The 9 Best Neighborhoods in Chicago to Spend a Weekend

Dive headfirst into the City by the Lake.

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.

Gold Coast

Viceroy Chicago
Viceroy Chicago

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.

Viceroy Chicago
Viceroy Chicago

Where to stay: 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 Devereaux 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.

Le Colonial | Photo by Neil Burger Photography

Best restaurants: 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. For a decidedly newer steakhouse, Maple & Ash offers the same glitz and glamor, albeit in sleeker digs. 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, Nico Osteria puts a spiffy spotlight on Italian seafood, Chicago Q offers a high-end take on Southern-style barbecue in a historic mansion, ad 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.

Museum of Contemporary Art Chicago
Museum of Contemporary Art Chicago

Things to do: At the apex of the Magnificent 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. Not everything necessarily costs an arm and a leg, though. For free fun, soak up some rays at Oak Street Beach or drink in the sights at the Museum of Contemporary Art Chicago. Pause to marvel at the historic Chicago Water Tower, a gothic castle-looking building that famously survived the Great Chicago Fire, then cross the Magnificent Mile to catch a show at the Lookingglass Theatre Company, where themed productions spotlight everything from Charlotte Brontë to glamping.

Logan Square

Flickr/Chris Christian

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 hipster 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 for 24 years), 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.

Where to stay: 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. It’s wild boar sloppy Joes and a deep bourbon list downstairs, with six intimate—and historically inspired—guest rooms upstairs, ensuring you needn’t go far after a night of whiskey-swilling.

Giant
Giant

Best restaurants: 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 still commanding lines—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. Later, cozy up at Owen & Engine, a bi-level ode to British pubs with bangers & mash, fish & chips, and one of the best burgers in town. 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 impossibly salivate over. On the newer front, head to 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.

Emporium Logan Square
Emporium Logan Square

Things to do: While it would be all too easy to confine your Logan Square activities to a farm-to-table foodie binge, the neighborhood is teeming with unique recreation, retail, and activities as well. The historic Logan Theatre, with its impossible-to-miss marquis looming over the square itself, is a local keystone for films new and old, plus open-mic comedy and movie trivia, in a space that feels timeworn and timeless, while also refurbished and stocked with a full-service bar. 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. In all its hipster glory, the neighborhood has also emerged as a hotspot for retro-inspired arcades, including the sprawling Emporium Arcade Bar and pinball aplenty at Logan Arcade. Round out your evening with a round of duckpin bowling at The Pink Squirrel, a retro-chic bar with a small bowling alley and boozy milkshakes.

A far cry from the ritzy—and touristy—storefronts downtown, Logan Square is loaded with indie boutiques for all occasions, be it a need for Chicago-inspired cards and David Bowie magnets from Wolfbait & B-girls, contemporary novels and poetry from City Lit Books, chic dresses by emerging designers from Felt, or VHS staples and vintage movie posters from Bric-a-Brac Records & Collectibles.

Maplewood Brewery & Distillery
Maplewood Brewery & Distillery

Bars and nightlife: From whiskey-soaked watering holes and glam cocktail haunts to bijou wine bars and nightclubs, Logan Square is an enclave that really comes alive at night. Long a mainstay for hallowed dives and music venues, like still-kickin’ Rosa’s Lounge, the neighborhood has filled in with a dizzying array of drinking establishments, including pioneering mixology masters like The Whistler and gin-centric Scofflaw. Billy Sunday, located right on the square, oozes romance and ambience with its antique-clad walls, candle-lit environs, and menu of classic drinks made with vintage spirits. Not dark enough for you? After a few tacos at Lonesome Rose, head downstairs to quasi-speakeasy Golden Teardrops for bracing cocktails in a windowless space so dark it feels like a non-threatening haunted house. On the brighter side, Estereo is a tropical oasis with garage-style windows, lush plants, and even lusher cocktails made with vibrant spirits like pisco, cachaça, and rhum agricole, while The Welcome Back Lounge serves up colorful patio murals with equally colorful cocktails and retro ‘70s-style ambience.

