When discussing seasonal travel itineraries in the United States, determining the very best road trips from Chicago in Winter is a topic that regularly comes up. As the nation’s third-most populous city, and one of the best cities I have personally visited, it’s a popular start point for road trips throughout the year. During winter, though, the city is an excellent launch point for a picturesque road trip, with its snowy vistas, delightful small towns, and impressive winter attractions sure to jump-start any journey.
Whether you aim for a family excursion, a skiing trip, a warm-weather getaway, or an extended winter road trip, there are numerous unforgettable options available from “The Windy City”. While we can’t possibly outline every option, we can make your job easier by narrowing it down.
This guide will outline the 5 best road trips from Chicago in Winter and offer a few additional winter road trip ideas. We lay out the best destinations, most beautiful routes, essential attractions, seasonal activities, and helpful travel suggestions to help you craft an extraordinary adventure from Illinois in the chill of winter.
The 5 Best Road Trips From Chicago In Winter
Road Trip From Chicago To New York City (Best For Christmas)
A road trip from Chicago to New York City is perhaps the most quintessential Christmas road trip you can take in the United States. This is because both Chicago and NYC are famed for their Christmas festivities, and we even included both on our list of the best places to spend Christmas in the US.
Let’s start with Chicago. Being situated so far north almost guarantees snowfall during the Christmas season, ensuring your plans for a white Christmas won’t be derailed by weather concerns. Santa figures fill the streets and department stores, while attractions like the ice-skating rink at Maggie Daley Park ensure there’s something to delight individuals of all ages.
Chicago is famous for its stunning Christmas decorations and light displays. From the bustling city streets to suburban homes, you’ll find everyone brings their A-game to create a scene reminiscent of a holiday movie. While the Chicago Christmas Tree and the Magnificent Mile Lights Festival are certainly highlight events, you can stroll along nearly any street to feel the festive spirit.
Moreover, there’s the Christkindlmarket, one of the longest-standing and most beloved Christmas markets in the country. True to the best Christmas market traditions, it is German-themed, with numerous stalls showcasing goods, snacks, and beverages characteristic of that culture. Enjoy walking around with a hot gluhwein, sampling its renowned sausages, and exploring the myriad stalls filled with handmade items like clocks and ornaments.
Then there’s New York City. When Americans envision Christmas, NYC often springs to mind, as the iconic city shines particularly bright during the festive season, showcasing its unique charm.
The season kicks off with the lighting of the tree at Rockefeller Center, an event held on the Wednesday after Thanksgiving. The televised ceremony draws large crowds to witness the tree being illuminated for the first time, marking the official beginning of Christmas celebrations in the city. Renowned as one of the world’s most famous Christmas trees, people travel across the globe to admire this stunning symbol. With an ice rink nestled at its base, this location exemplifies the spirit of Christmas in America.
Just moments away lies Saks Fifth Avenue. Each year, the store's exterior dazzles with an elaborate light-and-music display, inviting onlookers to share in the festive atmosphere. A short way north, Central Park transforms into a picturesque winter wonderland, with the park’s ice rink filled with the sounds of holiday music and skaters of all ages revelling in the fresh winter air. Horse-drawn carriage rides through the park are a magical experience, especially if you’re lucky enough to enjoy one amidst falling snowflakes.
Although Midtown Manhattan is the heart of the New York City Christmas experience, the enchanting spirit can be found throughout NYC. Streets and shops are adorned with festive decorations and lights, complemented by markets offering a variety of seasonal foods and gifts.
The Best Route For A Winter Road Trip From Chicago To New York City
A road trip from Chicago to New York City covers 790 miles and takes 12 hours and 30 minutes to drive. However, our suggested winter route is a little longer, at 855 miles and 13 hours and 45 minutes.
Follow I-90 east from Chicago, then use Exit 142 to join I-80, and continue southeast to Exit 344. Follow I-676 across Philadelphia, Pennsylvania, keep left to join the Vine Street Expressway, then merge onto I-95 and head north. At Exit 14, go east on I-78, across the Newark Bay Bridge and through the Holland Tunnel, to arrive in Lower Manhattan, New York City.
