A Chicago Weekend Guide For Creatives

 In Culture, Guide

Chicagoans have long known that the Midwest city was a unique middle-of-America hub for great food, arts and entertainment. Often thought of as the third American city to hit for a culturally enthused weekend, the rest of the U.S. needs to catch up with our brothers and sisters enjoying the western shores of Lake Michigan. We recently delighted in a long weekend through this Illinois metropolis. Skyscrapers peppered the skyline but didn’t shield us from a biting breeze that was so cold it may have ruined our moods if it weren’t for the incredibly prompt Uber, Lyft and taxi drivers.

Our trip was unique, in that we were searching for a particular experience. It wasn’t enough to just have a weekend holiday—we required a trip with a creative bent. We know what most tourists do when they have a few days in the Windy City: Cloud Gate in Millenium Park, Willis Tower, Navy Pier, Michigan Ave. While all are fantastic options, we wanted an inspiring three days that would trigger the next great story or stage the next beautiful photo. Let us be your guide.

Ace Hotel ALIVE Magazine Chicago

Ace Hotel; photo courtesy of Anjali Pinto.

Where To Stay: Ace Hotel
Ace has erected hotels in New Orleans; Pittsburgh; L.A.; London; Palm Springs, CA; New York; Portland; Seattle; and now Chicago. For their new installment, they chose a modern concrete-and-glass building in Chicago’s West Loop neighborhood, a place packed with award-winning restaurants and famous neighbors like Google and Twitter. The boutique hotel—only blocks from the nearest “L” station—is distinct from its sister hotels, embodying the spirit of Chicago. In fact, the young beverage director, Caitlin Laman, told us one evening during our visit that the hotel specifically hired (and listened to opinions from) Chicago natives while building Ace, so that the hotel would reflect the attitudes and desires of the city.

Upon entering the mid-century modern decor-filled lobby, you begin to notice that this hotel is not just a place to stay, but a place to chill. Stylish couches, rustic tables, mid-century tapestries and strategically placed outlets make the Ace lobby a focal point for tech-laden millennials to gather.

Two bars occupy the space—one on the first floor by the door that seems to be reserved for stylish Google employees and their dogs, or visiting musicians in town for a concert—and another, Waydown, with a stellar rooftop patio and view of the Chicago skyline. Select guestrooms are equipped with a Martin guitar or a selection of records, each with a description of what to do while listening to them. Clever.

Ace Hotel Room Chicago ALIVE Magazine

Ace Hotel Room; photo courtesy of Spencer Lowell.

Where To Eat Breakfast: The Allis
Not only does The Allis provide an Instagrammable interior, the food is also swell. Guests can be seated in an eclectic assortment of wing-backed chairs, or a long community table. And the people-watching is fabulous as Chicagoans walk by outside the floor-to-ceiling windows and retreat from Green Street into this brunch haven.

Where To Eat Lunch: City Mouse
If one is lucky enough to sleep in while resting under Ace’s Pendleton wool comforters, we recommend stumbling downstairs for brunch or lunch at City Mouse. The team, also responsible for local eatery Giant, serves a Midwestern-inspired seasonal menu comprised of burgers and a delightful avocado toast, created by executive chef, Pat Sheerin.

City Mouse Ace Hotel Chicago ALIVE Magazine

City Mouse, Ace Hotel; photo courtesy of Spencer Lowell.

Where To Eat Dinner: Boka
Boka shares a restaurant group with James Beard Award-winning restaurant The Girl & The Goat, but Boka is no slouch. Over the restaurant’s impressive 12-year run, the team has been nominated for three James Beard Awards themselves and have received the prestigious Michelin Star distinction since 2011. The atmosphere is perfect for a luxurious late-night dinner. Dark and moody lighting flows around deep booths with plated art arriving from the kitchen by way of flawless service. Make a reservation, because this Lincoln Park gem is always packed.

Where To Get Drinks: Waydown and Cindy’s
Both of these rooftop bars boast impressive views and are an easy pick for an evening cocktail. Since you’re staying at Ace, Waydown—named after Illinois native John Prine’s tune—is right upstairs on the seventh floor. The lounge hosts nightly musical entertainment with DJ sets and offers a menu, crafted by Laman that includes a no-nonsense combination of crafted cocktails and popular beer and wine.

Where To Be Inspired: Museum of Contemporary Art Chicago
It’s hard not to be taken aback when you see your first Andy Warhol. But this museum‘s permanent collection also includes the creepily beautiful “Marisol,” by Marisol Escobar (the institutions first purchase) and a 20-foot-high, 20-feet-long animal skeleton created by Maurizio Cattelan. Reality bends as you circle through MCA.

Where To Be Rejuvenated: The Garfield Park Conservatory
A weekend trip to Chicago during the winter months can at times be brutal. Trudging through the wet streets and shielding your eyes from the biting wind can make you rethink the whole trip. Enter the Garfield Park Conservatory. This free, glass-covered oasis is one of the largest spaces of its kind in America. Each distinct room evokes a lush atmosphere of plant life, all at a comfortable warm temperature.

Where To Listen To Music: Kingston Mines
Before heading back to Ace, hail a cab to this famous late-night blues bar that has been nurturing the Chicago music scene since 1968. Live bands play on two stages seven nights a week. And, on Saturday, they stay open until 5 a.m.

After a whirlwind getaway but before your trip to the airport, grab a coffee at Portland-based Stumptown (situated off the lobby of Ace Hotel Chicago).

Here’s hoping that your trip gets your creative juices flowing.


Thank you for supporting the businesses that keep ALIVE growing. This post has been made possible in part by Ace Hotel Chicago. Opening photo is by Sawyer Bengtson.


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