Known as the birthplace of the skyscraper, Chicago is home to award-winning restaurants, top sports teams and prized cultural treasures. But when you need a break from the excitement of the nation’s third largest city, there are countless getaways within easy driving distance. You can explore rural Illinois or enjoy neighboring Indiana, Wisconsin, Iowa or Michigan all within a weekend. Whether you’re planning a romantic getaway to a small-town bed-and-breakfast or a family-friendly trip to a water park resort, these nearby Midwest destinations will relieve the stress of big city life.
(Note: Some of the following activities, attractions and locations may be affected by the COVID-19 pandemic. New policies may be in place, including capacity restrictions, reservation requirements or mask mandates. Check with the Centers for Disease Control and Prevention, the U.S. Department of State and local tourism boards before traveling.)
Best Weekend Getaways from Chicago:
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Located along the picturesque Fox River on the western outskirts of Chicago lie the small towns that make up Illinois’ Fox River Valley. Stretching from the village of Antioch in the north to Ottawa – the gateway to Starved Rock State Park – in the south, this area is an ideal daytrip from the Windy City. Go biking, hiking and cross-country skiing along the 32-mile Fox River Trail or rent a kayak for paddling on the Fox River. In addition to outdoor pursuits, unique cultural attractions abound, including Broadway productions and musical events in Aurora’s historic and beautifully restored Paramount Theatre. Visitors rave about its exquisite decor and top-notch performances, applauding the Paramount for offering Broadway-caliber performances at Main Street prices. If you choose to overnight in the Fox River Valley, the Herrington Inn & Spa, which overlooks the Fox River in the small town of Geneva, would make for a romantic getaway.
New York has the Hamptons; Boston has Cape Cod. The summer playground for Chicagoans consists of eight glistening lakeshore towns dotting the coastline of southwest Michigan, collectively known as Harbor Country. Here you’ll find beaches, orchards and plenty of outdoor activities. At the southern end of Harbor Country, just over the Michigan-Indiana state line and about 70 miles from Chicago’s downtown loop, New Buffalo lures Chicagoans with its casual beach vibe and proximity. Families line up for burgers at The Stray Dog, but only adults can head up to the rooftop bar and patio. Patrons praise The Neighborhood Hotel Grand Beach for its modern design combined with cozy common areas, fire pits, ping pong tables and board games; they also appreciate the short walk to the beach and the heated pool.
Families will want to make the scenic 25-mile drive from New Buffalo north through the Harbor Country towns of Union Pier and Lakeside, past grand lakefront estates and bucolic farms, to St. Joseph, commonly called St. Joe’s. The family-friendly Silver Beach Pizza is housed in St. Joe’s former train depot, with diners saying it’s well worth what can be a half hour wait for the amazing pizza. Across the street is the restored 1910 Silver Beach Carousel, a great option for passing the time while waiting for your table if you’ve got kids along. St. Joe’s offers visitors the chance to step back in time with a beach, pedestrian-friendly downtown, boutiques and old-fashioned chocolate shops. One of St. Joe’s more unique shops is Third Coast Surf, where you can rent a surfboard and sign up for surfing or sandboarding lessons. Not expecting a surf shop in the Midwest? Visitors are often surprised when they first see Lake Michigan, known to Midwesterners as the Third Coast: It resembles an ocean more than a lake.
Located about 80 miles north of Chicago on Lake Michigan is the Brew City of Milwaukee, which boasts more than 200 breweries, museums, festivals and the Harley-Davidson Museum. As this city is home of the Milwaukee Brewers baseball team, no trip is complete without getting a taste for Milwaukee’s beer heritage. Visitors give Lakefront Brewery tours high marks for entertaining guides, extensive selection, riverfront views and its popular Beer Hall restaurant with live music on Fridays. Families will enjoy the lakefront museum campus, which includes the Discovery World science museum and Betty Brinn Children’s Museum, while culture lovers can visit the architecturally stunning Milwaukee Art Museum when the building’s “wings” open and close several times a day. Motorcycle enthusiasts will be in hog heaven at the modern steel-and-glass Harley Davidson Museum, which celebrates the machine invented in Milwaukee that’s come to symbolize the freedom of America and the open road.