Worthwhile stops along the way include Lake Michigan; Gary, Indiana; Indiana Dunes National Park; South Bend, Indiana; Toledo, Ohio; Lake Erie; Cleveland, Ohio; Cuyahoga Valley National Park; the Rock n Roll Hall Of Fame; Pittsburgh, Pennsylvania; Tuscarora State Forest; Lancaster, Pennsylvania; Philadelphia, Pennsylvania; and Newark, New Jersey.
Our guide to a perfect road trip from Chicago to New York takes you through the route and all its attractions in detail.
We also have helpful guides on the
best areas to stay in New York City, how to
enjoy NYC on a budget, and
the best things to do in New York City outside of Manhattan. This ensures you will find what you want, whether you are seeking cheap and cheerful motels or a 5-star hotel with a rooftop bar.
Road Trip From Chicago To Salt Lake City (Best For Skiing)
A road trip from Chicago to Salt Lake City, Utah, is a fantastic winter road trip for skiers, as it passes near many of the best and most iconic ski resorts in the United States, several of which are found in the hills above Salt Lake City.
The resorts begin popping up as soon as you climb into the Rocky Mountains near Denver in Colorado. The area around White River National Forest is home to one of the highest concentrations of ski resorts in the nation, with 11 resorts either fully or partially located within its area.
For a comprehensive skiing experience, Vail Ski Resort showcases vast expanses, famed Back Bowls, and an upscale village atmosphere. Aspen Snowmass Ski Resort caters to luxury seekers, offering four unique mountains along with top-notch dining, shopping, and nightlife. Breckenridge Ski Resort melds extensive terrain with a picturesque Victorian town, making it especially attractive to those seeking diverse slopes and vibrant après-ski scenes.
Renowned for its refined amenities and family-friendly vibe, Beaver Creek Resort is an excellent choice for novices and families. Keystone Resort is also a favourite with families and offers night skiing. Copper Mountain is known for its naturally varied terrain in a more laid-back environment.
As you near Salt Lake City, you’re met with a similar concentration of world-class resorts. The ski resorts near Salt Lake City are known for their outstanding powder, diverse terrain, and convenient access from SLC’s urban centre. All four principal resorts can be reached in 30 to 45 minutes.
Alta is particularly popular among traditional skiers, with its deep powder and demanding slopes. Snowbird caters to advanced skiers seeking steep descents, vast terrain, and an extended ski season. Brighton is a laid-back, family-oriented option that boasts excellent snow conditions, terrain suitable for all skill levels, and night skiing. Solitude provides a more tranquil skiing experience with appealing intermediate and advanced routes.
For those seeking a larger resort atmosphere, Park City Mountain encompasses over 7,300 acres of skiing terrain set against a vibrant historic town. Meanwhile, Deer Valley is recognised for its luxury, exceptional grooming, and superior guest services.
The Best Route For A Winter Road Trip From Chicago To Salt Lake City
Our Chicago to Salt Lake City winter road trip covers 1,530 miles and takes 22 hours to drive.
Take I-55 southwest to Exit 250B, merge onto I-80 and continue west for 780 miles to Exit 102. Follow I-76 to Denver, Colorado, merge onto I-70, and follow it 345 miles west. At Exit 157, go north on US Highway 191/Grand Army of the Republic Highway and remain on Grand Army of the Republic Highway when Route 191 bears right near Castle Gate, Utah. Merge onto US Route 89/National Park Highway in Thistle, Utah, and follow it north to Salt Lake City, Utah.
While we listed the best ski resorts, those desperate for more will comfortably find plenty of others in between. Other attractions on our route include:
Joliet, Illinois; Starved Rock State Park; Ronald Reagan’s Birthplace; Davenport, Iowa; Iowa 80 - World’s Largest Truck Stop; Herbert Hoover National Historic Site; Iowa City, Iowa; Amana Colonies; Des Moines, Iowa; Winterset, Iowa; Council Bluffs, Iowa; Omaha, Nebraska; Denver, Colorado; The Buffalo Bill Museum & Grave; Carbondale, Colorado; Grand Junction, Colorado; Canyonlands National Park; Arches National Park; Moab, Utah; Uintah & Ouray Reservation; Uinta Wasatch Cache National Forest; and Provo, Utah.