While Logan Square has emerged as a haven of cocktail culture in Chicago, the neighborhood’s diverse drinking scene offers a wide spectrum. This is where Revolution Brewpub planted its flagship taproom, forever changing the face of the modern gastropub in Chicago, and where places like cutesy Hopewell Brewing Co., Maplewood Brewery & Distillery, and Solemn Oath Brewery have since followed suit. On the wine front, legendary Webster’s Wine Bar is joined by newcomers Outside Voices and Parisian-style Soif. After your last sip of dessert wine, stay up late and dance into the wee hours at casual clubby fixtures like Cole’s Bar and The Owl, both home to cheap drinks, theme nights, and crowd-pleasing DJs, with the latter staying open until 5 a.m. on Saturdays.

Andersonville & Lincoln Square

Andersonville
Andersonville | James Andrews1/Shutterstock

Nestled north of the action-packed skyscraper district and its surrounding labyrinth, Andersonville and Lincoln Square serve as an ideal destination for those seeking the calmer corners of city life. Just a short L-ride away from the city’s longest stretch of beaches, with cafes, art, and antique stores lining quaint, sleepy streets, you’re far enough away from the downtown noise to feel as if you’re someplace completely new but close enough to the action to soak up the urban vibes.

Where to stay: The Guesthouse Hotel offers 25 accommodations featuring one- to three-bedrooms and has become a fast favorite for travelers desiring a more personalized stay in the big city. Thoughtful amenities, including fitness and business centers, boutique retail, a rooftop deck, and a spa (plus plenty of helpful perks for those traveling with kids, from baby monitors to strollers) add to the welcoming atmosphere.

Atelier | Photo by Neil Burger

Best restaurants: Gather is a go-to for American fare from chef Ken Carter, who offers options like sumac-glazed Pork Belly and hand-rolled Mafaldine pasta bolognese, while Luella’s Southern Kitchen celebrates the recipes of chef-owner Darnell Reed’s grandmother (who moved from Mississippi to Chicago in 1943, and whose gumbo was once voted Chicago’s best). For a pint and some low-key bites, head to Hopleaf, a favorite for craft beer enthusiasts. And those seeking a high-caliber dining experience will find it at a few of the area’s tasting menu destinations, including the newly minted Atelier or Goosefoot, where Chris and Nina Nugent impress with warm hospitality, decadent courses, and a housemade chocolate bar to-go.

Lost Larson
Lost Larson

Things to do: Since 1979, independent bookshop Women & Children First has been curating shelves upon shelves of must-reads, all while working diligently to promote equity, liberty, and justice for all. Keep an eye on their calendar—the team here hosts ample author readings and workshops. Afterwards, spring for a sugar fix at one of the area’s most sought after bakeries—A Taste of Heaven (for classic cake by the slice and cream puffs), Lost Larson (for Scandinavian-inspired delicacies), or Dorothy’s Sweet Shoppe, a one-stop-spot for coffee, croissants, and cookies that is run by and benefits those with developmental disabilities.

The Loop

Millenium Park
Millenium Park | Luis Boucault/Shutterstock

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.

Boleo | Photo by David Szymanski

Where to stay: One of the neighborhood’s splashiest newcomers is 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 chef Marcel Heiduk puts forth brasserie-inspired fare (including his signature Dry Aged Duck Breast). 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.

Photo courtesy of Bar Mar

Best Restaurants: 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 speakeasyMilk 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 Mediterranean vibes with a visit to Avli on the Park, where Greek fare and a gorgeous new rooftop entice passersby, or snag a stool at Bar Mar, where celeb chef José Andrés shines the spotlight on oysters, ceviche, and Caviar Cones.

The Art Institute of Chicago
The Art Institute of Chicago

Things to do: Explore the treasures of Millennium Park, including the Jay Pritzker Pavilion, Crown Fountain, Lurie Garden, and Insta-famous Cloud Gate, then cruise over to 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.

Hyde Park

The University of Chicago, located in the Hyde Park neighborhood
The University of Chicago, located in the Hyde Park neighborhood | STLJB/Shutterstock

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.

SOPHY Hotel
SOPHY Hotel

Where to stay: The ultra-chic Sophy Hotel, stashed near the massive, always fun Museum of Science & Industry, offers specials and packages for visitors (including the “SO - COZY” package, which provides hot cocoa, dinner credit, and tickets to the Museum of Science and Industry). 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.

Virtue Restaurant
Virtue Restaurant

Best restaurants: 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 Blackened Catfish with Barbecued Carrots or Cornbread with Honey Butter (save room for the Peach Cobbler). 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.

