High above Wicker Park’s iconic six-corner intersection of Damen, Milwaukee and North Avenue towers The Robey Chicago, housed in the historic Art Deco flatiron building. Formerly known as the Northwest Tower—it stands at 203 feet tall and is the only skyscraper for miles—The Robey captures the storied spirit of Chicago, a bustling, ever-changing, big-shouldered town. Located steps from the Blue Line Damen stop where two communities merge to form one of the city’s most unique, creative urban epicenter, it would be an ideal destination if only for immersing yourself in a Chicago neighborhood outside of downtown. But it offers far more than a fabulous location: the hotel was also named one of the best hotels in Chicago by Condé Naste Traveler.
Originally designed in 1929 as an office building, the hotel was transformed by Belgian design duo Nicolas Schuybroek Architects and Marc Merckx Interiors in 2016. They preserved its vintage charm with details like the stunning period lobby, hallway mail chutes, and Gothic relief carvings, but gave it a clean, contemporary feel with glass, chrome and timber elements. The light-filled guest rooms are furnished with midcentury modern furnitureand feature frosted glass embedded with chicken wire to give the bathrooms privacy.
“Wicker Park/Bucktown is popular for a lot of reasons, and not just the great food and the nightlife—of which there is plenty. A big draw is that it is one of the few walkable neighborhoods in the city.”
ROOMS & SUITES
The Robey has 89 rooms and suites, ranging from 215 to 675 square feet and offering king- or queen-size beds. Many suites provide a lounge area and workspace and stunning cityscapes, like the Panorama Suite with its 180-degree skyline views. Four rooms are modified for accessibility. The hotel is also family friendly, with rollaway beds and cribs that are free of charge. And, despite the building’s vintage layout, an elevator serves all floors of the building.
“You are so in contact with the energy of the intersection and also it feels very private.”
The Art Deco-meets-Modern motif features a mix of vintage and custom-designed furnishings, with iconic Schoolhouse Electric bedside lamps and retro phones that complement each room. Design features include Waterworks bath fixtures, custom terrazzo tile, bold accents of oxide red and Calcutta marble tabletops that are as suitable for work as dining.
Notable tech touches include blinds that lower at the touch of a button, bedside-controlled lights, Bluetooth sound systems and TVs that allow you to stream Netflix and other media.
In addition to the many room amenities you’d expect in a hotel of this quality, The Robey supplies Le Labo toiletries, bathrobes and felt slippers in the bathrooms. Room keys have an energy-saving feature: Lights only turn on when in place, and the key automatically turns everything off as you leave.
You can take advantage of dry cleaning, room service with special diet menus, shoeshine service, tours/ticket assistance, and wake up service. There are also complimentary bikes, provided by tokyobike.
The Robey is located in a neighborhood famous for live music and nightlife, chef-driven restaurants and countless art galleries. There’s no better area to sip and shop in the country.
The area has become a prevailing influence on Chicago’s Michelin-rated, James Beard Award-winning dining scene, boasting some of the city’s most sought after tables. Wicker Park and Bucktown are also known for their palate pleasing drinks, like those served in renowned brewery Piece and artisanal cocktails with roots in the pre-prohibition era at The Violet Hour. It’s also a draw for locals with Big Star, a fun bourbon and beer-focused taqueria with a large patio (note: they do not take reservations!); The Bongo Room, a popular brunch place with inventive pancakes like their famous Red Velvet Pancakes; and Dove’s Luncheonette, where you can grab big-hearted dishes such brisket burnt-ends and buttermilk-fried chicken in a lighthearted diner setting, served up 24/7.
Fun Fact: Damen Avenue was originally named Robey Street.
On the main avenues, you’ll find a blend of vintage shops and indie boutiques touting fashions for both men and women, such as Saint Alfred, Una Mae’s, Mildblend Supply Co., and Moth. Browse luxury home goods and beauty products at Credo Beauty, Aesop, and Asrai Garden. On the same blocks are nationally-recognized fashion and retail stores like Urban Outfitters, Scotch + Soda, and Free People, to satisfy the appetites of on-trend shoppers. The high concentration of a variety of shops (and styles) means that I can look through selections of hard-to-find cult French brands at Penelope’s or pick up a trendy oversized vintage tee at Moon Voyage while picking up my favorite shampoo bars at LUSH. You can also grab a coffee at La Colombe or The Wormhole, an 80s-themed rustic shop, then head over to Myopic Bookstore—one of Chicago’s oldest and largest, with three stories of floor-to-ceiling books.
