Apartments for Rent in the Oakland Neighborhood of Chicago, IL (523 Rentals) Page 4 of 11

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4418 S Drexel Blvd
2 to 3 Bedroom Apartments

4418 S Drexel Blvd

4418 S Drexel BlvdChicago, IL 60653
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425 E 41st St
1 to 2 Bedroom Apartments

425 E 41st St

425 E 41st StChicago, IL 60653
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421 E 41st St
Studio Apartments

421 E 41st St

421 E 41st StChicago, IL 60653
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537 E 43rd St
4 Bedroom Apartments

537 E 43rd St

537 E 43rd StChicago, IL 60653
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3918 S King Dr
2 Bedroom Apartments

3918 S King Dr

3918 S King DrChicago, IL 60653
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Pearl
Studio Apartments

Pearl

3836-3838 S Dr Martin L King Jr DrChicago, IL 60653
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Carolyn
Studio Apartments

Carolyn

3830-3832 S Dr Martin L King Jr DrChicago, IL 60653
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3631 S King Dr
Studio Apartments

3631 S King Dr

3631 S King DrChicago, IL 60653
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3633 S King Dr
Studio Apartments

3633 S King Dr

3633 S King DrChicago, IL 60653
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3629 S King Dr
Studio Apartments

3629 S King Dr

3629 S King DrChicago, IL 60653
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4213 S King Dr
1 to 3 Bedroom Apartments

4213 S King Dr

4213 S King DrChicago, IL 60653
Showing Results 151-200, Page 4 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 $1,025 to $3,723, with an average monthly rent of $1,786.

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 $1,215 to $2,350 with an average monthly rent of $1,427.

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 $1,836.

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 $3,723 - averaging $2,446 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.

decorative image for Renters Insurance 101: What It Is, What It Covers, and Why You Need It article

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.