
Apartments near Ashland & Roosevelt in Chicago, IL (1,763 Rentals)


1019 W 18th St

1826 W Cermak Rd

2239 W 18th St

Monroe Laflin Place

1702 S. Morgan St.

Residences on Racine

1259 W Adams St

1956 W 21st Pl

831 S Western Ave

6 Units in Pilsen - Beautifully Rehabbed

1000 S Western Ave

811-823 S Western Ave

2225 W 18th Pl

La Fama

1839-1843 S Carpenter St

32 S Ashland Ave

227 S Racine Ave

The Daily News Building

900 S Western Ave

918 S Western Ave

2242 W 18th Plz

1819-1835 W Cermak Rd

Park 1500

2049 W 21st St

1839 W Cermak Rd

1920 W Cermak Rd

1940 S May St

2057 W 21st St

221-225 S Racine Ave

1918 W Cermak Rd

225 S Racine Ave

1916 S Leavitt St

965 W 18th St

2416 W Arthington St

1400 W Monroe St

2136 W 21st St

301 S Leavitt St

2058 W 21st Pl

1937 W Cermak Rd

215 S Hamilton Ave

SkyTech Lofts

1823 W 22nd Pl

2276 S Blue Island Ave

Bldg A

Y Condominiums

2446 W Taylor St

Pilsen Apartments

2229 W Cullerton St

2332 W 18th Pl

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Frequently Asked Questions about Chicago
How much are Studio apartments in Chicago?
There are currently 8,243 Studio Apartments in Chicago with rent ranges from $600 to $15,622 with an average price of $2,081.
What is the current price range for One Bedroom Chicago Apartments for rent?
Today's rental pricing for One Bedroom Apartments in Chicago ranges from $800 to $9,885 with an average monthly rent of $2,480.
What does renting a Two Bedroom Apartment in Chicago cost?
The monthly rent prices of Two Bedroom Apartments currently available in Chicago range from $850 to $24,461. Today's average rental price for Two Bedrooms here is $3,073.
How expensive are Chicago Three Bedroom Apartments?
There are currently 5,045 Three Bedroom Apartments listings available in Chicago on ApartmentHomeLiving.com. The pricing ranges from $695 to $38,481 - averaging $3,717 for the location.
Expert Rental Resources
The rental experts at ApartmentHomeLiving.com provide you with top advice, tools, and tips for understanding the leasing process and finding the perfect rental. Here are a few helpful rental and leasing articles from our experts to guide you on your search.
Helpful Local Expert Guides

The Windy City Price Tag: Your Complete Guide to the Cost of Living in Chicago
Written by: Nicole Harms
When choosing a place to live, there are many things you must consider. Your employer, your shopping preferences, and even schools are all important to think about. Yet cost of living is also important to know and plan for.

Best Places to Live Near Chicago: 5 Cities That Keep the Windy City Accessible
Written by: Nicole Harms
I’m Nicole, you’re ApartmentHomeLiving.com Local Expert for Chicago. There’s no denying I love the Windy City. Yet there’s also no denying that rental homes in Chicago can be pricy, small, and hard to find.

Chicago Relocation 101: Mastering Utilities, Registration, and the CTA
Written by: Nicole Harms
Moving to a new city is always an exciting time, especially one as vibrant and diverse as Chicago. With world-class museums, a breathtaking lakefront, and numerous employment opportunities, there’s much to love about this city.

Explore the Windy City (But Watch for Falling Ice) - An Insider's Guide to Renting in Chicago
Written by: Nicole Harms
From Lake Shore Drive to the O’Hare Airport, the city of Chicago is a study in diversity, resilience, and culture.
Articles, How-To's, and Tips

Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags
Written by: Robin Stewart
Renters want to find a great apartment, the right place for them, one that checks all the boxes of location, rental cost, amenities, safety, and more.

First Apartment Regrets: Real Renters Share What They'd Do Differently
Written by: Robin Stewart
Hindsight is 20/20. Live and Learn. With age comes wisdom. We’re familiar with all those expressions, and all of them apply to lessons first-time renters learn.

Renters Insurance 101: What It Is, What It Covers, and Why You Need It
Written by: Robin Stewart
Insurance seems to be a part of life. In some states, having insurance is the law, as is the case for automobile insurance. Renters are no exception.

Apartment Occupancy Rates: Renter Attraction vs Renter Retention
Written by: Robin Stewart
There’s a tenet in marketing about client or customer attraction and retention. Studies and data have consistently shown it costs less to keep a current customer than to attract a new one.