Neighborhood Overviews

There is over 77 neighborhoods in Chicago and we’re hoping our brief overview of a few of them help you pick the perfect place for you to call home.

River North

River North is a bustling neighborhood just north of the Loop across the river, known for its upscale shopping, dining, fine nightclubs and cocktail bars. Opened in 1930, the expansive Merchandise Mart is housed in a former industrial estate and includes showrooms for home and office design that attract many visitors. The artist studios in former warehouses around the Mart contribute to the survival of the main galleries in the area.

The Square One Take: “River North is quiet and peaceful during the business day. The perfect on stop shop to grab lunch, hit the gym, and run errands. After 5pm it turns into a vibrant urban oasis. The perfect place to unwind, catch a show, and start your adventures.”-Michael

Insider Info: “Green Door Tavern: Here’s what you’ll do: Walk into Green Door, head to the back of the bar and hang a left to go down the stairs as if you were going to the bathroom. At this point, you may see already a line for the Drifter. If not, look for a knickknack-adorned door at the bottom of the stairs. Once you enter, you’ll be handed a few tarot cards, which double as the cocktail menu. You are welcome!”
– via Time Out Chicago

Old Town 

Old Town was founded in 1850 by German immigrants. It is particularly popular with the architecturally interested, who visit the Victorian buildings, the picturesque streets and stores sprinkled throughout the area. The tree-lined Wells Street features the famous Second City comedy club, traditional, charming pubs and cafes with exquisite coffee and original boutiques. St. Michael’s Church is one of the few buildings in Chicago that survived the Great Fire of 1871.

The Square One Take: “An Old Town with new life. A Second City, and Wells on Wells of fun and drinks. Enjoy!”- Malcolm 

Insider Info: You want a last minute laugh? UP comedy club is as spontaneous as our mood swings. Grab a drink and enjoy the show!



The Loop

The Loop is heart of the hustle and bustle of the city. It’s the financial hub of Chicago filled with skyscrapers full of offices, but it also has a large variety of restaurants, shopping, theaters and parks. You can find the tallest building in the Midwest, the 110-story Willis Tower, or if you are local Sears Tower, and countless other famous Chicago icons like Cloud Gate/The Bean. The highlight for tourists and Chicagoan’s alike would be the green space of Millennium Park, with its outdoor theatre full of activities in the summer, gardens and space to enjoy Chicago’s warmer months.

The Square One Take: “The heart of downtown-always something exiting happening here.” – Bonnie

Insider Info: Cindy’s Rooftop Bar has great cocktails and a stunning view of the downtown. It’s open year around and Chef Christian Regano is a food magician. You don’t want to miss out on this experience.

Lincoln Park 

The tree-lined Lincoln Park neighborhood offers a diverse nightlife, dining and entertainment. On North Lincoln Avenue, cocktail lounges, bars and concert halls such as Lincoln Hall are located. The renowned Steppenwolf Theater Company is located on Halsted Street.  The biggest park in the city, also called Lincoln Park, is located in the neighborhood is full of bike paths, beaches like North Avenue, Lincoln Park Zoo, and Chicago History Museum.

The Square One Take: “Lincoln Park is a neighborhood with a lot of history, chic and appeal.” – Rayford

Insider Info: Yes the big city life is the best, but sometimes and by sometimes we mean sometimes, you need a tiny getaway. The Alfred Caldwell Lilly Pool is an in the city oasis. Please don’t tell everyone.


Looking at Streeterville today you’d never guess it was never part of the original landscape of Chicago. Originally a sandbar, it got its boom of development in the 1920’s after the Michigan Avenue Bridge opened. It’s much more than Navy Pier and is full of incredible four-star dining options, a Northwestern University Campus, and views of the city and lake that can’t be beat.

The Square One Take: “Be sure to visit the Museum of Contemporary Arts, then grab a divi bike and enjoy the Lakefront.” -Norma

Insider Info: Streeter’s Tavern.This basement bar is on the west side of Michigan Ave. and has a lot of activities like beer pong, foosball, and giant Jenga. The DJ usually plays some great 90’s jams.


Lakeview is the perfect location of being far away from the busyness of downtown but close enough to get there quickly. Lakeview includes smaller “sub-neighborhoods” like Wrigleyville, Lakeview East and Southport Corridor. If all the options of dining, shopping and entertainment isn’t enough to make you want to call Lakeview home it has some of the best transportation options, along with miles of lakefront path to enjoy.

The Square One Take: “So welcoming and full of things to do. Go out and see some comedy.” -Kelsey

Insider Info: Go to Wrigley Field. It is the second oldest baseball stadium in the U.S and is just gorgeous. The secret tip: Go after or before the game to Murphy´s Bleachers and hang out with Eddie Vedder and Bill Murray.

Lakeshore East

Whether you call it Lakeshore East or New East Side, it has seen quite a few changes in the past view decades. It from a rail yard to golf course to now an area of architectural wonders. Though the area boasts some of the most iconic architecture in Chicago in recent decades like the Aqua skyscraper, you’ll find urban oases in the parks and green space in the area.

The Square One Take: “Wonderful little community along the river and Lake Michigan. Some fabulous buildings with astonishing views.” -Leif

Insider Info: III Forks: Spoiler Alert: Best Steak+Rooftop!

South Loop

The South Loop is one of the most accessible neighborhoods in Chicago. It boarders on Chinatown and the Chicago River. Hugged by the lake and Chi-town’s parks, it is one of the most diverse neighborhoods. It is perfectly lively and quiet at the same time.

The Square One Take: “The South Loop is my idea of the perfect neighborhood. Seriously, I moved here 3 years ago and it offers everything I could want in a neighborhood.” – Jason

Insider Info: Great hang-out spot “Spoke&Bird”. Great coffee, great people. You’ll become a regular for sure. There is just nothing not to love about this spot. Try it out 🙂 only home is better.

West Loop

The industrial area of the West Loop is known for its top restaurants and the quality bar scene. Stunning loft apartments and boutique hotels make this neighborhood on of the most unique ones.

The Square One Take: “From speakeasies to Michelin starred restaurants, there’s something for everyone in this culinary and artistic mecca!”- Anthony

Insider Info: Sushi Dokku turns into Booze Box if you clap three times as fast as you can or head to the alley just behind Sushi Dokku and look for the red light above a door that says Booze Box. If you can’t find it, the staff will be happy to escort you downstairs. Boozy cocktails, yay!