Winters are harsh, so summer is one endless celebration, with a multitude of neighborhood festivals, outdoor concerts and ethnic celebrations – check out German Fest at the end of July, honoring the city’s largest immigrant group. Summer excitement reaches a crescendo at the end of June with Summerfest, the world’s largest music festival. After a day of sightseeing or revelry, a top lodging choice is Milwaukee’s stately grand dame, the historic Pfister Hotel, offering Gilded Age elegance alongside 21st-century amenities like a pool with panoramic city views and a popular top-floor cocktail bar.
South Haven is a fun-loving beach town with a population that swells in the summer – especially in August for the National Blueberry Festival, since this Michigan destination claims to be the blueberry capital of the U.S. About 110 miles from Chicago, you’ll hear a lot of Jimmy Buffett playing in the bars and restaurants of this laid-back boating town where the harbors take center stage. Kick off your visit by learning about the area’s rich Great Lakes boating history at the Michigan Maritime Museum. (Note: The museum and campus are currently under construction and slated to reopen July 2022).
Along with its seven public beaches – some of the best beaches in Michigan – and iconic red lighthouse, South Haven also has a pedestrian-friendly downtown filled with unique shops and restaurants. Climb aboard the stationary Idler Riverboat, where casual dining combines with world-class waterfront views. Clementine’s is another local favorite, as is Captain Lou’s, which serves fresh perch and live music on the weekends. For a romantic getaway, consider Inn at the Park, a bed-and-breakfast one block from Lake Michigan: Guests praise the beautiful decor and sumptuous breakfasts, using locally grown blueberries. Travelers also love Yelton Manor Boutique Hotel for its manicured gardens, spectacular sunset views of Lake Michigan and proximity to town.
Looking for an active adventure? Only about 100 miles southwest of Chicago, this wilderness known for its deep sandstone canyons and waterfalls is perfect for daytrips – though with 18 canyons to hike, there’s plenty to keep you busy for a whole weekend. Walking along bluffs that lead to scenic lookouts over the Illinois River makes visitors feel immediately transported out of the flat Midwest heartland. Starving Rock State Park can be a weekend escape any time of year, but spectacular fall foliage makes it a favorite getaway for autumn in particular.
Starved Rock State Park has its own historic lodge with top-notch cabins, but kids may prefer going across the street to the family-friendly Grizzly Jack’s Grand Bear Resort, with its massive water park, mini-golf, indoor arcade and Northwoods decor. Camp Aramoni is a great choice for a romantic getaway, with luxury glamping in safari tents outfitted with hardwood floors, air conditioning and heating, and full bathrooms with showers. Nightly stays include chef-prepared farm-to-table dinner and breakfast using produce grown in on-site gardens that guests are welcome to visit. End your day at Camp Aramoni’s repurposed Airstream trailer that’s been turned into a bar.
Looking for high-adrenaline family fun? About 35 miles north of Chicago, just south of the Wisconsin border, lies the village of Gurnee, home to the Six Flags Great America amusement park. Thrill-seekers will love the 17 heart-stopping roller coasters, but dozens of other rides mean you’ll also find plenty for younger kids. Reluctant riders who want to steer away from high-speed coasters and intense drop rides can also enjoy the park’s shows and other entertainment. On a hot day, plunge down steep waterslides or splash around the wave pool at Six Flags’ 20-acre Hurricane Harbor water park. When it gets cold, a favorite local pastime is a stroll around Gurnee Mills, an outlet mall housing more than 170 stores.
Continue your Gurnee adventure with a stay at the Northwoods-themed Great Wolf Lodge, the most family-friendly hotel option in this destination. Guests say this water park resort makes even adults feel like kids again and rave about the endless family-friendly amenities, which include bowling, mini-golf, a ropes course and arcade – and, of course, the massive water park.
