The Coolest Neighborhoods in Chicago to Spend a Weekend

Chicago is a city of neighborhoods. There are 77 of them, in fact, spread across roughly 235 square miles (with lucky number 78 on the way), each with its own distinct vibe, attractions, views, and flavors. It’s a sprawling metropolis that offers a choose-your-own-adventure-style vacation, from the soaring glitz of downtown and the hipper haunts of Logan Square to the restaurant mecca that is the West Loop, a veritable Disneyland for foodies and Top Chef stans. Whether you’d like to be smack dab in the heart of the hustle and bustle, or cozied up in a quieter northside neighborhood surrounded by Belgian beer bars and feminist bookshops, rest assured that there’s an area of the city with your name on it. No matter if you’re a first-timer, a seasoned Chicago pro, or a resident itching for a staycation away from your roommate, here are 9 unique neighborhoods that offer an authentic taste of the Windy City.

One of the most on-the-rise neighborhoods in the city (and we mean that literally, with the recent completion of the 101-story St. Regis Chicago tower), Lakeshore East is finally finding its own footing, outside the shadows of nearby heavy-hitters like Streeterville and River North. Located at the nexus where the Chicago River merges with Lake Michigan, this metropolitan utopia boasts some of the foremost lake and river views in Chicago, along with optimal proximity to the Chicago River Walk, architecture cruises, and parks like Maggie Daley, Millennium, and Grant.

One of the newest public green spaces in the city, the Chicago Riverwalk has transformed a largely once-blighted stretch of riverfront into a 1.25-mile park lined with restaurants, seating, outdoor art, and boat docks, in case you’re traveling via your own private yacht. Notably, it’s also the best vantage point from which to drink in Chicago’s famed skyline, as it weaves from Lake Street towards the lakefront, through a veritable Grand Canyon of architecture.

One of the hottest new restaurants in the city, located on the second floor of The St. Regis, Tre Dita is a decadent homage to Tuscan cuisine, courtesy of Lettuce Entertain You Restaurants and Los Angeles-based star chef Evan Funke. Complete with soaring 40-foot windows overlooking Lake Michigan and the Chicago River, making this the ideal Lakeshore East destination, the restaurant features a humidity-controlled “pasta lab,” an exclusively Italian wine list, and a bi-level space clad in walnut timber paneling, arched portals, terracotta, wrought-iron light fixtures, and Tuscan marble. Next to the gilded dining room, Bar Tre Dita offers a slightly more casual Italian bar experience, spotlighting Italian spirits and wines. Funke’s menu mines regional recipes for standout dishes like Schiacciata Bianca, a rosemary and sea salt focaccia, ricotta-filled fried squash blossoms, prawns in Italian salsa verde, and a whole section of the menu dedicated to Prime steak. For something more casual, Brown Bag Seafood Co. makes up for its lack of 40-foot windows with a convincingly coastal menu of grilled shrimp tacos, fish & chips, and lobster rolls, while Avli on the Park offers Greek fare with a gorgeous—and underrated—rooftop.

The ritziest newcomer in town, the $1 billion St. Regis Chicago, is hard to miss, considering it resides in a sky-scraping tower 101 stories tall. Comprising the first 11 floors of the behemoth building, the high-end hotel offers more than 150 guest rooms and swanky suites (including a Presidential Suite with personalized butler service), along with a top-tier spa, indoor swimming pool, and in addition to Tre Dita, a modern Japanese stunner, Miru.

Emerging from the Logan Square Blue Line stop, you could be forgiven for thinking you’d mistakenly teleported to Portland at peak Portlandia. Chicago’s reigning artsy champ, Logan Square is a northwest side neighborhood known for its rigorously farm-to-table restaurants (like Lula Cafe, which has been holding it down since the late-’90s), quirky gift shops, indie theater, farmers’ markets attended by vintage-clad fashionistas, and more twee coffee shops than people. An easy L-ride from both downtown and O’Hare, and home to some of the city’s most popular watering holes, from negroni slushies to clubby dive bars, it’s an inclusive, boisterous, and must-stay place for a different side of Chicago.

Running every Sunday from May through October, the Logan Square Farmers Market is the place to see and be seen, oftentimes with strollers and/or dogs in tow. Well attended by chefs and area foodies, this massive market is one of Chicago’s most prized, where bike-powered smoothie machines churn out the season’s freshest slurps, locally sourced produce and meats are in abundance, and ready-to-eat foods run the gamut from bagels to arancini.

