Perfect Winter Road Trips for When You Need to Escape Chicago
Kick it into four wheel drive.
As a born-and-raised Chicagoan, I’m not going to try to convince you that winter is the Windy City’s best season, but just stick with me for a second. A few useful tips: Try not to fight it—it will be much more enjoyable if you lean into the droves of snow, the early sunsets, and the glove warmers. Sooner rather than later, the temperatures will be undeniably frigid and you’ll find yourself sipping a hot tea, officially entering winter’s “acceptance” stage. Keep at it, and you’ll reach the “appreciation” stage, where planning a fun and frosty getaway might even bring you incredible joy.
Just a short drive from the city sits pristinely powdered slopes ripe for skiing, sledding and snowmobiling, cozy, romantic cabins, soul-warming indoor pools, ice fishing adventures, caves to explore, horses to ride, and other thrilling and/or relaxing activities sure to ward off the winter blues. Here are 14 handpicked yuletide destinations perfect for your next weekend road trip.
Distance from Chicago: 365 miles, 5.5-hour drive
Who knew that there even was a Snowmobile Capital of the World? Eagle River, Wisconsin has held this title for years, and it's no wonder why. Hit the designated 600 miles of well-maintained trails winding through forests and over 2,000 lakes and you’ll undoubtedly blow off any pent-up winter steam. Bundle up and rent an “ATV for the snow” from Trackside or Toy Shop, who will make sure you have all the essentials to venture into this midwestern winter wonderland. And if you want to see how the pros shred, the World Championship Derby Complex—with its lineup of riveting events and competitions that have been going on since the 1960s—will not disappoint. Bonus: They even have vintage snowmobile races, so you can see some retro buggies attempting to prove themselves out on the snow. Haven't had enough yet? Peruse the halls at World Snowmobile Headquarters, where you can get up close and personal with the history of the motorized sport and the people behind it.
Of course, heavy machinery is not essential for enjoying the area’s many trails of blanketed pathways. Strap on some snowshoes or cross-country skis courtesy of Eagle Sports Center, and get lost in the trees at nearby Chequamegon and Nicolet National Forests, before winding down in idyllic comfort at local standbys The Eagle Waters Lodging or Wild Eagle Lodge.
Distance from Chicago: 346 miles, 5-hour drive
Ski slopes don’t usually come to mind when folks think of winter in the midwest, but Boyne Mountain Resort will have you mistaking northwestern Michigan for Park City, Utah (okay, maybe a bit of an exaggeration). Regardless, this snowy palace boasts 415 skiable acres, 60 downhill runs, seven terrain parks, and ski lifts soaring as high as 500 feet. There are plenty of options for all skill levels here, and if you’re just starting out (or just taking it easy), you can glide down the bunny slope to your heart's content without dropping any extra cash. Sister resort Boyne Highlands sports some more advanced slopes for those wanting a steeper challenge, and if you haven't had enough winter adventuring, head over to Gaylord State Forest, which boasts trails upon trails of natural beauty.
Between runs, check out other draws like ziplining, tubing, cross-country skiing, ice skating, fat tire snow biking, SNO-GO biking, and, if that wasn’t enough, a full-scale indoor waterpark for those who just can’t kiss summer goodbye. Local breweries like Hop Lot Brewery, Mackinaw Trail Winery & Brewery, Burnt Marshmallow Brewing, and Biers Inwood serve as prime respites for that much-needed apres-ski (or -waterslide). Before tucking into bed inside your villa or lodge, unwind at the onsite spa, packed with an array of body treatments, like facials, massages, and BEMER therapy. Because, hey, you’re worth it.
Distance from Chicago: 186 miles, 3-hour drive
If you're of a certain generation, the word “bobsled” instantly conjures memories of the infectious Cool Runnings theme song. Over at Muskegon Luge Adventure Sports Park in Muskegon, Michigan, you can finally realize your grade school dreams as you speed down an icy path on a, well, it’s a luge (close enough). The luge track was built by an Olympian and is one of only four in the United States, established with the intent to make the winter sport accessible to all levels while still getting you sliding at a thrilling speed of 30 mph. The fun park also sports a quarter-mile ice skating trail that guides skaters through a white pine forest and is lit at night for those with twilight urges. Elsewhere, grab a pair of snowshoes and float along the pillowy trails until you reach the top of the sand dunes overlooking Lake Michigan and Muskegon Lake.
The surrounding town provides plenty of opportunities to immerse yourself in a little history. Dive on over to the USS Silversides Submarine Museum to bask in the glow of gigantic underwater vessels or admire a restored Victorian home filled with decorative period furnishings at the ever-opulent Hackley and Hume. At the end of the day, hang up your parka and curl up with a heavy blanket inside a glowing cottage or bungalow—a holiday movie marathon awaits.
