Travel

The 15 Best Ski Destinations Within Driving Distance of Chicago

From dedicated trails to mountainside resorts stocked with winter fun, here are the Midwest's best ski trip destinations.

Granite Peak Ski Resort
Granite Peak Ski Resort
Granite Peak Ski Resort

We may not have the same dizzying, ear-popping altitudes as Utah’s Snowbird or Colorado’s Vail, but us Midwesterners still have plenty of ski-worthy slopes at our fingertips. And once you and your (vaccinated, boosted, and masked) buddies throw on those extra layers, it won’t take long to drive out to a place where you can cruise atop pristine white powder. If you’re a newbie and need some motivation, skiing is not only unbelievably exhilarating, it’s also an awesome substitute for your boring winter workout routine, improving coordination, strength, and flexibility. From bunny hills to Black Diamonds, here are 15 standout ski resorts within driving distance of Chicago sure to put an end to those mid-winter blues.

The Highlands at Harbor Springs
The Highlands at Harbor Springs
The Highlands at Harbor Springs

The Highlands and Harbor Springs Resort

Harbor Springs Michigan
Distance from Chicago: 370 miles; 6-hour drive
Since you’re already driving all the way up to Michigan, you might as well scout out a place where you can not only ski, but sleep, shop, and eat all in one place. The Highlands Springs Resort offers Michigan’s longest ski run, 10 lifts, 53 groomed runs, and, for the more advanced shredders in the group, four terrain parks. As if that wasn’t enough, the resort also accommodates snow tubing, snowshoeing, winter ziplining, and bonfires where s’mores are highly encouraged. When you’re ready to hit the hay, take advantage of the resort’s luxe lodging options which span condos, traditional hotel rooms, cottages, and entire homes for rent.

Sundown Mountain Resort
Sundown Mountain Resort
Sundown Mountain Resort

Sundown Mountain Resort

Dubuque, Iowa
Distance from Chicago: 188 miles; 3.5-hour drive
As the name suggests, Sundown Mountain Resort lets you glide down their cedar-lined slopes far past bedtime. The resort sports 21 trails catering to all levels, and when you’re ready to take a break, head over to one of their onsite lodges. Ben’s Den warms weary skiers by the campfire with s’mores and hot cocoa, while The Barn, located right off the slopes, provides drinks and bonfires. South Lodge’s Bottoms Up will get you fed while taking in sprawling views of the runs, and Northern Lodge is your spot to sip adult beverages and caro-load on pizza and sandwiches courtesy of Tips Up Food and Spirit. Clearly this place understands how to strike a fine balance between adventure and leisure.

Caberfae Peaks
Caberfae Peaks
Caberfae Peaks

Caberfae Peaks

Cadillac Michigan
Distance from Chicago: 283 miles; 4.5-hour drive
This 30-run resort features steep slopes, two peaks, five aerial lifts, and plenty of backcountry terrain if you’re in the market for a snowy path less traveled. Come for the day or kick back at the Mackenzie Lodge, conveniently stashed just below all the trails, where an outdoor heated pool, hot tub, and roaring fire pits offer many opportunities to get warm. And if inclines and declines aren’t really your thing, the Mckenzie Cross-Country Trail also offers Nordic Skiing over 10 miles of all-level trails traversing Huron-Manistee National Forest.

Wilmot Mountain
Wilmot Mountain
Wilmot Mountain

Wilmot Mountain

Wilmot, Wisconsin
Distance from Chicago: 66 miles; 1 hour, 15 minute drive
Wilmot used to be in the same class as suburban resorts that don’t amount to much more than a few slushy bunny hills, but the little mountain just across the Wisconsin border has seen some significant upgrades since Vail Resorts purchased the property in 2016 and cashed in $13 million worth of renovations. Featuring 120 skiable acres, 25 trails, 11 lifts, four terrain parks, and a 22-lane tubing hill, Wilmot is nowhere near being in the same conversation as Vail’s signature properties out West. But it does provide for some nice practice runs about as close to home as you can get.