Aside from maybe the West Loop, no neighborhood in Chicago has seen the rapid-fire restaurant boom in recent years like Logan Square. A lot of that can be attested to Lula Cafe, an early progenitor of farm-to-table cooking in the city at large when it opened an era ago in 1999. The beloved neighborhood cornerstone is still going strong—and winning James Beard Awards—for brunch, lunch, and dinner fare like smoked trout scrambles, marigold-flecked tomato toast, beet bruschetta, and chickpea and fennel tagines. It’s paved the way for a fresh slate of heavy-hitters, like Jason Vincent’s modern Midwestern mainstay Giant, Diana Davila’s lauded Mexican restaurant Mi Tocaya Antojeria, Alpine comfort food staple Table, Donkey and Stick, and Lardon, where European salumerias inspire a menu of whole-animal cookery and charcuterie.

Offering Instagrammable eats all day long, Logan Square is a neighborhood where you can start your day with a mug of esoteric java at Gaslight Coffee Roasters, followed by a slice of cannoli pie and a fluffy jam-stuffed biscuit at Bang Bang Pie & Biscuits. Or if you’d prefer your fish fry with a side of hush puppies, queue up at Parson’s Chicken & Fish, the enduringly cool hipster haunt with a colossal patio, Insta-famous Negroni Slushies, and all the surf & turf you could possibly salivate over. On the newer front, head to the new location of Daisies for pasta and pastries aplenty, or the vibrant Superkhana International, where the “flavors are Indian by way of the world.” And the butter chicken calzone is very much something you need in your life.

If one of the “B’s” in B&B stood for “bourbon,” Longman & Eagle would be the most idyllic abode. A contemporary homage to classic Chicago inns of yore, the kind where a few cozy rooms were nestled above dining and drinking establishments in outlying neighborhoods, this hip neo-tavern doubles as a nose-to-tail bar and restaurant, as well as a funky place to rest your head in artsy confines. Its wild boar sloppy Joes and a deep bourbon list downstairs, with six intimate—and historically inspired—guest rooms upstairs, ensure you needn’t go far after a night of whiskey-swilling.

As the name might suggest, things get pretty ritzy in the Gold Coast. A polished crown jewel among the downtown neighborhoods, nestled at the northernmost nexus of the Magnificent Mile, this is a sky-scraping neighborhood populated by the city’s poshest shops, most moneyed restaurants, and real estate that looks more like Beverly Hills. For a Chicago stint with guaranteed wow factor, it doesn’t get much slicker than this.

At the apex of the Mag Mile, there’s no shortage of swanky downtown shenanigans to get into, especially shopping at some of the most coveted stores in the city. On streets like Michigan Avenue, Rush Street, and Oak Street, you’ll find everything from Hermes and Versace to Chanel, Gucci, Tiffany & Co., and Armani.

It should come as no surprise that the highest-grossing restaurants in Chicago are in the Gold Coast. Gibsons Bar & Steakhouse is a longtime anchor at the epicenter of the Viagra Triangle, an intersection surrounded by lavish restaurants frequented by rich elders, shall we say, and it routinely ranks as the highest-earning independent restaurant in the city, amassing many millions of dollars annually. It’s clearly not cheap, by any means, but it’s well worth a visit to this hallowed institution for a taste of history—along with a Porterhouse, some Crab Legs, and Macadamia Turtle Pie. It’s not all fancy steak and potatoes in the Gold Coast, though. Killer breads, chocolates, and croissants can be accumulated at the jewelbox-sized Hendrickx Belgian Bread Crafter, Chicago Q offers a high-end take on Southern-style barbecue in a historic mansion, and Le Colonial remains a French-Vietnamese mainstay for power lunches and girls’ nights. Wind down with a rum-soaked nightcap at Sparrow, a sexy Cuban-inspired lounge awash in La Floriditas and Hotel Nacionals.

With swanky locations in locales like Saint Lucia and Serbia, the Viceroy hotel brand is perfectly befitting its towering Art Deco address in the Gold Coast. After all, if you’re gonna stay in a neighborhood called the Gold Coast, you might as well ball out at the Viceroy Chicago. Chic gold-accented guest rooms offer peeks at Lake Michigan through the nearby towers, while Pandan rooftop bar offers sophisticated cocktails and a pool with an 18th-floor vista. The hotel’s handy location will also have you in the heart of the ‘hood, and a mere stroll to area attractions, including restaurants where entrees might cost as much as your hotel stay.

While River North and the West Loop continue to see the densest population of dining and nightlife options, don’t overlook the Loop, where historic landmarks, culture, and some of the city’s most celebrated sights await.

Explore the treasures of the Midwest’s most-visited tourist attraction, including the Jay Pritzker Pavilion, Crown Fountain, Lurie Garden, and Insta-famous Cloud Gate, then cruise over to Grant Park to visit The Art Institute—one of the nation’s largest art museums and home to permanent works like Hopper’s Nighthawks, Picasso’s The Old Guitarist, and the ever-enjoyable Thorne Miniature Rooms.

