, tranquil wetlands, and along the picturesque shoreline of Lake Katherine itself. 

Lake Katherine is FREE to park and use.

Our Favorite Lake Katherine Trail

Personal Perspectives

Our favorite thing about Lake Katherine is the flock of swans that live here. They’re migratory, so not always around, but it’s extra sweet when we can catch a glimpse of them.

606 Trail

Chicago, Illinois (Humboldt Park, Logan Square, West Town)

The 606 Trail, an innovative elevated path in Chicago, transforms an old railway line into a vibrant green corridor that connects neighborhoods and encourages outdoor activity. Stretching nearly 3 miles, this unique trail offers a blend of walking, running, and biking routes, all set against the backdrop of stunning urban landscapes and lush gardens. As you traverse the trail, you’ll encounter art installations, scenic overlooks, and access points to parks, making it a lively hub for community engagement. The 606 is not just a trail; it’s a celebration of the city’s commitment to sustainability and connectivity, inviting residents and visitors alike to explore Chicago from a new perspective while enjoying fresh air and outdoor experiences.

The 606 Trail is FREE to use.

The 606 Trail

Warren Dunes State Park, Michigan

Sawyer, Michigan

Warren Dunes State Park, located along the scenic shores of Lake Michigan in southwestern Michigan, is a breathtaking destination known for its towering sand dunes and stunning natural beauty. Spanning over 1,900 acres, the park features miles of sandy beaches, lush forests, and scenic trails that invite outdoor enthusiasts to explore its diverse landscapes. Climbing the steep dunes rewards visitors with panoramic views of the lake and surrounding wilderness.

Warren Dunes requires a Michigan Recreation Passport. Non-resident daily use fee is $11, and there are a number of other options for annual and resident passes.

Our Favorite Warren Dunes Trails

Personal Perspectives

This is a bit of a jaunt from the city, but it’s worth it! The added distance means the views of Lake Michigan are not as hampered by industry as those from the Indiana Dunes. So you can enjoy the expansive crystal blue waters in their most natural form. The park is also west-facing, so an incredible place to watch the sunset. 

Packing List for Chicagoland Hikes

Related