Alpine Valley Resort Wisconsin
Alpine Valley Resort Wisconsin
Alpine Valley Resort Wisconsin

Alpine Valley Resort

Elkhorn, Wisconsin
Distance from Chicago: 90 miles; 1.5-hour drive
You probably know Alpine Valley as that place where you saw Dave Matthews that one time in high school. In winter, however, it’s the closest thing Chicagoland has to a respectable ski establishment. With a top elevation of 1,040 feet and a vertical drop of 388 feet, the 90 acres of skiable terrain is situated in a rolling forested area about 20 minutes north of Lake Geneva. It might be basic, but it’s definitely a thrill, providing a diverse ski experience for all ages with 12 lifts, three terrain parks, night skiing, and ski-in, ski-out accommodations, to boot.

Bittersweet Ski Resort
Bittersweet Ski Resort
Bittersweet Ski Resort

Bittersweet Ski Resort

Otsego, Michigan
Distance from Chicago: 159 miles; 2.5-hour drive
With 12 lifts, 20 runs, two terrain parks, and 100 acres of skiable terrain topping out at 850 feet with a 300-foot vertical drop, Bittersweet is typical of the small cluster of resorts in southwest Michigan that also includes Swiss Valley and Timber Ridge. They certainly won’t blow you away, but they won’t totally bore you either. Saddle up, cowboy.

Cascade Mountain
Cascade Mountain
Cascade Mountain

Cascade Mountain

Portage, Wisconsin
Distance from Chicago: 177 miles; 2.5-hour drive
With 47 runs, 11 lifts, and a peak elevation of 1,280 feet, Cascade officially enters the next level of Chicago-area ski experiences, complete with plenty of opportunities to go full Shaun White on big-air jumps spanning four terrain parks. Getting down the mountain via one of 15 snow tubing lanes also provides a fun alternative to the traditional wedge-and-scoot.

Chestnut Mountain Resort
Chestnut Mountain Resort
Chestnut Mountain Resort

Chestnut Mountain

Galena, Illinois
Distance from Chicago: 162 miles; 2.5-hour drive
Others on the list may have more snow and better runs, but few nearby ski destinations are this damn fun. Chestnut’s location in Galena (one of our top Midwest winter vacation spots) perched high on a bluff overlooking the Mississippi River provides a unique environment from which to survey your surroundings before tackling the resort’s 19 runs, three terrain parks, 10 lifts, and an impressive-by-Midwestern-standards 475-foot vertical drop.

Granite Peak Ski Resort
Granite Peak Ski Resort
Granite Peak Ski Resort

Granite Peak

Wausau, Wisconsin
Distance from Chicago: 275 miles; 4-hour drive
Located within the chilled-out Rib Mountain State Park overlooking the highest point in Wisconsin, this resort offers more room to roam than the crowded confines of popular alternatives like Cascade along with Wisconsin’s highest vertical drop measuring 700 feet. With a whopping 74 runs plus six terrain parks and one of the highest elevations in the Midwest at 1,942 feet, this resort, dating to 1937, is also one of the oldest in North America.

Crystal Mountain
Crystal Mountain
Crystal Mountain

Crystal Mountain

Thompsonville, Michigan
Distance from Chicago: 312 miles; 4.5-hour drive
Instead of being crammed into some broken down old lodge, you can rent badass private homes or high-end condos and throw your own socially distant après ski party at this Thompsonville stunner. With 58 runs spread out across 80 acres of skiable terrain plus a sizable backcountry and heaps of well-groomed cross-country trails, this family-owned resort overlooking the scenic Betsie Valley about 30 miles southwest of Traverse City might just be one of the Midwest’s best-kept secrets. Shhh.

Ski Brule
Ski Brule
Ski Brule

Ski Brule

Iron River, Michigan
Distance from Chicago: 339 miles; 5.5-hour drive
Often the first to open and the last to close each season, this sweet Michigan hideaway is a nice alternative to the megaresorts that often lay claim to the Midwest’s top runs. They have a few terrain parks, naturally, but how many resorts do you know that also house a full-on tubing park? We’re guessing just this one. With 17 runs and 12 lifts across 150 skiable acres, 30% of the runs are Black or Double Black Diamond-so it helps if you know what the hell you’re doing.