Our guide to the ultimate road trip from Chicago to Salt Lake City, Utah, details the route and each attraction in great detail.
Road Trip From Chicago To Yellowstone National Park (Best For Snow Activities)
A road trip from Chicago to Yellowstone is usually undertaken during Summer, when all of the park and its attractions are open, ready for you to embrace the great outdoors. However, Yellowstone National Park is an often-overlooked winter destination, as it’s bursting with unique snow activities to try.
Guided snowmobile tours are a fabulous way to experience the park at its most natural, without being surrounded by the mobs of tourists that descend on it during the summer months. You’ll get to see its iconic geothermal features and wildlife in all their glory, making it ideal for both thrill seekers and wildlife photographers. Even those not wanting to brave the elements can enjoy the experience with heated snow-coach tours.
Other winter activities in Yellowstone National Park include cross-country skiing and snowshoeing. Yellowstone Vacations offers great snow-coach and snowmobile rentals and tours. Yellowstone Expeditions also offers snow-coach tours and is our go-to for cross-country skiing and snowshoeing tours and rentals. Both operate out of West Yellowstone, Montana.
A short distance from Yellowstone National Park, you also have Jackson Hole, a valley that is home to Grand Teton National Park, Jackson, Wyoming, and three of the nation’s most outstanding ski resorts. Grand Teton NP offers a similar range of activities to Yellowstone NP. While the geothermal features are missing, the crowds are smaller, creating an even more natural experience.
The town of Jackson is Wyoming's 10th most populated. It’s known for Jackson Town Square, famous for its elk-antler arches and rich Western culture, marked by attractions like the Million Dollar Cowboy Bar and themed shops. The nearby National Elk Herd, the largest in the U.S., offers winter sleigh rides and hosts the Elkfest auction. The National Museum of Wildlife Art showcases local wildlife-inspired art, while the Center for the Arts highlights the town's vibrant arts scene. Jackson also serves as a base for the nearby ski resorts.
The three Jackson Hole valley ski resorts each provide a unique experience. The Jackson Hole Mountain Resort is the top choice for seasoned skiers, offering 2,500 acres of diverse terrain, ample deep powder, breathtaking views of the Teton Range, and challenging runs, including the renowned Corbet’s Couloir. Snow King Mountain is an easy access option located just minutes from Jackson Town Square, making it ideal for families, beginners, and those seeking a convenient skiing option, unique features like night skiing, or its varied non-skiing activities. Meanwhile, Grand Targhee Resort, located across the Tetons in Idaho, is famous for its plentiful powder, quieter slopes, and family-friendly trails.
The Best Route For A Winter Road Trip From Chicago To Yellowstone
The best route for a Chicago to Yellowstone road trip spans 1,400 miles, takes 21 hours to drive, and passes through Illinois, Iowa, South Dakota, and Wyoming. Attractions along the way include Davenport, Iowa; the Amana Colonies; Des Moines, Iowa; Sioux Falls, South Dakota; Badlands National Park; Wall Drug; Mount Rushmore; Wind Cave National Park; Crazy Horse Memorial; Deadwood, South Dakota; Devils Tower National Monument; and Cody, Wyoming.
Our perfect Chicago to Yellowstone road trip itinerary provides in-depth details on the route from Chicago to Cody, Wyoming, and all the attractions along the way.
To get from Cody to West Yellowstone, Montana, in winter, take WY-120 North across the Montana border (where it becomes MT-72) to Bridger. Head west on US-310 to Laurel, then merge onto I-90 West past Billings and Livingston. Exit I-90 at Bozeman and take US-191 South to West Yellowstone.
To get from Cody to Jackson in winter, head south on WY-120 South to Thermopolis. Continue south on US-20 East/WY-789 South through Wind River Canyon to Shoshoni, then follow WY-789 South into Riverton. Turn west onto US-26 West/US-287 North and follow it into Dubois and over Togwotee Pass (elevation 9,659 feet). As you descend into the Jackson Hole valley, the highway leads directly into Grand Teton National Park and Jackson.
