Chicago

The 7 Best Neighborhoods in Chicago to Spend a Weekend

Dive headfirst into the City by the Lake.

Photo by Alice Achterhof, Photo Courtesy of Choose Chicago
Photo by Alice Achterhof, Photo Courtesy of Choose Chicago
Photo by Alice Achterhof, Photo Courtesy of Choose Chicago

Spanning 77 diverse neighborhoods, each offering its own sights, sounds, tastes, and history, Chicago offers myriad adventures and points of exploration. Whether you’re a first-time visitor or a local looking to organize the ultimate staycation, any of these seven neighborhoods are perfect places to fall in love (or fall in love all over again) with the Windy City.

Andersonville & Lincoln Square

James Andrews1/Shutterstock
James Andrews1/Shutterstock
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.

Gather Chicago
Gather Chicago
Gather Chicago

Best restaurants: Gather is a go-to for American fare from chef Ken Carter, who offers options like Korean BBQ Short Rib and Grilled Mojo-marinated Flank Steak, 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 Brass Heart or Goosefoot, where Chris and Nina Nugent impress with warm hospitality, decadent courses, and a housemade chocolate bar to-go.

Lost Larson
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 some of the area’s most sought after bakeries like A Taste of Heaven (for classic cake by the slice and cream puffs) or Lost Larson (for Scandinavian-inspired delicacies-don’t sleep on the Princess Cake).

The Loop

Luis Boucault/Shutterstock
Luis Boucault/Shutterstock
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.

Pendry Chicago
Pendry Chicago
Pendry Chicago

Where to stay: The neighborhood just received one of the city’s most hotly anticipated hotel openings with 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 Donald Young puts forth brasserie-inspired fare (including his signature Dry Aged Duck Breast).

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 recently reopened Milk Room, an eight-seat speakeasy featuring ultra-rare vintage spirits and cocktails. Acanto is a must for all things Italian, thanks to regional specialties like Sicilian Arancini and Pork Milanese. Continue those Mediterranean vibes with a visit to Avli on the Park, where Greek fare and a gorgeous new rooftop entice passersby, or meander over to Kostali at The Gwen Hotel, where the team behind legendary Naha greet diners with plates of Fig and Tomato Jam Halloumi with Striped Bass with Chickpeas and Olives.

The Art Institute of Chicago
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

STLJB/Shutterstock
STLJB/Shutterstock
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
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 – In Love” package, which recreates the Obamas’ first date in the neighborhood). The hotel also 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
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. 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

John Gress Media Inc/Shutterstock
John Gress Media Inc/Shutterstock
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, house made Biscuits and Gravy, and Chili Butter Shrimp and Grits.

The Bristol
The Bristol
The Bristol

Best Restaurants: Find hyper seasonal American cuisine at The Bristol, where chef Larry Feldmeier serves an eight-course tasting menu for just $85. Sample through late-summer staples like Yellow Squash Gazpacho or Corn Tortellii while enjoying wine pairings throughout-and save room for the finale, when two desserts enter the scene (EVOO Cake and Buttermilk Sherbet). For Filipino fare, head to Kasama in nearby Ukrainian Village, where chefs Genie Kwon and Timothy Flores combine their Michelin-starred CVs to spin out daytime menus of Fried Pork Spring Rolls, Chicken Adobo, and the best damn breakfast sandwich in town stuffed with housemade longanisa sausage and a crispy hash brown patty. And come cooler months, it’s hard to top European mountain cuisine-the main event at Table, Donkey and Stick, as evidenced by a rotating selection of cheeses and charcuterie (the latter of which, along with all of the bread, is made fresh in-house).

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 the recently opened PRERY Collective, a boutique collaboration between local style curators Sararose Krenger and Emily McKenney.

Big Star Chicago
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

Kent Weakley/Shutterstock
Kent Weakley/Shutterstock
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
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.