Distance from Chicago: 145 miles, 3-hour drive
Chart a course due north along Lake Michigan for unparalleled hospitality at Destination Kohler. Guests here have options, starting with the five-star American Club Resort Hotel, with its variety of rooms and suites and luxe features like four-paneled glass fireplaces, luxurious showers and baths, and Peloton bikes. Overlooking Wood Lake perches the three-diamond Inn on Woodlake, great for a buddy trip and stacked with sleek modern amenities and beautiful views of the 11-acre lake. On the other hand, the Kohler Cabin Collection offers four lavish cabins outfitted as rustic-yet-refined homes away from home. The dwellings shine with expansive patios, outdoor firepits, indoor wood-burning stoves, and full kitchens to prepare any meal you could want—but what makes them extra special is their seclusion. Each is tucked away among a trove of snow-laden trees, so you can truly unwind and relax without interruption.
Get your festive fill at Winter Wonderland, an onsite complex spanning ice skating, ice bowling, snowshoeing, cross-country skiing, and guided trap shooting. Hungry? Settle into three squares and then some, from gourmet breakfasts and white tablecloth dinners to late-night bar snacks and cocktails at the inhouse bar. Two minutes on the property and wherever you stashed your car keys will be a distant, fading memory.
Distance from Chicago: 133 miles, 2.5-hour drive
Ever wanted to say, “Screw it all,” get rid of all your earthly belongings, and hole up in a hygge-ified tiny house in the middle of nowhere? Live out all your reclusive fantasies without actually tossing your stuff by booking a weekend in Grand Junction, a pastoral sliver of western Michigan about 15 minutes outside the lakefront hamlet of South Haven. That’s where you’ll find Getaway Barber Creek, a 79-acre dog-friendly glamp-ground outfitted with a handful of secluded cabins complete with parking spots, picnic tables, Adirondack chairs, and fire pits for all your marshmallow-melting needs. Each matte black hideaway is as practically appointed as it is aesthetically pleasing, stocked with a plush, super comfy bed, gorgeous floor-to-ceiling window, compact table, kitchenette with running water, and full bathroom with, yes, a real-deal shower.
Outside the confines of your new wintery oasis lies plenty of outdoorsy and less-outdoorsy activities, from hiking the converted railroad Kal-Haven Trail or sand-strewn Van Buren Park Dunes Trail to checking out the historic South Haven South Pierhead Light or stuffing yourself silly at area farm-to-table eateries and top notch breweries. Whatever you choose, embrace your new lifestyle—however temporary—by stashing your phone in the lockbox provided, bundling up with a good bottle of whiskey (preferably something camp-ready like Stillhouse), and reveling in the simplicity of it all.
Distance From Chicago: 193 miles, 3-hour drive
Wisconsin Dells is known not only for its killer collection of adult-friendly water parks, each of which offer a great escape from the freezing temps, but also for the Dells themselves: A magnificent gorge carved out by ancient glaciers, boasting powerful views of the sandstone cliffs lining the Wisconsin River. Dells of the Wisconsin River State Natural Area encompases five miles of beautiful winter hiking trails (weather permitting) following the curving river. And if that’s not enough, nearby Mirror Lake State Park has 18 miles of groomed trails for cross-country skiing plus scenic vistas and a boatload of other opportunities for brisk outdoor thrill-seeking. Nearby, Cascade Mountain is lined with cloud-like slopes popular with snow-tubers and skiers, while 25 miles northwest lies Castle Rock Lake, a go-to for both seasoned and novice ice fishing enthusiasts.
Apart from the literal endless amount of theme parks, water parks, and natural splendors, Wisconsin Dells is rife with other vacation-worthy charms. Rest your head at quaint bed and breakfasts like Oak Hill and Cedar Lodge, indulge your inner gourmand at countless restaurants (Brat House Grill, stationed in a colorful and gorgeously preserved Victorian home, is an absolute must), and kick back at small-batch breweries and wineries like Fawn Creek, Balanced Rock Winery, and the fan-favorite Moosejaw Pizza & Dells Brewing Co.
Distance From Chicago: 380 miles, 6-hour drive
Winter in Michigan's Upper Peninsula is truly outstanding, yet all-too-often overlooked by Chicagoans, as it lies just outside the traditional five-hour road trip radius. Don’t let the distance discourage you—Pictured Rocks National Lakeshore is well worth the extra effort, promising 42 miles of glorious panoramas dotted with frozen waterfalls, icy lakes, a plethora of rugged snow-dusted trails, and rocky technicolor ridges stretching as high as 200 feet above the shore. There are tons of wintery activities to keep you busy, like snowshoeing, cross-country skiing, snowmobiling, ice climbing, winter camping, and ice fishing. Whether you’re in the mood to trek through the trees or shred some backroads trails on a snowmobile, this natural paradise offers more than enough to occupy a full weekend of winter hijinks. And did we mention that Hiawatha National Forest and all its forested glory sits a mere 15 miles away? There you’ll discover the Rock River Canyon Ice caves—more popularly known as Eben Ice Caves—where water seeps through the sandstone, freezes, and creates spectacular curtain-like formations bound to put whatever Zoom background you’ve been staring at for the past six months to utter and absolute shame.