Catch some of the city’s best views at Cindy’s at the Chicago Athletic Association, a rooftop favorite for post-work happy hours and weekend brunching. Come evening, go full nerd with a stop into the CAA’s swanky speakeasy, Milk Room, an eight-seat nook featuring ultra-rare vintage spirits and cocktails. Acanto is a must for all things Italian, thanks to regional specialties like Sicilian Arancini and Chicken Piccata. Continue those European vibes with a visit to Bar Mar, where celeb chef José Andrés shines the spotlight on oysters, ceviche, and Caviar Cones. The Loop is also home to some of Chicago’s enduring old-school haunts, like the German-inspired Berghoff, Miller’s Pub (stop by during the holiday season for their famous Tom & Jerry’s), and the multi-story Al Capone haunt, Italian Village.

One of the neighborhood’s splashiest newcomers is the Pendry Chicago, a 364-room property in the city’s storied Carbide & Carbon Building. Head to the rooftop for an evening of sushi and light bites under string lighting at Chateau Carbide while taking in skyline views. Meanwhile, lobby-level diners are in impeccable hands at Bar Pendry or Venteux, where brasserie-inspired fare skews classic with Steak Frites, Trout a la Meuniere, and Ratatouille. Another soaring option is the Kimpton Gray Hotel, nestled in the heart of the historic Financial District. The color gray has never been sexier than these opulent rooms and suites, all of which are capped by a sultry and lush rooftop restaurant, Boleo, where South American flavors shine on plates and in cocktails.

Spend a weekend in Hyde Park, and you very well may fall in love. The neighborhood encircles The University of Chicago and plenty of historic sites, including the Frederick C. Robie house (designed by renowned architect Frank Lloyd Wright), as well as the homes of pioneering journalist Ida B. Wells, A Raisin in the Sun author Lorraine Hansberry, iconic boxer Muhammad Ali, and legendary trumpeter Louis “Satchmo” Armstrong. As such, the area overflows with art and culture, with many things to do open and free to the public.

For those looking to spend more time outdoors, Midway Plaisance—designed by Olmsted & Vaux, the renowned designers behind New York’s Central Park, for the 1893 World's Columbian Exposition—knits the South Side together, taking you from Jackson Park on the east to Washington Park on the west, the University of Chicago campus to the north, and Woodlawn at its southernmost point. Lined with trees and gardens, the park also boasts soccer fields, an ice rink, and special events, such as movies in the park. Later, skyline views and sunsets don’t get any better than those from Promontory Point.

Virtue, led by chef-owner and South Side native Erick Williams, has been voted one of the best restaurants in Chicago time and time again, with Williams often cited as one of many Black chefs at the forefront of American cuisine. Built on a foundation of warm Southern hospitality, the restaurant serves approachable, upscale takes on soul food, including Green Tomatoes with Gulf Shrimp or Blackened Catfish with Barbecued Carrots (save room for the butterscotch-kissed Carrot Cake). More of a night owl? The Promontory is half restaurant, half performance venue, offering a calendar of silent dance parties, salsa lessons, and live music acts among other festivities.

The ultra-chic Sophy Hotel, stashed near the massive, always fun Museum of Science & Industry, offers a boutique reprieve amidst tree-lined streets that look straight out of Mayberry. The hotel houses Mesler Kitchen, where breakfast, lunch, and dinner menus help guests feel constantly catered to (outdoors, too, where a patio with enclosed igloos warms visitors in winter months). For a more private stay, check out the Hamlin House Bed & Breakfast. Built in 1905 for Chicago opera singer George Hamlin, the property is beautifully restored, with five guest rooms with ensuite bathrooms, plus a Victorian-style dining room, and gardens. Visit the Smart Museum of Art during your stay, just steps away from the B&B’s front door.

Known for its indie-artist vibes, entrepreneurial spirit, and buzzing “six corners” intersection, the Bucktown-Wicker Park neighborhood stands as one of Chicago’s hippest destinations, intersected by walkable thoroughfares and an elevated park that stretches for nearly three miles. Milwaukee and North Avenues are go-tos for resale and record shopping alongside other eclectic finds (from coffee shops to beer gardens), while Damen Avenue and Division Street abound with upscale boutiques and award-winning restaurants.

