I have been blogging about adventures near Chicago ever since 2010, and I have been experiencing the adventures ever since I was ten. Not a bragger, but not many people know the outdoor adventure scene in and around Chicago and the Midwest. Many think Chicago is an outdoor adventure wasteland, but it is centrally located to many cool outdoor adventures within the city limits and within two-four hours away. Here are ten of my favorites.
Fall color was past peak in Forest Glen, but it lead to a beautiful carpet of leaves on the ground
Ten best outdoor adventures Chicago
Backpacking Forest Glen Preserve
What – Hiking and overnight backpacking
How far from Chicago – three hours south
Forest Glen Preserve is a little known pocket wilderness area tucked along the Vermilion River near Danville, Illinois. The highlight of the preserve from an outdoor adventure standpoint is the approximately 10 mile backpacking loop. The loop has two overnight campgrounds, so it is the best overnight backpacking area in Illinois that is closest to Chicago. Take a look at some of the adidas backpacks and hit the trail.
When one thinks of central or southern Illinois, most think of flat cornfields. Do not be deceived by its location. This is a rugged trail thanks to crossing ravine after ravine created by the creeks that empty into the Vermilion. It is listed as moderate by All Trails, so it is difficult, but not insanely difficult. What I love most about this trail is thanks to the deep ravines, you sometimes feel as if you are in the middle of Appalachian ridge and in a wilderness area, but civilization is deceptively close.
-Indiana Dunes State Park cross-country skiing
Cross-country skiing Indiana Dunes State Park
What – Cross-country or Nordic Skiing
How far from Chicago – one hour southeast
There are a lot of outdoor adventure opportunities in the Indiana Dunes, but many overlook the idea of cross-country skiing. When there is snow, there are two loops that start at the Nature Center. The A and B trail are 2 miles and 2.5 miles respectively. The B has better hills, but both are fun. The best part of these two trails is the state park is open until 11 p.m. at night. It is possible to leave Chicago after work, ski for hours and then return home before 10 p.m. The trails are not lighted, but it is easy to see without.
Amazing day fishing Lake Michigan
Waukegan Harbor Lake Michigan fishing
What – “Deep sea” fishing on Lake Michigan for trout and salmon
How far from Chicago – an hour to an hour and a half north
Last summer, for the first time, I went deep sea fishing on Lake Michigan with Jawzon Fishing Charters. It was an incredible experience, and I cannot believe I waited so long to try. We left Waukegan Harbor on a beautiful charter boat, and within an hour, we were nailing steelheads, king salmon, coho salmon, and even a rogue brown trout. I still have fish filets in my freezer, so not only do you get a fun fishing adventure, but you can enjoy many meals of fresh fish for weeks and months afterwards.
Related – Jawzon Charter fishing on Lake Michigan
Horserace Rapids from the Wildman Ranch was my last whitewater adventure
Outdoor adventures Chicago – Wildman Resort Whitewater Rafting
What – Whitewater rafting
How far from Chicago – four hours north
When one thinks of whitewater rafting, they probably think of wilderness areas far from Chicago like the mountains of Tennessee, the vast wilderness of Canada, or the Grand Canyon. Four hours north, Chicago adventurers can experience quality whitewater rafting on the Peshtigo River with class IV rapids in the Chicago Northwoods. Wildman Resort caters to whitewater rafting, zip lines, and has campsites and cabins. In the winter, they even run snowmobiling tours.
Outdoor adventures Chicago – My favorite photograph of spring warblers – A magnolia warbler *
Spring migration bird watching Montrose Point Bird Sanctuary
What – Birdwatching
How far from Chicago – Located in Chicago
Another outdoor pursuit one would not consider in or near Chicago is birding; however, Montrose Point features world class birding during a few weeks in May. The migration actually goes from late April to mid-June, but there are a few choice months in May when masses of warblers funnel through following the Lake Michigan shoreline north where the birding is just spectacular. I have counted 14 species of warblers on certain days. Montrose also features shore birds, waterfowl, birds of prey, so it is not just limited to songbirds.
Outdoor adventures Chicago (or near Chicago) Dusk on the Wisconsin River*
River canoe camping on the Lower Wisconsin River
What – River canoe camping
How far from Chicago – three and a half hours northwest
The last 92 miles of the Wisconsin River from the last dam at Sauk City to the confluence with the Mississippi River is characterized by sand bottom. It is one giant beach where during the right water levels, paddlers can camp along the river on sandbars. Enjoy lush green impenetrable shoreline and bluffs with bald eagles circling overhead and perching on what seems like every dead tree. This is a great experience to enjoy with a group of friends, where you can stop and swim at virtually every sandbar down the river. Wisconsin River Outings is the place to rent canoes and shuttle you and your friends to the river.
Outdoor adventures Chicago – Scuba diving gives a peek into another world
Scuba diving Haigh Quarry the Caribbean of the Midwest
What – Scuba diving
How far from Chicago – About an hour and a half south
This is the one adventure option on the list that I have not tried. A good friend of mine made me aware that one can become certified to scuba dive in the Midwest at Haigh Quarry. Although it is called the Caribbean of the Midwest, it is not warm or clear, but it is near if you live in Chicago. It is a great place to learn, and if you can learn, eventually you may be able to dive in Lake Michigan and check out a shipwreck.
Hiking Midewin National Tallgrass Prairie is a top outdoor adventure Chicago.
Outdoor adventures Chicago – Hiking Midewin National Tallgrass Prairie
What – Hiking
How far from Chicago – One and a half hours south
Midewin National Tallgrass Prairie is a wonderful place to hike near Chicago as it offers over 30 miles of trails. This was my oasis during Covid, and a great place for long distance hiking through reclaimed prairie. You might also see a buffalo as they have a herd that sometimes shows up near a trail. It is also one of the best places to see owls.
When I visit, I rarely see people, so it is a nice spot to find solitude for a couple of hours. Midewin also boasts great skies and beautiful sunsets, so make a point to end your hike in the evening.
Starved Rock State Park Wildcat Canyon
Starved Rock ice waterfalls, hiking, eagle watching, and kayaking, and camping
What – Hiking, camping, kayaking, eagle watching
How far from Chicago – 1.5 – 2 hour drive
Starved Rock is probably the most popular state park in Illinois with good reason. There are many canyons that produce waterfalls after rainfalls and ice waterfalls during certain times during the winter. Bald eagles also tend to congregate there during the winter but anytime is a good time to spot one. Kayak Morris offers kayak trips through this beautiful park with camping options nearby at a private campground. There is also a campground inside the park.
Ice Age Trail hiker – Hey that is me
Hiking or backpacking the Ice Age National Scenic Trail
What – hiking and/or backpacking the Ice Age National Scenic Trail
How far from Chicago – From 2-5 hours depending on the segment
The Ice Age National Scenic Trail winds its way through Wisconsin demarking the farthest south the last glacier covered the continent during the last ice age. The trail is not fully complete, but it will be over a thousand miles long when fully connected. The closest area to Chicago are the Kettle Moraine segments, which over overnight backpacking in reservable shelters.
I have hiked and camped on this beautiful trail in both south and north Kettle Moraine, in the Chequamegon-Nicolet National Forest, and the Hartman Creek section near Waupaca. Put on your adidas hiking boots and go.
Adventure on!