Since 1938 Wilmot Mountain has drawn visitors seeking wintertime leisure in the Midwest. About 25 miles northwest of Gurnee, just over Wisconsin’s state line, Wilmot Mountain Ski Resort makes for a great cold-weather attraction when Six Flags is closed. The big-name Vail Resorts purchased Wisconsin’s little ski hill in 2016 and rolled out plenty of upgrades, from improving terrain parks and snowmaking to adding chairlifts and elevating the dining experience. Enjoy winter sports over a variety of terrain at this alpine destination, whether you’re looking to ski, snowboard or snow tube. There’s no on-site lodging, but Gurnee’s Great Wolf Lodge is still a relatively short drive away.
This Wisconsin resort city makes for an idyllic weekend or daytrip. About 70 miles northwest of Chicago, Lake Geneva is described as the “Newport of the Midwest” because of its opulent lakefront mansions. You can come surprisingly close to these impressive residences by ambling along the Geneva Lakeshore Path, a rustic 25-mile walkway that encircles the lake, cutting right through the backyards of magnificent mansions and second homes. Amazingly, there aren’t any “No Trespassing” signs to scare away walkers; just beware the path is not intended for strollers, roller blades or bikes, since you’ll have to maneuver past steps and other obstructions. When you’ve finished your stroll, a lakefront cruise is another fun way to enjoy this city. Visitors give Lake Geneva Cruise Line excellent reviews for being informative and entertaining. A variety of daily cruises are offered, but one of the most unique is the mail delivery cruise. As Lake Geneva is one of the few remaining places in the U.S. where mail is still delivered by boat, about 75 lakefront homes receive their U.S. mail service via boat – and passengers are invited to come along for the ride.
Consider a stay at the Abbey Resort, the only full-service resort directly on the shores of Lake Geneva, during a summer visit. This lodging option offers complimentary adult and kids bikes, ideal for use on the Lake Geneva Bike Path, which connects many of the resort town’s amenities. The trail has five unique, color-coded segments, making it easy to find your way around. Things quiet down a bit in the fall, when the vibrant autumn colors set a serene scene.
Tourists descend on Lake Geneva’s charming downtown shops and restaurants in the summer, but the town has plenty to do year-round. One of the best winter attractions in this city is the Grand Geneva Resort & Spa, whose modest ski hill has three chair lifts, 20 runs and a terrain park. Grand Geneva Resort also has access to 5 miles of wooded trails for cross-country skiing and offers a limited number of ski rentals. Kids will love overnighting at Grand Geneva’s family-friendly Timber Ridge Lodge and Waterpark for indoor aquatic fun while adults relax at the spa. Time your winter visit to coincide with Lake Geneva’s Winterfest so you can observe one of the country’s biggest snow sculpting competitions.
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Turkey Run State Park is the crown jewel of Parke County and one of the Hoosier State’s oldest and most popular state parks. Eleven trails ranging from a half-mile to 2 miles wind through rugged ravines surrounded by the park’s signature sandstone cliffs – providing Midwest hiking at its best. Turkey Run Inn, a popular lodging option situated within the park, is appreciated by guests for its friendly staff and cozy atmosphere. There’s an indoor pool and plenty of public sitting areas with fireplaces, whether you want to play a board game or read a book. Choose from rooms within the historic lodge or the adjacent cabins. Even if you don’t stay at Turkey Run Inn, you can still enjoy its restaurant, The Narrows, which diners recommend for the catfish dinners as well as the fried biscuits and hot apple butter.