Back at the hotel, street-level Café Robey is a neighborhood restaurant that serves Chef Kevin McAllister’s modern American dishes at brunch and dinner daily.
The restaurant is cozy and intimate, with lots of natural light from its large windows. Its sleek, modern space sports red booths with a view into the kitchen and a bar toward the back. The whole space has a bright, open feel to it, despite its small footprint.
Breakfast ranges from light (fruit plate or avocado toast, $9 each) to hearty (smoked salmon Benedict, $16). Don’t miss the decadent Cuban sandwich, stuffed with pork loin and shoulder, gruyère, avocado, jalapeño and red onions—served with a side of fries, of course. The small, curated menu has something for everyone’s taste, including vegetarian and vegan options. The portions are on the smaller side, so get a few to share.
Just upstairs from Café Robey is the second-floor lounge, the perfect place to order an espresso, plug in for work or a grab a round of handcrafted cocktails with friends. The lounge is outfitted with reclaimed retro furniture from local shops like Salvage One. This area serves as the hotel’s living room, breakfast room for guests, and all-day bar. Whatever you’re there for, prepare to be distracted by the view: it’s the best seat in the house for gazing out on the street action.
THE UP ROOM
The Up Room is The Robey’s rooftop cocktail lounge, boasting a breathtaking 180-degree view of the Chicago skyline. Highlights of the cool craft cocktail menu include the Duck Fried Rice (Sesame Infused Aylesbury Duck Vodka, Lemongrass Infused Ford’s Gin, Bitterman’s Tepache) and a dealer’s choice option if you’d like your bartender to call the shots, which I LOVE! You tell them the type of drink or flavors that you typically prefer or want to try in a cocktail (I prefer sweet) and they will drum up a tasty concoction. There’s also an extensive list of wine, locally brewed beer, whiskey and bourbon.
The Grotto—a secluded, private alcove nestled within The Robey’s bell tower—is sure to impress for those special occasions. It is heated in the winter and they provide fuzzy lap blankets for added warmth. A glass-enclosed indoor lounge at the center includes a small retro bar that seats four, surrounded by a wide wraparound exterior deck.
“The inspiration for this hotel is a bit of Edward Hopper and that all-American experience.”
You’ll need to get your name on the guest list the instant you check in, because access is not guaranteed even if you are staying in the hotel. At present, the Up Room opens at 6 p.m. on weekdays (1 p.m. on weekends). The view is distinctly different from what you’ll see from its downtown counterparts. At night, the lights on Milwaukee Avenue and the parallel L track lead your eyes straight to the Chicago skyline; by day, the same view expands to include Lake Michigan.
Cabana Club is the Robey’s sixth-ﬂoor rooftop pool and deck, which overlooks the entire Wicker Park neighborhood. Cabana Club serves summer classics like house-made chips and guacamole and a variety of small bites, all available poolside. You can also get a local favorite, Jeni’s Ice Cream, for dessert. Cabana Club is equipped with two full bars—indoor and poolside—the perfect place to relax with fun frozen cocktails and food while soaking up the sun.
Fun fact: In the late 1800s, Wicker Park was called the Windy City’s “Polish Gold Coast.”
Cabana Club also has amazing skyline views. To the east, you’ll spot Chicago’s John Hancock Center as well as the tops of lower-altitude neighborhood churches. A refreshing triangular pool is neatly slotted into the rooftop terrace, so pack your swimwear. Cabana Club is open from May through September.
THE ROBEY HALL
The Robey Hall is a multifunctional event space with a unique ambiance, located in the adjoining former Hollander Fireproof Warehouse. It’s great for standing cocktail receptions, concerts, fundraisers, galleries—the list goes on! Here you’ll ﬁnd street-level access, two large bars, lounge seating with custom-designed furniture by Delordinaire architects and presentation capabilities, all with that authentic Wicker Park vibe.
