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9 underrated weekend getaways near Chicago

Get out of town and hit one of these unique Midwestern destinations this fall

Wolverine Brewing in Ann Arbor

It’s time to cash in those spare vacation days and hit the road for a fall-fueled road trip. Whether you want to stroll through a pumpkin patch, take a scenic drive or discover fantastic seasonal eats and sips, you won’t have to go far. We explored nine Midwestern destinations that are oozing with character and fun. The best part? They’re all within five hours of Chicago.

Eau Claire, WI

Eau Claire, WI

5hrs from Chicago

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. 937 Water St (715-835-0088, riversidebikeskate.com)

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. 516 Galloway St (844-692-6932, theoxbowhotel.com). $140–$190/night. —Zach Long

Iowa City

Iowa City

3hrs 30mins from Chicago

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 campus turns into a postcardworthy 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 University of Iowa’s campus surround the Old Capitol Museum. 21 N Clinton St (319-335-0548, oldcap.uiowa.edu)

Stay here: Bunk up at the super modern hotelVetro, which has 56 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. 201 S Linn St (800-592-0355, hotelvetro.com). $171–$200/night. —Morgan Olsen

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Spring Green, WI

Spring Green, WI

3hrs 30mins from Chicago

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 (5481 County Rd C; 608-588-7900, taliesinpreservation.org)

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. 5754 State Rd 23 (608-935-3639, thehouseontherock.com)

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. 6279 County Hwy C (608-588-7828, springvalleyinn.com). $99–$137/night. —Laura Rote

Cedarburg, WI

Cedarburg, WI

2hrs from Chicago

Located just a few miles north of Milwaukee, Cedarburg is an ideal place to wind down and take things slow. The charming small town is brimming with old-world architecture, friendly Midwesterners and culture galore.

Do this: Get your fall fix at Cedarburg Creek Farm, a sprawling family-owned operation that has pumpkins, flowers, an impressive petting zoo, free hayrides and a corn maze. The season starts September 24 and runs through November, when freshly cut Christmas trees become available. 649 Hwy 60 (414-333-5600, cedarburgcreekfarm.com)

Stay here: You could retreat to Milwaukee for the evening, but when you see the historic Washington House Inn, you’ll want to stay put. Guests choose from nearly 30 rooms, each with different decor like fireplaces, floral wallpaper and canopy beds. W62 N573 Washington Ave (262-375-3550, washingtonhouseinn.com). $162–$337/night. —MO

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Kalamazoo, MI

Kalamazoo, MI

2hrs 30mins from Chicago

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. 9191 W Main St (269-372-1237, hustedfarmmarket.com)

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. 100 Monroe St (269-344-1827, hendersoncastle.com). $129–$199/night; spa and romance packages are also available. —Grace Perry

Toledo, OH

Toledo, OH

4hrs from Chicago 

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. 7605 Garden Rd, Holland, OH (419-865-2916, macqueenorchards.com)

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, dine at the Lodge’s restaurant, hit the links at an 18-hole golf course or go for a hike on a nearby trail. 1750 State Park Rd #2, Oregon, OH (800-282-7275, maumeebaystateparklodge.com). $180–$220/night; golf packages available. —ZL 

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Ann Arbor, MI

Ann Arbor, MI

4hrs from Chicago 

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. 113 E Liberty St (734-369-3979, spencerannarbor.com)

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. 615 E Huron St (734-769-8693, graduatehotels.com/ann-arbor). $188–$497/night. —MO

Bloomington, IN

Bloomington, IN

4hrs from Chicago

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. 581 E Hillside Dr (812-822-0222, feastcateringonline.com)

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. 310 N Grant St (812-334-2353, grantstinn.com). $159–$209/night. —LR

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Louisville, KY

Louisville, KY

4 hrs 45mins from Chicago

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. A current exhibition, “Pop Stars!” (through March) looks at the intersection of pop culture and art since the 1960s. The hotel is also home to one of Louisville’s finest restaurants, Proof on Main, where chef Mike Wajda crafts Southern fare using seasonal ingredients sourced from the Ohio River Valley. 700 W Main St (502-217-6300, 21cmuseumhotels.com/louisville). $279–$519/night—Kris Vire

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