8 Awesome Midwest Getaways

Stay in the heart of downtown at one of the city’s most historic hotels, Hotel Phillips. The landmark, which recently emerged from a massive facelift, is a living monument to the roaring 20’s in Kansas City—complete with its own underground speakeasy, PS. From here, take the streetcar to the Crossroads arts district to shop at local spots like Coki Bijoux, a French-inspired jewelry boutique tucked away in a brick alley, and Hammerpress for exquisitely designed cards and posters fresh off the printing press. The art scene in KC is thriving—you can catch a concert at the Kauffman Center for the Performing Arts, or browse the Bloch Galleries at the Nelson Atkins Museum of Art (we especially love the new collection of Impressionist art and Art Nouveau artifacts). Enjoy a nightcap at Tom’s Town, a swank art deco bar with house-distilled gin and vodka martinis, and some jazz at nearby Green Lady Lounge. Keep the party going with Sunday brunch at Ça Va, a champagne bar serving crepes and cheesy Croque Monsieurs. The Build Your Own Mimosa bar is the highlight with housemade bitters, syrups, fresh juices and edible flower garnishes.

Chicago is the quintessential Midwest city for a reason: tons to do and see, but somehow the city living maintains a perfectly easygoing Midwest pace—not to mention the happy hospitality. Speaking of which, lay down your bags at the newly renovated Chicago Athletic Association Hotel. The hotel overlooks Millennium Park with killer views from its bar, Cindy’s Rooftop, and is a great place to hang at night with billiards, bocce, shuffleboard and clinking glasses reminiscent of the old club days. As the biggest city in the Midwest, Chicago has no shortage of fine restaurants. Culinary master Stephanie Izard recently opened her latest venture, Duck Duck Goat, and the daring Asian food and exotic cocktails exceed all expectations. Other excellent options are Piccolo Sogno for upscale Italian with a drool-inducing housemade pasta menu and Dove’s Luncheonette for a tongue-in-cheek take on diner culture serving Southern inspired Mexican cuisine morning, noon and night. Shopping, of course, abounds on Michigan Avenue, but don’t pass up on the boutique scene in Lincoln Park or vintage at Kokorokoko—its collection of ‘80s and ‘90s threads is wild.

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Cleveland may get a bad rap, but the city has undergone a rebranding of sorts, embracing its gritty side in an artistic renaissance. In their own words: “we’ve got world class experiences without the world class ego, and for that, you’re welcome.” The Schofield Hotel is the perfect place to get a taste of the unapologetically funky vibes taking over this town. Downtown Cleveland is quickly becoming home to a coffee movement, so start your weekend off with a quality cup at Pour Cleveland. Of course you have to check out the Rock & Roll Hall of Fame, but don’t stop there: the Museum of Contemporary Art might be even more rock & roll than the hall of fame itself. For lunch, head to the beautifully preserved West Side Market. The oldest marketplace in the city, West Side vendors serve up everything from cinnamon chipotle pork chops to filled-to-order cannoli. If you’d rather sit down for a fine meal, French restaurant L’albastros Brasserie + Bar has one of the most epic cheese offerings you’ll ever behold.

Lay down your bags at Hewing Hotel, the perfect combination of masculine, contemporary design and rustic lakehouse vibes. The brick-and-timber warehouse is over a century old, and original pine timber beams give way to walls covered in work by local Minneapolis artists and photographers. Located on the North Loop, it’s a great starting point to check out dining destinations like The Bachelor Farmer, a charming yet modern Scandinavian restaurant, and especially Bar La Grassa, oft credited with leading the charge in the hottest neighborhood in the city. Minneapolis is a haven for boutique shopping, a trend you might say trickled down from the troves of handmade shops dotting smaller towns on the lake. Housed in a former brass factory, The Foundry Home Goods encourages simple living, and sells handcrafted wool blankets, delicate porcelain dishware and other carefully curated home goods. Once you’ve snagged the perfect take-home gift, head to Parlour Bar to celebrate with a craft cocktail concocted from rare artisanal spirits.

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There is no better home base than the ultra-luxe Four Seasons St. Louis. Take in the spot-on views of the Arch right from your plush king bed, and be sure to enjoy the spa and rooftop pool while you’re there. A couple of obvious attractions here: Anheuser-Busch Brewery, to name the King of Beers, is open to the public with great tours, and of course you can catch a Cardinals game at Busch Stadium. But the under-the-radar beer scene is really where it’s at. Sip suds at small micro-breweries like Urban Chestnut or order a flight at the rapidly growing Schlafly. Swing by Boxwood Farms in the afternoon to take home some succulent souvenirs (plus solid advice from the staff on how not to kill them). When you’ve worked up an appetite, go to town on the spicy hot chicken at Southern. For a more upscale evening, head to happy hour at the cute gas station turned garden bar Olio, followed by dinner at Olive + Oak, an inventive American Restaurant getting nods from the likes of James Beard.

If you really want to dive into the Midwest, fly into MCI airport and drive an hour west to beloved Lawrence, Kansas. The quintessential college town hosts a thriving and surprisingly upscale farm-to-table restaurant scene, thanks to all the nearby farmland. See it for yourself at Mass Street, a hub of shops, bars, restaurants and more. Check out RND Corner Grille, an old drugstore now home to chef Simon Kass’s hallmark KC cuisine: a perfectly cooked steak. Pair that with a glass of red from their extensive wine list, all of which they offer by the glass—even the big names like Silver Oak. Wander down the street afterwards to Sylas & Maddy’s Homemade Ice for a sugary-sweet cone, then prepare to shop. Delaney & Loew Kitchenalia has every kitchen gadget you could imagine, as well as some wonderful small-batch local products like cocktail mixes and bitters, candied nuts, and quality vanilla extracts. If you’re interested in art, design and printmaking, visit Wonder Fair for exhibitions, adult coloring books and a huge selection of unique posters. End your night in a suite with city views at The Oread Hotel, a Lawrence mainstay with a knack for excellent martinis.

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Don’t be fooled by Nebraska—Omaha is no farm town. This city was one of the first to jump on the trend of rehabbing their downtown, paving the way for one of the Midwest’s most darling districts, Old Market. Brick-lined streets, alleyway shops, and contemporary restaurants are just a few gems you’ll find in the area, all walkable from Hotel Deco, a lavish art deco stay with an unbeatable location. Wheatfields Eatery & Bakery makes the kind of cinnamon rolls you’ll be dreaming about years later, and Aromas coffee is a favorite among locals. Beer lovers should check out Benson Brewery, a remodeled 1910’s movie theater with exposed brick walls and hand-crafted beer. And if you’re in the Midwest for the comfort food, we don't blame you: head straight to Mark’s and order the mac & cheese.

For a taste of small-town life, head north of Kansas City to bucolic Weston, Missouri. The historic downtown district is frozen in time with a Main Street that looks straight out of a country Western. Copious B&Bs, antique shops and small wineries make it more than worth a weekend away. The cozy accommodations, weekend wine tastings and homemade pastries at Hatchery House Bed & Breakfast will lull you into instant easy living. Spend the whole day shopping the tiny antique shops along Main Street. When the evening rolls around, taste some wine under an ivy canopy at Pirtle Winery, choose from a large selection of hand-rolled cigars at Weston Tobacco and head to Weston Brewing Company for some great Irish pub fare, local brews and live music down in the cave-like bar. On your way home, make a pit stop at Green Dirt Farm’s Creamery for a fresh sheep’s milk grilled cheese sandwich and sheep’s milk ice cream—a truly unique, tangy treat.