Rates at The Robey vary, but a double-occupancy room starts at $165 (excluding tax at 17.4-percent). The hotel also charges an additional resort fee of $18.00 per room per night on check-out. Rates do not include breakfast: an American breakfast is $12, or choose from the à la carte menu.
- The Robey offers a café, lounge, rooftop, pool terrace and private event space
- Triangular-shaped Corner Suites afford the best city views
- 180-degree views of the skyline from The Up Room and Cabana Club
- Located near an award-winning dining scene
- Le Labo toiletries in all the rooms
- 24-hour front desk and security
- In-room snacks, 2 bottles of water and 2 local beers, refreshed daily
- Discounts at participating local shops
- Located a 15-minute drive or train ride from the Loop, Chicago’s central business district
WHO SHOULD GO?
The people are one of the main reasons visitors love the “second city.” We welcome tourists with a friendly, hardworking and down to earth attitude and are happy to share the pride and passion we have for the city including our top dining and drink options, iconic attractions, and accommodations such as The Robey.
You also don’t have to go far to have an awesome vacay. Turns out Chicago is a pretty great spot for a staycation, so why would you want to leave if you can have that perfect getaway right here in your own city? The Robey is a great option when you have extra vacation days to burn or need some time away where you can disconnect while enjoying local offerings in the neighborhood or downtown.
Business travelers should be aware that the hotel is about a 15-minute drive or train ride from the Loop. The nearest El stop is steps away (light sleepers may be able to hear it; the hotel provides complimentary ear plugs).
WHEN TO GO
Downtown Chicago is one of my favorites, but if this isn’t your first time in the city, the best local experience is at The Robey. If you are still looking for that downtown atmosphere, spend a night or two at The Robey before staying at Chicago Athletic Association or The Silversmith Hotel that will allow you to take advantage of the other abundant Chicago activities and attractions. The best times to visit Chicago are May through September when the temperatures are warm, a variety of festivals take place and crowds are manageable. You’ll find higher rates during these seasons, but you’ll also escape Chicago’s notoriously bitter winters. Chicago experiences frigid temperatures from November to March, but if you can hack it, hotel and airfare deals are easy to find.
The Robey’s allure is the combination of its unique refurbished interior and views with the attractions of the surrounding neighborhoods. The area’s restaurants and shops are thriving within an arts and culture-centric community, all beneath the historic steel girders of the city’s L train. Wicker Park is a great choice for travelers interested in culture, city walks and city trips. Plus, the bordering area of Bucktown—with its charming storefronts and roots in the arts community—creates an irresistible mix that draws locals and visitors alike.
- Wicker Park (0.1 miles)
- Chicago Theatre (3.5 miles)
- Steppenwolf Theatre (1.6 miles)
- United Center (2.2 miles)
- Second City (2.5 miles)
- Lincoln Park Zoo (2.9 miles)
FOOD + DRINK
- Big Star (0.1 mile)
- urbanbelly (0.1 mile)
- Piece Brewery & Pizzeria (0.1 mile)
- Taxim (0.1 mile)
- The Violet Hour (0.1 mile)
- Paradise Park (0.1 mile)
- Umami Burger (0.2 miles)
- etta (0.2 miles)
- Jeni’s Ice Cream (0.2 miles)
- Handlebar (0.4 miles)
MOST POPULAR LANDMARKS
- Wrigley Field (3.7 miles)
- Lakeshore Drive (5 miles)
- Willis Tower (3.6 miles)
- Magnificent Mile (3.5 miles)
- John Hancock Center (3.8 miles)
- Millennium Park (3.9 miles)
- Art Institute of Chicago (4.4 miles)
- Navy Pier (4.4 miles)
Location: Wicker Park
Category: Boutique Hotel
Check-in: 3 p.m.
Parking: $45 per car / overnight
TripAdvisor Rating: 4.5/5 stars | #44 of 204 Hotels in Chicago
Yelp Rating: 3.5/5 stars
Have you stayed at The Robey? Locals, have you popped in for a drink? What are your thoughts? Share them in the comments!
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