Anyone who spends time in Chicago is likely well familiar with the six-corner intersection where Damen, Milwaukee and North Avenues meet. This the place where Wicker Park and Bucktown brush up against one another as well, the two combining to create what has over time become one of the most impressive sections of any city in the Midwest, a vibrant, very cool place brimming with cafes, nightspots, high-end boutiques and acclaimed restaurants that feels almost New York-like in its coolness. (Not that you'd ever want to mention New York's name to anyone around here, of course. Not unless you were looking for a lecture.)
Once just another scruffy commercial district centered around a Blue Line elevated train stop between Chicago's Loop and O'Hare airport with a Polish luncheonette among its chief attractions, the last decade or two have seen extraordinary change in Wicker Park and Bucktown, along with so much of the rest of the city.
While the area is now firmly on the list of places you absolutely should visit, once you wear out the soles of your shoes exploring Chicago's monumental and more vibrant than ever city center, for the longest time, there was always something missing. This was one of those good-for-a-night-out sort of places – you came up here to dip your toes in the neighborhood's particular brand of cool, before heading back downtown to your pleasant but relatively unimaginative lodgings.
This winter, everything has changed. Right at the busy intersection, in its most iconic building – the flatiron-shaped, art deco jewel that is the Northwest Tower – not one but two hotels have opened for business. First, there's the Robey, quite easily the first hotel in the city to combine cool and chic quite so effortlessly. Then there's the Hollander, a terrific little hostel where you can sleep affordably without sacrificing style. Both projects are the brainchild of Grupo Habita, the Mexico City-based boutique hoteliers that have all but changed the way many travelers experience Mexico; this project mirrors the dual-purpose Downtown Mexico hotel, the group's popular hotel/hostel combination carved out of a 17th century residential building in Mexico City's gorgeous historic center.
Not that you'd know who was behind all this, stepping into the property and lounging in its gorgeous first-floor café and bar, or the more mellow, second-floor lounge (not to mention its greenhouse-style rooftop bar, with stunning city skyline views). With all the terrazzo and wood grain and frosted glass and things upholstered in olive green and navy blue, the mood is entirely classic Chicago – a celebration of the genre not typically seen outside of those masculine old skyscrapers in the Loop. It is, quite simply, one of the best hotels this city has ever seen, part of a tiny group of lodgings that feel authentically cool.
In the end, however, it's not just about new hotels, as nice as they are – this is about how their arrival in this part of town changes the game for visitors to Chicago. No longer must visits revolve around the city center and the lakefront – it's now entirely feasible to spend a satisfying weekend break in an entirely different version of the city, a Chicago that feels worlds away from downtown's mass tourism – even if you'll always be able to see the skyline, one of the world's best, from your hotel room. Eager to switch things up on your next visit? Here are the five essential first stops.
A decade in the making, a decommissioned, elevated railbed stretching for 2.7 miles (and right through Bucktown) is now one of Chicago's best parks. Unlike New York's narrower High Line, there's lots of room for everyone – cyclists included – up here, making this a great place to get some exercise in, as well as engage with some of the city's most interesting neighborhoods. (Maps and information at the606.org)
The Flatiron Arts Building
Across the bustling six-corner intersection from the hotel, this handsome building is filled with studios belonging to every type of creative type you can think of, from tattoo artists to costume designers. Open to the public, you can always drop by to see what's happening – there's always new art to check out and events taking place many evenings. If you like a sure thing, come around the first Friday of each month – that's when most everyone opens their doors for a festive and fun evening. (1579 North Milwaukee Avenue)
A pleasingly sophisticated Tex-Mex menu is the co-star at this alluring, nearly chic update on the classic counter joint – the almost intimidatingly-cool spot just out from underneath the elevated tracks is one of those worth-a-journey places that's garnered its share of national acclaim for good reason. It's one of many places that is helping to cement Chicago's status as one of the best places to dine right now in North America, full stop. (1545 North Damen Avenue)
No matter which pricey burger chain you currently swear loyalty to, prepare to have your world rocked by this humble but rather magnificent outpost of Au Cheval, home to one of the country's most talked-about cheeseburgers (and for good reason). The burgers here are slightly less elegant than the originals, but they're also cheaper –served up with impeccable, fresh-cut fries, you can combo it up for about $11. That's roughly the same or not much more than so many vastly inferior burger joints now cropping up across the land. This place might even be – gasp! – better than Shake Shack. Oh – they do shakes and serve booze, too. (1732 North Milwaukee Avenue)
Whether you stay here or not, the hotel's magnificent second floor lounge – with big windows looking out on to the busy heart of the neighborhood – has its own coffee bar and waiter service throughout the day. It's becoming a popular place for locals to work and mingle throughout the day and into the cocktail hour. If it's not full of hotel guests, make sure to stop for a civilized drink at Up and Up, the rooftop lounge. (2018 West North Avenue)
Looking for more to do while in Chicago? We have a few more ideas: