Uptown may have originated as a summer resort town in the early 1900s, but nowadays, it boasts being one of the most diverse neighborhoods in Chicago, Illinois. Contributing to this area's vibrant culture are world-class ethnic restaurants, a lively music scene, historic architecture, and an ever-growing theatre district and entertainment district. However, not everything in Uptown differs from a century ago—it is still a highly sought-after destination for both entertainment and leisure on the lakefront thanks to the expansive Montrose Beach. Neighborhoods within Uptown include Buena Park, Sheridan Park, Argyle Street (also known as Asia on Argyle district), Margate Park, and the Uptown Square historic district. Andersonville is also often lumped into this area. It is an upscale neighborhood on the north-side of Uptown with lively streets that are a popular haunt for retail therapy.
Neighboring Ravenswood, Uptown is the go-to for fun with its bustling nightlife and endless entertainment options. Catch a rock show or some Latin dancing at the Aragon Ballroom or pop on over to the Riviera for some live theater. Want some pre-show cocktails while enjoying some smooth jazz? Check out The Green Mill. Then there is always a tourist favorite, Graceland Cemetery. Architecture, art, and design lovers won't want to miss the final resting place of historical Chicagoans like Louis Sullivan, and Ludwig Mies van der Rohe.
For some fun in the sun, a stretch of greenspace nestled between N Marine Dr and Lake Michigan offers a tranquil city escape. This leisurely lakefront area that is collectively known as Lincoln Park stretches 7 miles, making it the largest public park in the city. Here you will find the expansive Montrose Beach, Montrose Dog Beach, and the Clarendon Park Community Center. Cricket Hill is also in this area, which is a hotspot for sledding in the winter and known for its annual kite festival.
The CTA red line that feeds in from The Loop makes everything that Uptown has to offer highly accessible. Beyond the CTA, the bus is also an excellent option since it has many major bus routes running through the area. And you can't forget Lake Shore Drive, which offers an easy transportation option to the city at large.
Uptown is one of Chicago's most affordable neighborhoods and home to some of the most magnificent rehabilitation projects in the city. Here you will find many historical apartment buildings with magazine-worthy architectural detailing and luxury amenities. However, these apartments are more than just exquisite aesthetic and comfort—they're a magnificent blend of Chicago’s past and future.
A few notable Uptown Chicago apartment buildings include:
There is a reason dog owners flock to Uptown. With the walking trails that snake along the shore and the Montrose Dog Beach, your four-legged friends can stretch their legs and swim a few laps. Pet-friendly apartments in Uptown include 4070 N Kenmore Ave in Lakeview, The Bachelor (1136 W Wilson St), and Buena Shores (833 W Buena Ave). If you want to be just blocks away from the Montrose Dog Beach, The Lawrence House is also an excellent option (1020 W Lawrence Ave. Chicago, IL). Want a freshly renovated pet-friendly apartment? The June was recently constructed in 2020.
Whether you are craving a freshly brewed cup of coffee or some karaoke and beer, Uptown has you covered. With its assortment of restaurants and international cusine, you are sure to find something that satisfies your taste buds. Here are a few of our favorites.
Coffee & Snacks
Dinner & Drinks
Originally an apartment hotel—famous for housing musicians from the Aragon Ballroom and talent from the silent film production house Essanay film studios—The Lawrence House has preserved the spirit of the roaring '20s in contemporary apartment living. The lobby is open to the public and features an art deco barrel-vaulted skylight with a co-working table, lounge seating, a Heritage Outpost coffee shop, and Larry's bar. 3 Squares Diner is connected to the lobby and offers breakfast, lunch, and dinner. This Uptown gem offers historic Chicago charm with access to luxury hotel-style amenities. These luxury amenities include a gym with a restored mosaic-tiled pool, a boxing ring with regular boxing classes, strength training, and cardio. Additionally, there is a rooftop lounge, deck, and backyard, providing ample seating for spring and summer fun with gas grills and seating areas. The Lawrence House offers studio, lofted studios, 1-bedroom, and 2-bedroom apartments.
This former Synagogue's exquisite exterior was preserved after being slated for demolition and converted into studio, 1-bedroom, and 1-bedroom lofted apartments. Architectural details provide visual interest and Flats partnered with local organizations to donate historic and religious artifacts.
The Bachelor is just steps from the newly renovated Wilson Red Line CTA station and across the street from Truman College. Studio and 1-bedroom apartments feature in-unit laundry, have subway tiling, and poured concrete floors in the typical Flats fashion.
The Draper will offer apartments with building amenities such as a full gym, roof deck and lounge, media/game room, lobby with a coffee shop, and other ground-level retailers.