The Robey is an art deco icon with a flatiron footprint and light-flooded rooms revamped by up-to-the-minute modern design. The Cabana Club's rooftop pool and cocktail bar look out to the downtown skyline, but there’s every chance you won’t miss the bright lights of the city with two of Chicago’s hippest ‘hoods on your doorstep. Wicker Park and Bucktown – either side of the hotel – are the Chicagoan’s Chicago: tourist-light creative hubs where the bands are still making it and the snow globes are only ever ironic. They say that Chicago is the pulse of America; this is the pulse of Chicago.
Double rooms from £112.84 ($140), including tax at 17.4 per cent. Please note the hotel charges an additional resort fee of $24.65 per room per night on check-in.
Rates do not include breakfast; à la carte dishes range from $4-16.
One of our all-time, top five favourite cult rom-coms, John Cusack’s High Fidelity, was based and filmed in Wicker Park, despite the original Nick Hornby story being set in London. The closest thing to the fictional Championship Vinyl record store is the comparably old school Reckless Records (1379 N Milwaukee Ave), although Dick and Barry almost certainly don’t work inside.
At the hotel
Cocktail bar, lounge bar, café, free WiFi throughout. In rooms: Cable TV, Bluetooth stereo, iPod dock, minibar, hairdryer, Le Labo bath products.
Our favourite rooms
Every room gets a healthy dose of sunlight, but it’s the triangular-shaped Corner Suites which have the best views. They, along with the jumbo Panorama Suite, have windows along all but one of their sides, giving 180-degree views of the neighbourhood below and beyond that, the city skyline.
A refreshingly unheated triangular pool is neatly slotted into the rooftop terrace. There are ledge-side sunloungers and tables looking out over the city, and drinks service, so its worth packing your swimwear in anticipation now.
Binoculars, to make the most of the expansive views. In season, don’t forget your swimsuit for the rare-in-Chicago rooftop pool. For the young or young-at-heart, a kite – it is the Windy City, after all.
The communal areas and four King rooms are fully accessible to guests with mobility issues and have the ADA stamp of approval. There is a lift to all floors of the building.
All ages welcome. Highchairs and full-size or travel baby cots are available on request.
It looks out on the bustling six-corner intersection where Wicker Park meets Bucktown, so a people-watching window seat is a must.
Insider designers to fit in and stand out in Wicker Park; think Kamm pants and mules.
Modern-American comfort food: words to get the saliva glands going. Chef Michael Elliott oversees Café Robey’s brunch menu, which features a range of breakfast and all-day bites (booking recommended). Tuck into buttermilk pancakes or a wholesome breakfast salad of baby kale, lemon poppy vinegarette, strawberries, toasted sunflower seeds, goats cheese and poached eggs. Each dish is carefully crafted in the open kitchen and served up at sleek tables beneath the double-height ceiling. Up in the second-floor, the elegant Lounge (open September to May) serves dinners of potato gnocchi, 9oz teres major with blue cheese cream or roasted salmon with black lentils and curried cauliflower alongside an impressive cocktail and wine list.
The Robey is the highest building for miles around; the view from the Up Room, on the rooftop, confirms it. Low-slung sofas are slouch-ready by the bar, or beyond the floor-to-ceiling glass, there’s the terrace looking out to the twinkling skyline and up to the iconic Robey spire. Guests can secure their spot with priority access at 4:30pm, half an hour before the bar opens to the outside patrons. The Second Floor lounge, above Café Robey, is designed for work or play; it’s as well suited to a laptop-side coffee from Colectivo coffee as it is to refined cocktails and light bites with one eye on the streetscape outside. Head to the rooftop Cabana Club ($15 per person) for drinks with a view; to the east you'll spot Chicago's soaring John Hancock building and the tops of neighbouring churches – you might even catch a passing L train or two.
Cafe Robey is open from 7am to 9pm (10pm on Friday and Saturday). The lounge serves dinner from 3pm to 11pm, with last orders at 10pm. The Up Room bar is open from 5pm until late and Cabana Club from 11am to 11pm (11am and 12am, on Friday and Saturday).
A selection of modern-American yummies based on the Café Robey menu is available in your room, 8am to 10pm daily, as is dinner from the Lounge menu from 3pm to 10pm.
The Robey sits on the bustling intersection of Damen and Milwaukee Avenues, where the creative neighbourhoods of Wicker Park and Bucktown meet. It’s just over three miles to the Loop, Chicago’s skyscraper-laden central business district.
The mighty Chicago O’Hare airport is an international hub and a half, with flights all over the world including most major cities in the US and Europe. It’s 30 minutes by cab to the hotel (around $60, or $99 with a private transfer arranged by the hotel). Or arrive like a local on the L (elevated) train; take the Blue Line to Damen station. Chicago’s second airport, Midway International, is the same distance away as O’Hare, on the other side of the city.
From the hotel you could almost flick a dime into Damen station. The L train runs there into Downtown in about 20 minutes. For altogether longer journeys, head to Union Station (also on the L train Blue Line), where trains depart to New York, California, and plenty of places in between.
Roadtrippers can avoid the downtown crush by taking the 90/94 highway to W North Avenue, then driving west for half a mile to the hotel. Valet parking is available for $49 per night on a limited and first come first serve basis.