The Southport Grocery & Cafe
The Southport Grocery & Cafe
The Southport Grocery & Cafe

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). For dinner, check out Coda di Volpe for Italian fare from chef Phil Rubino, who wins over guests with homemade pastas and pizzas plus one epic display of Chicken Diavola (with Calabrian Chili Honey Glaze and Grilled Broccolini). Those on-the-go can visit Foxhole, the restaurant’s takeaway window, where Focaccia Squares and bottled Negronis help round out the workweek. 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.

Joe Hendrickson/Shutterstock
Joe Hendrickson/Shutterstock
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

Felix Mizioznikov/Shutterstock
Felix Mizioznikov/Shutterstock
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: 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), The Kennison (contemporary American fare), Sushi Suite 202 (show-stopping sashimi and nigiri), or The J.Parker (year-round rooftop cocktails with panoramic city views).

Alinea
Alinea
Alinea

Best Restaurants: Farm-fresh produce is front and center at Range, as evidenced by brunch orders like the Carrot Omelet (with smoked beans and rosemary) or the Zucchini-Pea Benedict (with cilantro-pesto hollandaise and cucumber), and dinner staples like the Peach-Tomato Flatbread or Pan-seared Half Chicken with corn polenta and fennel. Greek enthusiasts will do well by Avli Taverna, a neighborhood corner spot with a Mediterranean-influenced menu and mighty patio scene. 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
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

Antwon McMullen/Shutterstock
Antwon McMullen/Shutterstock
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
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. 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
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 Paneer, and Ethiopian Beef Tartare. 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. Explore the convergence of Italian and Croatian cuisines with orders like Tortellini Djuvec or Beef Burek.

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.

The Darling Chicago
The Darling Chicago
The Darling Chicago

Bars and nightlife: Drinking at The Darling is like falling down Alice’s rabbit hole into Wonderland (the good parts, at least). Charming, intimate, and featuring a reservation-only library with hidden entrance and pop-up cabaret performances, the beloved lounge serves a number of exquisitely balanced cocktails and food options while hosting some of the city’s best DJs. 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).Want more Thrillist? Follow us on InstagramTwitterPinterestYouTubeTikTok, and Snapchat.

Nicole Schnitzler is a contributor for Thrillist.

Chicago

Robyn DaCultyre Is Doing It for the Culture

"The cool thing about Ohio is that there is literally a place for everyone."

Photo by Kayode Omoyosi
Photo by Kayode Omoyosi
Photo by Kayode Omoyosi

I was introduced to Robyn DaCultyre at an Untitled Queen show at C’mon Everybody in late January, and it was one of the most unique drag shows I’d seen in a while. Afterwards, I tracked down this self-described “drag creature” and video chatted about her drag origin story, the state of drag in her native Ohio, and the dual identities that make up her persona. Thrillist: I want to ask you about how Robyn DaCultyre came about and your point of view behind your performance.

Robyn DaCultyre: I’ve been travelling around the country from a young age in ministry and Christian studies. I moved to Chicago right after high school. Four years later, moved back to Columbus and decided I didn’t really want to do church anymore; that wasn’t where my heart was.

I had a really low point in my life and had a suicide attempt and then really found drag and started doing drag as a coping mechanism and way to let off steam. I started in July of 2019, and it was really a lot of punk and metal music. I created this drag creature of sorts and they were really out of this world and celestial and all of those fun alien type terms.

And then we went into a global pandemic and I had a lot of time to figure out who I wanted to be. Digitally I was still doing a lot of drag creature-esque numbers and all of that, but I had this moment where we’re on the front lines getting hit with pepper spray and rubber bullets and pepper spray-all of those lovely things. And I said, I have this platform and I need to start showcasing what’s happening.