Most have never heard of this tiny town 140 miles north of Chicago, but Kohler is home to Wisconsin’s only hotel to receive AAA’s highest five diamond rating. The American Club Resort Hotel – part of the Destination Kohler Resort – is still owned by the family who built it: The Kohlers are best known for high-end plumbing and bathroom fixtures. The American Club’s luxurious Kohler Waters Spa specializes in hydrotherapy, giving guests a chance to experience all the legendary bath and shower products Kohler is known for. Should you want to recreate that luxury spa experience in your own bathroom at home, a few steps away from the spa is the sleek, multistory Kohler Design Center, filled with model bathrooms and design ideas sure to give most of us bathroom envy. Amid your self-care ventures in Kohler, enjoy plenty of outdoor activities. Fall brings a boisterous bounty of color to this rural area, while winter experiences at The American Club include ice skating, curling, snowshoeing and cross-country skiing across miles of trails that wind through woodlands and meadows.
Ten miles from American Club Resort Hotel sits the Kohler-owned Whistling Straits Golf Course, which some golfers describe as reminiscent of the legendary Pebble Beach. Whistling Straits ranks among the top public courses in the country and has hosted 2021’s Ryder Cup and three PGA championships. The two Pete Dye-designed courses at Whistling Strait offer stunning views of Lake Michigan or rolling green hills. Golfers will feel transported to Ireland’s tranquil grassland or its rugged coastline as this course winds its way along the bluffs and dunes overlooking Lake Michigan.
It’s easy to see why Saugatuck is one of the best places to visit in Michigan. Nicknamed the Art Coast of Michigan, this hip resort town about 130 miles from Chicago is stocked with galleries, boutiques, excellent dining and beaches. Perhaps surprisingly for a town of less than a thousand people, Saugatuck is also known for its lively nightlife and for being an LGBTQ-friendly destination. Take a seat at the counter of the century-old Saugatuck Drug Store and you’ll get a taste of the town’s more traditional side, served up via a classic malt or ice cream soda. Visitors are in for another nostalgia trip when you board the chain ferry: Operating since 1838, it claims to be the only remaining chain-driven ferry in the U.S., transporting passengers across the Kalamazoo River between downtown and Oval Beach. After disembarking on Oval Beach, active beachgoers love climbing the 302 steps to the top of Mount Baldhead – known as Mt. Baldy – and getting a bird’s eye view of the area. Overlooking Lake Michigan, Saugatuck’s Lake Shore Resort is applauded by patrons for its breathtaking views and many complimentary amenities, including bikes, kayaks, yoga and a heated pool.
About 190 miles northwest of Chicago is the ultimate Midwest family getaway: the “Waterpark Capital of the World.” If traveling with kids to Wisconsin Dells, stay at one of the immensely popular water park resorts, such as the flagship property of Great Wolf Lodge. Guests appreciate the original Great Wolf Lodge for its signature Northwoods decor, endless amenities and the feeling of being in a tropical paradise year-round.
Beyond its myriad indoor and outdoor water parks, Wisconsin Dells boasts a wide variety of kid-friendly entertainment options, from zip lines to animal parks. Catch a performance at the Palace Theater, which offers everything from concerts to comedy shows to children’s plays and Broadway-style productions; some theatergoers swear there isn’t a bad seat in the house. More fun for the whole family can be found at the Rick Wilcox Magic Theater shows, which wow audiences with both humor and illusions that keep you guessing. Want to escape the indoor attractions for a natural one? Head over to Mirror Lake State Park for a scenic hike along a tranquil, no-wake lake set among sandstone bluffs. Pontoon boats, kayaks and stand-up paddleboards are available to rent here.
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Billing itself as the covered bridge capital of the world, Parke County, Indiana – about 160 miles south of Chicago – maintains 31 of these Instagram-worthy symbols of a bygone era. Visitors descend on the area every October for the Parke County Covered Bridges Festival, Indiana’s largest annual festival. The popular biker bar Thirty Six Saloon is a family-friendly roadhouse in Rockville, the town where the popular fall festival is headquartered. Kids may be mesmerized by Thirty Six Saloon’s vast collection of taxidermy, with animals from the region mounted throughout the restaurant. Diners compliment everything from the burgers and ribs to the fish sandwiches and unique decor. Another popular culinary option is the tenderloin sandwich at the Mecca Tavern in Mecca. Parke County’s oldest tavern overlooks Mecca’s historic schoolhouse and covered bridge. Locals and visitors alike say stopping by Wheelhouse Donuts is another must: This adorable bakery lets you design your own doughnut.
