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The 25 best weekend getaways from Chicago

Eat, play and explore a different city (without venturing too far) by booking an amazing weekend getaway from Chicago.

Written by
Time Out Chicago editors
Allison Yates
Lindsay Eanet

Although we adore our city’s endless restaurants, museums and attractions, a change of scenery is always nice. Luckily for us, the Midwest has plenty to offer with exciting destinations only a few hours’ drive from Chicago. You can lounge in transparent waters and hike sand dunes in the “Malibu of the Midwest,” recharge at a bed and breakfast on a farm surrounded by friendly sheep, and marvel at modernist architecture in a small southern Indiana town. Many of these places are also great for a day trip or family-friendly getaway. So if you're looking to skip town, here are the best weekend getaways from Chicago.

The most unique day trips from Chicago
Historic Airbnbs near Chicago

Top weekend getaways from Chicago

Driving time from Chicago: One and a half hours

Our neighbors to the north will make you feel right at home with a seemingly endless supply of craft beer and cheese. Leave time to explore world-class cultural institutions before hopping on the Amtrak for a stress-free ride back to Chicago.

Do this: Start your day at the Milwaukee Art Museum, an architectural masterpiece along the shores of Lake Michigan that houses almost 25,000 works of art. Quite honestly, the building itself—designed by Spanish architect Santiago Calatrava—is a masterpiece in its own right, even if you don't want to splurge on admission.

Stay here: Sleep in the heart of the city when you check into the Kimpton Journeyman Hotel in Milwaukee's Third Ward. Located within walking distance of some of the city's best restaurants and bars, this beautiful boutique hotel also has a jaw-dropping rooftop terrace and rooms that are outfitted with lavish touches—perfect for a weekend away.

Kohler, WI
Photograph: Courtesy of Kohler Co.

2. Kohler, WI

Driving time from Chicago: Two hours and 15 minutes 

New York City’s Central Park architect Frederick Law Olmsted left his legacy in several places in the Midwest, including rural Wisconsin when the Kohler Company commissioned him in the early 1900s to design its new planned “industrial garden community” five miles west of Sheboyan. Today, this community of 2,000 is ideal for unplugging. 

Do this: Climb the dunes at Kohler-Andrae State Park before indulging in a spa service at Kohler Waters Spa, the only five-star spa in the Midwest. After your treatment, take advantage of the hydrotherapy circuit, a combination of cold plunges, steam room and sauna visits, and a relaxation pool.

Stay here: Splurge on one of the three Destination Kohler lodging options—a luxury resort, a lakeside inn or one of the cabins—or opt for the more moderately priced and equally exciting Velvet Sheep Farms Bed & Breakfast and Fiber Farm, just a ten minute drive north of Kohler. Embrace the slower pace of life as you get to know the farm’s beloved sheep by name and take a tour of their fiber production facilities.

Galena, IL
Photograph: Shutterstock

3. Galena, IL

Driving time from Chicago: Three hours

A charming, small Illinois town known for its history, 19th-century architecture and resorts. 

Do this: Make your way through over a hundred shops and boutiques in the downtown area. History buffs can head over to the Ulysses S. Grant Home to tour the city’s proudest attraction. Once you’ve worked up an appetite, stop into Log Cabin Steakhouse, which has been in operation since 1937. During the third weekend of June, tourists and locals alike gather for the annual Great Galena Balloon Race.

Stay here: The 6,800-acre Eagle Ridge Resort & Spa has everything you could need for a relaxing vacation. Play a round of golf on any of the four courses (there are 63 holes in total), book a spa treatment or go for a swim. The resort also offers 22 miles of hiking and biking trails, three restaurants on site and lodge-style rooms outfitted with jacuzzi bathtubs.

Indianapolis, IN
Photograph: Shutterstock

4. Indianapolis, IN

Driving time from Chicago: Three hours 

Indianapolis’s nickname may be “Naptown,” but there’s nothing sleepy about the locally-owned and farm-to-table restaurants, busting jazz clubs, bookstores and quirky gift shops found around Indy. Fanning out from Monumental Circle, the heart of downtown Indy, Indianapolis’s neighborhoods are home to a friendly and welcoming cultural scene.

Do this:  Spend your time browsing the stores, spotting art (and fairy homes!) and eating in the Fountain Square Cultural District, a diverse and LGBTQ+ friendly neighborhood just south of downtown. By day, make time for coffee and snuggles at Nine Lives Cat Cafe and at night, see a drag show at White Rabbit Cabaret or coincide your visit with swing dancing at the historic Fountain Square Theater Building, a longstanding Indy tradition. 

