Like brunch spots and Starbucks, boutique hotels often herald urban gentrification. But not in Wicker Park and Bucktown: These adjacent Chicago neighbourhoods already offered just about every urban amenity one could want – from vintage fashion boutiques and record shops to taco stands, cocktail bars and even a landscaped rail path – years before Mexican hotel developer Grupo Habita simultaneously opened the Robey and the Hollander in late 2016 on the six-corner intersection unfortunately known as "the Crotch."
Arriving too late to be harbingers of development, the adjacent properties instead fill a glaring gap in WP&B's travel credentials. Now visitors can jet into Chicago O'Hare, take the "L" train directly to the Damen stop, and step into a uniquely beguiling streetscape that finally features stylish and versatile accommodations to match. And should guests wish to explore the more famous diversions of "the Loop," as central Chi-town is known, the area provides an ideal jumping-off point.
Stay
The Hollander, a hotel-hostel hybrid boasts plenty of beautiful exposed brick and distressed paint in its lobby, an homage to the space’s industrial roots.
Handout
The Robey: Name-dropping this 69-room hotel still seemed to thrill local merchants more than two weeks after it opened. And no wonder: Full-service luxury accommodations, and their affluent out-of-town guests, are relatively few and far between outside the Loop.
Along with the standard-issue comforts of its luxury-chain rivals on the Magnificent Mile – plush robes and slippers, fine linens, fine dining, Bluetooth-enabled sound systems and so on – the Robey delivers plenty of the art-deco flair for which Chicago is famous. Housed in the 12-storey Northwest Tower, a flatiron-style landmark that rose over WP&B in 1929, the Robey's vintage flourishes adorn everything from the compact lobby's checkerboard floors and dark-wood panelling to the gleaming elevator doors. The literal capper: The "Up and Up" lounge and rooftop terrace, where an ornate chambered spire bisects glorious views of Chicago's skyline.
Four room configurations start at $175 (U.S.) a night and range from stylishly minimalist units with queen- and king-sized beds to an aptly-named "Panorama Suite" with separate living room. The tower's triangular footprint in a low-rise neighbourhood, combined with generous windows, means most rooms afford superb city views and are bathed in natural light. The flip side: With the noisy "L" train mere steps away, light sleepers may want to request quarters on the opposite side of the building. 2018 W. North Ave., therobey.com
The Hollander: Like the Robey next door, this hotel-hostel hybrid embraces its historic namesake home – a century-old five-storey warehouse – with plenty of exposed brick and artfully-distressed paint in the airy lobby/café/bike shop.
The self-serve laundry facilities, day lockers and eight dorm-style rooms (starting at $45) are the stuff of hostels, to be sure, but make no mistake: The Hollander provides a spotless and pleasingly versatile option for families and groups. A dozen private rooms (starting at $125) all include ensuite bathrooms, small refrigerators and flat-screen TVs, with bunks and queen-sized beds cleverly incorporated into the spartan, vaguely industrial decor. 2022 W. North Ave., thehollander.com
Eat and drink
Mindy’s Hot Chocolate is a popular joint in the neighbourhood, serving an eclectic brunch menu and eight varieties of hot chocolate.
Scott Shigley
Big Star: This guide could only avoid using the word "hipster" for so long. But the casual eatery that started Chicago's so-called "hipster taco" trend in 2010 is the furthest thing from standoffish or pretentious.
Friendly, knowledgeable serving personnel help guests navigate the nine taco varieties on offer – three or more will fill you up – while saying "surprise me" is bound to yield something delicious in the lively, roomy dining room or out on the expansive patio. 1531 N. Damen Ave., bigstarchicago.com
Mindy's Hot Chocolate: Yes, the eight hot chocolate varieties are moniker-worthy – especially when topped with an extra house-made marshmallow – but there's much more than warm beverages here. Brunch is especially popular and eclectic, with the char siu fried rice melding barbecued pork, peas, carrots, eggs and scallions and the buttermilk pancake topped with cider apples and dripping in caramel butter. 1747 N Damen Ave., hotchocolatechicago.com
Café Robey: The art-deco-style eatery on the Robey's ground floor makes the most of the wedge-shaped building with floor-to-ceiling windows that are ideal for people-watching. The French-American menu, meanwhile, features contemporary twists on standards such as steak frites and duck confit. The cozy second-floor lounge above is ideal for after-dinner cocktails such as the pompadour, a lively concoction of rum, pineau de charentes, lemon juice and peychaud's Bitters. 2018 W. North Ave., therobey.com
Publican Anker: Continue watching the world go by in this brand-new gastropub that's kitty corner to the Robey. Sip one of 14 draft beers and nibble on smoked mackerel behind windows that are straight out of Edward Hopper's Nighthawks. 1576 N. Milwaukee Ave., publicananker.com
Shop
Vintage Charm Bucktown: WP&B's many vintage boutiques are as carefully curated as any, but this charming option stands out with vintage-inspired attire, accessories, housewares and decor items that are not actually vintage. All the style, none of the mustiness. 1735 N. Damen Ave., shopvintagecharm.com
Una Mae's: Amid the fast-fashion chain stores that have popped up on bustling North Milwaukee Avenue, this multi-level independent boutique offers an appealingly retro collection of menswear and womenswear – think skinny jeans, peacoats and eccentric costume jewellery – along with handmade toiletries and whimsical housewares. 1528 N. Milwaukee Ave., unamaeschicago.com
deciBel Audio: Audiophiles will exult in the new and used stereo receivers, amplifiers, turntables, speakers and accessories. High Fidelity fans will exult in the deciBel Audio T-shirts worn by John Cusack in the 2000 film, which was set in Wicker Park. 1429 N. Milwaukee Ave., decibel.com
Local secrets
The 606: Named for the first three digits in every Chicago zip code, this elevated train track-turned-greenway runs 4.3 kilometres from the less-gentrified Logan Square district to the eastern fringe of Bucktown. The sculpture-dotted path, which opened in 2015, is a boon for strollers, joggers and cyclists and hosts seasonal events such as an "Arts Blitz" in September and a "Block Party" in June. the606.org
The writer was a guest of the Robey and the Hollander. They did not review or approve this article.