About 150 miles west of Chicago, in the northwest corner of Illinois, the charming Mississippi River town of Galena regularly makes national lists of best small towns. Its elegant dining, historic sites, quaint shops and bounty of bed-and-breakfasts make Galena an excellent choice for a romantic getaway. Because the glaciers that flattened most of the Midwest didn’t reach here, the pastoral farmland is hillier, perfect for a Sunday drive. The 19th-century buildings in this old mining town have been painstakingly preserved, with 85% on the National Register of Historic Places – including the Ulysses S. Grant Home State Historic Site, a residence gifted to the nation’s soon-to-be 18th president in 1865 by Galena citizens.
One memorable overnight option would be a stay at the former county jailhouse – now the luxurious Jail Hill Inn. For a more romantic atmosphere, the Goldmoor Inn is beloved by guests for its stunning views of the Mississippi River, in-room fireplaces and two-person hot tubs. Galena is gorgeous any time of year, with plenty of travelers drawn here during harvest time for apple and pumpkin picking amid the abundance of fall colors. Winter brings its own charm with shops along Main Street resembling something out of a Norman Rockwell painting. The small town also houses a popular old-school ski resort: Guests say Chestnut Mountain Resort’s decor and amenities are a bit dated, but its 19 ski runs provide scenic views of the river below.
Head 170 hundred miles west of Chicago, cross the Mississippi River, and you’ll be in Dubuque, Iowa. Get a feel for how important the river is here by visiting the National Mississippi River Museum and Aquarium, or take a ride on a riverboat for another scenic way to experience the Mississippi. Visitors give the Celebration Belle river cruise high marks for being fun, informative and affordable. Another must-see attraction is Fenelon Place Elevator, a steep funicular railway providing fabulous views of the surrounding area. History lives on at the elegant Hotel Julien Dubuque, which guests compliment for its charm and friendly service. Baseball fans will want to make the additional 25-mile drive west to the town of Dyersville to explore the Field of Dreams, one of the best tourist attractions in the U.S. Play on the baseball diamond and tour the home where the movie “Field of Dreams” was filmed.
About 230 miles northeast of Chicago, Ann Arbor is a quintessential college town, filled with independent bookstores and great live music. University of Michigan alumni are a proud bunch – and not just on game days, when they march clad in blue and yellow to what’s known as The Big House, the largest sports stadium in the country. Ann Arbor also scores an A when it comes to food and culture. The world-class University of Michigan Museum of Art displays works by Picasso, Monet and Warhol. A few blocks away on Liberty Street is the edgier public art canvas known as Graffiti Alley, just steps from the historic Michigan Theater and State Theatre, which delight visitors with film screenings, festivals and live music throughout the year (as long as you follow the theaters’ COVID-19 regulations). A pastrami sandwich at Zingerman’s Deli is a 40-year tradition, but if you’re hungry for a more budget-friendly option head to Frita Batidos and take a seat at one of the communal tables for Cuban-inspired street food. Hit the books at Literati, a beloved independent bookstore. A fun hotel choice is Graduate Ann Arbor with its University of Michigan-themed decor.
About 140 miles northwest of Chicago, Madison is more than just a cool college town: It’s also the capital of Wisconsin. No trip here is complete without visiting the beautiful, white-domed Wisconsin state Capitol building; free tours are given throughout the day. Madison’s isthmus location on a narrow strip of land between two lakes means waterfront biking and hiking trails abound. Foodies will also get their fill at Fromagination, a cheese lover’s paradise popular with Wisconsin cheeseheads as well as out-of-town visitors. Located across from the Capitol, this delightful cheese shop features dozens of one-of-a-kind artisanal Wisconsin varieties. If visiting Madison between April and November, head to Capitol Square on Saturday morning for the Dane County Farmers’ Market, the country’s largest producer-only farmers market. The 72-room, collegiate-themed Graduate Madison hotel is an easy walk to campus, dining, shopping and nightlife. Decorated in the University of Wisconsin colors of red and white, the hotel gets high marks from guests for its nostalgic decor and artwork, including collages of political buttons, a nod to the town’s legacy of social activism.