Get some fresh air along The 606, a 2.7-mile elevated rail trail that takes the cake as the longest greenway initiative of a former rail line in the country. Upon your descent at Milwaukee Avenue, swing into Ipsento 606 for some cold brew and tiny doughnuts (their specialty), then stroll the shops of Damen Avenue, including Moth, a dainty Nordic-meets-Japanese storefront stocked with elegant clothes, candles, art, pottery, tea kettles, and more.

In the morning, follow the inevitable line down the block—and the aroma of buttery brioche—to Mindy’s Bakery. The buzzy bakeshop from legendary pastry chef Mindy Segal, the cafe slings a daily dose of bagels, bialys, Hot Fudge Cheesecake Muffins, raspberry-filled Rugelach, Candy Bar “Pop Tarts,” Cinnamon Rolls with vanilla bean-sour cream glaze, and oodles more. Later, Piece Brewery and Pizzeria is a timeworn staple that brews its own beer and serves lanky New Haven-style slices and pies heaped with garlicky clams. For modern Mex, stroll down Milwaukee to Antique Taco, an adorably twee taqueria peddling Garlic Shrimp Tacos, Fried Chicken Burritos, and Blueberry Basil Margaritas.

The Robey is a favorite for its industrial-chic design and prized location (placed conveniently on the aforementioned six corners intersection and offering unobstructed views of downtown). Check in, then check out any of the property’s common areas, including Cabana Club and Up Room, and two rooftop options for those seeking a little sun with their stay. Come morning, scope out brunch at Café Robey, a quaint corner eatery with a knack for contemporary American comfort fare —e.g. S’mores Croissants, French Toast with Horchata Cream Cheese Icing, Duck Hash.

Looking to be among the city’s most trendy? The West Loop, just blocks away from Chicago’s Greektown and the United Center (home of the Chicago Bulls and Chicago Blackhawks), is defined by boutique shopping, public art, and most especially, cutting-edge dining. Ready your social handles—chances are that anything you eat, drink, or do here will be Instagrammable.

Around here, eating and drinking is the foremost form of entertainment, and in addition to a slew of restaurants from Top Chef alumni, the West Loop’s bar scene has been on a serious upswing of late. For a heightened drinking experience alongside seriously impressive snacks, book it to After, the after-dinner counterpart to Curtis Duffy’s Michelin-adored Ever. Here, one of Chicago’s most esteemed chefs pairs masterful mixology—think: Espresso Martinis infused with truffles—with Caviar Service and Vietnamese Duck Wings. Don’t miss Kumiko, where multi-award-winning barkeep (and 2020 Thrillist Local Hero) Julia Momose helms a menu of Japanese-inspired drams to pair up with plates from two-Michelin-starred chef Noah Sandoval (Oriole). Or keep it leisurely at Lone Wolf, a hipster tavern slinging frozen cocktails, bracing Old Fashioneds, and tamales. Then there’s Blind Barber, a funky barber shop that doubles as a speakeasy with seasonal drinks, Espresso Martinis, nightcaps, and snacks like Korean Korn Dogs (not a misspelling) and Smash Burgers.

Some of Chicago's top restaurants call West Loop’s Restaurant Row and the surrounding areas home. Sushi enthusiasts should reserve a spot at Mako, where chef BK Park serves an omakase menu that has earned him and the team a Michelin star and several rave reviews, or keep things casual at his newest Japanese venture, Tamu, where sushi hand rolls are the bill of fare. And Top Chef fans will be eager to snag a table at Rose Mary, the first restaurant opening from Season 15 winner Joe Flamm, exploring the convergence of Italian and Croatian cuisines with orders like Tortellini Djuvec or Pork Ribs Pampanella, while another Top Chef alum, Sarah Grueneberg, oversees Monteverde, a pasta-centric temple of all things Sweet Pea and Sausage Gramigna, Sheep’s Milk Ricotta Tortelli, and Pappardelle with tomato-braised lamb sugo.

Perched on the border of the West Loop and equally flashy Fulton Market District, The Hoxton draws well-heeled crowds for its upscale-artsy aesthetics and invitation to the creative lifestyle, as evidenced by a shared workspace and “flexy time” check-in/out that suits a guest’s schedule. What’s more? Three dining outlets (including Cabra from Top Chef icon Stephanie Izard) are on deck, plus a vibrant events calendar that beckons a night in. More recently, Chicago welcomed its very own Nobu Hotel, an uber-modern luxury property with 115 rooms and suites, a rooftop bar, and an outpost of sushi-famed Nobu Restaurant. For more of a home-away-from-home experience, head to The Publishing House Bed & Breakfast, where modern style meets Midwest hospitality in a historic—you guessed it—publishing house. The inn only hosts 24 guests at a time across 11 private rooms, each with an ensuite bathroom (complete with clawfoot tub), highly personalized service, and customized breakfast options.

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