
2 Bedroom Apartments for Rent in the Woodlawn Neighborhood of Chicago, IL (122 Rentals)


Oglesby Towers Apartments

Academy at Drexel

Total Monthly Price
738 E Marquette Rd, Unit 1

6603 S Kimbark Ave, Unit 3

6525 S Evans Ave, Unit 1

6657 S Minerva Ave, Unit 1142-1W

6657 S Minerva Ave, Unit 6657-1N

6557 S Minerva Ave, Unit 2B

6656 S Woodlawn Ave, Unit 3
Renting with Roommates: Realistic Expectations for Shared Lease
Sharing a lease? Learn how to set clear expectations with your roommates on routines, bills, and cleaning to ensure a successful and peaceful shared living arrangement.

6525 S Evans Ave, Unit 1

6618 S Maryland Ave

6223 S Kenwood Ave

1169 E 61st St

6426 S Ingleside Ave

941 E Marquette Rd

6550 S Drexel Ave

6525 S Evans Ave

6634 S Greenwood Ave

964 E 62nd St
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When searching for a roommate, follow this list of essential steps and set clear expectations to create a solid foundation for a harmonious living situation.

1367 E 64th St

Lakefront Place

Parkland Condominiums

Kimbark Estates

The Grant at Woodlawn Park

6147-6149 S Woodlawn Ave

6621 S Ingleside Ave

6235 S Ellis Ave

The Kenwood Apartments

6512 S Ingleside Ave
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Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.

6420 S Woodlawn Ave

6213-6215 S Greenwood Ave

6605 S Kimbark Ave

1431 E 66th Pl

6427 S Kimbark Ave

6646 S Greenwood Ave

6605-6607 S Greenwood Ave

6657 S Minerva Ave

855 E 64th St

814 E 67th St
Renting Smart: Lease Basics Every Renter Needs
Demystify Your Rental Lease. Learn the basics about renting, deposits, and tenant/landlord responsibilities. Rent smart and avoid surprises. | Renter University at ApartmentHomeLiving.com

6639-6641 S Ellis Ave

6550 S University Ave

1131 E 61st St

6541 S University Ave

1534 E 65th Pl

Woodlawn

Renaissance Apartments

Ingleside

6138-6140 S Woodlawn Ave

6405 S Ingleside Ave
Renters Insurance 101: What It Is, What It Covers, and Why You Need It
From theft to fire to water damage, the unexpected can happen to any renter. Discover why renters insurance is one of the smartest and most affordable investments you can make as a tenant.
Woodlawn, Chicago, IL Local Guide

