Here’s your guide to an unforgettable weekend in the Windy City.
Many people know Chicago by many different names: Chi-Town, the Windy City, Mud City, Paris on the Prairie…the list goes on. But whatever you choose to call it, America’s beloved Second City is simply second to none.
Chicago has built a reputation for being one of the country’s most diverse and enthralling cultural hubs, punctuated with stunning skyscraping architecture, world-class culinary icons, and more than enough attractions to keep you busy for a lifetime. But if you’re just passing through, you’ll want to hone in on the highlights.
While it’s impossible to list everything worth exploring during a stay in Chicago, our comprehensive guide is a solid place to start. So read on to learn more about our favorite places to eat, drink, and stay in the Windy City that are guaranteed to blow you away.
Coffee Lab & Roasters
The charming Lakeview neighborhood recently celebrated the opening of their newest coffeehouse, Coffee Lab & Roasters. The location is a triumphant follow-up to their popular Evanstown joint known for serving premium locally roasted specialty coffee.
They also offer a premium selection of organic loose-leaf teas, freshly baked pastries delivered daily, and light snacks for a more serious case of the munchies. Jumpstart your day with a cup of their Kono Pour-Over coffee (one of the best in the city) or opt for a classic cappuccino or espresso.
Tucked away in the ritzy River North neighborhood is The Drifter, a 1920s inspired speakeasy that seems timeworn yet polished at the same time. The subterranean cocktail bar is hidden beneath The Green Door Tavern and is celebrated by locals for the creative tipples.
They have a small stage that plays host to a diverse range of live entertainment each night, including musical performances, magic demonstrations, burlesque shows, and more. With no set drinks menu, bartenders instead follow an ever-changing cocktail list presented on tarot cards. Although they don’t accept reservations, it’s absolutely worth swinging by during any visit to Chi-Town.
The Ladies’ Room at Fat Rice
Fat Rice is a local Logan Square staple renowned for their creative focus on Macanese cuisine, which is generally described as a fusion of Chinese and Portuguese ingredients, recipes, and culinary techniques (with additional Southeast Asian influences). While the acclaimed eatery’s unique dishes have been making headlines for years, it’s their inventive cocktail bar, The Ladies’ Room, that’s also deserving of critical acclaim.
The Ladies’ Room delivers a one-of-a-kind drinking experience that combines Midwestern flair with international flavors and ingredients. Aside from the intimate setting, guests especially love their house-made infusions, elixirs, and potions. Order a White Negroni (made with gin, Malort, white vermouth, and wild lemon liquor) or try The Thunderstorm (an amped up take on the classic Dark and Stormy).
To avoid the throngs of tourists and see a slice of local life, hop in an Uber and head north to Andersonville. One of the North Side’s most colorful neighborhoods, Andersonville is known for its Swedish roots and is also home to one of the city’s largest queer communities.
Since 1992, beer fanatics have flocked to this mom-and-pop district thanks to Hopleaf Bar. The Belgian-inspired bar provides an impressive list of bottled and draft brews in a no-frills, laid-back atmosphere. Expect to find an eclectic array of beer, cider, mead, and wine that’s sure to quench any thirst.
For one of the best brunches in Chicago, make a beeline for BEATNIK. Opened in 2017, this West Town restaurant is the stuff Instagram dreams are made of. The expansive restaurant offers a whimsical escape, combining lush Bohemian vibes with the over-the-top grandeur of yesteryear. The space is decked out with 15 enormous crystal chandeliers and a collection of worldly curiosities hand picked from far-flung destinations such as Bali, Egypt, and Spain.
Appearances aside, the menu is also just as praiseworthy, featuring an experimental collection of globally inspired plates, pulling from Italy, France, Morocco, Japan, Peru, and more. For brunch, indulge in their Smoked Baba Ghanoush, Shakshuka with Duck Eggs, or Smoked Salmon Toast. And don’t forget to order one of their specialty cocktails to wash it all down (we recommend a My Boy Blue slushie made with a house rum blend, Blue Majik, pineapple, coconut, lime, and bitters).
What kind of tourist would you be if you didn’t treat yourself to a slice of Chicago’s world famous pizza? When it comes to finding the city’s best interpretation, locals are quick to rattle off their favorite spots. Some claim Gino’s reigns supreme, while others swear by long-standing staples like Giordano’s or Lou Malnati’s. But for an unexpected twist, pay a visit to Pequod’s Pizza in Lincoln Park.