Things to do: Snag tickets to a show at Court Theatre, The University of Chicago’s campus venue known for showcasing an array of works, from familiar classics to new productions from up-and-coming voices. Seven Ten Social is a retro-style hipster bowling alley, which features food that’s far better than the bowling alley standards, like Brisket Fries, Pumpkin Seed Hummus, and Smash Burger Sliders. 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.

Bucktown & Wicker Park

Chicago's Wicker Park & Bucktown neighborhood
Chicago's Wicker Park & Bucktown neighborhood | John Gress Media Inc/Shutterstock

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. 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.

Where to stay: 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 American comfort fare (with some Southern-inspired twists)—e.g. Duck Hash, Nashville Hot Chicken Thighs, and Peanut Semifreddo with crispy marshmallow.

Photo courtesy of Antique Taco

Best Restaurants: In the morning, follow the inevitable line down the block—and the aroma of buttery brioche—to Mindy’s Bakery. The hotly anticipated 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. The pizzeria also collaborates with local chefs and restaurants for specialty pies, like the Bayless Family Pizza, inspired by the one and only Rick Bayless, which features tomatillo salsa, pepper Jack and goat cheeses, red onion, bacon, jalapeño, and cilantro. For more modern mex, stroll down Milwaukee to Antique Taco, an adorably twee taqueria peddling Mushroom Fajita Tacos, Fried Chicken Burritos, and Rosemary Margaritas.

Things to do: 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.

Big Star Chicago
Big Star Chicago

Bars and nightlife: Grab a round of expertly tailored tipples at Violet Hour, the covert drinking den that helped kick off the city’s now-booming cocktail scene when it opened nearly 15 years ago. Afterwards, head across the street to Big Star, where late nights are just as fun as the day drinking, by way of plenty of tacos, tequila, and tunes.

Wrigleyville and Southport Corridor

Wrigley Field
Wrigley Field | Kent Weakley/Shutterstock

After the Cubs won the 2016 World Series, Wrigleyville has been undergoing an impressive overhaul, bringing with it multitudes of new restaurants, bars, shops, and hotels that are quickly changing what city dwellers once thought of the area (read: baseball and beer). Meanwhile, Southport Corridor only continues to grow cooler, thanks to the arrivals of on-trend retailers and lively eateries.

Hotel Zachary
Hotel Zachary

Where to stay: You can’t get any closer to the action than with a stay at Hotel Zachary, a 173-room boutique hotel located directly across from Wrigley Field. Cubs fan or not, expect a memorable stay thanks to striking mid-century modern interiors and generously sized rooms. Opt for an east-facing one for views of the park and adjacent Gallagher Way (where early morning yoga and HIIT classes are on offer during warmer months, only to morph into an ice rink and Christmas market come winter). Dine at The Bar at Hotel Zachary, where a menu of light bites accompanies a fleet of classic cocktails.

Itoko | Photo by Boka Restaurant Group

Best Restaurants: Southport Grocery and Café has gained a loyal following since its 2003 opening for its all-day breakfast and lunch—not to mention its city-famous cupcakes (your choice of chocolate or yellow cake layered with a sheet of vanilla buttercream). While waiting for your order (go with the Southport Cuban or Walnut Coffee Cake), peruse their shelves of artisanal goods, from Niloofar Persian Trail Mix to any of their preserves (most of which are made in-house). GG’s Chicken Shop is the new neighborhood hotness, courtesy of Boka Restaurant Group and acclaimed chef Lee Wolen, where Fried Chicken Sandwiches, Chicken Burgers, and Rotisserie Chicken are served in a funky diner-esque setting in the historic building that once housed Southport Lanes. For dinner, Boka doubled down on Southport with adjoining Itoko, a Japanese and robata hot spot from Gene Kato. In the morning, head straightaway to Southern France Patisserie, where chef-owner Amanda Tommey Terbush serves some of the best croissants in town (credit a three-day process and meticulous dough-handling). While there, don’t miss the chance to try any of their other French specialties, from the Paris-Brest to the Far Breton.

Music Box Theater
Music Box Theater | Joe Hendrickson/Shutterstock

Things to do: Find plenty of adventure beyond the ballpark here, starting with the shops of Southport Avenue, home to a medley of big-box names and boutiques alike (think Anthropologie, Sephora, and Lulu Lemon alongside local gems like Alice & Wonder, Krista K, and Foxtrot Market). Come evening, check out a screening at The Music Box, a historic theatre that hosts a roster of indie and foreign films. Keep an eye on the calendar at Uncommon Ground, too, a coffeeshop-come-concert venue (plus organic brewery) that spotlights local and touring up-and-comers.

