Chicago’s West Loop is arguably the city’s trendiest neighborhood. From flashy cocktail bars to hip hotel rooftops and some of the best dining options in the city, it seems there’s no shortage of ways to spend a weekend here. Of course, those endless options can also be a bit overwhelming. Think of this list as a primer for the range of experiences the area has to offer, from restaurants and bars to more unique experiences.
The Hoxton is the latest addition to Chicago’s ever-expanding roster of boutique hotels, and while it has some stiff competition in the surrounding neighborhood, what truly sets it apart is its beautiful, expansive lobby. The Hoxton lobby takes Soho House’s airy Instagrammable aesthetic and blows it up by a factor of ten, folding in a coffee counter, a full-service bar and a surprisingly delicate Mediterranean menu courtesy of in-house restaurant Cira. It’s all wrapped up in a tasteful Art Deco-inspired presentation of the brass fixture and muted pastel variety, complete with a seemingly endless array of seating options. Whether you’re looking to dine, drink, do some work or just lounge, the Hoxton’s spacious lobby has a space for you.
Maybe $15 cocktails and Instagrammable lobbies aren’t your thing. Maybe your thing comes in the form of scuffed-up sneakers and cans of PBR and the clacking of wheels on concrete. If that’s the case, the House of Vans on Elizabeth Street might be more your speed. The converted warehouse is part skatepark, part concert venue, part multi-use art space. It’s held performances from artists such as Vic Mensa and Iceage, multimedia art installations, artist-led workshops and free open-skate sessions with complimentary pizza and beer. Oh, and there’s a food-truck in back. Check Vans’ website to see what’s on the roster for your visit. Then go dig out those ratty old Sk8-His.
Down the street from the Hoxton is Punch Bowl Social, the one-stop shop for classically American games. The huge space is home to a miniature bowling alley, a billiards table, a faux-hearth with obligatory armchairs, private karaoke rooms and much, much more. It’s also eminently Instagrammable – look no further than the bevy of tagged posts featuring the now iconic multicolored laundromat facade in the bar’s lobby. Snapshots, pool shots, regular old alcohol shots – it’s all here.
Another contender in the West Loop’s expansive boutique hotel landscape, the Ace Hotel off Fulton Market is a must for anyone looking to soak up the sun during Chicago’s brief yet wondrous patio season. The Waydown bar and terrace, located on the seventh floor, boasts one of the best views in the city, a veritable wide-lens portrait of Chicago’s famous skyline that looks especially brilliant when illuminated by the setting sun. Waydown is also jam-packed with events, performances and more, featuring DJ sets, artisan exhibitions and weekly midday coffee talks from local creatives. There’s room to roam on the terrace, so head on up and stake your claim.
Take a stroll down Fulton Market past midnight and you’ll come across a strange sight: a line of people waiting to get into what appears to be an empty barbershop. It’s all a ruse, of course; while the front parlor at Blind Barber is a real, functioning shop during the day, at night it turns into one of the coolest clubs around. Head through the shop to the back room to find a low-lit lounge complete with wood-paneled walls, low-backed couches and a killer roster of cocktails. Depending on the night, you might also find yourself rubbing elbows with members of Chicago’s creative community; the back room often plays host to Aux Cord DJs, a monthly dance party in which DJing duties are handled by a different local creative each month. Get there late, but not too late, or you might be left looking in on that empty storefront. For more nightlife check out our guide to the best bars in Chicago.
So you’ve had your fill of eating and drinking. You want something new, something out of the ordinary, something to get your heart pumping. If that’s the case, climbing up a sheer rock face at Brooklyn Boulders just might be what you need.The rock climbing gym features both bouldering and belay climbing options ranging in intensity from beginner to veteran. You can dive right in on the free climbing with a $25 day pass, but to access the roped climbs you’ll have to take an hour-long course, in which you’ll learn the basics of climbing before being set loose to scale the walls. When your hands are sore and your arms are aching, head up to the in-house co-working space to unwind before heading back out. Whether you’re a thrill seeker, a workout junkie or just looking for something out of the ordinary, make a trip to Brooklyn Boulders – you won’t regret it.
Just look for the white hand on the black door. That will lead you down to this hidden ramen joint, situated underneath perennial lunch favorite Green Street Smoked Meats. High Five can usually be found with a line out the door and wait times of around two to three hours. Its low seat count is part of the appeal, of course; it really does feel like a back alley shack. The secret is all in the timing, however. Get there at the right time and you and a date could slip right in and find yourself a spot at the counter. Of course, you can always drop your name at the door and spend the intervening hours hanging around the neighborhood. We’ve had the best luck when making it the last stop on a night out. The low-key, dim vibe makes it perfect for late-night munchies, and you may have better luck finding a seat after midnight. To plan the culinary side of your trip in more detail, eat your way through our guide to the best restaurants in Chicago.