Nub's Nob Ski Area
Nub’s Nob Ski Area
Nub’s Nob Ski Area

Nub’s Nob

Harbor Springs, Michigan
Distance from Chicago: 376 miles; 6-hour drive
This loveable little resort named after founder Nubby Sarns opened in 1958 and continues its affable family-friendly vibe to this day. With 53 runs scattered across 248 skiable acres with nine lifts and a 427-foot vertical drop, it’s nestled in one of the most picturesque parts of northern Michigan, just 30 minutes south of the launch point to lakefront oasis Mackinac Island.

Big Powderhorn Mountain Resort
Big Powderhorn Mountain Resort
Big Powderhorn Mountain Resort

Big Powderhorn

Bessemer, Michigan
Distance from Chicago: 408 miles; 6-hour drive
With 253 skiable acres featuring one of the largest vertical drops in the Midwest, Big Powderhorn is a classic Upper Peninsula getaway offering a wide variety of terrain across 45 trails and three terrain parks. With nine lifts and one-third of the resort dedicated to Black or Double Black Diamond tears, check out the Cannonball or Blunder trails for some of the most delightfully challenging terrain in the region.

Boyne Mountain Resort
Boyne Mountain Resort
Boyne Mountain Resort

Boyne Mountain

Boyne Falls, Michigan
Distance from Chicago: 358 miles; 5.5-hour drive
Stretching across a massive 415 skiable acres near the northern tip of Michigan, the Midwest’s most famous ski resort is tough to beat. The sheer shredability across such a dizzying array of well-groomed runs is first-rate, but then again, so is the snow biking, horseback riding, and ziplining. With 60 trails, 12 lifts, and seven terrain parks, one thing you won’t find at this iconic resort is boredom. When it comes to skiing in the Midwest, this is about as good as it gets.

Big Snow Resort
Big Snow Resort
Big Snow Resort

Big Snow Resort

Wakefield, Michigan
Distance from Chicago: 401 miles; 6-hour drive
Formed in 2014 after a merger between two of the Midwest’s premier resorts-Indianhead and Blackjack-this monstrous destination offers everything you need for a Midwestern ski weekend at its best. 56 trails and 15 lifts punctuate a combined 400 acres of skiable terrain, with Indianhead being the mountain of choice thanks to a 638-foot vertical drop and some of the finest trails in the region.

Elanor Bock is a contributor for Thrillist.

Jay Gentile is an award-winning freelance journalist specializing in travel, food & drink, culture, events and entertainment stories. In addition to Thrillist, you can find his work in The Washington Post, The Guardian, CNN Travel, Chicago Tribune, Lonely Planet, VICE, Outside Magazine and more. Follow @thejaygentile

Travel

13 Reasons to Drive to Palm Springs

Rest, relaxation, and happy hour await you in the desert.

Photo courtesy of Palm Springs Aerial Tramway
Photo courtesy of Palm Springs Aerial Tramway
Photo courtesy of Palm Springs Aerial Tramway

SoCal winters may not cause locals to flee toward warmer weather, but it does remind us that now is a good time to visit Palm Springs. This time of year is the sweet spot where it’s not too hot during the day and the nights are perfect for a dip in a hot tub. Covered in kitsch, with a culture that encourages you to day drink and lay by a pool all day, it’s no wonder that the desert town has long been a refuge for weekend warriors looking for an escape. Bonus: You can pack up and drive, and be there in less time than it takes to binge a new Netflix series.

Palm Springs is home to a vibrant LGBTQ community-including the nation’s first all-LGBTQ city council-plus art and culture, as well as an abundance of mid-century modern architecture. A field of wind turbines welcome you to town, and once you’re there you’ll be welcomed by leaning palm trees and craggy mountain ranges that keep inspiration flowing. Here you can find warm weather, outdoor activities, and an abundance of restaurants and shops. You’ll also find plenty of opportunities to lounge poolside and do close to nothing, if that’s more your vibe. Use our recommendations below to craft your perfect weekend. You deserve it.

Editor’s note: The city of Palm Springs requires proof of COVID-19 vaccination status or a recent negative COVID test result for entry into the city’s indoor bars and restaurants. Make sure you plan accordingly.

Photo courtesy of Fleur Noire
Photo courtesy of Fleur Noire
Photo courtesy of Fleur Noire

Chill out in style

So you decided to make the good choice to spend a weekend in Palm Springs and need a place to stay. Sure, you could go the Airbnb route, of which the town has many. Or you could enjoy the luxury and amenities of one of Palm Springs’ beautifully designed hotels.

If you’re traveling with a whole posse, consider the boutique hotel, Limón. Their interiors are bright, cheery, and inspired by mid-century modern and 1960s Mexico City. The seven-room property books as one unit and can accommodate you and 13 of your pals. It includes a communal kitchen, an entertainment room, pool, and BBQ area. During your stay, let their staff take the wheel and plan your days. They can assist in creating the perfect stay, like a night out for a bachelor/ette party, a hot air balloon excursion, or a personal chef to cook for you and your crew.

For those looking for an intimate stay for two, try the adults-only hotel, Dive. It’s hard not to feel romantic in their elegant rooms inspired by the 1960s French Riviera. Personally, we fell in love at “free glass of rosé upon check-in.” During Valentine’s Day weekend they will up their complimentary glass by offering a complimentary bottle of French Pool Toy Rosé and two chocolate-covered strawberries per room.

You can’t miss Fleur Noire, with its black exterior that makes it stand out amongst Palm Springs’ otherwise brightly colored architecture. The interiors feel airy, modern, and are punctuated with wallpaper bearing large floral prints. The property consists of an array of casitas, studios, and standard rooms surrounding the communal pool. The hotel is near Palm Springs’ famed Palm Canyon Drive with shops and restaurants. However, if you want to stay a bit closer to your home-tel, you can access Sandfish Sushi & Whiskey through their back gate. Try their signature Black Mussels served with hijiki seaweed, scallions, and miso sake broth. On the Fleur Noire property, you can grab a drink at their rosé and champagne bar, La Boisson.

Aptly named Tiki Hotel is a nod to the 1950s & ‘60s affinity for tiki culture. If you don’t like kitsch and bold design, this is not the place for you. The 11-room property boasts island-themed decor, with vibrant colors and patterns galore. You can lounge by their pool or jump on one of the provided beach cruisers to explore the Palm Springs Design District and nearby shops and restaurants.

Photo by Jenni-Kate Rogers, courtesy of Boozehounds
Photo by Jenni-Kate Rogers, courtesy of Boozehounds
Photo by Jenni-Kate Rogers, courtesy of Boozehounds

Try out the Palm Springs food scene

At some point you might want to stop taking your food and drinks poolside and head into a restaurant. Palm Springs has something for everyone and at least one restaurant for the dogs. Boozehounds makes you wonder: is this a dog-friendly restaurant or a human-friendly dog restaurant? Either way, we’re all in! The restaurant has a large patio perfect for your pooch or if you prefer to dine sans dog, they have an indoor dining area. They serve a wide selection of food, from Japanese yellowtail to a Double Cheeseburger, all inspired by Southern California. They even have a menu just for dogs. with items like a bowl of skirt steak, steamed rice, and sweet potato. As the name suggests, they have a great selection of booze in the form of cocktails, wine, and beer. Not to leave dogs out, you can order your fur baby a weenie-teenie, a concoction of chicken broth, chicken whipped cream, and a dog biscuit crumble. Non-alcoholic, of course.

Eat brunch or lunch outdoors at El Patio, a family-owned Mexican restaurant. Try the Breakfast Enchiladas that come with squash, spinach, corn, cheese, and topped with your choice of green or red sauce and two fried eggs. Or opt for the Bone-in Chicken covered with mole poblano and pipian sauces, garnished with red onion, sesame seeds, and pumpkin seeds. Make sure to save room for their churro cart that comes with three different dipping sauces and sprinkles.

