Designed as an ornate Spanish courtyard and completed in 1926, the Aragon Ballroom was one of the biggest entertainment venues for big bands in Chicago during the 1940s. Today, it’s used as a concert venue for rock, pop, and electronic music artists. With easy access to and from the El, the Aragon Ballroom is one of the most popular and certainly one of the most unique performance spaces in all of Chicago.
Aragon Ballroom, 1106 W Lawrence Ave Chicago, IL, USA, +1 773 561-9500
Historical figures from George Pullman, inventor of the Pullman railway car, boxer Jack Johnson, and film critic Roger Ebert found their final resting place in this Victorian era cemetery. Serene and hauntingly beautiful, Graceland Cemetery has many elaborate and imposing tombs and mausoleums befitting the prominence of the many important Chicagoans buried here. History, art, and architecture buffs will find sculptures, Egyptian Revival architecture, and some of the city’s biggest names at this site; the rest of us can enjoy the green space and fresh air.
Graceland Cemetery, 4001 N Clark St Chicago, IL, USA, +1 773 525-1105
Before Hollywood dominated the US film industry, Chicago was a major center for silent film during the early 20th century. Most notably, many early Charlie Chaplin films were produced and filmed here, including Chaplin’s iconic movie The Tramp. Chaplin, along with the rest of the American cinema, moved his productions to California and Essanay studios were in poor financial health in the years afterward. Today, it is a part of St. Augustine college and, while no guided tours exist, it is a protected landmark and the iconic sign for the studios remains intact.
Essanay Studios, 1345 W Argyle St Chicago, IL, USA, +1 773 878-8756
Swedish American Museum Center
Chicago was one of the main immigrant destinations in the late 19th and early 20th centuries and this museum pays homage to the thousands of Swedish immigrants and their descendants who settled in and around Chicago. Andersonville, a neighborhood in the northern part of Uptown, had one of the highest concentrations of Swedish immigrants in the entire country and the Swedish American Museum helps to preserve that heritage. Along with the museum’s permanent collection cataloguing the history of Swedish-Americans in the area, the museum also has special exhibits and a large genealogical center.
The Green Mill Cocktail Lounge
A cheeky allusion to the Moulin Rouge in Paris, the Green Mill was a favorite hangout of silent film actors and Chicago gangsters, so much so that Al Capone’s gang became part-owner of the establishment. Jazz, poetry slams, and a variety of local bands now perform regularly at this Uptown nightlife favorite. The Green Mill, though no longer having the same concentration of filmmakers it once did, has been featured in dozens of films, including High Fidelity and Prelude to a Kiss, establishing it as one of Chicago’s preeminent attractions.
Since Uptown is located right on the shoreline of Lake Michigan, it is endowed with wide and sandy beaches, much to the shock of those not native to the Midwest. Chicago has some of the best beaches anywhere on the Great Lakes and in the whole country, and Montrose Beach is as good a beach as any in Chicago. An added bonus: it’s officially dog friendly so dog-owners and lovers will feel right at home during all four seasons.
Montrose Beach, 4400 North Lake Shore Drive Chicago, IL,USA, +1 773 363-2225
The Kiss Kiss Cabaret
Elaborate, classy, and sexy, the Kiss Kiss Cabaret offers entertainment you won’t find anywhere else in the Midwest. Burlesque, vaudeville, comedy, magic shows, and fine drinks have been offered here since 2009. The winner of ‘Best Burlesque Troupe’ as voted by Chicago Reader, the cabaret’s new location is right next to the aforementioned Green Mill Cocktail Lounge.
The Kiss Kiss Cabaret, 4707 N Broadway St #309 Chicago, IL, USA, +1 773 867-1946
Once an elaborate movie palace built in 1917, it has now been converted into an ornate concert venue that houses mainly punk, hip-hop, and indie groups. Lauded for its sound quality, historicity, decor, and amazing views from the balcony, this piece of 1920s history is not one you’ll want to miss, even if you don’t enjoy the music commonly performed there.
Riviera Theatre, 4746 N Racine Ave Chicago, IL, USA, +1 773 275-6800
By Jediah Johnson