Explore Chicago's Hippest Neighborhood From This Mid-Century Modern Hotel

Imagine sipping Champagne above a cliff overlooking the Pacific Ocean, or indulging in a heavenly spa treatment with the Manhattan skyline in view. Even if your wallet can't quite stretch to a full-blown luxury getaway, sprinkling a touch of luxe into your travels can turn an ordinary trip into a memorable adventure. That idea sparked our new series, Flights of Fancy, where we take you along for a trip to the luxury experiences around the cities we adore.

Chicago is the U.S.’s third-biggest city, and one of its most exciting. While the city is undoubtedly the financial and cultural center of the Midwest, Chicago shouldn’t be relegated to a regional hub. A true global city, this diverse and sprawling metro has a lengthy history of influence in architecture, music, design, and the culinary arts, not to mention comedy and theater.

One of the benefits of taking a trip to Chicago is that it doesn’t have to cost an arm and a leg. Sure, it’s not going to be super cheap to visit any major city, but in comparison to the U.S.’s coastal hotspots, Chicago is a fantastic deal. If you’re particularly intrigued by the Windy City’s emphasis on architecture and design, you shouldn’t miss The Robey hotel.

Located in one of Chicago’s hippest and most bustling neighborhoods — Wicker Park — The Robey stands out for its mid-century modern design, many amenities, and fantastic location for exploring the local shops, eats, and nightlife.

About the Neighborhood

One of the biggest benefits of The Robey is its surrounding scene. Wicker Park has made countless lists of the coolest neighborhoods in the country, and for good reason — from the art murals adorning its historic buildings to the many thrift shops, speakeasies, and gourmet bakeries gracing its streets, it has all the makings of a hipster oasis, even if it’s a little more established these days. Ukrainian Village also borders Wicker Park to the South along Division Street, and has its own share of incredible shops, restaurants and bars.

Here’s how to get the most out of visiting this iconic hotel, no matter your budget. Plus, what to do in the neighborhood!

Stay At The Robey (Budget: $160+)

Booking a room at The Robey can be pretty reasonable. You can score the best deal by booking in the off season, staying Sunday through Monday, and springing for a Queen-sized room. Even The Robey’s most modest rooms are stunning design-wise, boasting decor that looks straight out of a West Elm catalog.

The main draw of every room at The Robey may be the decor, but a close second is the Wicker Park neighborhood’s buzzing energy. You’ll get to view the city lights through your window and revel in all the neighborhood has to offer once you step outside The Robey’s doors.

Every room comes with full access to the hotel’s amenities, which include rooftop pool (open seasonally), personal care items from Le Labo (like we said, this place doesn’t mess around when it comes to good branding), and complementary bikes you can use to traverse the bike-friendly near northwest side of Chicago. You’ll be right on Milwaukee Ave., a busy corridor that has a bike lane connecting the fashionable neighborhoods of Wicker Park, Logan Square, and Avondale.

Dine At The Robey (Budget: $50+)

If a stay at The Robey isn’t in your budget, consider checking out the hotel via Cafe Robey. Chef Michael Elliott serves up comfort food with a seasonal twist, and get this — you can get brunch at any time of day. Dreams really do come true.

If The Robey’s all-day brunch is what you’re craving, spring for the Duck Hash, Biscuits and Gravy, or the Chilaquiles, accompanied by refined yet indulgent sides like the Maple Glazed Pork Belly or the Whipped Ricotta with cherry pepper jam, honey, and sea salt.

More in the mood for dinner fare? We can’t recommend the Roasted Chicken enough, but if you’re more in the mood for something carby, the Ricotta Gnocchi is where it’s at. Wash whatever you choose down with Cafe Robey’s curated wine list or one of their many carefully crafted cocktail options.

Grab Drinks At The Robey (Budget: $20+)

If your budget is pretty limited but you still want a little bit of the Robey experience, head to one of the hotel’s three stunning bars. You could stay ground-level and check out Clever Coyote, a ‘90s inspired nostalgia bar that serves up tiki-style drinks and delicious bar food, all while letting you people watch from a cozy table in a gorgeous environment.

Got your sights set a little higher? Take the elevator up to the Up Room, The Robey’s 13th-floor lounge that allows you to take in the city skyline for miles and miles. The building is the tallest in the area, so nothing will block your view of the endless city lights.

Somewhere in the middle (more specifically, on the 6th floor) is the Cabana Club, which offers some great views that are a little more down-to-earth, though just as exciting. Take in all the sights and sounds of the city, from the El train passing by to views of the iconic John Hancock tower. This is also where the rooftop pool is located — and it’s open to all during the summer months!

Spend The Day In Wicker Park

Sure, you’ll find mainstay shopping destinations like Lululemon, Aesop, Free People, and Yeti along the corridors, but you’ll also discover some amazing and unique shops. Head to Una Mae’s for stylish clothing and gifts, or Kokoroko for curated vintage finds and kitsch items straight out of decades past.

Some must-visit culinary destinations include Big Star (seriously, the world’s best craft tacos and margaritas), Ina Mae tavern, and Folklore, an Argentine grill just steps away on Division. Oh, and cap off the evening with drinks at Violet Hour, the neighborhood’s famed speakeasy, or The Rainbo Club, an infamous dive bar that’s been in business since 1933.

In addition to all the shopping and eating you can do, there are plenty of opportunities to simply people-watch and spend time outdoors, too. Check out the neighborhood's eponymous Wicker Park, located right in the heart of the neighborhood. Sprawl out and admire the brick Chicago-style homes that line the street, or take a quick walk up to the 606, an old El train line that’s since been converted into a walking path and greenspace-boasting connecting corridor between many of the city’s neighborhoods.

With all that just outside your doorstep, it might be easy to forget the incredible scenery and culinary pleasures that await you when you return to your hotel for the night.

Main Photo: The Robey

Follow along for all your summer travel needs with our Flights of Fancy series and Jetset Journeys series.