Lincoln Park

Lincoln Park Zoo
Lincoln Park Zoo | Felix Mizioznikov/Shutterstock

Known for its tree-lined streets and Brooklyn-esque brownstones, Lincoln Park is a quiet respite from the city’s louder pockets—and one that also brims with destination-worthy shopping, world-renowned restaurants, and impressive culture (including one of the nation’s only free zoos).

Where to stay: Experience home-away-from-home vibes at The Neighborhood Hotel, where 14 stylish suites welcome travelers and feature all of the comforts one seeks in such a stay (from fast WiFi to a well-stocked kitchen). Hotel Lincoln is situated directly across from Lincoln Park’s sprawling grounds, making it the perfect landing pad for those looking to explore North Avenue Beach, Lincoln Park Zoo, or the celebrated Green City Market. Enjoy its cozy confines in between visits to any of its popular dining outlets, including Elaine’s (coffee and pastries), Sushi Suite 202 (show-stopping sashimi and nigiri), or The J.Parker (year-round rooftop cocktails with panoramic city views).

Alinea
Alinea

Best Restaurants: Farm-fresh produce is front and center at Range, as evidenced by brunch orders like the Mushroom Omelet or the Winter Squash Benedict with apple-pecan salad and beet hollandaise, and dinner staples like the Turnip-Apple Flatbread or Pan-seared Half Chicken with blue potato puree and sunflower shoots. Ramen enthusiasts will do well by Ramen-san, a sprawling spin-off location of one of Chicago’s ramen pioneers in River North. And for a true splurge, book an evening at Alinea, the city’s only three Michelin-starred restaurant featuring dozens of courses from mega chef Grant Achatz.

Green City Market
Green City Market

Things to do: An array of charming stores dot Armitage Avenue, from independently owned (Art Effect, Lori’s Shoes) to bigger names (Paper Source, Allbirds, Marine Layer). The best part? They are punctuated by the likes of Jeni’s Splendid Ice Creams, La Colombe Coffee, Berco’s Popcorn, and Beacon Doughnuts, ensuring plenty of fuel along the way. Once caffeinated (or sugared-up), explore the vendors at Green City Market (Wednesdays and Saturdays), a local haven for flowers, produce, and baked goods. Continue from there to the Lincoln Park Zoo, a 35-acre animal adventure founded in 1868, making it one of the oldest zoos in the country (and one of the only ones with free entry, too).

West Loop

West Loop
West Loop | Antwon McMullen/Shutterstock

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 cutting-edge dining. Ready your social handles—chances are that anything you eat, drink, or do here will be Instagrammable.

The Hoxton, Chicago
The Hoxton, Chicago

Where to stay: 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 champ and local darling 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 92 rooms, 23 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.

Proxi
Proxi

Best restaurants: Some of Chicago's top restaurants call West Loop’s Restaurant Row and the surrounding areas home. At Proxi, gorgeous, spacious interiors beckon diners, who will only continue to be floored by the flavors they encounter in plates like Tempura Elotes, Coal-roasted Sea Scallops, Sweet Potato Chaat, and Foie Gras Steam Buns. 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. 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 Artichoke Caramelle, Tortelli Verde, and Chitarra with black truffle sausage ragu.

Things to do: In the mood for a little retail therapy? Stop by M2057 by Maria Pinto, the local designer celebrated and worn by the likes of former First Lady Michelle Obama, and treat yourself to some affordable luxury via quality Italian ready-to-wear. Kristin Cavallari’s Uncommon James is also on-hand, along with popular brands like Free People and Anthropologie. Plus, there’s an insider-approved Goodwill for those who love a good deal and surprise finds.

Blind Barber | Photo by John Stoffer

Bars and nightlife: For a heightened drinking experience alongside seriously impressive snacks, book it to 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 casual 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 Berbere Hot Chicken Tenders and Crab Rangoon.

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Nicole Schnitzler is a contributor for Thrillist.
Matt Kirouac is a travel writer working on a memoir about the epic ups and downs from life on the road as a gay couple—and the lessons learned along the way. Follow him on IG @mattkirouacofficial.