The Robey

Booking a highrise hotel in downtown Chicago may be the default, but if experiencing the city like a local is more your style, consider The Robey. It’s situated right at the six-cornered intersection of Milwaukee, North and Damen avenues, where Wicker Park and Bucktown converge. 

After the Great Chicago Fire, this area was settled by the city’s German, Polish and Norwegian immigrants in the late 1800s, and later evolved into an enclave for musicians, artists and other creative types (the Rolling Stones famously played a surprise show here in the late ’90s). Though these spots aren’t as gritty as they once were—as evidenced by the number of daycares, dentistry studios and medspas—they still deliver plenty of cool options for dining, drinking and shopping. 

The location’s convenient, sure, but what makes The Robey so special is that it spans two historic buildings, now adjoined: the triangular Art Deco-style Northwest Tower (the first building of its size built outside of downtown in 1929) and the Hollander fireproof warehouse built in 1905. The combination gives the hotel a quirky layout that packs plenty of personality into a relatively small footprint. Here’s what I thought of my stay. 

What are the rooms like at The Robey?

The 89 single-bed rooms in the Tower hint at the building’s former life as an office building. It’s all Mad Men-meets-boutique hotel with hardwood floors, moody charcoal paint, white window sheers, and furniture that leans mid-century. Rooms with multiple beds in the former Hollander warehouse—now called the Annex Loft—have an industrial feel with high ceilings, concrete floors, and exposed plumbing. Bunk-style beds, locker-style cubbies and separate sink and water closet areas are holdovers from the building’s short-lived time as a hostel and have the added bonus of working well for groups. 

If you prefer cushy comforts, you might find the rooms in both buildings a bit spare, but the coolness factor is undeniable. Toiletries are courtesy of much-obsessed-over New York City perfumery Le Labo (Santal 33, of course). And the corner king rooms are wedge-shaped with the bed facing two walls of windows, so you can fall asleep to the glow of the downtown skyline and let the sun rising over the city wake you in the morning. Hard to imagine what could be more romantic for an urban rendezvous. 

What is the service like at The Robey?

Warm and easy-going. At check-in, José at the front desk made sure I knew the happy hour deals at the hotel restaurants ($3 tacos until 3pm at Solana and $9 menu items at Clever Coyote) and exactly when I could expect a tray of freshly baked chocolate-chip cookies to land in the lobby (that would be 4pm). Service here isn’t as formal and in-your-face attentive as you’d experience at a high-end downtown hotel—for example, room service drink buckets left in the hallway weren’t collected until the next day—but the more laid-back style aligns with the neighborhood’s vibe. 

What is the food like at The Robey?

On the tower’s first floor, Cafe Robey serves brunch all day. Pancakes are impossibly fluffy and thick wedges of hashbrown casserole accompany the breakfast sandwiches. At nostalgic ’90s-themed bar Clever Coyote on the tower’s second floor, you can sip tiki-inspired drinks while you shoot pool, play arcade games or face off with a drinking buddy at the shuffleboard table. On the tower’s 13th-floor rooftop you’ll find The Up Room, a stunner of a cocktail bar where outdoor tables face the balcony’s stone edge to maximize the view. Hotel guests get early access at 4.30pm, so you can sneak in your Instagram snaps before it opens to the public at 5pm. On the Annex Loft’s sixth floor, poolside perch Solana has a walk-up taco bar. And the Robey’s owners also operate Valedor next door, where you can score complimentary tapas with your cocktails during Cantina Hour (5-7pm). 

With these options alone, you could eat and drink well without ever leaving the hotel. But then you’d miss out on the insanely tasty pastries at Mindy’s Bakery, falafel at Sultan’s Market, ice cream sundaes at Margie’s Candies, burgers at Small Cheval, rosemary margaritas at Antique Taco … I could go on.

What are the facilities like at The Robey?

Hotel pools in Chicago are hard to come by, let alone triangular heated rooftop pools like The Robey’s. Though it’s petite in size, the panoramic views and bar serving fruity frozen margaritas and piña coladas makes the sixth-floor deck feel genuinely close to paradise on a sweltering summer day. Since it’s open to the public, I was worried it would be slammed, but special guests-only hours (8-11am) along with a row of lounge chairs reserved the rest of the day meant I easily found a place to kick back poolside. 

There’s no onsite gym, but thanks to a partnership with Bucktown Athletic Club down the street, guests can take fitness classes or use equipment there with a pass provided at the front desk. 

What’s the area like around The Robey?

Head north on Damen Avenue (called Robey Street prior to 1927) to shop Bucktown’s boujiest beauty and fragrance boutiques—think Credo, Bluemercury, Diptyque, and Aesop. If scouring racks of vintage threads is more your style, head southwest on Milwaukee Avenue, Wicker Park’s diagonal main drag, for a bevy of resale shops. Whether by bike or on foot, checking out The 606 is a must. This elevated trail built on a former rail line connects several street-level parks and also features public art installations and scenic lookouts. Conveniently, bicycles and helmets are available to check out at The Robey’s front desk. 

DETAILS

Address: 2018 W. North Avenue, Chicago

Price: Starting around $195, with many dates in the $250-$550 range depending on the season

Closest transport: 0.5-block walk to CTA Blue Line (Damen station), with service to O’Hare Airport (30 minutes) and Chicago’s downtown district (20 minutes).

Book now: via Booking.com

➡️ Check out Time Out’s full list of the very best budget hotels in Chicago. 

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