Uptown is an upscale neighborhood that is a destination for shopping, dining, and entertainment.
It is a fun environment with lots of public art and local businesses that are supported by residents.
Uptown was originally populated by German and Swedish farmers. By 1890 it became a developed neighborhood for Chicago’s wealthy patrons. Although it was known for being an elite neighborhood, things would change when the Great Depression and the housing crisis of World War II would hit. The once large apartment and hotel buildings were being divided for the poor while the wealthy stayed on the north side of the neighborhood. Once the economy started to change, things were looking up in Uptown and the Uptown Chicago Commission was formed. This group successfully sought out the designation of Uptown as a conservation area in 1966. It soon became acknowledged as a Model Cities area by the federal government.
The architecture of Uptown is a wide variety of old-world revivals including Venetian Gothic, Art Deco, and Spanish Revival which all give Uptown its distinct look. One of the most well-known buildings in Uptown is the Spanish Revival-style Aragon Ballroom. It has been used as a roller rink and boxing venue but now is used for concerts.
Uptown offers a vast variety of dining experiences. From Ethiopian cuisine to Thai and Italian, Uptown has so many different flavors to choose from. Demera is a casual Ethiopian restaurant with shared plates and house-roasted coffee. It is delicious and great for a night out with friends! Pokiology is a great place for lunch! These Hawaiian poke and sushi bowls are easy, quick, and refreshing. Hearth & Crust offers a taste of Northern Italy. Have some yummy pizza and pasta with a nice wine pairing! Urban Vegan is a great option for vegans and vegetarians!
Larry’s has the nostalgia of a low-lit bar and craft cocktail bar. Vintage artwork fills the walls and during warmer months the patio and fire pits offer a great place to have a drink. The Green Mill offers entertainment while having a nice drink. There is live music performed by bands and poetry slam Sundays. This iconic bar has so much character and will provide a fun night out. Big Chicks is a lively and colorful, LGBTQAI+ friendly bar. Every weekend there are DJs that provide a great atmosphere to enjoy the night in.
There are so many things to discover in Uptown. Walking the streets during the day offers a look into local businesses, parks, and Montrose Beach. At night there are many things to do from seeing a Cabaret show to a concert at the Aragon Ballroom. The Chicago Pride Parade goes straight through Uptown in celebration of the LGBTQAI+ community. When Uptown, there is never a dull moment!
Walking Score:
Bike Score:
Transit Score:
CTA L: Red Line and Purple Line
CTA Bus:
#36 (Devon & Clark)
#81 (Jefferson Park)
#151 (Clark & Arthur)
Metra: UP-N
Renaissance - 901 W Argyle St
$1,412
Uptown Regency - 5050 N Sheridan Rd
$1,472
Buena Terrace - 4242 N Sheridan Rd
$1,266
Covington - 4600 N Clarendon Ave
$1,455
Sheridan Plaza - 4607 N Sheridan Rd