20 Microescapes to Make Your Chicago Winter Awesome

by Justyna Frank
awesome Chicago winter microescapes

Chicago winter is not for the meek.

It can be difficult to find motivation to go outside, and it’s so tempting to cocoon indoors near a heat source! The cold can be penetrating, the wind unforgiving, and short daylight hours make it hard to drag yourself out. Plus, there’s nothing to do outside.


That may be true –if you are feeling meek. But if you’re willing to grab the Chicago winter by its icy horns, you’re sure to be rewarded.

Despite the need for some initial planning and a bit of careful preparation to protect yourself from the weather, you’ll find that winter adventures offer an exhilarating experience that’s completely different from the summer vibe. With most people staying indoors, you may enjoy a trail, a local woods, or even an entire campground without seeing anyone. And the quiet landscape –gripped in ice, or muffled in snow– will help you leave big city pressures far behind, regardless of how far you’ve actually traveled.

So, where to go, what to do?

Here are 20 suggestions for short winter outings in or near Chicago, along with a few longer trips snuck in for good measure. Try one, try them all –one for each week of the season, and more. Or use them as a springboard to devise your own microescapes.

Winter sunrise over Lake Michigan marsh
chicago winter breakfast outside
Chicago winter breakfast
Raceway Woods MTB Trail in winter
  1. Cook breakfast outside. This is probably my favorite weekday treat any season of the year. You can set off on foot or by bike. Since you won’t be on the road long, you don’t really need any specialty gear beyond a small camp stove. A portable chair makes things more comfortable. This post has some of my preferred cooking methods. My favorite spots for Chicago winter breakfast al fresco are LaBagh Woods, Linne Woods, Gillson Park, and the lakefront near the Montrose Bird Sanctuary, but the possibilities are endless.
  2. Got that portable stove? Bring it to work, head out to a local park on your lunch hour, and brew your coffee outside. You’ll need a small pot to boil water, a pour-over filter and holder, and a thermal mug. And your favorite coffee and fixings. Who knows? Next week your co-workers may want to join you.
  3. Hike to or from work. Seriously, pick a nice day when snow is gently falling, lace up your boots, grab a backpack and just walk to work. OK, if the distance is too great, you may need to take the train and get off at an earlier stop. The distance of 2-3 miles is probably doable on the way in, but after work, I’ve walked 5-6 miles to get home and enjoyed the special charms of Chicago winter after dusk.
  4. Although urban hiking has its appeal, you can also sneak in some nature time before work. Simply leave 1-2 hours earlier than you need to for a morning hike in the local woods or forest preserve (you can combine this with items 1 or 2 above!).
  5. Build a campfire in the back yard (yours or a friend’s). Clear some snow around the fire pit (or build the fire right on the ground), set up a couple of chairs, bring blankets, something to roast on sticks, and perhaps a bracing beverage. For extra credit, you can cook a meal over open fire. You might forget you’re not actually camping.
  6. If that sounds like fun, push it up a notch and try camping out in your back yard. Why would you want to do that? Well, why not? It might be fun, and is probably the safest way to try winter camping if you’re not completely convinced.
  7. Or, if you’re ready to tackle the elements, head out for an actual overnight winter camping trip. Winter camping is available in Cook County Forest Preserves (Camp Bullfrog Lake is especially nice), and many state parks in Illinois, Indiana, Wisconsin and Michigan. Most will have access to water and at least a rudimentary bathroom. However, don’t count on being able to purchase firewood, so be sure to plan accordingly ahead of time. You may literally get the entire campground to yourself.
  8. Set out on foot for a day tour of a city. If you stay in Chicago, pick an outlying neighborhood or suburb to explore, and adopt a tourist mindset. Or visit a smaller city nearby (Milwaukee, Madison, Rockford, St. Louis or Michigan City, for example), and plan to spend a day getting to know it. Bring food, or a way to prepare it, a hot beverage in a thermal flask, and live out of your backpack for a day.
  9. Hike the Ice Age Trail. Not all of it. The whole thing is 1000 miles. But several of the most scenic sections are easily accessible from Chicago. Check this guide for day hike ideas.
  10. How about a nano-bike tour? For this, you may want to choose a crisp, dry, Chicago winter day. Head out on your bike for the day, plan to cook a meal over a camp stove or open fire, chill out for a bit, maybe crack open a beer (bring extra layers or even a sleeping bag for the time you’re just hanging out), and then ride home before nightfall.