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Those who have more time could leave the bright lights of Chicago for the serenity of Michigan’s Traverse City to visit Sleeping Bear Dunes National Lakeshore and its 64 miles of pristine coastline and mountains of sand dunes. Traverse City is about 300 miles from Chicago, but you’ll be rewarded with breathtaking beaches, peaceful hikes, top-notch cuisine and the added perk of what’s considered the “Napa Valley of the Midwest”: the 24 wineries of the Leelanau Peninsula Wine Trail. When the temperatures drop and the snow arrives, a great winter weekend getaway involves cross-country skiing in Pere Marquette State Forest or the Leelanau Trail, which runs from Traverse City to Suttons Bay. Traverse City and northern Michigan are also filled with summer lake resorts: Top options include Lake Leelanau’s Fountain Point Resort, the upscale Homestead Resort and the all-inclusive White Birch Lodge in nearby Elk Rapids. With White Birch known for its water sports program, teens and tweens will love water-skiing, tubing and ending the day swapping adventures with new friends around a beach bonfire.
Best known as the location of the Kentucky Derby, Louisville sits 300 miles south of Chicago and has a whole lot more going on than just horse racing. About 95 percent of the world’s bourbon is made in Kentucky; for a taste of the state’s signature liquor, head to downtown Louisville’s historic Whiskey Row. Here you’ll find distilleries, unique restaurants and live music. Topping any sports lover’s itinerary should be a visit to the Louisville Slugger Museum and the Muhammad Ali Center, which visitors applaud for honoring the boxer’s life, faith and humanitarian service. Art lovers would enjoy staying at the 21C Museum Hotel Louisville, which houses its own contemporary art museum.
About 300 miles southwest of Chicago, just over the Illinois border along the Mississippi River, sits this Missouri city. St. Louis is well worth a weekend trip for its plethora of restaurants, breweries and cultural treasures. Nicknamed the Gateway City for its iconic Gateway Arch, St. Louis gives travelers the chance to take a tram ride to the top of this engineering marvel. After getting a bird’s-eye view of the surrounding area, head over to the nearly 1,300-acre Forest Park, site of the 1904 World’s Fair, now home to the Saint Louis Zoo and several museums. Music lovers can’t miss the National Blues Museum, which sings the praises of that melancholy American music form. If you find yourself in need of more music lessons, make your way to the Scott Joplin House State Historic Site, where the king of Ragtime lived. After a busy day sightseeing, Drury Plaza Hotel St. Louis at the Arch makes a good place to rest. Guests rave about the unbeatable value of the hotel’s free breakfast and happy hour with complimentary hot food and drinks.
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The Twin Cities of Minneapolis − St. Paul straddle the Mississippi River, about 450 miles northwest of Chicago, with Minneapolis as Minnesota’s most populous city and St. Paul as the state capital. Minneapolis is known as a city of lakes, but visitors also like to walk along the riverfront, taking in the magnificent Mississippi. Groundbreaking pop musician Prince was born in Minneapolis; now his legacy lives on at Paisley Park, a sprawling complex in the nearby town of Chanhassen that was once the artist’s studio and home. Millions more travel here to visit the largest mall in the Western hemisphere, Mall of America, located in the nearby suburb of Bloomington. As much an entertainment complex as a retail center, this mall houses the indoor amusement park Nickelodeon Universe, a highlight for kids. Guests give Minneapolis’ Hewing Hotel stellar reviews for its character, charm and stunning views from the rooftop lounge.