How much does it cost to rent an apartment in Woodlawn?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Woodlawn Studio Apartments | $951 | $726 | $1,244 |
| Woodlawn 1 Bedroom Apartments | $1,325 | $1,169 | $1,656 |
Woodlawn 2 Bedroom Apartments | $2,082 | $1,200 | $3,525 |
| Woodlawn 3 Bedroom Apartments | $2,447 | $1,665 | $4,200 |
| Woodlawn 4 Bedroom Apartments | $2,616 | $2,495 | $2,980 |
Browse Apartments in this Neighborhood
There are currently 122 rentals with your search options within a 2 mile radius of the Woodlawn Neighborhood of Chicago, IL.
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Woodlawn, Chicago, IL Local Guide
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Largest Available Woodlawn 2 Bedroom Apartments
The largest available 2 Bedroom apartment unit in the Woodlawn area of Chicago, IL is found at 5715-5725 S. Kimbark Avenue and is listed at 1,392 square feet priced from $3,300. Here is today’s list of the largest available 2 Bedroom units in the area:
| Apartment Listing | Model Name | Square Footage | Priced From |
|---|---|---|---|
| 5715-5725 S. Kimbark Avenue | 57152bb | 1,392 Sq Ft | $3,300 |
| Cloisters | clo-2b2a | 1,290 Sq Ft | $3,599 |
| Oglesby Towers Apartments | 2 Bedrooms Floor Plan B2B | 1,215 Sq Ft | $1,846 |
Cheapest Available Woodlawn 2 Bedroom Apartments
Currently the lowest priced 2 Bedroom apartment unit Woodlawn of Chicago, IL is the 2 Bedrooms Floor Plan B1B Model starting from $1,811 at Oglesby Towers Apartments. The average price for all 2 Bedroom apartments in Woodlawn is currently $2,082. Here is today’s list of the cheapest available 2 Bedroom options in the area:
| Apartment Listing | Model Name | Priced From |
|---|---|---|
| Oglesby Towers Apartments | 2 Bedrooms Floor Plan B1B | $1,811 |
| 5715-5725 S. Kimbark Avenue | 57152ba | $3,095 |
| Cloisters | clo-2b2b | $3,350 |
Best Neighborhoods to Rent in Near Chicago's Top Employers: A Guide for Renters
A Local Expert's Guide to The 10 Best Chicago Neighborhoods near Major Local Employers. Find your perfect Chicago, IL apartment, condo, or rental home today at ApartmentHomeLiving.com
Read ArticleA Local Expert's Top Student Friendly Neighborhoods to Rent Near Colleges in Chicago
A Local Expert's guide to the Best Student Friendly Neighborhoods Near Colleges in the Chicago, IL metro area for affordable living. Find your perfect Chicago Student apartment, condo, or rental home today at ApartmentHomeliving.com
Read ArticleReal Estate and Rental Term Glossary | ApartmentHomeLiving.com Renter University
From the letter A all the way to the letter Z, the Real Estate and Rental Term Glossary from the content team at ApartmentHomeLiving.com provides our visitors and shoppers with a little clarity and helpful guidance in navigating the real estate world through definitions and explainers for the top subjects and terms that someone may come across during the leasing, buying, or selling process.
Read ArticleQuick Rent Budget Calculator
How much rent can you afford?
The common "Rule of Thumb" is that rent should be no more than 30% of your income. How much is that? Enter your monthly income and click "Calculate My Budget" to find out.
Best Local Schools in Woodlawn, Chicago, IL
Carnegie Elementary School
Hyde Park Academy High School
Wadsworth PreK-8th STEM School
School data provided by Great Schools
Frequently Asked Questions about 2 Bedroom Woodlawn Apartments
What is the Cheapest apartment in Woodlawn with 2 Bedroom?
Currently the most affordable 2 Bedroom in Woodlawn is at Oglesby Towers Apartments listed at $1,811.
What is the largest available 2 Bedroom Woodlawn Apartment for rent?
Today's apartment with the most square footage in Woodlawn is a 1,392 square feet unit starting from $3,300 at 5715-5725 S. Kimbark Avenue.
What is the average size for Woodlawn 2 Bedroom Apartments for rent?
The average size for a 2 Bedroom rental in Woodlawn is currently 0 sq ft.
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

A Local Expert’s Guide To 10 Budget-Friendly Neighborhoods to Rent in Chicago
Written by: Nicole Harms
I’m Nicole, your ApartmentHomeLiving.com Local Expert for Chicago, IL. As a resident of the Chicago area for over 20 years, I’ve learned which neighborhoods are great and which are best avoided.

Top Student Friendly Neighborhoods to Rent Near Colleges in Chicago
Written by: Nicole Harms
With world-class museums lining its streets, Chicago is a place people go to learn. It’s not surprising, therefore, that it’s also home to multiple colleges and universities with national and global reputations.

Best Neighborhoods to Rent in Near Chicago's Top Employers
Written by: Nicole Harms
Whenever life takes me into the city, I’m always impressed with the sheer amount of industry and commerce that it holds. With all of that commerce comes a wide range of employment options.

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.
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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.

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.

How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide
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Evaluating rental properties for clients draws many parallels to house-hunting. Whether an apartment, loft, townhouse, or other rental, finding the right place means finding “home” for your client.

Pet-Friendly Renting: Everything You Need to Know Before You Move
Written by: Christine Leonard, Esq.
For so many of us, pets are the best companions and a big part of our lives. For this reason, a pet-friendly house or apartment is often a very important - and nonnegotiable - part of a move.