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Fort Wayne riverfront and boat
Photograph: Courtesy Visit For Wayne

The 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
Zach Long
Morgan Olsen
Allison Yates

Places like Door County, Galena, and Michigan's Southeastern shore have long been popular weekend jaunts for Chicagoans (especially for the best hiking near Chicago), but there’s a host of untapped food, arts and culture scenes beyond the well-known favorites. From post-industrial cities reclaiming their place on the Midwest map to small-town university towns proving they’re more than just a temporary destination, you’ll find underrated weekend getaways from Chicago within a five-hour drive of the city. When you've run out of thing to do in Chicago, explore, rejuvenate or get weird at unexpected attractions any time of the year—your next weekend getaway from Chicago is waiting.

RECOMMENDED: The best day trips from Chicago 

Best 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.

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 all year. 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 11 ornate rooms, spa amenities, a steakhouse, a craft cocktail lounge and high-tea service.


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 Bakery Cafe, 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.

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.


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 now has five tourable distilleries, including Evan Williams, Angel’s Envy and Bulleit

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

Once a popular stop on the railway line between Chicago and New York, Toledo is still worth a visit. Surrounded by farmland, the former industrial hub is ground zero for fall-harvest overload.

Do this: Pumpkins may be the most beloved seasonal crop, but there’s nothing sweeter than a crisp, autumnal apple. You’ll find bushels of them at MacQueen’s Apple Barn and Cider Mill just outside of Toledo, where you can pick 16 varieties. The family-owned farm also sells fresh fruit–infused baked goods, including pies, fritters and addictive cider donuts.

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.


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 13 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.

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.


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.

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. 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.

Fort Wayne, IN
Photograph: Courtesy Visit For Wayne

11. 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 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

12. 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 elevator? Head to Fenelon Place Elevator Co for a 186-foot trip from Fourth Street to Fenelon Place, where you can take in an aerial view of the city.

Stay here: One of Iowa’s only remaining pre-Civil War era hotels, the Black Horse Inn is located just outside of town. All four rooms in this historic bed and breakfast overlook the Mississippi River.

Carbondale, IL
Photograph: Courtesy Shawnee Hills Wine Trail

13. 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

14. 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 architecture tour of more than 30 of Columbus's 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’s 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

15. 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 rooftop bar as you watch the sun set over the river.

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