Stay here: Housed in the restored art-deco architecture of a former Coca Cola Bottling Plant, Indy’s Bottleworks Hotel was used by Indianapolis Public Schools for years before becoming one the city’s most unique luxury accommodations. The Bottleworks grounds also includes a food hall and several small businesses.

Madison, WI
Photograph: Courtesy of Focal Flame Photography

5. Madison, WI

Driving time from Chicago: Two and a half hours

Life in “Lake City,” as Wisconsin’s second largest city is often referred to, is undeniably beautiful—and full of year-round water-focused recreation. Between the parks and shorelines of lakes Mendota, Monona, Waubesa, Kegonsa and Wingra, visitors can expect to be in close proximity to nature and green living. In fact, wherever you live in Madison, you’re no further than 10 minutes from a park. 

Do this: Spend a day at Olbrich Park along the shores of Lake Monona. In the summer, rent a kayak, canoe, or stand-up paddle to relax on the water, and in the winter, opt for snowshoes and remind yourself there’s no bad weather—only bad clothing. After, head to Giant Jones Brewery, one of the best boozy destinations from Chicago

Stay here: One of Madison’s newest hotels is the centrally-located boutique Hotel Indigo Madison Downtown, housed in the former Mautz Company Paint Building. It’s a short walk from Giant Jones. And as far as we’ve heard, the fumes are gone.

Door County, WI
Photograph: Shutterstock

6. Door County, WI

Driving time from Chicago: Four and a half hours

The 300 miles of shoreline separating Green Bay and Lake Michigan offers vacationers a mix of natural beauty, history and locally sourced food.

Do this: Start with breakfast at Blue Horse Cafe, where you can dig into eggy breakfast sandwiches and delightful baked goods. That should provide you with the energy for hiking on the Ice Age National Scenic Trail, which features dramatic landscapes carved by glaciers 12,000 years ago.

Stay here: Historic bed and breakfast White Gull Inn is a quaint experience that dates all the way back to 1896. All of the rooms have been meticulously restored with modern amenities through the years, ensuring guests get a comfortable night’s rest. In the morning, wake up to French toast stuffed with Wisconsin cream cheese and Door County cherries, served with Door County maple syrup.


Driving time from Chicago: Four and a half hours

The renaissance of Detroit has brought with it a vibrant downtown area, oodles of amazing restaurants and bars and several destination-worthy boutique hotels—all the makings of a weekend trip away.

Do this: Plan your visit around award-winning restaurants like Selden Standard and Sister Pie. Between bites, hit up John K. King Used & Rare Books, a four-floor emporium of old tomes, as well as Belle Isle Aquarium along the Detroit River.

Stay here: Book an affordable room at the Siren Hotel, a 106-room property in the historic Wurlitzer Building. You don't have to go far for a great cocktail—downstairs watering hole, the Candy Bar, serves funky creations in an all-pink, chandelier-adorned room.

Des Moines, IA
Photograph: Shutterstock

8. Des Moines, IA

Driving time from Chicago: Five hours

Iowa’s capital city doesn’t get the love it deserves, but you’ll find plenty to do in a weekend, with tons of art, food and breweries and a packed summer calendar of local events and festivals. 

Do this: There’s a lot of beauty in Des Moines, including at the sprawling indoor-outdoor Greater Des Moines Botanical Garden, and the six-mile Art Route connecting more than 80 pieces of public art. Plan your trip around one of the city’s many massive summer festivals, like the packed indie music celebration 80/35, the inspiring Des Moines Arts Festival and Interrobang Film Festival, and—you guessed it—the Iowa State Fair

Stay here: For luxe accommodations, it’s hard to beat the Surety Hotel, featuring modern rooms and the elegant Mulberry Street Tavern downstairs. Grab a martini at the bar at the punnily-named Des Lux Hotel before an evening on the town, or just curl up in your room with a fireplace. 

Traverse City, MI
Photograph: Courtesy Traverse City Tourism

9. Traverse City, MI

Driving time from Chicago: Four hours and 50 minutes 

Situated in Grand Traverse Bay’s 180 miles of Lake Michigan shoreline, Traverse City is a small town with arts, culture, water recreation and summer street festivals. There's also easy access to the Old Mission Peninsula, Leelanau Peninsula, Sleeping Bear Dunes and the strings of other small towns dotting the pastures and hills of what Michiganders call “Up North.” 

