Uptown Neighborhood Guide

Between Andersonville and Lakeview lies Chicago’s Uptown neighborhood. Filled with dazzling architecture, diverse entertainment, and reasonably priced, Uptown is the epicenter of the northside. Located on Chicago’s northeast side, interlocked by Foster Avenue to the north, Montrose to the south, and Clark Street to the west, the neighborhood borders Lake Michigan², and locals use the lakefront trail as a backyard. In the center of Uptown is Broadway Avenue, which is the community’s cultural and commercial hub. With easy CTA access and historic theaters, Uptown has been a Chicago entertainment destination for over a decade. 

Uptown’s legacy began at the turn of the 20th century with a housing boom initiated by Chicago’s world fair in 1893¹. According to Explore Uptown, large entertainment venues appeared alongside new residential buildings in the 1900s, including one of Chicago’s most celebrated concert halls, the Aragon Ballroom⁹. In its early years, The Aragon hosted the most prominent big band musicians, like Duke Ellington and Benny Goodman; in addition to being a music venue, the Aragon has also been a roller rink, a disco, and a boxing arena. Throughout its history, the theater has continuously invited different performers to its stage, with names like Queen, Metallica, Buddy Guy, and Smashing Pumpkins having graced the marquee.

Chicago’s oldest jazz bar, The Green Mill, is also in Uptown. As the Uptown population grew, demand for entertainment venues increased, leading to the introduction of jazz and blues clubs like the Green Mill. Throughout the 20s and 30s, The Green Mill had some of the most prolific artists of the time perform there, including Billie Holiday and Louis Armstrong⁴.  

Uptown’s music scene is still thriving and The Riviera Theatre on Racine and Broadway is one of the neighborhood’s most recent additions. Converted from a movie theater in 1986, “The Riv” hosts an eclectic array of musical genres, including contemporary rap, pop, and rock artists.  

Uptown is a community with tremendous ethnic, racial, and economic representations. Uptown is a premier destination for Ethiopian food with Demera⁶, named one of the best restaurants in Uptown by Time Out Magazine. Sitting right on the busy corner of Lawrence Avenue and Broadway, Demera has been serving up delicious and authentic Ethiopian dishes for over 15 years. 

Broadway Avenue is home to one of Chicago’s most famous Chinese restaurants, Furama. For more than 35 years, this local favorite has served authentic favorites like soup dumplings and chop suey. The restaurant constantly receives praise for its small plates, gaining accolades from Time Out and Eater as a top contender for the best dim sum spot¹⁰ in Chicago.  

One of the neighborhood’s most famous streets is Argyle, home to Chicago’s best Vietnamese restaurants and grocery stores. Lovingly known as Asia on Argyle, the area saw a considerable increase in Vietnamese and Cambodian residents during the 1970s. Today, the neighborhood still hosts Chicago’s largest East Asian and Southeast Asian populations and the free Argyle Night Market is an annual event that features food from local Argyle restaurants, plus live cultural and musical performances during summer evenings³.  

The Taste of Uptown is a bustling restaurant crawl that brings local restaurants together on a route of small plates and samples of various cuisines. A Passport to Haiti, hosted by the Haitian American Museum of Chicago, offers Haitian drinks and dishes, as well as lessons in making Pikliz, a traditional pickled relish from the island nation. Chicago’s Pride Parade⁸ famously starts in Uptown, marching from Broadway and Montrose to Diversey Parkway and Sheridan Road ending in Lincoln Park. The Uptown Art Fair is an annual showcase for murals that occurs every August, highlighting the city’s public arts, and features activities for all ages, from interactive art projects to installations hosted by local businesses. 

Shopping for local produce is easily accessible in this neighborhood, with several grocery stores available and Uptown’s grocery cooperative, Chicago Market, set to open in the former Red Line Broadway station with the support of the community. The Uptown Farmers Market offers delicious, locally-sourced goods from Illinois and Wisconsin farmers, like organic produce, meats, cheese, and honey. Operating every Wednesday from May through November in the Sunnyside Mall, the outdoor market offers Chicagoans plenty of time to pop over and peruse the more than 20 vendors it hosts weekly.   

Since the neighborhood directly borders the lakefront path and Lake Michigan², Uptown residents have convenient access to miles of outdoor space and sprawling park land. outdoor space is almost endless for its residents. In addition to the iconic lakefront trail perfect for running, walking, or biking, there’s also Buttercup Park, an urban green space with a playground perfect for younger kids. Just a 1-mile walk southeast from Buttercup Park, you’ll find Montrose Beach, which hosts one of the city’s only dog beaches to the north, an iconic dog park, and the city’s only bird sanctuary. The Montrose Point Bird Sanctuary is entirely free, and a short walk through its winding path allows watchers to see hundreds of thousands of migrating birds⁵.  Montrose Beach is the premier spot to lounge in the summertime. 

From the regal Aragon Ballroom to the vivacity of Asia on Argyle, there are unlimited opportunities to experience arts, entertainment, and culture in Uptown. For more than 100 years, Uptown has remained the preferred place for incredible music and innovative theater. With great restaurants on every corner and ample outdoor amenities, this neighborhood is a must-visit and a great place to call home.