One of the most exciting restaurants in Palm Springs right now is Bar Cecil. The culinary commander of the place is Gabe Woo, a Coachella Valley native and local celeb known for his dinner series at Sparrows Lodge and Holiday House that were hard to get into. Woo takes bistro-style foods and expands on it while using seasonal produce from local farms. We can’t promise you it’ll be easy to get a table but we can say that their bar area takes walk-ins where you can order a juicy, flavorful burger and a delicious pork chop with a hint of smokiness. Or order from their “Why Not” menu where you can find swanky items like their infamous $50 martini-Beluga vodka with a kiss of Alessio vermouth is poured tableside in a perfectly chilled glass. The drink is served on a silver tray with a Regiis Ova caviar-topped deviled egg and a bowl of sunchoke chips.

Seymour's
Seymour’s
Seymour’s

Grab a cocktail or two

Drink across decades at Truss & Twine, a cocktail bar that celebrates the history of drinks in America. The interiors may be dark and dramatic, but their staff are friendly and happy to share their knowledge on libations with you. We recommend trying one of their original cocktails like the Game Changer that comes with gin, lime, cucumber, sugar, onion brine, sea salt, and celery bitters. They also serve food that does not resemble typical bar food fare, like their Wagyu Oxtail Grilled Cheese with cheddar, caramelized onion, and green chile aioli. For a mellow night, take a trip to the local speakeasy Seymours, located next to Mr. Lyons Steakhouse. Enter through the unmarked side entrance and step into a bar with chill vibes, moody lighting, and an intimate atmosphere with extraordinary bartenders. They also offer outdoor seating. Try their Oaxcan Hemingway with mezcal, maraschino liqueur, grapefruit juice, and simple syrup.

Photo courtesy of Fantasy Balloon Flights
Photo courtesy of Fantasy Balloon Flights
Photo courtesy of Fantasy Balloon Flights

Take in the scenery

September through May, Fantasy Balloon Flights will show you the world… or at least the vastness of the Coachella Valley from the sky. Rest assured, the hot air balloon company has been at it for some time (since 1981 to be exact). For those that need a bit of liquid courage, champagne balloon adventures are available.

Hop on the world’s largest rotating tramcar at the Palm Springs Aerial Tramway. The car takes you on a ten-minute ride up and along the cliffs of Chino Canyon for picturesque views of the desert until you arrive at your destination, Mt. San Jacinto State Park. At the top, there are places to grab food, observation decks, and over 50 miles of hiking trails. And if you go during the winter there’s a good chance there will be snow.

Bon Vivant Palm Springs
Bon Vivant Palm Springs
Bon Vivant Palm Springs

Load up on new and new-to-you goods

Look for retro wares in the land of mid-century modern majesty. Palm Springs may not have invented the style but they sure do embrace it. Go on a vintage crawl on Palm Canyon Drive and gander at shops like Bon Vivant, Modernway, and Revivals. There you can find eccentric accents and mid-century modern furniture to buy or give you major design inspo. While you’re around, you might as well spruce up your wardrobe at vintage boutiques like The Frippery, Iconic Atomic, and Bazar.

If you prefer to be the first owner of your items, check out the Mojave Flea Trading Post. Contrary to its name, the indoor department store features about 95% new and 5% vintage goods. Browse the stylish works of 40+ local artisans and find art, jewelry, clothes, natural beauty products, home goods, and more.

Photo courtesy of Toucans Tiki Lounge & Cabaret
Photo courtesy of Toucans Tiki Lounge & Cabaret
Photo courtesy of Toucans Tiki Lounge & Cabaret

Support the LGBTQ community

For a bar that has a mission statement that is as good as its food, try Blackbook. Named after the black book in Nevada, a list of notorious people not welcomed in casinos, owner Dean Lavine explains, “We like to think that everyone has been on a blacklist at some point in time. Gay, bullied, racially excluded, Raiders fans, etc.” The bar prides itself on being inclusive and welcoming to all, with some of the best food in Palm Springs. We’re partial to their Palm Springs-style nachos, a version they invented that ensures every chip has cheese so no one is left with a cheese-less chip when sharing. We can’t forget about their drinks. They have a full bar with the largest whiskey selection in the valley, with over 450 different bourbons, ryes, scotches, and international whiskeys, along with beers and other adult canned and bottled beverages.

