Apartments for Rent in the Oakland Neighborhood of Chicago, IL (523 Rentals) Page 8 of 11

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4400 S Calumet Ave
1 to 3 Bedroom Apartments

4400 S Calumet Ave

4400 S Calumet AveChicago, IL 60653
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235 E 35th St
Studio Apartments

235 E 35th St

235 E 35th StChicago, IL 60616
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4218 S Indiana Ave
2 to 4 Bedroom Apartments

4218 S Indiana Ave

4218 S Indiana AveChicago, IL 60653
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1157 E 47th St
Studio Apartments

1157 E 47th St

1157 E 47th StChicago, IL 60653
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4238 S Indiana Ave
3 to 4 Bedroom Apartments

4238 S Indiana Ave

4238 S Indiana AveChicago, IL 60653
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3446 S Prairie Ave
2 to 3 Bedroom Apartments

3446 S Prairie Ave

3446 S Prairie AveChicago, IL 60616
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539 E 46th Pl
2 to 4 Bedroom Apartments

539 E 46th Pl

539 E 46th PlChicago, IL 60653
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4530 King Dr
1 Bedroom Apartments

4530 King Dr

4530 King DrChicago, IL 60653
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4550 S King Dr
3 Bedroom Apartments

4550 S King Dr

4550 S King DrChicago, IL 60653
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Gwendolyn Place
1 to 3 Bedroom Apartments

Gwendolyn Place

109 E 43rd StChicago, IL 60653
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4522 S Calumet Ave
2 to 3 Bedroom Apartments

4522 S Calumet Ave

4522 S Calumet AveChicago, IL 60653
Showing Results 351-400, Page 8 of 11

Frequently Asked Questions about Oakland

What is the current pricing and availability for apartments for rent in the Oakland area of Chicago, IL?

As of today, August 24, 2026, there are currently 523 available Oakland apartments priced from $1,045 to $3,720, with an average monthly rent of $1,778.

What is the current price range for One Bedroom Oakland Apartments for rent?

Today's rental pricing for One Bedroom Apartments in Oakland ranges from $1,190 to $2,350 with an average monthly rent of $1,428.

What does renting a Two Bedroom Apartment in Oakland cost?

The monthly rent prices of Two Bedroom Apartments currently available in Oakland range from $1,450 to $2,700. Today's average rental price for Two Bedrooms here is $1,840.

How expensive are Oakland Three Bedroom Apartments?

There are currently 95 Three Bedroom Apartments listings available in Oakland on ApartmentHomeLiving.com. The pricing ranges from $1,720 to $3,720 - averaging $2,436 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

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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.

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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.

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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.

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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

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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.

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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.

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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.

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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.