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Spending 48 Hours in Chicago, IL

Chicago’s architecture, art, and green spaces galore make the Windy City one of the most visited spots in the country—and one that continually blows guests away.

Written By:  Jennifer Kornegay

Photographers:  Supplied

Photo courtesy City of Chicago

48 Hours in Chicago

Chicago’s abundant (and awe-inspiring) architecture and art, diverse shopping, widespread dining options, and green spaces galore combine with its lakeside setting to make the Windy City one of the most visited spots in the country—and one that continually blows guests away. There’s enough to see, do, and eat to keep you busy for weeks, but if you’ve only got 48 hours, here are a few highlights.


4 p.m.
Check in at the The Alise Chicago, a chic and contemporary, yet cozy, boutique hotel that boasts all three of real estate’s most important points: location, location, location. Just a few blocks off of one of the city’s main thoroughfares, Michigan Avenue, it’s within easy walking distance of several major attractions and areas of interest.

7 p.m.
Head out to dinner at one of the newest iterations of a Chicago institution, the steakhouse. Sitting on the edge of the city’s Ukrainian Village, in a building that was formerly a butcher shop, Boeufhaus is small, intimate, and dimly lit (with chandeliers burning real candles), and it is the perfect place to heartily indulge in a massive, cast-iron-skillet-seared, dry-aged ribeye, with a side of fries that are crisped in beef fat.

10 p.m.
Make your way to Wicker Park’s Big Star, a taco joint that transforms into a bourbon-heavy bar at night. A large patio is the place to soak up the party vibe, sip a whiskey-based cocktail (or a tangy margarita), and listen the funky blend of old country and new rock blaring from the sound system.


9 a.m.
The Randolph Street area in the West Loop neighborhood is just right for breakfast at Little Goat. Hearty culture-clash items, like This Little Piggy Went to China (a sesame-cheddar biscuit with eggs, Szechuan pork sausage, and chili-garlic sauce), provide plenty of fuel for a full day.

10 a.m.
Spend the morning shopping this neighborhood, where posh stores replace high-rises. Check out Southern-sourced designer Billy Reid’s Windy City digs; peruse modern, minimalist furniture at Morlen Sinoway Atelier; and do some high-end treasure hunting amid the antiques and eclectic vintage finds (jewelry, records, art, and more) at the once-monthly weekend Randolph Street Market.

12:30 p.m.
Fill up with the cheeseburger that’s been hailed one of Chicago’s (and America’s) best at the hip, always happening, Au Cheval, also on Randolph Street. Wash it down with a Boo Radley cocktail.

2 p.m.
It may be “touristy,” but you shouldn’t miss the vertigo-inducing views from the skydeck atop the 110-story, 1,450-foot-high Willis Tower (formerly the Sears Tower), the second tallest building in America. Step inside one of the deck’s glass boxes for a suspended-in-air sensation that will literally steal your breath.

3 p.m.
Make your way back toward Lake Michigan to spend the afternoon exploring Chicago’s museums. Check out the sparkling hall of gems at the Field Museum of Natural History, the colorful, glowing collection of Tiffany stained glass at The Driehaus Gallery, and the rooms upon rooms of paintings, drawings, photographs, and sculptures at The Art Institute of Chicago, which houses 300,000 works spanning centuries and styles.

7 p.m.
On your way to Alinea (where you must have reservations, made well in advance), prepare to be wowed. The fluctuation of bold, then nuanced, flavors of chef Grant Achatz’s experimental, unpredictable cuisine are matched by the emotions they’re designed to evoke, and the powerful dinner experience here led the James Beard Foundation to name it the country’s “outstanding restaurant” in 2016.


10 a.m.
Grab some complimentary coffee in the hotel’s sleek lobby, and walk over to Millennium Park. Snap the obligatory selfie in front of the mirror-surfaced Cloud Gate sculpture before losing the crowds and strolling through the Park’s Lurie Garden, a quiet spot bursting with colorful blooms (including brilliantly indigo Virginia bluebells) in spring.

12 p.m.
Before bidding Chicago farewell, savor a nontraditional brunch at Belly Q, an Asian barbecue eatery offering creative twists to wake up your taste buds, like the breakfast fried rice with ground sausage and scrambled eggs, topped with a strip of bacon and house-made, intense-orange Belly Fire hot sauce.

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