  11. Ride a fatbike across a frozen beach at Illinois Beach State Park or Indiana Dunes. Never tried a fatbike? There are places near Chicago that offer rentals and groomed trails, such as Love Creek Park near Berrien Spring, MI., and even instruction, such as Brooks Adventures in Salem, WI.
  12. Bike across a frozen lake. For this one, you’ll have to travel a bit, but virtually every winter you can join the annual Bike Across Bago, a nearly 20 mile adventure across the ice of Lake Winnebago in northeast Wisconsin
  13. Go on a full moon night hike out your back door. Leave at at dusk and walk to a place near open water or field, set up you camp chair, bundle up in a sleeping bag, and hang out with the lonely satellite. Full moon dates for winter 2022-23 are December 7, January 6, February 5 and March 7.
  14. Because we’re lucky to be on the western shore of Lake Michigan, we can enjoy million dollar views on any given morning. Rising early to witness a winter sunrise in Chicago can be particularly rewarding. Get out before dawn and watch the sunrise on an ordinary day before work.
  15. Go snowshoeing at Miller Woods, Indiana. If you’ve never tried snowshoeing, you can try it free at the Paul H. Douglas Center in the Indiana Dunes National Park (call first to check on trail conditions, since there has to be adequate snow cover). You can then explore the three miles of trails at Miller Woods including oak savanna and duneland, which is quite a new experience when they are covered in a layer of snow.
  16. Visit an ice cave. Tucked away in southwestern Wisconsin is Kickapoo Valley Reserve rich in geological history that created the perfect conditions for wintry masterpieces. Numerous natural rock shelters turn into spectacular ice caves as groundwater trickles down and forms frozen waterfalls over the rock openings.
  17. Head for the beach! The Lake Michigan shoreline in winter undergoes a radical transformation as powerful waves push ice and sand ashore, and the cycles of freeze and thaw shape the deposits into ice mountains and caves reminiscent of a lunar landscape. You can experience this anywhere along a stretch of sandy beach, but the effects are particularly dramatic along the Indiana Dunes, where long stretches of beach allow for the formation of ice mountains, inland pools and even small ice caves. These formations can be dangerously unstable, so make sure you stay well inland, and on solid ground.
  18. Visit an island. Cut off from the physical connection of mainland hustle and bustle, islands have a bit of a mystique regardless of the season. But there are few things as intriguing as a desolation of a northern island in winter. In the summer, Washington Island at the tip of Door County is a popular tourist attraction. In winter, it will be just about your own to explore. The car ferry service continues through the winter, but be sure to bring your own food and provisions, as most public services are closed or maintain unpredictable hours.
  19. For a quick Chicago winter escape try mountain bike trails at Raceway Woods. The relatively short, easy-to-moderate singletrack trails are accessible to riders of all skill levels (you can always walk any section beyond your riding skills). After just a short ride up, you will emerge into a snow-covered evergreen grove that will make you feel like you’ve suddenly landed on an Alpine slope far far away.
  20. Winter in the big city can sometimes seem like a drag, and any Chicago winter can at times become less than joyous. When this happens, escape to a place that embraces winter in all its glory. Muskegon Luge Adventure Sports Park is such a place. You can learn to luge, but you can also ice skate through the woods, xc ski on lighted trails at night, and snowshoe along Lake Michigan shoreline. Equipment is available to rent, and you will be surrounded by people who know how to love winter.
Ice formations turn rock shelter into a cave.
coffee outside chicago winter
Fully armed for winter coffee break
Deserted early winter campground

There are so many ways to dip your toe into the snowbank of winter adventures! Some require a bit of commitment, but others don’t take a lot of time, and will still leave you completely recharged. A crisp winter microescape is just the thing to cure the relentless cabin fever. It may not be easy, but doing not-easy things is part of the fun! Chicago winter may be the perfect setting to launch you on the pursuit of a more adventurous life. The moment you decide to seize adventure —a trip, a challenge, a bold plan or simple experience outside of routine— every cell in your body will simply be rearing to go.

Got any favorite Chicago winter escapes of your own? IPlease share in the comments.

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