Chicago might be hundreds of miles from open sea, but those Great Lakes are all but an inland ocean. In summer, several ships cruise out across Lake Michigan, some even as far as Toronto and Montreal in Canada.
Worth getting out of bed for
Outside the Robey doors lie Wicker Park and Bucktown, two of the city’s most achingly trendy neighbourhoods, with enough vintage clothes stalls, bookshops and high-end boutiques to make it prime territory for a rummaging urban ramble. To explore the area, walk the 606 ( also known as the Bloomingdale Trail); the stretch of abandoned rail line runs through Wicker Park, Bucktown, and neighbouring Logan Square and Humboldt Park. Top of the shops are Robin Richman for a curated collection of designer threads, Una Mae’s for classic Americana fashion and an array of take-me-home knick-knacks, and Shinola, for Midwest-made clothes, watches and leather bags from the Detroit-based brand. Local art galleries include LVL3 and Jackson Junge, and Corbett vs Dempsey; the latter displays work by up and coming artists from the local area. There’s a farmers’ market on Sundays, and every summer Green Music Fest (mid June) and Wicker Park Fest (late July) bring lip-licking street grub and live music to Damen and Milwaukee Avenues.
For heroic Greek food go to Taxim, or head to Antique Taco for habanero popcorn, horchata milkshakes and tacos, glorious tacos. Booking is essential at Alinea, the Chicago instituation which has been named 'The Best Restaurant in America' three times.
You can’t go wrong with the single-origin brews at coffeeshop mini chain La Colombe; Fairgrounds Coffee and Tea is an artisanal alternative. For big-hearted dishes in a lighthearted diner, grab a counter stool at Dove’s Luncheonette; grits, brisket burnt-ends and buttermilk-fried chicken star on the deep-south-meets-Mex menu, served up all day and night long.
Fill up at Big Star, a 1940s gas station revamped as a basement-priced bourbon and beer bar where the long nights are played out to a rocking, rolling, honky-tonk kind of soundtrack. Speakeasy-styled Violet Hour shakes up artisan cocktails in sophisticated surrounds. No visit to Chicago would be complete without a visit to an authentic speakeasy – The Drifter has a rotating list of over 100 cocktails presented on Tarot cards and quirky nightly performances.
En route from the airport after a trip to visit Mr Smith in North Carolina, I call the Robey to angle for an early check-in – they oblige with a cheery ‘No problem’. I’m delighted already, and I haven’t even set foot in the building yet…
Driving down North Avenue, I spot my destination from almost a mile away – this pie-shaped piece of prime real estate towers over Wicker Park, the hipster heart of Chicago, and though I’ve lived in this city for 10 years, the thought of sleeping in it gives me butterflies.
Rolling up to the Robey, I’m greeted by a smiling doorman who collects my bags and makes me laugh as if I’m a regular. After a seamless check-in, I excitedly take the elevator to my room: 1104. Like all the rooms ending in ‘4’, it’s an exceedingly spacious triangle; like a ship’s prow overlooking the action below. There’s a king-sized bed, a sumptuous seating area, some covetable denim robes in the closet, and a TV with one of Chicago’s iconic Blues Brothers on it, beckoning me to sync my bluetooth and unwind to the music of my choosing. I’m surrounded by the smooth sounds of Gary Clark Jr in no time.
Hungry, I venture down to Café Robey on the first floor and find a comfortable seat in which to eye-up passing dishes (and those ordering them). It’s a local neighborhood triumph – elegant, comfortable, laid-back. As for the food, I highly recommend the frisée salad and fried chicken sandwich…
I retreat back upstairs with the intention of tackling a heaving inbox of emails, but I can’t help but succumb to the big white bed and its cashmere throw… Well rested, I rise to get ready to meet a girlfriend and find the bathroom well-stocked with Santal 33 (including, pleasingly, its much-loved Le Labo fragrance).
I’d tried once before, unsuccessfully, to drink in the Robey’s well-named top-floor bar, the Up & Up. This time, though, I’m there promptly at 6 to find my friend waiting on a cosy couch and we order champagne from our amiable host, who soon suggests a second round. As an admitted lightweight, I decline, but enquire instead after something that’ll wake me up a bit. He returns with two more glasses anyway (on the house) and a conspicuous little baggie. It was sugar, but the laugh we get out of the exchange was worth his effort.
We decide to head out onto the open catwalk that stretches all the way around the glass-enclosed bar to take in the night air and say our goodbyes. As we’re making our move, I spy none other than Chicago mayor, Rahm Emmanuel, enjoying a glass himself. Making eye contact and having a little moment with the mayor: this was a first for me in Chicago – thanks, Up & Up!
After a restorative night’s sleep, I wake to a drizzly day and head down to the second floor for a coffee uplift: a cup of tasty local blend, Metric. I find a seat and admire my surroundings (and mentally applaud the always-on-point music that’s soundtracking my stay). Not only is the Robey gorgeously designed and well-appointed, but there’s a Grupo Habito-styled hostel next door, I find out. Had this been around when I was in my early 20s, I’m certain I’d have used it as a fancy place to stay on the cheap.
For now, though, a return visit to check out the rooftop pool when it opens this summer has shot straight to the top of my to-do list. There’s nothing like Chicago in summertime and, I’m convinced, there’ll be nowhere better to enjoy it than here.