Do this: Meander by car or bike around the wineries of Leelanau Peninsula Wine Trail. Featuring over 20 award-winning Michigan wineries, you’ll pass rolling hills with views of Lake Michigan. Stop for lunch at  the tranquil Farm Club for a selection of al dente pastas, local meats, pan-seared vegetables and leafy salads straight from the garden.

Stay here: Cozy up in one of the six rooms at downtown boutique hotel The Flats and Iron + Union. The 1890s-era building housed many beloved local businesses throughout the past century and is now a prime location for visitors.

Driving time from Chicago: Four hours and 45 minutes

Kentucky’s largest city, just across the Ohio River from southern Indiana, is steeped in bourbon and long on charm.

Do this: The home of the old-fashioned and the mint julep embraces its role as the gateway to Bourbon Country. The city has a number of tourable distilleries, including Evan Williams, Angel’s Envy and Old Forester.

Stay here: True to its name, 21c Museum Hotel is part boutique hotel, part contemporary art locale. With more than 75,000 square feet of exhibition space, there's bound to be something for everyone. The hotel is also home to one of Louisville’s finest restaurants, Proof on Main, where chefs craft Southern fare using seasonal ingredients sourced from the Ohio River Valley. 


Driving time from Chicago: Four hours

Situated just west of Detroit, Ann Arbor is home to University of Michigan, a slew of breweries and a handful of phenomenal restaurants. If you’re a roaming foodie or beer nerd, this is the low-key vacation spot you’ve been searching for.

Do this: You’ll want to make it a point to visit Spencer, an exquisite neighborhood spot that offers pastries and coffee in the morning and a selection of seasonal small plates, cheese and wine when the sun goes down.

Stay here: Graduate Hotels is a collection of boutique properties that celebrate the youthful feel of college days past, and Ann Arbor is one of the group’s many locations in the country. The space is outfitted in Persian rugs, plaid chairs, velvet couches, reclaimed wood and gorgeous chandeliers. Think of it as the prep school of hotels.

St. Louis, MO
Photograph: Shutterstock

12. St. Louis, MO

Driving time from Chicago: Five hours

If you only know the big Arch, Busch Stadium and deep-fried ravioli, we assure you there’s a lot more of STL to explore. 

Do this: Like Chicago, one of the best ways to get to know St. Louis is by visiting its neighborhoods—browse local makers and antiquers on Cherokee Street, explore a host of breweries like Side Project and Schlafly, and savor a traditional red-sauce meal on The Hill. The 1,300-acre Forest Park, one of the most stunning urban green spaces in the country, is a must. If you’re traveling with kids (or kids at heart), don’t miss the interactive, immersive City Museum, an educational playground with slides, sculptures you can play on and even vintage pinball machines. 

Stay here: The art deco Royal Sonesta Chase Park Plaza St. Louis offers views of Forest Park and renovated guest rooms in the popular Central West End. The quirky Moonrise Hotel on the Delmar Loop leans into the lunar theme and offers an enticing all-seasons rooftop bar. 

Peoria, IL
Photograph: Courtesy of Discover Peoria

13. Peoria, IL

Driving time from Chicago: Two and a half hours

Once a small riverfront European settlement in early Illinois history, Peoria is now a safe haven for the Midwest LGBTQ+ community looking for affordable housing. Plan a visit during the River City Pride Festival to support local LGBTQ+ artists and vendors and enjoy arts, culture and food.

Do this: Drive the two and a half mile scenic Grand View Drive, one that Theodore Roosevelt famously reported was the “Most Beautiful Drive in the World.” The panoramic views of the Illinois River are stunning no matter the season, but visitors flock to Peoria for fall foliage spotting. 

Stay here: There are plenty of small, historic bed and breakfasts in and around Peoria, but for a unique experience, opt to stay 20 minutes west of downtown Peoria at Wildlife Prairie Park’s converted Santa Fe train caboose or old grain bin.

Eau Claire, WI
Photograph: Andrea Paulseth/Volume One

14. Eau Claire, WI

Driving time from Chicago: Five hours

You’ve been to Madison and Milwaukee, but a trip to the Chippewa Valley in northern Wisconsin is an experience unto itself. You’ll find rolling hills and colorful foliage, plus plenty of beer and cheese to smuggle back to Chicago.

Do this: Hiking is nice and all, but if you really want to see what autumn looks like here, hit the Chippewa River. Head to Riverside Bike & Skate in downtown Eau Claire, where you can rent kayaks and hire a shuttle service to drive you upstream.

Stay here: Bon Iver frontman and Eau Claire native Justin Vernon is one of the partners behind the Oxbow Hotel, so it’s no surprise that it’s easily the trendiest joint in town. The renovated motel has its own bar and restaurant, and each room contains a turntable. You probably won’t write a hit indie-rock album in your room, but at least you can listen to one.

