
2 Bedroom Apartments for Rent in the Madison Square Neighborhood of Chicago, IL (161 Rentals)


162 N La Crosse Ave, Unit 2nd Fl.

4340 W Maypole Ave, Unit Garden Unit

5309 W Jackson Blvd, Unit 2ndfloor

4622 W Jackson Blvd

5331 W Congress Pkwy

4702 W Fulton St

5356 W Madison St
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5354 W Madison St

5344 W Madison St
The Art of the Rental Viewing: What to look for during a property tour
Touring a rental? This guide helps you know exactly what to look for, from safety features to hidden flaws, so you can confidently sign your lease or keep searching.
Smart Renter's Guide: Calculating Affordable Rent & Housing Costs
Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.
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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.
Chicago's Best Affordable Neighborhoods
Learn about Chicago and the best places to live with original content written by our Chicago, IL Local Expert Nicole Harms
Madison Square, Chicago, IL Local Guide

How much does it cost to rent an apartment in Madison Square?
Bedroom | Average Rent | Cheapest Rent | Highest Rent |
---|---|---|---|
Madison Square Studio Apartments | $840 | $840 | $840 |
Madison Square 1 Bedroom Apartments | $1,107 | $1,100 | $1,115 |
Madison Square 2 Bedroom Apartments | $1,485 | $900 | $1,860 |
Madison Square 3 Bedroom Apartments | $1,751 | $1,300 | $2,300 |
Madison Square 4 Bedroom Apartments | $1,850 | $1,850 | $1,850 |
Browse Apartments in this Neighborhood
There are currently 161 rentals with your search options within a 1 mile radius of the Madison Square Neighborhood of Chicago, IL.
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Madison Square, Chicago, IL Local Guide
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Largest Available Madison Square 2 Bedroom Apartments
The largest available 2 Bedroom apartment unit in the Madison Square area of Chicago, IL is found at 200 N Kenneth and is listed at 1,000 square feet priced from $1,275. Here is today’s list of the largest available 2 Bedroom units in the area:
Apartment Listing | Model Name | Square Footage | Priced From |
---|---|---|---|
200 N Kenneth | 2BR/1.0BA | 1,000 Sq Ft | $1,275 |
4814 W Monroe | 2 Bedroom 1 Bathroom Apartment | 801 Sq Ft | $1,265 |
5328 W Harrison | 2 Bedroom 1 Bath Apartment | 800 Sq Ft | $1,205 |
400-02 S Kilbourn Ave | 2 Bedroom, 1 Bath | 716 Sq Ft | $1,195 |
5100-04 W Madison St | 2 Bedroom 1 Bathroom Apartment | 680 Sq Ft | $1,080 |
Cheapest Available Madison Square 2 Bedroom Apartments
Currently the lowest priced 2 Bedroom apartment unit Madison Square of Chicago, IL is the 2 Bedroom, 1 Bath Model starting from $1,045 at 5201 W Washington Blvd (old). The average price for all 2 Bedroom apartments in Madison Square is currently $1,485. Here is today’s list of the cheapest available 2 Bedroom options in the area:
Apartment Listing | Model Name | Priced From |
---|---|---|
5201 W Washington Blvd (old) | 2 Bedroom, 1 Bath | $1,045 |
5100-04 W Madison St | 2 Bedroom 1 Bathroom Apartment | $1,080 |
400-02 S Kilbourn Ave | 2 Bedroom, 1 Bath | $1,130 |
5328 W Harrison | 2 Bedroom 1 Bath Apartment | $1,205 |
4814 W Monroe | 2 Bedroom 1 Bathroom Apartment | $1,265 |
200 N Kenneth | 2BR/1.0BA | $1,275 |
Quick Rent Budget Calculator
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Pet Friendly LifestyleMadison Square, Chicago, IL
Ranked #86
Among neighborhoods in Chicago, IL for Apartment listings with Pet Friendly Amenities
Pet Friendliness Lifestyle Score
2.5Pet Friendly
Frequently Asked Questions about 2 Bedroom Madison Square Apartments
What is the largest available 2 Bedroom Madison Square Apartment for rent?
Today's apartment with the most square footage in Madison Square is a 1,000 square feet unit starting from $1,275 at 200 N Kenneth.
What is the average size for Madison Square 2 Bedroom Apartments for rent?
The average size for a 2 Bedroom rental in Madison Square is currently 1,049 sq ft.
Expert Rental Resources
Helpful Apartment Articles, How-To's and Tips
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.

A Local Expert’s Guide To 10 Budget-Friendly Neighborhoods to Rent in Chicago
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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.

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Written by: Cheryl Bowman
A fantastic way to save money and enjoy a built-in community is to share an apartment. However, a bad roommate situation can turn your dream rental into a nightmare.

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You’ve scrolled through countless listings, walked through a blur of rentals, and finally found what feels like the one. The pictures? Fantastic. The neighborhood seems just right.

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Written by: Lauren Harrington
Renting an apartment or house isn’t just about looking through online ads, choosing a few apartments or homes you want to tour, filling out an application, and putting down a deposit. Those things are all necessary and important.