Chicago has 77 diverse community areas with multiple neighborhoods in each. One of the best areas to explore on the north side of Chicago’s loop is Uptown. The roaring twenties history continues to influence this area, which has remained a hub for nightlife and abundant entertainment. Here, you’ll find great beaches — for dogs and people, jazz music, a timeworn cemetery, burlesque shows, and Asian dining and shopping. Discover the top seven things to do in this vibrant full-of-history enclave with the aid of our guide.
The Uptown theater district, much different from Chicago's Broadway-style downtown theaters, is worth a look-see for the architecture and history alone. The Riviera Theatre is a stunning French Renaissance Revival building, built in 1917, originally created to be a movie theater. In the mid-eighties, it morphed into a private nightclub. Now, as one of the largest independent producers of live entertainment in America, it’s home to one of the best places in the city to see a concert. Popular notable acts include: Morrissey, Ben Folds Five, Silversun Pickups, The Cranberries, AC/DC, The B-52’s, Red Hot Chili Peppers, Ice-T, Indigo Girls, Lenny Kravitz, Bob Dylan, Ramones and The Allman Brothers Band.
The best part about this beach is that if you have a dog, you can bring them to the designated dog beach (MonDog) on the north end of Montrose Beach. Watch your fur ball swim and fetch balls, while romping around the sand with other pooches. Wash your dirty canine afterward at the pay-to-use washing station. Entrance to the pup beach is free and parking is also available. While the dog beach is off-leash and fenced-in, you’ll need a leash to walk your dog in from the parking lot.
If you would like to sun yourself and enjoy the lake without dogs running over your beach towel, then visit the other side of Montrose Beach. Purchase snacks and drinks, rent a kayak or volleyball net, and set up shop on the sand for a day of fun. Showers and restrooms are also available as well as a pay parking lot and street parking. And, if you’re a distance swimmer, you can get a good workout — entrance for serious swimmers is at Tower 4, just north of the boat house. If you’re car-free, take the CTA train at Lawrence or Wilson stations.
One of the most iconic experiences you can have in Chicago is a night out at the Green Mill Cocktail Lounge, known for its jazz music, spoken word and mob history. Pop Morse’s Roadhouse was the original name in 1907, followed by a title inspired by Paris’ Moulin Rouge (Red Mill): Green Mill Gardens. Jack McGurn, part of Al Capone’s Chicago Outfit, was a co-owner during the Prohibition era (gangsters used tunnels underneath the Green Mill). Visit and see Al Capone’s booth of choice, which still sits at the end of the bar. Now you can visit to hear jazz — Patricia Barber and Kurt Elling were regulars — and other musical acts as well as weekly poetry slams. The 21-and-over joint is cash-only and there’s no dress code — expect a fee to get in at the door. Don’t bother asking for a tunnel tour, they won’t oblige the request.
After 50 years on Clark St. in the River North neighborhood, near Chicago’s loop, The Baton Show Lounge made a big move to Uptown in 2019. This mecca for lively entertainment and the art of female impersonation and seduction has enticed celebrities, athletes and bachelorette parties through its doors for decades. If you’ve never seen a drag show, add this experience to your must-do list. The shows feature group and individual numbers, with mixed genres, and the atmosphere is upbeat and approachable. Reservations are recommended, admission prices vary depending on show and dates, and expect a two-drink minimum. No food is available or allowed and only visitors ages 21 years and over are permitted. Grab a bite to eat before hand. One last thing: wear your dancing shoes.
Eat, Shop and Enjoy the Culture: Argyle Street’s Restaurants and Stores
There have been many monikers attached to the area at Argyle Street, between Sheridan and Broadway: New Chinatown, Little Saigon, Little Cambodia, Vietnamese Town, Little Vietnam and Argyle. No matter what you call it, you’ll find a plethora of Asian grocery and hardware stores, gift shops, nail salons and a mural depicting a century of immigration and life on Argyle Street — The Roots of Argyle, located on the corner of Argyle and Winthrop. Grab a bite to eat at Miss Saigon, Ba Le, Argyle Night Market, Tank Noodle, Hon Kee or Pho 777. The rich immigrant and cultural history of the area is part of what makes Chicago such a diverse and spirited city.
See the burial sites of Chicagoans from nearly 160 years ago at Graceland Cemetery. Historical figures like George Pullman, inventor of the Pullman railway car, Kate Warne, the first female detective, and famous film critic, Roger Ebert have their final resting places here. Several victims of the 1903 Iroquois Theater fire, where more than 600 people died, are buried here. Visit the bronze sculpture, Eternal Silence, also known as the Statue of Death, created by Lorado Taft (Taft also rests here). Beautiful and evocative, the tombs are both commanding and simple, kept safe with walls designed with wrought iron spear-point fencing. The history and architecture — Egyptian Revival, anyone? — is worth seeing as well as the park-like grounds full of trees and greenery. The main entrance can be found at Clark Street and Irving Park Road or get off the Red Line, CTA, at Sheridan. Pick up a free map in the cemetery office before heading out and visit the website for a self-guided audio tour.
During the inception in 1926, Aragon Ballroom was one of the most elaborate and expensive venues of its time, built at a cost of two million dollars. Huge chandeliers, intricately-designed balconies, arched entryways and terra-cotta ceilings, built in the Moorish architecture style to resemble a Spanish village, set the scene for this venue. The tunnels under the Green Mill Cocktail Lounge are said to connect to the Aragon’s basement. Past uses included a roller skating rink, championship boxing, and a disco called the Cheetah. Stevie Wonder, Chuck Berry, Fats Domino, ZZ Top, Fleetwood Mac, Aerosmith, Grateful Dead, and The Rolling Stones have all performed here. In 2015 Aragon Ballroom was used in the filming of "Batman vs Superman: Dawn of Justice" (Thomas and Martha Wayne are shot in the scene). In 2017, Live Nation took over management and now produces English and Spanish language pop and rock concerts.