Iowa City, IA
Photograph: Think Iowa City

15. Iowa City, IA

Driving time from Chicago: Three and a half hours

Nothing says fall like holing up in a college town and reminiscing about football tailgating, dorm food and campus crushes.

Do this: Starting in September, the walkable University of Iowa campus turns into a postcard-worthy scene that spans from the downtown pedestrian mall to the darling surrounding neighborhoods. Start your self-guided tour in the epicenter of it all, the Pentacrest, where four buildings on the campus surround the Old Capitol Museum.

Stay here: Bunk up at the super-modern Hotel Chauncey, which has 51 spacious suites outfitted with sleek furniture, floor-to-ceiling windows and minimalistic accents. Toss in a rooftop deck, gym and in-room kitchens, and it’s no wonder this place books up early during football season.

St. Joseph, MI
Photograph: Shutterstock

16. St. Joseph, MI

Driving time from Chicago: One hour and 45 minutes

This Michigan beach town and its twin city Benton Harbor offer picturesque sandy shores, as well as plenty of wine.

Do this: Soaking up the sun on beaches is the most obvious attraction, but once you’ve gotten your fill of vitamin D, hit up the nearby Lake Michigan Shore Wine Trail. It’ll take you to wineries up and down the coast, and you can easily spend an entire weekend just swirling, sniffing and sipping.

Stay here: Located along the St. Joseph River, the Inn at Harbor Shores boasts waterfront views and amenities like a spa and a golf course that’s close by. If you don’t feel like leaving the hotel, grab a seat on the patio of the in-house restaurant, Plank’s Tavern on the Water, for a relaxing meal.

Spring Green, WI
Photograph: Courtesy House on the Rock

17. Spring Green, WI

Driving time from Chicago: Three and a half hours

Quiet and quaint, it’s easy to see why the scenic village of Spring Green on the Wisconsin River attracted the likes of Frank Lloyd Wright, who made his summer home here at the must-see Taliesin.

Do this: Get weird and head to the House on the Rock, a curious wonderland of oddities and artifacts that’s set quite literally on a giant rock surrounded by panoramic views of towering trees. Don’t miss the massive indoor carousel or the Infinity Room, an engineering wonder with 3,264 windows that juts out 218 feet over the valley.

Stay here: Step back in time at Spring Valley Inn, designed by the Frank Lloyd Wright School of Architecture. The small inn on 10 acres of wooded prairie offers unbeatable views of the valley, plus a relaxing bar, patio, fire pit, indoor pool, hot tub and workout room.

Bloomington, IN
Photograph: Shutterstock

18. Bloomington, IN

Driving time from Chicago: Four hours

This next-level college town has all the big-city amenities you crave, but it’s tucked in the middle of hills, forests and nearby lakes. 

Do this: Fill up at the intimate Feast Market and Cellar, a family-owned kitchen with a lovely corner porch. The restaurant makes everything from scratch daily, so you know you’re consuming fresh eats, from the mayonnaise to the bread to the macarons.

Stay here: Grant Street Inn, which is within walking distance of downtown and the attractive Indiana University campus, has four-star hotel accommodations with bed-and-breakfast charm. Choose from the main house, built in the 1890s, or any of the other four buildings, each with unique themes and features, from those done up in traditional antique decor to the newest space, a LEED-certified addition.

Toledo, OH
Photograph: Courtesy Destination Toledo

19. Toledo, OH

Driving time from Chicago: Four hours

Once a popular stop on the railway line between Chicago and New York, Toledo is still worth a visit, full of Great Lakes history, native greenery and other surprises.

Do this: Toledo is a paradise for flâneurs—wander the Old West End to take in beautiful Victorian homes that line the peaceful streets, or take a nice, pastoral break in the Swan Creek Preserve. The National Museum of the Great Lakes offers a fascinating look at the region's history. For a livelier evening, take in some minor league baseball with the Toledo Mud Hens.

Stay here: Get a room with a view of Lake Erie at the Maumee Bay Lodge, located amid 1,336 acres of natural splendor in Maumee Bay State Park. When you’re not enjoying the private balconies and patios, grab food from the Lodge’s restaurant, hit the links at an 18-hole golf course or go for a hike on a nearby trail.

Fort Wayne, IN
Photograph: Courtesy Visit For Wayne

20. Fort Wayne, IN

Driving time from Chicago: Three hours

Indiana’s second largest city was once a booming industrial hub with more than 300 churches. But make no mistake—there’s no shortage of small-town charm and plenty of places to let loose.

