
2 Bedroom Apartments for Rent in the Woodlawn Neighborhood of Chicago, IL (126 Rentals)


Academy at Drexel

Oglesby Towers Apartments

Total Monthly Price
1140 E Marquette Rd

6557 S Minerva Ave, Unit 2A

6525 S Evans Ave, Unit 1

6439 S Kenwood Ave, Unit 14W

6525 S Evans Ave, Unit 1

6557 S Minerva Ave, Unit 2B

6656 S Woodlawn Ave, Unit 3
The Windy City Price Tag: Your Complete Guide to the Cost of Living in Chicago
Chicago may cost more than the national average, but with the right neighborhood, a smart transit strategy, and a few local insider tips, living well in the Windy City is more achievable than you might think. Our local expert breaks down everything from rent and groceries to transportation and healthcare so you can plan your move with confidence.

853 E 64th St

6621-23 S Ingleside Ave

6541 S Ellis Ave

1151 E 61st St

6618 S Maryland Ave

6550 S Drexel Ave

6529 S Kimbark Ave

6525 S Evans Ave

6225 S Dorchester Ave

6634 S Greenwood Ave
Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags
Looking for the perfect new rental? Learn great ways to spot the perfect apartment for you, identify common red flags, and avoid rental issues and scams with these expert provided actionable tips.

6700 S Paxton Ave

6714 S Chappel Ave

6104 S Dorchester Ave

6453 S Ingleside Ave

6453 S Ingleside Ave, Unit 3S

6529 S Kimbark Ave, Unit 2R

Lakefront Place

Parkland Condominiums

Kimbark Estates

6700-12 S Chappel
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!

6711 S Chappel Ave

1508 E 67th Pl

Crandominium on the Lake

Renaissance Apartments

825 E 61st St

6719 S Cornell Ave

6729 S Chappel Ave

The Burnham at Woodlawn Park

6500-6502 S Cottage Grove Ave

The Grant at Woodlawn Park
Chicago Relocation 101: Mastering Utilities, Registration, and the CTA
Moving to Chicago? This essential relocation guide offers a complete checklist for new residents, covering finding the right neighborhood, setting up utilities (ComEd, People’s Gas), and mastering high-rise moving logistics and vehicle registration.

6147-6149 S Woodlawn Ave

1425 E 66th Pl

6621 S Ingleside Ave

6235 S Ellis Ave

6512 S Ingleside Ave

6420 S Woodlawn Ave

6213-6215 S Greenwood Ave

6605 S Kimbark Ave

1431 E 66th Pl

6427 S Kimbark 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 | $946 | $726 | $1,439 |
| Woodlawn 1 Bedroom Apartments | $1,419 | $1,279 | $1,673 |
Woodlawn 2 Bedroom Apartments | $1,865 | $1,200 | $2,999 |
| Woodlawn 3 Bedroom Apartments | $2,362 | $1,665 | $3,599 |
| Woodlawn 4 Bedroom Apartments | $2,400 | $1,625 | $2,980 |
Browse Apartments in this Neighborhood
There are currently 126 rentals with your search options within a 2 mile radius of the Woodlawn Neighborhood of Chicago, IL.
See all Apartments in ChicagoExplore Chicago
Woodlawn, Chicago, IL Local Guide
- Nearby Chicago neighborhoods
- Nearby Cities
- ZIP codes
- Local Counties
- School Districts
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 $2,999. 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 | $2,999 |
| Cloisters | clo-2b2c | 1,385 Sq Ft | $3,295 |
| Oglesby Towers Apartments | 2 Bedrooms Floor Plan B1B | 1,200 Sq Ft | $1,716 |
Cheapest Available Woodlawn 2 Bedroom Apartments
Currently the lowest priced 2 Bedroom apartment unit Woodlawn of Chicago, IL is the STUNNING + SPACIOUS 2 Bedroom apartment in quie... Model starting from $1,650 at 6700-12 S Chappel. The average price for all 2 Bedroom apartments in Woodlawn is currently $1,865. Here is today’s list of the cheapest available 2 Bedroom options in the area:
| Apartment Listing | Model Name | Priced From |
|---|---|---|
| 6700-12 S Chappel | STUNNING + SPACIOUS 2 Bedroom apartment in quie... | $1,650 |
| Oglesby Towers Apartments | 2 Bedrooms Floor Plan B1B | $1,716 |
| 5715-5725 S. Kimbark Avenue | 57152bb | $2,999 |
| Cloisters | clo-2b1c | $3,285 |
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 6700-12 S Chappel listed at $1,650.
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 $2,999 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 1,108 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

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.