Celebrate Winter's Last Hurrah With These 4 Midwest Getaways

Snow is never a guarantee for Midwesterners seeking a late-season winter getaway, but the Great Lakes Region may continue to look like winter past the March 1 start of meteorological spring, according to some new spring forecasts.

Here are four getaways worth considering, one each in Illinois, Michigan, Wisconsin and Minnesota. Or, a person could take take in chill experiences in a four-state road trip celebrating winter’s last hurrah.

Float The Chicago River In A Hot Tub

Don’t count on snow in Illinois, though it could happen. But it doesn’t matter. Here are some ideas for a chill weekend getaway to Chicago, one of America’s great cities, that work with or without snow.

One example: Floating down the Chicago River in a hot tub boat from the Chicago Boat Rental Company. The 800-pound capacity boat cruises at a leisurely speed of 1 mph through the heart of the Chicago cityscape, heading west toward Michigan Avenue or west toward Wells Street. Be aware that if the temperature dips below 20 degrees Fahrenheit, the boats may not run. Check availability.

Another way to embrace the chill is to grab a drink or dinner at one of Chicago’s cozy winter rooftops — outdoor dining options with fire pits and heated igloos.

Chicago is also known for its blues clubs. A couple of the best downtown are Buddy Guy’s Legends in the Loop and Blue Chicago in River North, both known for attracting renowned blues musicians. Chicago’s downtown also has a bustling theater district.

There are plenty of museums to explore. The lakefront Museum Campus is home to the acclaimed Field Museum, Adler Planetarium and the Shedd Aquarium. Others nearby are the Art Institute of Chicago, one of the country’s oldest and largest art museums, and the Griffin Museum of Science and Industry.

Shopping along the Magnificent Mile is always an option, too.

The Loop or River North are the best places to stay because they offer easy access to major tourist attractions and public transportation connections.

Where to base your stay depends on what you’re ofter. The West Loop is best for foodies, Lincoln Park is best for families and Wicker Park has a trendy vibe, according to Chicago tourism sites.

Explore Up North In Michigan

Northern Michigan is a good place for winter sports enthusiasts to plan a getaway, and the state is one of those that could see some late-winter snow, according to an AccuWeather spring 2025 forecast.

Boyne Mountain Resort has decent snowpack right now, offering endless fun, whether skiing down a mountain slope, snowshoeing or giving ice fishing a whirl. The 1,200-foot-long, 118-foot-high SkyBridge Michigan, the world’s longest timber-lowered suspension bridge, dazzles all winter long with more than 200,000 twinkling lights.

After a stroll across the bridge, warm up by a cozy fire pit, treat yourself to something from a resort food truck or head inside the Eagle’s Nest for steaming cup of cocoa before heading back to the base.

Back at the resort, the Avalanche Bay Indoor Waterpark offers endless fun for the kids — adults, too. There’s also an on-site spa, Alpine Oasis.

Another option is Traverse City, which sits in the purlicue between the thumb and forefinger on Michigan’s famous “mitten.” The quintessential “Up North” town has a vibrant restaurant scene with local and farm-to-table options and a growing list of microbreweries, cideries and distilleries.

This town of about 15,700 people has so much going for it in natural beauty and attractions that The Wall Street Journal included it along with only two other places in the United States in the “10 Best Places to Go In 2025.” (The other U.S. locations on a global list that includes Morocco and Amsterdam are Maui, Hawaii, and Macon, Georgia.)

Winter sports opportunities in the Traverse City area include skiing at Crystal Mountain Resort in nearby Benzie County, or at the smaller ski areas such as Mt. Holiday and Hickory Hills, which are located in Traverse City.

Timberlee Hills, just north of Traverse City, is Michigan’s largest snow tubing hill, and there are also good runs at Mt. Holiday.

Go Snow-Kiting In Wisconsin

For something completely different, book a kiteboarding lesson with Kite Riders in Fitchburg, Wisconsin, which is located on the southern outskirts of Madison.

Kiteboarding, for the uninitiated, uses a kite and board to glide across water, snow or sand. The rider is pulled by the kite, which is powered by the wind. Also called kitesurfing, it’s easier to learn on snow and ice-covered lakes than in the water, according to Kite Riders.

Madison is a great outdoor city in cold weather. There are still a few Frozen Festivals on frozen lakes, snow sports, fat bike races, and cozy getaways at off-the-beaten-path inns.

Madison has a creative culinary scene. It’s also known as one of the 5 Best Drinking Cities in the World, in large part because of a craft beverage scene that began with breweries but has expanded to include wineries, cideries and distilleries that create well-regarded grain- or grape-to-glass drinks. Bars throughout the city take handcrafted approaches in the creation of innovative cocktails that aren’t found anywhere else.

The city also has a vibrant arts culture with a variety of free museums and galleries.

Settle Into This Minnesota Gem

Winona, a picturesque college town nestled on the banks of the Mississippi River and limestone bluffs of southern Minnesota, is a hidden gem. And it’s easy to get to via Amtrak’s newish Borealis route, connecting Winona to the Twin Cities and Chicago.

The home of Winona State University has a permanent population of about 26,000 and offers a pleasing blend of natural beauty, cultural richness and historic charm. The Mississippi brought great wealth to Winona, established in 1851, and its homes and business are of an opulent style that isn’t common in Minnesota.

Winona is known as the “stained-glass capital” of the United States because of the number of homes and businesses with stained-glass windows from Tiffany and other studios catering to the wealthy class. Downtown Winona has more than 100 sites on the National Register of Historic Places.

The downtown is alive with shops offering unique gifts, a variety of places and things to eat, and live music. Just outside of downtown, the Minnesota Marine Art Museum features great art inspired by water, from historic exhibitions to contemporary art work, and pushes the boundaries of what marine art can be.

Winona has multiple city parks, including Garvin Heights, which offers spectacular views of the Mississippi, and Sugar Loaf Park, where Winona’s most iconic landmark, an 85-foot rock formation known as the Sugar Loaf.

The border town is central to five state parks, three in Minnesota and two in neighboring Wisconsin. As well as two national wildlife and fish refuges: Upper Mississippi River National Wildlife and Fish Refuge and Trempealeau National Refuge.

Those public spaces make Winona a year-round playground with opportunities including skiing, snowshoeing, ice skating and ice climbing. Take note: Winona’s ice-climbing hills were still open last weekend for an ice festival despite warmer-than-normal temperatures.

Winona has plenty of places to stay, ranging from the grandeur of a restored riverfront mansion to a low-cost hotel with a swimming pool where the kids can splash.