Untitled [Queen] stepped in at the right time and messaged me and said, “I’m doing this show for Independence Day called Untitled in America with 52 different performers and I want you to be a part of it.” It was at that moment I was able to take the footage I had been recording on the front lines and incorporate it into digital content. I did a song called Black Like Me by Mickey Guyton that talks about white picket fences, but if you want to see how America is, then you should try being Black like me. The imagery of what’s literally happening in Columbus in that digital performance really spearheaded me into focusing on people who look like me.

Nina Simone is one of my biggest inspirations, and one of her quotes that resonates with me is that it’s the duty of the artist to resonate with the times. My art is politically charged. I like to entertain, but there will definitely be a time when you come to a show expecting to have your drink and be chill and that might not be the case.

How did the name Robyn DaCultyre come about?

I was smoking with Ursula Major, who was on season one of Dragula, and the first time I introduced myself to her I was Robyn Banks, which is my drag name originally. She said, “Well, do you just not want to be original at all?” [Laughs] And I sat with that for a couple of months, and I got really stoned one day and was listening to Janelle Monae, and she talks about doing it for the culture, and I said “I do it for the culture, too!” And the rest is history.

And you started a series called Melanated.

We started Melanated last February. I told the idea to my show director that there were no shows specifically run by Black people that only featured Black entertainers. I wanted to do this show for a night and she said, Why don’t we do it once a week for the whole month? The first show happens, and it’s a sold out crowd, and [my director] comes back and says we should do this every month. So I sucked it up and here we are a year later.

Melanated is the only fully Black show in all of the state. It’s a horrible marketing tool and not something I want to promote, but it is just a fact. It amazes me that we are the 13th largest city in America and there’s nothing here that’s fully focused on Black entertainers. The name also comes from Janelle Monae; she says she’s highly melanated and I said, that works.

Photos by Chay Creates LLC (left) and Bridget Caswell (right)
Photos by Chay Creates LLC (left) and Bridget Caswell (right)
Photos by Chay Creates LLC (left) and Bridget Caswell (right)

You refer to yourself as a drag creature, as opposed to drag queen or king…

This is actually the first time I’m making this public. I am in this place where I want to separate the alternative creature from who this melanated goddess or whatever is. DaCultyre is definitely the person who runs Melanated and then Robyn is this drag creature that is out of this world and really loves punk and alternative music. And both intertwine to make Robyn DaCultyre.

You also do pageants. Tell me about that.

In 2020 I was appointed by Nina West, who is from Columbus, as the representative from Ohio for National Entertainer of the Year in Louisville, Kentucky. I placed ninth out of 13 contestants and I really fell in love with the system and fell in love with the pageantry and loved the idea of reigning and being different. I want to show that we as alternative performers, as bearded performers, you can come into these systems and shake things up.

Is there a uniquely “Ohio” style of drag?

No, and I think that’s one of the things that makes it so amazing is that everyone has their own unique style, and it’s all pretty much accepted. I started as a performer and a drag creature and there was space that was afforded to me and I transitioned to more glamor and pageantry and that’s afforded to me as well. I’ve been a bearded entertainer for a year now. The cool thing about Ohio is that there is literally a place for everyone.

I think I have everything I need. Is there anything else I didn’t ask you about that you want to bring up, or‚Ķ

I don’t think so. Are there any generic questions you haven’t asked?

Generic questions‚ĶI think I asked all of them already [laughs]. I like to ask what you’d be doing if you weren’t doing drag?

It’s a great question. I have a day job that is very demanding so I need drag to get away. I’m also very creative and artistic. I used to do web design and all these other things to pull into my creativity. Drag is the longest thing I’ve stuck with in all parts of my life, so I don’t think it’s going anywhere anytime soon.

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John deBary¬†is a drinks expert and writer. His first cocktail book,¬†Drink What You Want, is available now, and his next book,¬†Saved by the Bellini, is expected in early 2023. He is also the co-founder and president of the¬†Restaurant Workers’ Community Foundation, which is dedicated to improving the lives of hospitality industry professionals through advocacy, grant making, and impact investing.

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