Road Trip From Chicago To Florida (Best For Warm Weather)
A road trip from Chicago to Florida is particularly popular during winter with people who aren’t fans of the cold. As we touched on above, Chicago is bitterly cold during winter, so swapping it for the year-round warm weather of “The Sunshine State” is a no-brainer. As for where in the state to go, perhaps nowhere in Florida offers as much around Christmas as the greater Orlando area.
The Santa Workshop Experience at ICON Park offers families a chance to experience Christmas magic through activities like meeting Santa, festive treats, and train rides. EPCOT showcases global holiday foods and traditions, including the Candlelight Processional. SeaWorld provides a colourful display with over three million lights, ice skating, and visits with Santa.
Disney's Very Merriest After Hours at Magic Kingdom Park features character interactions, parades, artificial snow, rides, roller coasters, and winter festivities.
Universal Orlando Resort hosts the Holiday Parade Featuring Macy’s and iconic characters, and themed attractions. Its Wizarding World of Harry Potter is particularly noteworthy at this time of year. Fans can experience Christmas at iconic franchise locations, such as Hogwarts, Hogsmeade, and Diagon Alley, while embracing festive wizarding traditions.
The Orlando Museum of Art's Festival of Trees presents artistic Christmas displays, while the Winter Park Ye Olde Hometown Christmas Parade highlights local traditions. The town of Christmas, Florida, serves as a year-round festive destination. Founded on Christmas Day, it is particularly famous for its unique post office, where you can meet Santa and post letters stamped with a special Christmas postmark.
If all of this wasn’t enough, our route passes very close to Cincinnati, Ohio. This is a great bonus around Christmas, as “Cincy” is the best place in the United States for Christmas markets, thanks largely to its rich German heritage.
It features two main markets: the Christkindlmarkt, held in November with Bavarian food, entertainment, and traditional crafts, and the Cincideutsch Christkindlmarkt, part of the Macy’s Light Up The Square event, which includes live music and fireworks. Additionally, visitors can enjoy the Greater Cincinnati Holiday Market in November, showcasing over 300 vendors and family-friendly activities.
The Best Route For A Winter Road Trip From Chicago To Florida
A road trip from Chicago to Florida spans 1,155 miles and takes 17 hours to drive. However, our preferred route is slightly longer, at 17 hours and 45 minutes and 1,200 miles.
Take I-90 south to Exit 17, then follow I-65 south to Nashville, Tennessee. Merge with I-24, head southeast, and use Exit 185A to join I-75. Go south 390 miles to Exit 435, then drive east on I-10 to its conclusion. Merge onto I-95, head south, use Exit 260 C-B-A, then take I-4 southwest to Orlando, Florida.
There is an incredible range of attractions along the route, without including Cincinnati, which we mentioned above. These include:
Gary, Indiana; Indianapolis, Indiana; Louisville, Kentucky; Bardstown, Kentucky; Jim Beam Distillery; Fort Knox; Mammoth Cave National Park; Bowling Green, Kentucky; Historic Mansker’s Station; Nashville, Tennessee; Lynchburg, Tennessee; Chattanooga, Tennessee; Nantahala National Forest; Atlanta, Georgia; Jackson, Georgia; Macon, Georgia; Osceola National Forest & Wildlife Management Area; Jacksonville, Florida; St. Augustine, Florida; and Daytona Beach, Florida.
Our guide to the best road trip from Chicago to Florida covers all these, and our preferred route in great detail.
Road Trip From Chicago To Los Angeles (Best All-Round)
A road trip from Chicago to Los Angeles, California, may seem very similar to a Chicago to Florida road trip; a great way to swap “Chi-Town’s” ice and snow for warmer pastures. While that sentiment is a big part of the appeal, there are also a few unique selling points which differentiate the two Chicago road trips.
