Our Ultimate Weekend Guide to Chicago

Everything about this Humboldt Park coffee shop spells cool, from its vintage furniture (think: atomic sputnik light fixtures, vintage Pan Am posters, distressed wood-plank walls) to its young, creative clientele. Located in the back of a dive bar, the coffee shop whips up delicious spiked coffee drinks, like Cuban Lattes, which combine rum, caramel and espresso, and the Scotch & Honey (a belly-warming mix of Famous Grouse, almond and honey). If you’d rather skip the booze, there’s also creamy cortados, Cuban cigars, and and to-die-for doughnuts.

This historic hotel arguably has the most coveted address in all of Chi-Town: across from Millennium Park, and steps from such attractions as Anish Kapoor’s Cloud Gate, the Pritzker Pavilion and the Chicago Institute of Art. You’d be remiss, however, not to check out all the amenities closer to home before venturing outside. A landmark institution that was designed by Henry Ives Cobb in the 19th century, the former sports and social club—which was brought up-to-date by the renowned design team at Roman & Williams (of New York’s Ace and The Standard fame)—has a Game Room complete with shuffleboard, bocce, billiards and more; a rooftop bar, where Chicago’s pretty people gather around fire pits to sip classic cocktails; and Stagg Court, the restored gymnasium. Guest rooms nod to the building’s storied past with retro sporty details like leather wingback chairs, linen lampshades, and pommel horses at the foot of the beds.

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Walk into this retro pie and soda spot and you’ll be greeted smell of butter wafting through the air. From there, take a seat on a spinning bar stool, and order the roasted beet Ruben sandwich, a classic vanilla milkshake, and whatever pie is on special (we had a slice of the hibiscus key lime with blueberry compote). A husband-and-wife duo are behind the warm and inviting space, whose focal point is a 1928 Bastian Blessing soda fountain.

“Pared down,” “clean lined,” and “contemporary” are all words that have been thrown around to describe The Robey. Set in Wicker Park in an art deco tower, the hotel rises 12-stories above ground, making it one of the one of the only skyscrapers for miles. The property's highlights include a 2,100-square-foot rooftop bar, a French-American ground-floor eatery, and a Cabana Club and rooftop pool.

The casinos in Macau, China inspired this Logan Square cocktail bar—an atmospheric joint that has a “ritzy, dirty” feel, with its hazy ruby lights and vintage Asian pin-up posters and cigarette ads. Go early to get a seat in the tiny bar, which seats fewer than 20, and shakes up creative cocktails made with house-infused liquors, such as a white Negroni with reverse-engineered Malört.

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Southern Italian comfort food is on the menu at this Southport eatery—a cozy, bustling space with bronze mirrors, leather U-booths and rich blue-green walls adorned with spurn brass sconces. Start things off with the baby arugula salad, a tangy medley of pickled grapes, pecorino cheese and fried almond, then tuck in to a Neapolitan wood fired pizza (we’d recommend the quattro formaggi) and the squid ink spaghetti, which is topped with chili flakes and bread crumbs. Leave room for dessert—in this case, a pumpkin spice brioche stuffed with creamy sweet potato gelato and a pumpkin crème anglaise.

This trendy boutique looks like a Pinterest board come to life: soaring white ceilings, geometric wall art, stacks of eclectic textiles and one-of-a-kind jewelry. The owner, who started her career working in contemporary art galleries, curated the store’s eclectic panoply of art, home decor, apparel and vintage finds, featuring wares by local artists including Leah Ball and Ashley Kukulski. If you don’t have a trip to Chi-town in the works, you can shop the store’s finds here.

It can be a tall order to find a good mint julep or old fashioned in the Midwest, but at this cozy whiskey parlor, Southern-inspired cocktails are the main focus. Order a William Houston (an apricot-colored cocktail with rum, madeira, lemon juice, house-made jasmine green tea syrup and cherry bitters) or sample the bar’s impressive collection of vintage American whiskies. Pimento cheese, fried pickled shrimp, and other Southern-inflected bites are also on the menu, should you work up an appetite.

A budget-friendly stay with a high-design aesthetic, The Freehand is a popular sleep among a hip, college-age crowd. Pick among private rooms, shared quads (where curtains make snoozing next to a stranger less awkward), or one of two penthouses, which are better suited for traveling groups. Cocktails and street-food fare is served at hotspot Broken Shaker, where hipsters drink bespoke cocktails until the early hours, and at Cafe Integral, the hotel's breakfast nook, dine on Mesoamerican comfort food like baked yucca fries and Cuban sandwiches.

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If you find yourself out on the town and craving fast food, resist the temptation to scarf down a Big Mac, and make a beeline to this West Loop hotspot instead. Old-school hip hop blasts through the speakers and dim-lighting gives the place a club-like feel—a vibe that is only compounded by the lineup, which invariably wraps out of the restaurant and down the street. But don’t be deterred by the (potentially three-hour) wait; Bon Appetit declared Au Cheval’s cheeseburger the best in America, as have celebs like Aziz Ansari.