After eating, sing your heart out at Quadz, where VJs are playing clips of beloved musical theater. You will have a great time at this lively bar even if musicals aren’t your “thing.” However, after a few of their notoriously strong and affordable drinks, you may be belting out Streisand with the best of them. Reserve a spot at Toucans and see a performance at Palm Springs’ longest continuously running drag show. Drag shows are Thursday-Monday with a different theme each night. No matter what day you go, it’s always a good time at Toucans, making it a favorite for tourists and locals alike, but pro-tip: Monday nights are free.

Photo courtesy of Palm Springs Art Museum
Photo courtesy of Palm Springs Art Museum
Photo courtesy of Palm Springs Art Museum

Get your art and culture fix

It may be hard to peel yourself away from basking in the sun, but take a break and explore the Palm Springs Art Museum. You can find modern and contemporary art, architecture, and design objects that reflect Palm Springs’ unique history, culture, and place.

Photo courtesy of Feel Good Spa
Photo courtesy of Feel Good Spa
Photo courtesy of Feel Good Spa

Recharge at a spa

Between work, existential crises, and living through a global pandemic, we all could use a relaxing spa moment. Book a massage at the Ace Hotel’s Feel Good Spa. Try their Rose Goodness, where a masseuse will use quartz massagers to get deep into your muscle tissue. The use of rose quartz is said to help replace toxic emotions and blockages to the heart chakra with loving energy. Release tension and stress and gain clarity through a holistic treatment at The Spa at The Colony Palms Hotel & Bungalows. They offer a wide range of services, including massages, facials, body treatments, vibrational sound healing, and acutaping.

Big Wheel Tours
Big Wheel Tours
Big Wheel Tours

Go on a tour

Cruise through the desert landscape on two wheels (or by Jeep or by hiking) with Big Wheel Tours. If your interests are more architecture than nature, check out Modern & More Bike Tours and see architecturally and historically significant homes in South Palm Springs.

If biking is not your style, hop in Palm Springs Mod Squad‘s van and take part in a mid-century modern architecture tour. Choose the martini option to learn more about the cocktail and cap off your tour with James Bond’s favorite drink. Their expert will explain why martinis are shaken and not stirred. They also offer socially distanced options for those that prefer to stay in their own car.

Indian Canyons & Tahquitz Canyon
Indian Canyons & Tahquitz Canyon
Indian Canyons & Tahquitz Canyon

Hike historic trailheads

If you prefer to see the desert terrain by foot, Indian Canyon Trails offer a plethora of hiking options that include cool streams and lush oases. You may even see a BigHorn Sheep. Indian Canyons is the ancestral home of the Agua Caliente Band of Cahuilla Indians, and you can learn more about their history through preserved rock art, irrigation ditches, and food preparation areas.

The Living Desert
The Living Desert
The Living Desert

Explore desert plant life

See desert animals and plants thriving at The Living Desert Zoo and Gardens. The world-class wildlife and botanical park has almost 430 animals, including cheetahs, giraffes, and camels as well as creatures native to the area. After that, head to Moorten Botanical Garden aka Cactus Castle, and explore over a dozen arid biomes and thousands of specimens sourced from all over the world. Plus, see rocks, crystals, fossils, gold-mining relics, and desert tortoises. If you feel inspired to become a plant parent after your visit, Moorten’s has a nursery for you to take home your own prickly bundle of joy.

Palm Springs Windmill Tours
Palm Springs Windmill Tours
Palm Springs Windmill Tours

Take a windmill selfie

The rows and rows of wind turbines off the I-10 on your way to Palm Springs are almost as iconic to the area as palm trees. If you’ve ever been curious about what they do, reserve a tour with Palm Springs Windmill Tours to see these 300-foot behemoths up close and learn how they power the entire Coachella Valley.

The Lights at Indio GC
The Lights at Indio GC
The Lights at Indio GC

Tee off after the sun goes down

If you burnt too much daylight at the pool or on hikes and weren’t able to get a round of golf in during the day, The Lights at Indio Golf Course has you covered. The Desert’s only night-lit course allows you to hit the links after dark.Want more Thrillist? Follow us on InstagramTwitterPinterestYouTubeTikTok, and Snapchat.

Keisha Raines is a LA-based freelance writer born and raised in the Palm Springs area with a tattoo of the San Jacinto mountains to prove it.

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