Firstly, we suggest driving a very specific route to Los Angeles: Historic Route 66, perhaps the most famous road in the United States. A Route 66 road trip is bursting with historical and cultural attractions and landmarks from start to finish. It gives you the chance to soak in a diverse array of the nation’s landscapes, while enjoying a trip that is equal parts entertaining and educational.
Next up is something you may not expect to find when heading this far south: ski resorts. Arizona surprisingly has several great ski resorts, most of which are conveniently located on I-40/Route 66, primarily around Flagstaff. Cross-country skiing enthusiasts can also visit Arizona Nordic Village, located west of Flagstaff, which offers an array of groomed Nordic ski and snowshoe trails.
The state's leading ski destination, Arizona Snowbowl, is 15 miles north of Flagstaff. Nestled in the San Francisco Peaks, it boasts roughly 55 ski runs, a vertical drop of 2,300 feet, modern lift systems, and terrain catering to skiers of all skill levels, from beginners to advanced. On clear days, guests can see stunning vistas that extend all the way to the Grand Canyon.
For families and those at an intermediate skill level, Sunrise Park Resort in the White Mountains offers another fantastic choice. Requiring a brief detour south near the Arizona–New Mexico border, it stands as the state’s largest ski resort, featuring around 66 trails distributed across three mountains. This resort is celebrated for its laid-back vibe, diverse terrain, and additional winter activities such as tubing and sleigh rides.
The final unique attraction on a Chicago to Los Angeles winter road trip is found just past Flagstaff, in Williams, Arizona. Home to the Grand Canyon Railway Depot, which offers memorable train rides to the Grand Canyon, they offer a magical Polar Express experience in November and December.
The 90-minute evening journey takes passengers through the winter landscape to a festive “North Pole,” where Santa Claus and his reindeer await. Along the way, passengers can enjoy hot chocolate, cookies, Christmas music, and a reading of The Polar Express. Santa boards the train to greet children and present each with a special gift.
This is all before arriving in Los Angeles. Beyond its warm weather washing your wintry woes away, it has a surprising amount to offer around Christmas for such a sun-kissed city.
The Hollywood Christmas Parade runs down Hollywood Boulevard on the first Sunday after Thanksgiving. Universal Studios Hollywood showcases Grinchmas and festive events in The Wizarding World of Harry Potter. L.A. Zoo Lights turns the zoo into a stunning exhibition of illuminated animal figures. The Enchanted Forest of Light at Descanso Gardens offers a mile-long pathway featuring interactive light displays throughout the gardens.
Torrance’s permanent Bavarian-themed Alpine Village has an annual Christmas fair, showcasing German beers, traditional foods, glühwein, charming stalls featuring handmade crafts, lively music, entertainment, and visits from Santa Claus. Huntington Beach has a German Christmas market dubbed the “best Christmas market in California” and a Swedish Christmas Fair that sells festive gifts, clothes, handcrafted goods, and traditional Swedish foods and drinks.
Santa Monica Pier has an 80-foot-tall snowman, a surfing Santa, a Christmas puppet show at Bob Baker’s Marionettes, ice skating, and beautiful lights and decorations including reindeer and icicles. Visitors can even take in the Christmas decorations and lights on Rodeo Drive and in Beverly Hills, try Here & Now bar’s seasonal cocktail menu including highlights like the Gin-gle All The Way, partake in outdoor ice skating at Pershing Square, or explore festive displays in Griffith Park.
The Best Route For A Winter Road Trip From Chicago To Los Angeles, California
The best route for a winter road trip from Chicago to Los Angeles is Historic Route 66. However, as you can’t drive it in its entirety anymore, you will need a little help. Our guide to a Route 66 road trip from Chicago to Los Angeles, California, will explain precisely how to follow the original route as closely as possible, provide vital information, such as how long it takes, and detail all the fantastic things to do and see along the way.
We also have a helpful guide on where to stay in Los Angeles when you arrive.
Best Hidden Gem Day Trip Destinations
The following three hidden gems are both a short drive from the Windy City, located around an hour away from Chicago, making them ideal choices for those seeking a quick, 1-day trip that doesn't require overnight accommodation, such as families with kids.
