While the Loop is Chicago’s geographical heart, it can often seem impenetrable when trying to find a good spot to let loose and have some fun. It is, after all, the central hub of business for the Windy City.
The Loop is where skyscrapers loom, taxi cabs blare and the El Train clatters without end. But do a little digging – or climbing – and you’ll find a vibrant cultural wonderland hidden just beneath all the gleam and glimmer. From swanky rooftops to corner dives, Culture Trip has gathered 13 of the best places in the Loop to grab a drink and hang out.
Bar, American, African, Cocktails, Wine, Beer, $$$
At the top of the Chicago Athletic Association on the Magnificent Mile is Cindy’s, perhaps the crown jewel of Chicago rooftop bars. With unbeatable views of Millennium Park and an exquisite roster of craft cocktails, Cindy’s is the prime choice for those looking to experience the height of luxury in Chicago. It’s not cheap, but that’s the point.
The second rooftop bar on this list comes atop the classical Chicago architecture of the LondonHouse hotel on Wacker Drive. The views from up top capture the glory that is the Chicago riverfront – the beautiful old stoneworks and shining new spires, the low iron bridges and the soft yellow pumping of traffic. The tri-level rooftop bar is best observed from the comfort of the limited array of couches, so be sure to reserve seating if you can.
The third bar on this list is Cerise, located on the rooftop at Virgin Hotels. Where Cindy’s and LondonHouse speak to the aristocratic set, Cerise is geared more towards the musically minded. The 26th-floor terrace is a cool half-in, half-out setup that wraps around half the building and features a central dance floor that has played host to many international DJs. Down on the 25th floor lies a mini-stage that has hosted local rockers and rappers alike. You can’t go wrong with either floor, so head on up and see what Cerise has in store for you.
Boutique Hotel Restaurant, Brazilian, Guatemalan, $$$
Boleo offers Peruvian-street-food-inspired small bites | Courtesy of Boleo
This rooftop restaurant, located on the 15th floor of the Kimpton Gray in the heart of the Loop, is the most foodie-oriented of all the hotel-attached spots on this list. Chef de cuisine Franklin Perdue’s menu features South American staples such as fried yucca and ceviche de mahi alongside a tailor-made cocktail service of similarly sub-equator creations like fernet and cola or seasonal piscos. It’s all housed under a retractable glass rooftop so that you can enjoy the taste of the tropics rain or shine.
Monk’s Pub is a neighborhood classic on Lake Street and a rarity in the Loop, remaining in continuous operation for over 40 years in a part of town that often favors the shiny and new over the tried-and-true. It’s the classic pub food, huge beer selection and no-frills decor that keep customers coming back, though. With a facade like an old German drinking hall and an ambience to match, Monk’s feels like a comfortable slice of low-stakes fun in the middle of all the rooftop pageantry.
For a restaurant with even deeper roots, look no further than The Berghoff – one of the most entrenched institutions in the Windy City. It first opened in 1898 and has remained in almost continuous operation since, closing for just one year in the mid-2000s for renovations and transitional tidying up. The restaurant features a mix of classic German fare and lighter, more contemporary offerings, while The Berghoff Bar and The Berghoff Cafe feature extensive draft selections and quick lunch options. It wouldn’t be complete without the luxurious old-world ambience, which makes you feel as if you’ve stepped into Prohibition-era Chicago.
City Winery Chicago lies on the Chicago Riverwalk | Courtesy of City Winery
City Winery Chicago lies on the beautiful Chicago Riverwalk. For those working in the heart of the city, it is the spot to visit for lunch and happy hour. The tableau of the river and surrounding buildings is serene, and the riverwalk features enough built-in seating to accommodate a crowd. The selection features, naturally, a hearty wine selection alongside craft cocktails and an array of dishes ranging from light appetizers to pasta entrées. During the winter, City Winery Chicago converts its patio space into heated domes so you can drink and dine no matter the temperature. During just about any time of year, you can be sure to find a crowd letting loose right alongside the Chicago River.
Revival Food Hall has many vendors, offering something to suit every taste | Courtesy of Revival Food Hall
Revival Food Hall is a chic, surprisingly packed spot featuring an array of Chicago favorites. There’s Brown Bag Seafood Co. with its truffle parmesan tots, Antique Taco Chiquito’s proven Mexican fare, Smoque’s barbecue sliders, and many more local legends. At 5pm, the Revival Café-Bar becomes a bustling post-work hang-out spot, with a solid selection of beer and cocktails. There’s even a small corner store that sells books, vinyl and other knick-knacks. If you’re looking for a one-stop shop for all of your consumption needs, Revival is your best bet.
Play darts while sipping cocktails at Flight Club Chicago | Courtesy of Flight Club Chicago
Do you like darts? Then Flight Club Chicago should be on your list. You don’t need to be a dart extraordinaire – but it does help. Billed as “Social Darts,” Flight Club Chicago is a gastropub built around that classic American bar sport. There are five unique versions of dart games available, tailor-made to accommodate groups of up to 20 participants. It’s a great venue for big groups, with a selection of bites available so you never have to leave your designated dart dojo. Of course, you can drink at the beautiful Art Deco-inspired bar, if that’s more your speed. No sharp throwing skills required.
While technically just outside the Loop proper, the House of Blues, a nationally renowned chain, is one of the few music venues still standing in the neighborhood – outside of a handful of jazz clubs. The House of Blues is, of course, a great place to catch Chicago blues acts, but it also has plenty of big-name artists for those in the mood for something more contemporary. There’s an attached restaurant and bar, which makes for the perfect pre- or post-concert stop. There’s also the Gospel Brunch on Sundays, which features an extravagant buffet spread accompanied by local talent performing gospel standards. What better way to spend your day of rest?
The Emerald Loop Bar and Grill has many TVs for sports enthusiasts | Courtesy of Emerald Loop
The Emerald taps into the Irish side of Chicago’s ancestry, featuring Irish classics such as shepherd’s pie or bangers and mash alongside more traditional pub fare. While there’s ample patio space for the summer months, the barroom is a no-frills expanse of unadorned tables. It makes for a great brunch spot, especially if you’re in the mood for a full Irish breakfast.
On the other side of the adornment spectrum lies Beatnik, a perennial favorite for the Instagram crowd due to its killer decor and riverside placement. The ambience lies somewhere between Moroccan hideaway and Parisian parlor, complete with lush greenery and frilly parasols. Its riverside seating is the obvious draw, but the whole space is immaculately decorated and features a streetside coffee bar and patio space. The menu is similarly photo-friendly, featuring a blend of the Spanish and Mediterranean dishes that made the bar’s West Town sister restaurant so popular.
How else to round out this Loop list but with one last rooftop spot? This one isn’t quite as stratospheric as the other contenders – residing on the third floor – but its riverfront placement and unique elevation level make for a more relaxed atmosphere that’s matched by the ample floor space and bite-friendly menu with plates primed for sharing among friends. An ideal destination for those with a fear of heights or an aversion to the overly glamorous, RAISED is the perfect middle ground between all the Loop has to offer.