
2 Bedroom Apartments for Rent in the Woodlawn Neighborhood of Chicago, IL (127 Rentals)


5715-5725 S. Kimbark Avenue

Oglesby Towers Apartments

Academy at Drexel

Total Monthly Price
6100 S Dorchester Ave, Unit 2

Total Monthly Price
1140 E Marquette Rd

6657 S Minerva Ave

6557 S Minerva Ave

1140 E Marquette Rd

6557 S Minerva Ave
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.

6716 S Merrill Ave

6100 S Dorchester Ave

6108 S Dorchester Ave

6701 S Crandon Ave

6426 S Ingleside Ave

6150 S University Ave

1452 E Marquette Rd

6730 S Clyde Ave

6538 S Kenwood Ave

941 E Marquette Rd
Roommate Matching: Finding the Right Fit and Avoiding Pitfalls
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.

6716 S Merrill Ave

6523 S Greenwood Ave

6527 S Kimbark Ave

6550 S Drexel Ave

6634 S Greenwood Ave

6457 S Kenwood Ave

6133 S Drexel Ave

6700 S South Shore Dr, Unit 22B

Lakefront Place

Parkland Condominiums
Navigating the Rental Market: Tips for First-Time Renters
Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.

Kimbark Estates

The Grant at Woodlawn Park

6147-6149 S Woodlawn Ave

6100-6102 S University Ave

University of Chicago Faculty Apartments

6658 S Drexel Ave

6620 S Greenwood Ave

6101 S Kenwood Ave

6427-6429 S Drexel Ave

6631-6633 S Woodlawn Ave
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

6457-6459 S Cottage Grove Ave

1461 E 66th Pl

6612 S Greenwood Ave

6156 E Kenwood Ave

Carmel Fields

6635-6637 S Drexel Ave

6600 S Maryland St

Ingleside

6138-6140 S Woodlawn Ave

6405 S Ingleside Ave
Best Places to Live Near Chicago: 5 Cities That Keep the Windy City Accessible
Looking for a rental near Chicago? These five cities offer excellent options! From small-town charm to excellent business options, you can't go wrong!
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 | $803 | $726 | $1,110 |
| Woodlawn 1 Bedroom Apartments | $1,288 | $1,175 | $1,356 |
Woodlawn 2 Bedroom Apartments | $2,052 | $1,250 | $3,195 |
| Woodlawn 3 Bedroom Apartments | $2,268 | $1,665 | $3,760 |
| Woodlawn 4 Bedroom Apartments | $2,577 | $2,495 | $2,980 |
Browse Apartments in this Neighborhood
There are currently 127 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 Oglesby Towers Apartments and is listed at 1,215 square feet priced from $1,846. Here is today’s list of the largest available 2 Bedroom units in the area:
| Apartment Listing | Model Name | Square Footage | Priced From |
|---|---|---|---|
| Oglesby Towers Apartments | 2 Bedrooms Floor Plan B2B | 1,215 Sq Ft | $1,846 |
| 5715-5725 S. Kimbark Avenue | 57152ba | 1,070 Sq Ft | $3,095 |
| 6715 S Dorchester | 2 Bedroom 1 Bath Apartment | 804 Sq Ft | $1,235 |
| 5748 Blackstone By 3L Living | Two Bedroom | 700 Sq Ft | $1,549 |
Cheapest Available Woodlawn 2 Bedroom Apartments
Currently the lowest priced 2 Bedroom apartment unit Woodlawn of Chicago, IL is the 2 Bedroom 1 Bath Apartment Model starting from $1,235 at 6715 S Dorchester. The average price for all 2 Bedroom apartments in Woodlawn is currently $2,052. Here is today’s list of the cheapest available 2 Bedroom options in the area:
| Apartment Listing | Model Name | Priced From |
|---|---|---|
| 6715 S Dorchester | 2 Bedroom 1 Bath Apartment | $1,235 |
| 5748 Blackstone By 3L Living | Two Bedroom | $1,549 |
| Oglesby Towers Apartments | 2 Bedrooms Floor Plan B1B | $1,811 |
| 5715-5725 S. Kimbark Avenue | 57152ba | $3,095 |
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 6715 S Dorchester listed at $1,235.
What is the largest available 2 Bedroom Woodlawn Apartment for rent?
Today's apartment with the most square footage in Woodlawn is a 1,215 square feet unit starting from $1,846 at Oglesby Towers Apartments.
What is the average size for Woodlawn 2 Bedroom Apartments for rent?
The average size for a 2 Bedroom rental in Woodlawn is currently 1,100 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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A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back
Written by: Lauren Harrington
I’m going to talk with you as a seasoned property manager and friend. So, let’s start with your security deposit. I want you to think about this guide as insider information. You deserve your deposit back.

Expert Solutions for Creating the Perfect Work-From-Home Apartment Layouts
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This article is based on first-hand experience managing apartment communities and helping renters adapt to their spaces after moving in.

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This article draws from first-hand renter experiences and recurring financial challenges reported after moving in.

Maximizing Your Refund: Essential Tax Tips for Renters
Written by: Christine Leonard, Esq.
Other than tax professionals, I can’t think of anyone who looks forward to tax season. For everybody else, April is a stressful month to collect information and meet deadlines.