The pizza wizards at Pequod’s have built a loyal local following that keeps the people coming back for more. Here, hungry patrons line up out the door in search of their doughy pies and crisp, caramelized crusts that deviate slightly from the traditional deep-dish variety. They also serve up thin-crust Chicago-style pizza in addition to other mouth-watering options like buffalo cauliflower, Italian sausage sandwiches, and tricolor tortellini.
Luella’s Gospel Bird
In addition to pizza, Chicago also happens to be a winner when it comes to outstanding fried chicken. And this brand new spot in Bucktown has already built a ton of buzz for itself among the city’s in-the-know foodies. Meet Luella’s Gospel Bird (which, thankfully, is open for brunch, lunch, and dinner).
A spin-off of Lincoln Square’s beloved Luella’s Southern Kitchen, this chicken-centric sequel gets imaginative with its short-but-sweet menu. Their classic Buttermilk Fried Chicken is already a star, but don’t be afraid to step out of your comfort zone. Try an order of the Smoked Jerk Chicken or opt for The Gospel, which features fried chicken smothered in its namesake tangy Gospel sauce. Pair your meal with a side of Luella’s candied yams or mac and cheese for an unforgettable stick-to-your-ribs lineup.
Chicago’s epicures were outraged when Bellemore was snubbed by the latest Michelin Guide—and for good reason. The highly anticipated addition to the ever-trendy food-obsessed West Loop neighborhood opened in late 2017 to critical acclaim, with celebrated chef Jimmy Papadopoulos at the helm. To date, it’s still one of the best meals I’ve ever eaten in my life. The brainchild of the Boka Restaurant Group, Bellemore serves up an ingenious menu teeming with “Artistic American” fare in a relaxed but sophisticated space.
The lofty 6,000-square-foot eatery boasts a sleek aesthetic showcasing brass, wooden, and leather design elements throughout. In other words, it provides the perfect setting to celebrate a special occasion, or simply enjoy a romantic night on the town. As described by Chef Papadopoulos, the menu can be described as “bold, bright, and beautiful.” Look for decadent dishes such as their Venison Tartare (made with cave-aged cheddar, pickled Asian pears, seeded rye, spicy Tokyo turnips, and black lime); Hand-Cut Pappardelle (served with braised lamb, olives, ricotta, and mint); or their Wild Arctic Char (roasted in brown butter with hedgehog mushrooms, Treviso, tamarind, and apples). And trust us when we say you definitely don’t want to miss out on a slice of The Oyster Pie.
This year will see The Hoxton continue its expansion throughout the United States, with their next opening slated for the Windy City. The iconic hospitality group (owned by Ennismore and headquartered in England) has generated a cult-like following thanks to its open house, design-focused hotels inspired by the characters and neighborhoods that surround each property.
The 182-room outpost is expected to open its doors this spring, straddling the border of the West Loop and Fulton Market neighborhoods. The room design will be reminiscent of the building’s industrial heritage, paying homage through warehouse-style design details. It will also feature a spacious lobby, all-day restaurant, cozy basement piano bar, state-of-the-art fitness center, rooftop eatery, and swimming pool.
The Gwen Hotel
A relatively recent addition to Chicago’s hospitality scene, The Gwen first opened its doors to guests in 2015. Situated just off Michigan Avenue in the heart of downtown, the boutique hotel features an effortlessly cool, art-deco atmosphere reminiscent of Chicago in the 1930’s.
Inspired by the golden era of the city’s grand hotels, The Gwen represents Chicago’s storied past while looking toward the future by introducing all of the luxurious perks a 21st Century traveler expects. Book one of their comfortable guest rooms or sprawling suites with balcony views overlooking the frenetic city below. Or, if you’re feeling slightly more adventurous, opt for an urban glamping experience on the private terrace of the Gwen Lux Suite (only available from May 28 through September 30).
Deer Path Inn
Itching to escape the hustle and bustle of city life? If so, look no further than the award-winning Deer Path Inn. Hidden away on the North Shore in picturesque Lake Forest, the warm and welcoming retreat is just a short drive or train ride from Downtown Chicago, but feels worlds away. Inspired by a 15th Century Tudor manor, the landmark inn traces its roots back to 1929 and has been enchanting guests ever since.
Personalized service, timeless accommodations, and exceptional culinary experiences have made this beloved property a favorite amongst locals and travelers alike. It’s the kind of place where no detail is overlooked. Here, the team of gracious employees is always quick to remember a guest’s name or offer thoughtful recommendations to curious visitors. The English-inspired White Hart Pub is the perfect spot to enjoy a beer and classic tavern specialties like Shepard’s Pie or Bangers and Mash. But for a more refined meal, reserve a space at The English Room to enjoy plates such as Seared Diver Scallops, Scottish Salmon, and Braised Beef Short Rib.