Internationally recognized chefs, striking architecture, world-renowned museums, and a friendly Midwestern attitude come together to make Chicago one of the country’s best cities. Conde Nast Traveler’s readers have awarded it the Best Big City in the United States for five years in a row.
We also love the Windy City. The Magnificent Mile, Chicago Loop, Lincoln Park, Lakeview, and the Lakeshore waterfront are some of our favorite haunts. Like most tourists, we tend to stick to these tried-and-true neighborhoods, hanging out in the city’s more famous stamping grounds. But Chicago is home to 77 neighborhoods; recently, we took a closer look at three lesser-known but buzzing burgs.
Plenty of people lament the arrival of the Gen-Zs, Gen-Xers, and millennials to this neighborhood, and its resulting gentrification. Yet, we think it’s still one of the coolest, edgiest areas in the city. Tucked into the west side of Chicago, it’s full of vintage shops, used book and record stores, hidden speakeasies, live music venues, contemporary art, and bustling nightlife.
We checked into The Robey Chicago, a sleek, contemporary 89-room hotel, housed in a historic 203-foot-tall Art Deco high rise, located in the heart of the neighborhood. Sunlit rooms are minimalistic yet comfy, with wood floors, neutral hues, and platform beds topped with cushy mattresses and linens. Extra cool are the sixth-floor Cabana Club with an outdoor pool and The Up Room at the 13th-floor rooftop bar with Chicago skyline views. We had lunch at the popular Café Robey (duck hash and Nashville hot chicken!) and then headed out to explore the neighborhood.
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Do this: Check out the cluster of vintage clothing and secondhand stores on Milwaukee Ave., like Vintage Underground, known for its impressive collection of vintage jewelry and accessories, and Kokorokoko for throwback ‘80s and ‘90s apparel. You’ll find some funky clothes at Round Two and trendy men’s and women’s wear at Una Mae’s. Reckless Records is the place to go for vinyl and new and used CDs and DVDs.
Grab a coffee at Ipsento 606 and then take a walk on the 606, a.k.a. the Bloomington Trail, a 2.7-mile elevated greenway that draws walkers, bicyclists, runners, dogs, and kids.
Start (or end) your evening with cocktails at The Violet Hour, a very sexy speakeasy, with candlelight, dark corners, and delicious cocktails. You’ll need to look hard for its hidden door if there’s not a line forming outside.
Also, nearly hidden is Dorian’s Through The Record Shop, an elegant, intimate lounge with live entertainment, tucked behind a door in the corner of — yep — a record store. Other places for cocktails and entertainment include the Cabaret-style Bordel (the Burlesque shows are very sultry) and Subterranean, a longstanding concert venue.
Eat here: Lively Amaru offers an artful blend of Latin, Caribbean, and American cuisine. We’ve tasted some standouts here, like the charred octopus, three-day marinated chicken with Peruvian corn pickle salad, and the Cuban oxtail stew. For casual Mexican, you can’t beat Big Star, located in a former 1940s gas station. If you’re craving a burger, stop by Small Cheval, and for Italian comfort food, try Club Lucky.
It’s been called a village within a city, a liberal and intellectual enclave, and one of the most culturally and racially diverse neighborhoods in Chicago. It’s the stamping grounds of former President Barack Obama and his family, and the future home of the Obama Presidential Center. The Lake Michigan waterfront neighborhood, about 7 miles south of downtown Chicago, is anchored by the prestigious University of Chicago and the vast Museum of Science and Industry. It feels untouristy and well-established, with leafy parks, brownstone row homes, old-school barbershops, and independent bookstores, but the ongoing addition of new restaurants and hotels makes it a great base for a weekend getaway.
The luxe Sophy Hyde Park is the place to stay, a contemporary 98-room boutique hotel with art and custom-designed flourishes that pay homage to the arts and sciences (lamps in the shape of brass instruments, and Erlenmeyer flasks used as wine decanters). The expansive lobby/lounge is a great gathering spot, with a large two-sided fireplace and several sitting areas. Rooms are spacious with marble baths, wall-size art pieces, custom-made Crosley record players, and a selection of vinyl records by local musicians.
