Located on Chicago’s North Side, Andersonville feels more like an adorable small town than a subset of the city. The streets are lined with beautiful homes and unique local businesses, such as Women and Children First Bookstore, one of the last remaining feminist bookstores in the country; the Andersonville Galleria, which showcases and sells the work of local designers and artists; and AlleyCat Comics, whose entrance is literally in an alley.
Residents of this neighborhood are considered to have pioneered Chicago’s “shop local” movement. It is also one of the most queer-friendly areas of the city. Andersonville is filled with passionate people who stand up for what they believe in and is definitely worth a visit.
This South Side neighborhood holds so much Chicago history. It’s the site of the 1893 World’s Columbian Exposition, otherwise known as the Chicago World’s Fair. It has a home designed by Frank Lloyd Wright, and it is also the former residence of President Barack Obama. There is even a plaque on the corner of 53rd Street and Dorchester Avenue commemorating where Barack and Michelle Obama shared their first kiss.
Both the University of Chicago and the Museum of Science and Industry lie within Hyde Park’s borders, as does a portion of the beautiful Jackson Park. Hyde Park is also on the shores of Lake Michigan, giving residents and visitors beautiful views and easy access to the 18-mile lakefront running and biking path.
Logan Square is a quiet West Side neighborhood filled with beautiful architecture, lovely parks and a great mix of bars and restaurants. It is also known for its charming Sunday farmer’s market that runs from May through October. While you’re there, be sure to check out Best Intentions, a dive bar owned by two bartending brothers with decades of experience who make unbelievable craft cocktails. Distiller Magazine rated Best Intentions one of the top 22 bars in the world. (Full disclosure: the brothers are the author’s cousins.)
Located on the city’s Lower West Side, Pilsen is a predominantly Mexican-American community with incredible food and art scenes. Visitors to Pilsen will find street vendors selling delicious tacos and elotes, restaurants with live music and cozy local coffee shops. On the art side, gorgeous murals by famous street artists adorn buildings all over the neighborhood. Pilsen is also home to the National Museum of Mexican Art, which offers free admission and whose 10,000-piece collection celebrates Mexican art and culture.
The West Loop is an industrial zone turned chic foodie paradise near Chicago’s business district. It has become a hotspot only over the past decade or so, but Chicagoans flock to this neighborhood for its bevy of modern, upscale bars and restaurants. It is home to the famous Girl and the Goat, where those vying for a table must make reservations months in advance, as well as to the French Market, an indoor food market featuring an eclectic (and delicious) mix of vendors. Other great spots to check out are The Publican, Bar Siena, Duck Duck Goat and Parlor Pizza.
The home of the Chicago Cubs’ Wrigley Field, Wrigleyville is a baseball heaven on the North Side of the city. The area surrounding the stadium is lined with souvenir shops and sports bars where fans can enjoy the game. Since the Cubs won the 2016 World Series, the neighborhood has been completely revamped. New hotels, restaurants, bars and shops seem to sprout up every day.
Bronzeville is considered the center of Chicago’s own 20th-century Harlem Renaissance and is the former South Side home of such greats as Louis Armstrong, Richard Wright, Bessie Coleman and Ida B Wells. It is also the site of Chicago’s Bud Billiken Parade, the largest African American parade in the country, held every August since 1929.
While the neighborhood has experienced significant economic hardship since the Great Depression, it is currently undergoing a revitalization. Not only are new shops and restaurants opening, but the neighborhood is also re-establishing itself as an arts center, with beautiful public art displays as well as the Bronzeville Art District, a group of six visual-arts spaces in the neighborhood. Visitors can even take a free Trolley Tour hosted by the Bronzeville Art District to learn about the neighborhood’s art.
The Southport Corridor is a shopping hotspot on the Northeast side of the city, lined with restaurants and clothing stores and also containing the city’s first Amazon bookstore. The Southport Corridor is a fantastic neighborhood in which to spend a Sunday trying on clothes and enjoying a delicious brunch.
This enclave of Lakeview was the first gay neighborhood in the country to gain official recognition by a city government. The neighborhood is marked by a series of rainbow pylons lining its streets, installed in 1998 by Chicago’s then mayor, Richard M Daley, in a historic move to legitimize the neighborhood. Boystown’s main street is filled with queer-focused bars and businesses and is the site of Chicago’s annual June Pride Parade. It is also the location of the Center on Halsted, the largest LGBTQ community center in the Midwest.
Wicker Park has long been known as one of Chicago’s hipster neighborhoods, anchored by unique local bookshops, cafés, art galleries and cocktail bars. Running through this neighborhood (as well as Logan Square and Humboldt Park) is an elevated 2.7-mile (4.3-kilometer) running and bike path called the 606 – a converted railroad now brimming with beautiful greenery and public art installations.
Old Town is a historic district on Chicago’s North Side, home to beautiful buildings as well as the world-famous comedy club The Second City. If you’re looking for a fancier night out, Old Town offers some great locales. This neighborhood also holds St Michael’s Church, one of only seven buildings to survive the Great Chicago Fire of 1871.
Bridgeport is the location of Guaranteed Rate Stadium, home of the Chicago White Sox. It’s a great neighborhood to visit to catch a game, whether inside the stadium or at one of the area’s many Sox bars. It is considered one of the most diverse neighborhoods in the city, is the birthplace of five Chicago mayors and is also home to the beautiful Bridgeport Art Center, a popular art and event venue.
Rogers Park is another beautiful lakeside neighborhood and the location of Loyola University. It is the northernmost neighborhood of the city and feels almost like a delightful little town of its own. Rogers Park has a large immigrant population, which also means it has a vast array of delectable restaurant choices, from Peruvian to Indian to Greek to Korean to Pakistani.
Nestled within the neighborhood of Edgewater lies the beautiful Bryn Mawr Historic District that will have you feeling like you’ve stepped back into the early 1900s. It’s a charming area to wander and enjoy the remarkable architecture.
The swanky neighborhood of River North is near Chicago’s central business district and a popular location for after-work dinner and drinks. It is bursting with bars, restaurants and nightlife and is also home to a number of upscale art galleries. It also lays claim to the famous Wrigley Building, an architectural marvel on Michigan Avenue’s Magnificent Mile. You may know it by its beautiful clock tower reaching into the sky from the building’s center.