Do this: Spend an afternoon at Promenade Park where locals congregate on the riverfront for festivals, picnics and water recreation. Grab pizza and beer from local favorite Pint & Slice and don’t miss the photo opportunities in front of murals in the alley.

Stay here: Located in the heart of downtown, The Bradley is a 124-room, nine-suite boutique hotel featuring murals and decor from local artists. Get great views of the city from the hotel’s rooftop bar, Birdie’s.

Dubuque, IA
Photograph: Courtesy Elevate Images

21. Dubuque, IA

Driving time from Chicago: Three hours

This historic Mississippi River settlement’s attraction goes far beyond a visit to the Field of Dreams. It’s easy to get lost in the vivid murals, craft breweries and outdoor art galleries.

Do this: What’s a weekend getaway without a ride up the world’s shortest and steepest scenic railway? Head to Fenelon Place Elevator Co for a 189-foot trip from Fourth Street to Fenelon Place, where you can take in an aerial view of the city.

Stay here: The century-old Hotel Julien Dubuque is full of elegance, blending modern luxury with historic charm. It offers 133 rooms and amenities like an indoor pool, spa and fitness center.

Carbondale, IL
Photograph: Courtesy Shawnee Hills Wine Trail

22. Carbondale, IL

Driving time from Chicago: Five hours

This Southern Illinois university town was developed as a result of the railroad, but today is a great jumping off point for exploring Shawnee National Forest and nearby wineries.

Do this: With Carbondale as your home base, take your time exploring the 11 wineries that make up the 40-mile Shawnee Hill Wine Trail. Between wineries, pick up one of The Iron Whisk’s famous Dutch babies (a puffy pancake made in a cast iron pan) from a converted auto garage kitchen in Cobden.

Stay here: Referencing Carbondale’s past as a railroad destination, the Train Inn is a four-room bed and breakfast in a renovated early 1900s bungalow featuring art deco styling and train memorabilia. Owner Paul Lewers will make your breakfast according to any dietary preferences, but he encourages those willing to venture outside their typical palate to try his red-eye gravy, a speciality made from country ham and coffee.

Columbus, IN
Photograph: Shutterstock

23. Columbus, IN

Driving time from Chicago: Three and a half hours

In the heart of Southern Indiana, Columbus is an unexpected center for boundary-pushing architecture—in fact, the American Institute of Architects ranked the city sixth in the nation for architectural innovation.

Do this: Take an Architectural Highlights Tour of more than 30 of Columbus' structures and learn how this city became the state's award-winning arts and design destination. Once you’ve worked up an appetite, stop by Columbus Bar, the oldest bar and restaurant in town.

Stay here: Columbus’ Hotel Indigo is a perfect place for architecture- and design-lovers to rest their heads, outfitted with an in-house gallery featuring pieces by regional artists.

Davenport, Iowa
Photograph: Courtesy Visit Quad Cities

24. Davenport, Iowa

Driving time from Chicago: Two and a half hours

You’ve tried Quad Cities-style pizza, but now it’s time to explore Davenport’s museums, gardens, parks and charming riverfront.

Do this: Glimpse permanent and rotating exhibitions of international and regional works at the Figge Art Museum situated downtown just blocks from the river. Then, make you way to the German American Heritage Center to learn about German immigration and culture—and why some consider Davenport to be the most German city in the U.S.

Stay here: Built on the site of Davenport’s first hotel, the city’s industrial and agriculture roots mingle with modern art and design at The Current Iowa, decorated with split canvas photographs of freight cars and colorful paintings of pastoral scenes. Sip the hotel’s namesake cocktail with gin, elderflower, lavender and mint and relax at the UP Skybar as you watch the sun set over the river.

Kalamazoo, MI
Photograph: Shutterstock

25. Kalamazoo, MI

Driving time from Chicago: Two and a half hours

Western Michigan boasts spectacular fall foliage and, in turn, excellent apple-picking conditions. Make Kalamazoo your home base for an excursion and reap the benefits of the lively Midwestern town.

Do this: Husted's Farm Market & Cider Mill is one of several autumnal havens in the region, featuring fresh, pickable produce June through October. When the asparagus, rhubarb and strawberries are gone, you’ll find pumpkins, apples (23 varieties) and gourds in their place.

Stay here: Enjoy the royal treatment at the Henderson Castle Inn, a bed-and-breakfast in a historic 19th-century mansion. The inn features 12 ornate rooms, spa amenities, a steakhouse, a craft cocktail lounge and high-tea service.

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