In terms of creature comforts, Munising is studded with all kinds of restaurants and cafes—plus a host of inviting hotels, motels, cabins, and resorts if chilly off-season camping isn’t quite your thing.
Distance From Chicago: 60 miles, 1-hour drive
Michigan City is an adorable town perched along the southern shoreline of Lake Michigan, engulfed by the venerable and incredibly diverse landscape of the Indiana Dunes. In the winter, Indiana Dunes State Park and Indiana Dunes National Park combine for miles of sandswept, snow-covered mounds traversed by a bounty of trails wandering through dense woodland. Snowshoes or cross-country skis can be rented for free at the Paul H. Douglas Center for Environmental Education, which is a nice touch. Those interested in sleeping under the stars can do so year-round within the State Park or at several area all-weather camp and RV grounds (though you may want to cop a home on wheels via RVshare, as the temperatures can creep pretty low). Otherwise, book a stay at The Brewery Lodge, an unforgettable rustic-chic boutique hotel set on over 40 splendid acres, or snag a room at the retro-cool 4411 Inn & Suites, a renovated roadside motel offering private back patios and communal fire pits.
Prefer to balance your outdoor pursuits with a dose of small town charm? Michigan City is overflowing with things to do, from shopping at the massive outlet mall to sledding down the eponymous hill at Sunset Hill Farm alongside other their planned winter activities. A Michiana booze crawl is always in order, with standout producers Burn ‘Em Brewing, Shoreline Brewery, Zorn Brew Works, Shady Creek Winery, and nearby Journeyman Distillery, among others, leading the belly-warming charge. And when hunger strikes, post up at polished restaurants like The Brewery Lodge’s onsite Supper Club, Fish Camp, and Fiddlehead or chill out at laid-back favorites like Bridges Waterside Grill, Hammers, and Barker Pub.
Distance From Chicago: 147 miles, 2.5-hour drive
Maybe you’re not exactly keen on heading to another city for your winter escape, but this college town gem will undoubtedly change your mind by merging urban perks like a quality dining scene and world-class cultural venues with an onslaught of nature activities like winter hiking, skiing, and ice fishing in surrounding Lake Mendota, Lake Waubesa, and Lake Kegonsa. Rent some skates and glide atop the glassy ice at Ice House or head out to sled under the crisp night sky over at Elver Park. Lace up your boots to tackle one or more of Madison’s many winter-friendly trails like Picnic Point, Ice Age Trail, and Cherokee Marsh, then clean up, mask up, and reward yourself with a stately meal—head-turning restaurants are another local specialty.
Make a point to stroll the always vibing State Street promenade to scope out satisfying casual and global eateries or reserve a table at one of the many farm-to-table gems scattered around town. Save room for beer from craft champions like Ale Asylum, Lone Girl, Young Blood, and Funk Factory Geuzeria, and when it comes time to crash, AC Hotel Madison Downtown, The Livingston Inn, The Edgewater, and the upbeat Graduate Madison have you covered—literally.
Storybook winter views will be there to greet you once you’ve had a good night’s sleep. The University of Wisconsin Arboretum is nestled within the city proper, with both paved and dirt trails crisscrossing its eclectic expanse. And you don’t have to be an architecture nerd to have your mind totally blown at Frank Lloyd Wright's famous Taliesin estate, a majestic and artfully preserved UNESCO Heritage Site located just south of nearby Spring Green, Wisconsin. On your way back to the Chi, stop off at Blue Mounds State Park for some awe-inspiring panoramic views of the life-sized snowglobe below courtesy of the region’s highest lookout point.
Distance from Chicago: 80 miles, 1.5-hour drive
There’s a reason why Lake Geneva has been Chicago’s number one vacation destination for generations. It’s got everything you could possibly need in a weekend oasis… all just 90 minutes from the city. One of America’s top lake towns in the summer, it also boasts an array of winter activities from a stellar dining scene to serene snow-covered lakefront trails. And the nice thing about Geneva in the winter is that it’s much tamer than the extremely busy summer months. However, if you find the postcard-perfect downtown still abuzz with tourists, get some fresh air by walking the entire length of the lakeshore along the town’s open-to-the-public Lake Shore Path before taking refuge in under-the-radar Lake Como, home to the epic Mars Resort and its newly expanded patio. February brings the lauded Winterfest to town, with bonfires on the beach, mind-boggling ice sculptures, and more. Elsewhere, the lesser-visited nearby towns of Williams Bay, Fontana, and Lake Delavan are more than worthy of exploration any old time of year.