Do this: Visit the Museum of Science and Industry, one of the largest science museums in the world, filled with immersive and interactive exhibits. Descend into a coal mine; board a World War II submarine; become a pilot on a state-of-the-art flight simulator; see the world’s largest display of Lego art, and much more. After, stroll beautiful Jackson Park, home to the Japanese-style Garden of the Phoenix and Yoko Ono’s Skylanding sculpture. Continue in Midway Plaisance Park, a mile-long greenway flanking the Gothic, ivy-clad buildings of the University of Chicago. Nearby is the Frederick C. Robie House, a National Historic Landmark, designed by Frank Lloyd Wright and considered one of the finest examples of his Prairie-style architecture. Public tours are offered.
A variety of exhibits, with artifacts, photos, and video storytelling, explore African-American history at the DuSable Black History Museum and Education Center. Particularly moving is the new “The March” exhibit, produced by Time and executive producer Viola Davis. You’ll don headphones and stand among the more than 250,000 people who joined the 1963 March on Washington for Jobs and Freedom to hear Martin Luther King Jr. deliver his iconic “I Have a Dream” speech.
Eat here: The destination-worthy Mesler Chicago is the top place to dine in Hyde Park, a sophisticated, contemporary restaurant with colorful art and sleek furnishings (love the buttery yellow leather chairs!). Brunch favorites include the chicken and sugar waffles and the braised lamb shoulder with poached eggs and grits. For dinner, we’d go for the prime beef bavette or the seafood bucatini. Valois, a downhome, cafeteria-style breakfast and lunch joint, was one of President Obama’s favorites; it’s a neighborhood standby. 2022 James Beard award-winning chef Erick Williams creates crave-inducing Southern cuisine at Virtue Restaurant & Bar. We can’t stop thinking about his gizzards and dirty rice, the green tomatoes topped with gulf shrimp, the stewed collard greens with smoked turkey, and the short rib with creamed spinach.
“Ever hear of the word mestizo?” Salvador Cerna, director of community outreach for the Pilsen Economic Strategies Development Corporation, asked as we toured the neighborhood. “It’s an infusion of cultures, the blend of indigenous and American experiences. It’s Pilsen.”
Pilsen has always been a working-class, immigrant community. Today, it’s one of the largest Mexican communities in Chicago, a vibrant neighborhood with traditional restaurants, local specialty shops, art galleries, and colorful street art.
For a good introduction to the neighborhood, join the Chicago Architecture Center’s Walk Pilsen guided tour. Then explore on your own.
Do this: Walk around the neighborhood and you’ll see dozens of murals. The National Museum of Mexican Art offers a guide to five significant ones, including a work by muralist Hector Duarte, who has painted more than 50 murals across Chicago, and a mural by artist Joseph “Sentrock” Perez, featuring one of his signature characters, a person with a bird mask over his face who he calls “a symbol of freedom.” Next, walk 16th Street along the rail embankment, where you’ll find a mile-long wall of murals.
Visit the National Museum of Mexican Art, with one of the largest collections of Mexican art in the country, spanning some 3,600 years, with more than 18,000 pieces from pre-Cuauhtemoc Mexico to the present.
Browse traditional shops like Centro Botanico Guadalupano, with more than 200 herbs and curated medicinal herbal remedies, and a knowledgeable staff formally trained in traditional herbal medicine. Artesamias D’ Mexico imports ceramics and handicrafts from eight states across Mexico. For traditional pastries and homemade tortillas, check out Panaderia Nuevo Leon.
Eat here: 5 Rabanitos is known for their hefty, home-style dishes — all your favorites are here from tacos to goat adobe barbacoa, served in an unfussy, simple setting. Taqueria Los Comales is well-known for its tacos and tortas and is a good place to get a traditional Mexican breakfast. There are several places to feast on carnitas, but Carnitas Don Pedro is a standout. La Luna is a fine place for cocktails and dinner; start with the mango, tomatillo, and Quemada salsa flight or the ceviche de Cameron, followed by entrees like the mole con pollo asado, roasted cauliflower tacos, or chimichurri lamb chops.
For more information, visit www.choosechicago.com.
Diane Bair and Pamela Wright can be reached at bairwright@gmail.com
Work at Boston Globe Media