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Old Town Luxury Apartments

Living in Old Town means experiencing all the best parts of Chicago! Old Town luxury apartments in this neighborhood bask in all the quirky, Bohemian charm the area’s known for — while putting you walking distance from River North, North Avenue Beach and the Chicago Riverwalk.

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Apartments for Rent in Old Town, Chicago

Chicago's Old Town, A Neighborhood Rental Guide

Living in Old Town holds a special pride that ties neighbors together and forms lasting bonds. In this friendly and historic neighborhood, you'll see people on their patios or stoops chatting with passersby, and dog owners convening at the dog park with their two-legged and four-legged friends.

Don't be surprised if your street is temporarily closed for a day in lieu of a neighborhood block party — complete with picnic tables, games, a live band and lots of home-cooked dishes to pass.

Downtown Apartment Company specializes in connecting you with the best of Old Town apartment buildings and high-rise apartments. If you’re interested in one of our listings, simply reach out to speak with a leasing specialist today! We are happy to help find your dream home in Old Town!

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Rates vary on luxury apartments in Old Town, Chicago. Explore listings, and you’ll find a wide range of property values throughout the area that suit any budget and living preference.


he apartments for rent in Old Town can be the perfect fit for many lifestyles. When you live in an Old Town apartment, expect an easy-going and quaint community to surround you.


This is a dog-loving neighborhood with a lot of opportunities to get outside and enjoy the outdoors.


Old Town offers easy access to both Interstate 90/94 (Kennedy Expressway) and Lake Shore Drive.


The Second City is a well-known comedy clubs — Bill Murray is among its alumni — but it also hosts improv classes and conducts touring shows.


One of the best parts of choosing apartments in Old Town is the convenience. Given the small size of the neighborhood and its proximity to downtown and Lincoln Park, Old Town makes it easy to get around the Windy City. Living here, you’ll be a short walk to most errands or destinations within the area. And, for going any farther, there's easy-to-access public transit, taxis or driving your car.

2 cta routes

10 bus routes

0 metra routes

10 notable landmarks

Recreation / Entertainment

In the summer, Old Town explodes with fun and excitement as folks come from all around to visit the neighborhood street festivals, which are among the most beloved in Chicago. Known for hosting its annual art festival, this neighborhood is rich in cultural history.

A Red Orchid Theatre

A Red Orchid Theatre is an ensemble theatre located in the Old Town district of Chicago. Founded in 1993, it’s now in its 21st year of producing.

Bauler Playlot Park

Locals love this nook of green space surrounded by trees, starring a children's playground with slides and swings.

159 restaurants bars & coffee shops


Even though Old Town is a predominantly residential locale, certain restaurants have been in the area longer than most homeowners, becoming community institutions that are as much a part of the neighborhood culture as the residents who live here.


Casual Dining

Fine Dining

Fast Food

Kapéj Coffee Roasters

Serving coffee from around the world, Kapéj Coffee Roasters offers a laid-back atmosphere with outdoor seating in the summer months. The focus is on delicious coffees and customer service that makes you feel like family.

La Fournette

This traditional French bakery features rustic wood decor and offers fresh-baked breads and sweet treats.


What would the luxury apartments of Old Town, Chicago be without a local Starbucks? Visit this Seattle-based coffeehouse chain for its signature roasts, light bites and Wi-Fi availability.

Old Jerusalem Restaurant

Veteran neighborhood cafe for casual Middle Eastern dining with BYOB & indoor-outdoor seating.

Topo Gigio Restaurant

Restaurant serving traditional Italian cuisine in a warm setting with an outdoor patio.


Japanese dining plus traditional sushi in a bi-level modern space with an upstairs lounge & patio.

Topo Gigio Restaurant

rant serving traditional Italian cuisine in a warm setting with an outdoor patio.

Quiznos Sandwich Restaurants

Classic, long-running fast-food chain known for its burgers, fries & shakes.


Classic, long-running fast-food chain known for its burgers, fries & shakes.

Nightlife / Bars

The bar scene in Old Town is concentrated on Wells Street, but there are a few other establishments scattered about the residential blocks that are just as lively as the pubs on the main strip. So, take your pick, or make the rounds and have yourself a ball in this quaint, yet happening near north side neighborhood.


Old Town Ale House

Relax and unwind at this laid-back, cash-only dive bar. Set near Second City, it features a storied past, old-school jukebox and funky art.

The Glunz Tavern

Enjoy this historic tavern, which features a European-style menu, a tin ceiling, a mahogany bar and hardwood floors.

Woodie's Flat

Woodie’s Flat is a lively two-story spot with a collegial vibe and a creative menu of wood-smoked burgers and craft beers.


You’ll love this lively sports bar with a wide range of bar food from salads to steaks, plus a patio and a rooftop deck.

Old Town Pizza Pub

This brick-walled pub showcases old-world style and has a long bar for beers and tables for whole pizzas.


In the Old Town Triangle, Wells Street is home to the neighborhood's retail shops and boutiques. Found amid the restaurants are a handful of storefronts that offer residents a variety of unique fashion items and other goods that are always handy to have close to home.

300+ retail shops

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