
Apartments near Ashland & Roosevelt in Chicago, IL (1,759 Rentals)


3121 W Monroe St

651 N Milwaukee Ave

2900 S Union Ave

City Towne Lofts

729 N Hoyne Ave

464 W 27th St

3012 W Warren Blvd

904 W Erie St

2901 S Union Ave

246 W 24th St

2121 W Superior St

2100 W Superior St

226 W 23rd Plz

268 W 24th Pl

669 N Milwaukee Ave

Lofts at Avenir

683-685 N Milwaukee Ave

2828 S Wallace St

1006 S Keeley St

3155 W Jackson Blvd

478-480 W 28th St

243 W 24th St

The Monroe Residences

3125 W Cermak Rd

Six91 Milwaukee

2859 S Lowe Ave

2353 S Whipple St

2806 S Normal Ave

2844 S Wallace St

250 W 24th Pl

445 W 27th St

3134 W 5th Ave

707-709 N Milwaukee Ave

2845 S Wallace St

2858 S Wallace St

2841 S Wallace St

738 W 30th St

2346 S Whipple St

3142-3144 W Cermak Rd

2320-2322 W Huron St

223 W Lake St

2849-2853 S Wallace St

1032 W 31st Pl

945 W Huron St

River West Two Condo Association

2902 S Wallace St

2431 S Whipple Rd

2955 W 25th St

501 W 28th 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.