Kenosha, Wisconsin
Kenosha serves as a delightful winter destination along the shores of Lake Michigan, offering a charming waterfront alongside a range of museums, historic sites, and outdoor recreational opportunities. Guests can visit the Kenosha Public Museum, Dinosaur Discovery Museum, and Civil War Museum, take a leisurely walk by the lakefront and harbor, or partake in winter sports such as ice skating, snowshoeing, and cross-country skiing.
Seasonal festivities in Kenosha include the annual Snow Daze Festival, enhance the winter experience.
Additionally, Wilmot Mountain, located nearby, offers panoramic views and options for skiing, snowboarding, and tubing, while the downtown area of Kenosha features local shops, dining spots, and breweries. Geneva Lake, a popular resort town during the winter months, is slightly further afield and offers skiing, snowboarding, and ice fishing, as well as the fabulous Yerkes Observatory.
From Chicago, simply head north on I-94 until you reach Kenosha. The distance from Chicago is approximately 58 miles (93 km), with a usual driving duration of about 1 to 1¼ hours.
Starved Rock State Park
Starved Rock State Park is widely recognized as one of the most picturesque natural sites in Illinois. Located along the Illinois River, 94 miles southwest of Chicago, Starved Rock features striking sandstone bluffs, deep canyons, waterfalls, and over 13 miles of hiking trails.
Visitors can discover well-known locations such as Starved Rock, French Canyon, and Wildcat Canyon, and during winter, the park showcases frozen canyons and waterfalls and provides chances for ice climbing.
From Chicago travel southwest on I-55 toward Pontiac, then switch to I-80 west heading for Ottawa. Take the exit for IL-178 south toward Utica and follow the directions leading to Starved Rock State Park.
Indiana Dunes National Park
Indiana Dunes National Park is the third-newest and fifth-smallest national park in the U.S., covering 15,000 acres. It features 25 miles of dunes along Lake Michigan and over fifty miles of trails, and offers a variety of recreational activities such as hiking, swimming, and birdwatching. While not a prime location for wildlife, it is still popular with nature lovers as it is home to rare plant species like American columbo and Mead’s milkweed, as well as animals like bald eagles and Indiana bats.
During winter, the snow-blanketed dunes, icy shorelines along Lake Michigan, and tranquil trails are ideal for hiking, photography, and observing wildlife.
From Chicago use I-90/I-94 heading east toward Indiana, and then continue on I-94 to Exit 26 for IN-49 north, which leads directly to the park’s Visitor Center; its approximately a 1-hour drive from Chicago.
Best Weekend Trips
If you want something between an epic road trip and a one-day adventure, the Midwest is bursting with ideal winter road trip destinations, boasting everything from charming towns to frozen waterfalls. The following suggestions are all a three hour drive from Chicago and take at least five hours for a round trip. This means they are slightly too far for a day trip, but perfect for a fun weekend break.
Grand Rapids, Michigan
Grand Rapids serves as a delightful winter getaway, featuring a vibrant downtown alongside numerous outdoor activities. Guests can engage in ice skating at Rosa Parks Circle, discover the city’s assortment of museums, or dine at various restaurants, while beer lovers can sample local craft brews. Other winter pursuits include hiking trails, snowshoeing, and fat-tire biking.
The yearly World of Winter festival showcases bright and interactive art displays in the downtown area, while the nearby Cannonsburg Ski Area provides options for skiing, snowboarding, and tubing.
On the way to Grand Rapids you also pass near Saugatuck, Michigan. Known for its artsy atmosphere and winter activities, it could make for a great additional stop if you wanted to extend your trip.
From Chicago, head east on I-90/I-94 towards Indiana, then proceed on I-94 through Michigan toward Benton Harbor. Take I-196 north/east heading to Grand Rapids, continuing until you arrive in the city. The trip spans approximately 175 miles (280 km) and typically lasts about 2¾–3¼ hours.
