While packed with great restaurants, sporting events, improv performances, and other fun things to do, sometimes you just need a break from a city as cool as Chicago. Luckily, numerous amazing places within a few hours’ drive make for an incredible weekend getaway. Small towns, national and state parks, and waterside destinations where you can live your best lake life await when you venture out of the Second City. So pack your bags for a midwestern-style endeavor—the deep-dish pizza will be waiting for you when you return.
Here are 7 incredible weekend getaways from Chicago.
For National Park Seekers: Indiana Dunes National Park, Indiana
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A national park located less than an hour’s drive from Chicago? Yes, please. Indiana Dunes National Park, on the southern edge of Lake Michigan, is an excellent choice for a weekend getaway for so many reasons, but especially because it’s so close to the Windy City. Speaking of wind, that’s precisely what helped shape the 15 miles of Indiana’s dune-filled shoreline behind the park’s namesake (that, and the waves). With more than 50 miles of trails weaving their way through 16,000 acres of sandy dunes, wetlands, forests, and prairies, visitors will get a multifaceted experience while exploring the park. A great, all-around route to try is the 6.8-mile Glenwood Dunes trail. The park is also a playground for various other activities, including fishing, camping, swimming, horseback riding, and stargazing, to name a few. This is a fantastic option for those who don’t have access to a car, as the South Shore Railway stops at the park.
For City Swappers: Milwaukee, Wisconsin
Sometimes you just want a change of scenery, but still want the city atmosphere. For those looking to delve into a different urban landscape for the weekend, Milwaukee offers the perfect city swap, particularly if you love breweries and cultural activities. At only an hour and 45 minutes from Chicago, you won’t have to spend too much of your few days away in the car, and can dedicate more time exploring. It’s a city of several nicknames, including ‘Brew City’ for its abundant craft breweries, and the ‘City of Festivals’ due to its full line-up of cultural events throughout the year, ideal for planning your trip around.
Don’t leave without snacking on some cheese curds, an iconic appetizer the state gets creative with (think: pancake-battered or fried!). More than 40 local breweries make up the brew trail, so it’s a beer lover’s haven. Stop into Sprecher Brewery, the city’s original craft brewery. Hop over to the well-known Lakefront Brewery for tried and true classics and events from live music to bingo, or pop into Eagle Park Brewing and sample their unique Milkshake IPA for a little something different. In between all that eating and drinking, wander the city on an art walk, led by a free public mural map of downtown.
For Lake Lovers: Elkhart Lake, Wisconsin
Treat yourself to a laid-back lake weekend in gorgeous Elkhart Lake, where the water is impossibly clear. At just under 3 hours from Chicago, it’s doable for a weekend getaway of nature exploration, dining, and shopping. The picturesque village positions you for heaps of outdoor activities, whether you’re into cycling, hiking, paddling, or golfing. One of the top attractions is the nearby Road America, a famous racetrack hosting NASCAR events. If that’s not really your speed, rent a boat or kayak on the lake with Elkhart Watersports. Birders should bring their binoculars and head to the Sheboygan Marsh Wildlife Area to spot species such as waterfowl and Blue Herons. With everything from cafes to elevated farm-to-table eateries, there are plenty of restaurants to try in Elkhart Lake, but make sure to save room for ice cream at Gessert’s Ice Cream and Confectionery, one of the oldest ice cream parlours in the country.
For Those On a Budget: Starved Rock State Park, Illinois
Less than 2 hours from downtown Chicago is a whole other world, one filled with waterfalls, to boot. Starved Rock State Park is ideal for nature lovers looking to check out the glacier-carved canyons, cascades, and wildlife. With so many outdoor activities to enjoy, you won’t break the bank either. There are 13 miles of trails throughout the park, where you can take in the bluffs, canyons, and seasonal waterfalls (spring is the best for more robust cascades). For shorter treks, try French Canyon, clocking in at .8-miles, and for a longer jaunt, you can hike past French, tacking on Wildcat and LaSalle Canyons for a total of four miles. Keep an eye out for bald eagles as they’re known to be spotted in the park. In between adventures, the city of Ottawa has a range of spots to grab a bite. The Lone Buffalo by Tangled Roots Brewing slings beers and delicious pub fare, or head to Walk-up Station, a popular food truck hub for cheap eats.
For Families: Lake Geneva, Wisconsin
An hour and a half northeast of Chicago is a destination filled with museums, parks, a theater, and a zoo, waiting to entertain the family. Lake Geneva is loaded with fun things to do lakeside, of course, but the resort city has a ton of unique kid-friendly options too, from an indoor waterpark to a drive-through safari. Grab tickets to the Dancing Horses Theatre or the Tristan Crist Magic Theatre for an evening of unique live entertainment and magic. Get outdoors and walk the Lake Geneva Shore Path, putt-putt some golf balls at Paradise Miniature Golf Park, or go swimming or paddling at Big Foot Beach State Park. If you’ve got some daredevils in your family, get their adrenaline going north of the city, zipping your way through the course at Lake Geneva Ziplines & Adventures on their canopy tour.
For Couples: Door County, Wisconsin
Between Green Bay and Lake Michigan is Door County, a peninsula with a whopping 300 miles of shoreline and quite a bit of romance to indulge in. Depending on where you go, it’ll take anywhere from four to four and a half hours by car to get there, but it’s well worth the effort. You’ll find a plethora of beautiful beaches, state parks, charming towns, breweries, and wineries. You can even buy tickets for a trolley tour and make a day of visiting a few different wineries. Spend some time taking in the natural attractions of Door County, from sunrise and views of the limestone ledges at Cave Point County Park, to hiking the 30 miles of trails or stargazing at Newport State Park, a designated Dark Sky Park. There are 11 historic lighthouses throughout the peninsula as well, which make for fantastic photo opportunities with an extra scenic view. If it’s a romantic sunset you’re after, head to the town of Ephriam and Peninsula State Park, where almost anywhere will give you a sunset vista for the books.
For Architecture Appreciation: Galena, Illinois
History buffs and architecture appreciators will find that the tiny town of Galena has more preserved historical buildings than not. Dating back to the 19th century, many of the structures are on the National Register of Historic Places, now housing everything from restaurants and bars to antique and other local shops. Tour the ornate Belvedere Mansion & Gardens, built in 1857, and check out the Old Market House, which functioned as the city market space as well as a venue for government offices, and even hosted some jail cells at one point in time. Galena is approximately 3 hours from Chicago, and depending on the time of year you take your getaway, you’re almost guaranteed to encounter an event or festival. From a haunted mansion tour to the Great Galena Balloon Race, this is a town that likes to have fun. You can even take a quirky hike with goats while sipping a root beer float.
For Spa-like Getaway: Book a Hotel or Cabin With a Jacuzzi
Whether you’re escaping the city for a few days with your partner, family, or friends, it’s nice to have a relaxing place to stay after a day of exploring. All of these weekend getaways from Chicago have accommodations with jacuzzis or hot tubs to make your trip more enjoyable. You’ll find a variety of hotels and resorts that offer hot tubs or private jacuzzis in their rooms when visiting Door County, Wisconsin. If you’re in search of a private rental, this waterfront cabin in Door County is the perfect romantic spot with unbeatable views. We found an upscale hotel with a soaking tub in Milwaukee for approximately $300 a night, and a budget-friendly hotel with a jacuzzi in Chestertown, one of the ideal spots for a home base when venturing to Indiana Dunes National Park, for approximately $85 per night.