Distance from Chicago: 351 miles, 5.5-hour drive
No one is going to mistake Illinois for Big Sky Country, but the Land of Lincoln has one ace up its sleeve: Shawnee National Forest, a brilliant stretch of approximately 280,000 acres covering a large portion of Illinois’ southern tip. In other words, it’s the perfect spot to take a much-deserved break from the endless crush of news for a few days. Tent, RV, and dispersed camping sites are generally up for grabs through December 15, but do your research ahead of time, lest you find yourself scrambling for shelter as the sun makes its frosty descent.
Wherever you stay, set aside some time to bask in the solitude of the National Forest’s monstrous focal point, Garden of the Gods Wilderness—one of seven such wilderness areas in the park—before peacefully meandering through the pastoral surrounding towns with their antique shops and mom and pop restaurants, taking full advantage of everything this nearly Rhode Island-sized midwestern getaway has to offer.
Distance from Chicago: 164 miles, 3-hour drive
As one of the best small towns in America, Galena has you covered if you're into strolling snowy cobblestone streets amidst historic mansions and fairytale rolling hills. It also happens to be home to Chestnut Mountain Resort, Illinois’ only ski-ready “mountain.” With the entire Galena Historic District—spanning more than 1,000 buildings constructed before 1900—listed on the National Register of Historic Places, you won’t have to wander far to realize why Ulysses S. Grant chose to call this little village home. Get that Christmas shopping done early with a trip to Main Street, where you’ll find unique shops like Galena Apothecary and The Grateful Gourmet among other retail curiosities. Feed your inner creative by stopping in for a class at Galena Spoon Company, where you can learn how to carve gorgeous wooden spoons, or whip up a custom holiday candle over at Scent Workshop.
If you're feeling outdoorsy, Galena also has incentives for the adventurous at heart, including an excursion to the nearby resort at Chestnut Mountain as well as a number of cool bluff hikes overlooking the Mighty Mississippi. Settle in off the beaten path at the LeFevre Inn, nestled on 100 acres of land just outside of town. And to stretch your legs amid winter’s bounty, your best bets include the historic Stagecoach Trail and the always-lovely Apple River Canyon State Park.
Distance from Chicago: 139 miles, 2.5-hour drive
Saugatuck is famous for its pristine Oval Beach (cited by the Tribune as the Midwest's very beach), where winter visitors can still roam its 10 miles of prime Lake Michigan real estate. Snowy sand dune hikes will always vie for your attention, but during the cooler months, when the water grows choppy and the winds start to kick, Saugatuck’s world-class arts scene sets it apart from the beachy pack.
Known as “the art coast of Michigan,” Saugatuck and the neighboring towns of Douglas and Fennville are home to dozens of galleries and unique shops tailor-made for serious collectors and amateur onlookers alike. The open-minded community is also famously welcoming to all, with more than 140 LGBTQ+-owned and -friendly businesses making it one of the most queer-friendly resort towns in America. While known primarily for its summers, winter is an equally excellent time to visit, with price-drops at fun-loving lodging options like queer mecca Dunes Resort and vintage roadside charmers like Pines Motorlodge And Cottages and Saugatuck Retro Resort Motel. A wealth of seasonal activities is also on hand, including a number of festive wintery events, and since it’s just a hop, skip, and a jump from Chicago, you may as well enjoy the journey by ticking off all the boxes on this road trip bucket list.
Distance from Chicago: 276 miles, 4.5-hour drive
Door County is a picture-perfect assemblage of more than a dozen little villages situated on a beautiful 75-mile peninsula surrounded by the shimmering waters of Lake Michigan and Green Bay. With 53 public beaches, five state parks, and 300 miles of shoreline, there's a lot to like (and do) here. And while winter’s thinning crowds do make for a nice break from their more raucous summertime counterparts, you’d still be wise to explore some of the area’s lesser-known attractions such as the 7,000 acres of chilly open-air space carefully watched over by the Door County Land Trust, or the peaceful lighthouse-strewn Ridges Sanctuary, prime territory for listening to nothing but the sound of snow crunching beneath your boots. Additional hidden gems like Baileys Harbor Ridges County Park or the breathtaking Hotz Memorial Town Park teem with similar outdoorsy appeal. A full slate of official winter activities, including December’s Tree Festival, a polar bear swim in January, and the Fire and Ice fest in February, keep things interesting.
Limit your interaction with other humans by opting for a carry-out meal from a stash of excellent local restaurants (Wild Tomato is a no-brainer), and be sure to book a stay at one of the area’s many waterfront resorts, rustic log cabins, or inviting inns when you need your beauty rest.