Green Bay, Wisconsin
Green Bay is an excellent winter retreat, especially for those who appreciate snowy outdoor pursuits and the culture of American sports. Football aficionados can tour the iconic Lambeau Field, while the city boasts various museums, dining options, and the vibrant Titletown area. Popular winter activities include ice skating, tubing, snowshoeing, cross-country skiing, and fat biking, with Titletown being particularly favored for its skating rink and 46-foot tubing hill.
Those who want to venture further northeast into Door County will be met by remote frozen shores offering stunning views and activities like snowshoeing.
From Chicago, head north on I-94 towards Milwaukee, and then merge onto I-43 north toward Green Bay. The drive is roughly 208 miles (335 km) and typically takes about 3 to 3½ hours.
Elkhart Lake, Wisconsin
Elkhart Lake is a delightful village by the lake that transforms into a serene, snow-covered retreat during winter. Guests can partake in activities such as snowshoeing, cross-country skiing, and hiking amid the picturesque Kettle Moraine landscape. The lake's frozen surface is ideal for those who enjoy ice fishing, and the tranquil streets create an ideal setting for a restful escape.
The village boasts cozy dining spots, unique boutiques, and wellness facilities, making it an excellent choice for a weekend winter retreat. Additionally, seasonal festivities, including holiday events, enhance its charm.
From Chicago drive north on I-94, merge onto I-43, heading for Sheboygan, then follow local routes westward to reach Elkhart Lake. The total distance is about 147 miles (237 km), typically taking around 2¾–3 hours.
Wisconsin Dells, Wisconsin
Wisconsin Dells serves as a vibrant winter retreat, especially favored by families for its renowned indoor waterparks, offering a cozy refuge from the cold weather. In addition, visitors can partake in skiing, snowboarding, and snow tubing at nearby attractions like Cascade Mountain and Christmas Mountain Village. For those interested in outdoor activities, Mirror Lake State Park and Devil’s Lake State Park provide options for snowshoeing, cross-country skiing, and winter hiking. The town is also home to indoor amusement parks, arcades, restaurants, and various family-friendly attractions, ensuring that even in frigid temperatures, there’s plenty to keep everyone entertained over a winter weekend.
From Chicago follow I-90 west toward Rockford, and then follow I-90 north through Madison, the capital of Wisconsin and a vibrant college town, to reach Wisconsin Dells. The total distance is approximately 193 miles (311 km), with a travel time of about 3 to 3¼ hours under typical conditions.
Eagle Ridge Resort & Spa
Eagle Ridge Resort & Spa, also known as the Eagle Ridge Inn, is a picturesque retreat in The Galena Territory, encompassing 6,800 acres of lush woodlands and scenic countryside. It's just a short distance from the historic 19th-century town of Galena, which is known for its scenic charm and boutiques.
The resort provides a range of accommodations, including cozy rooms, villas, and homes, as well as a full-service spa, a hot tub, a heated indoor pool, dining options serving delicious food, golf courses, and extensive hiking and biking paths. During the winter months, the serene environment makes it an inviting location for a tranquil rural escape or romantic weekend, with Galena's shops, dining establishments, and historical sites nearby.
Go west on I-90 towards Rockford, then switch to US-20 west heading towards Galena. Proceed past Elizabeth and adhere to the signage directing you to Eagle Ridge Resort & Spa; the journey covers about 150 miles from Chicago, typically taking 2½–3 hours under normal conditions.
Final Thoughts On The Best Winter Road Trips From Chicago In Winter
That concludes our guide to the best road trips from Chicago in Winter. You should now have all the information you need to complete each trip yourself, including why you should go, the best route, how long it takes, and what to see along the way, while remembering that top winter destinations near Chicago also include Galena and Lake Geneva, the latter about 75 miles northwest of Chicago.
We also have a helpful guide on where to stay to begin your trip in Chicago, so we hope to have a little something for everyone, whether you want budget-friendly, sophisticated style, or Illinois' answer to Beale Street. All you have left to do is work out what to take with you and start budgeting and booking everything, then you can look forward to enjoying it all for yourself.
Remember that all travel times are influenced by traffic and winter weather conditions, and drive with caution as icy roads can be slippery. You should also ensure you check weather forecasts for your route and destination before setting off, and pack plenty of emergency essentials.
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