Cheap Homes for Rent in Uptown Neighborhood of Chicago, IL from $1,000 (126 Rentals)

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Search the lowest-cost Homes available for rent right now in the Uptown area of Chicago.

What Does “Rent Burdened” Mean? How Much Rent Is Too Much

Learn the official definition (spending 30% or more of your gross income on housing) and how to calculate your exact rent-to-income ratio. This guide offers expert tips on factoring in total housing costs (including utilities and fees) and budgeting accurately to avoid unnecessary financial strain.

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Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between

Thinking about getting a co-signer for your rental application? We break down what a co-signer is, the potential benefits, and the serious risks for both parties. Find out if it's the right choice for you.

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Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting

Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.

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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.

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property at 5020 N Sheridan Rd

$1,486 - $2,128

Total Monthly Price

Total Monthly Price

Base Rent
$1,486 - $2,128
Total Monthly Price
$1,486 - $2,128

1 Bedroom, 1 Bath Condo for Rent

Available Now

5020 N Sheridan Rd

ChicagoIL60640

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!

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Uptown, Chicago, IL Local Guide

Cheapest Available Uptown Apartments for Rent

 

The cheapest available apartment rental in the Uptown area of Chicago, IL is a Studio unit found at 3838 N. Broadway priced from $1,195. The Edison has the second lowest priced unit, which is a Studio apartment currently listed from $1,248. Here are the most affordable Uptown apartments for rent in Chicago, IL:

Apartment ListingModel NameBed/BathPriced From
3838 N. BroadwayStudioStudio,1BA$1,195
The EdisonStudio | 1 bath - EFFRStudio,1BA$1,248
The Lawrence HouseA1 - 60% AMI AHSAPStudio,1BA$1,260
930 W. WinonastudioStudio,1BA$1,275

Best Value Apartments for Rent in Uptown, IL

As of June 03, 2026 the best value apartment in the Uptown area is the $0.31 price per square foot 910 W Gunnison St Model at 910 W Gunnison St, Unit G1 in the in the Uptown Chicago neighborhood starting from $3,100. The second greatest value Uptown apartment is the 1338 W Winona St Model at 1338 W Winona St, Unit 3 starting at $3,250 with a $1.30 price per square foot in the Uptown Chicago neighborhood. Here is today’s list of the best values for Uptown apartments based on price per square foot:

Apartment ListingModel NameBed/BathPrice Per Sq.Ft.
910 W Gunnison St, Unit G1910 W Gunnison St3BR,2BA$0.31
1338 W Winona St, Unit 31338 W Winona St3BR,1BA$1.30
1520 W Sunnyside Ave, Unit 1WS1520 W Sunnyside Ave3BR,2BA$1.92
1455 W Wilson Ave, Unit 21455 W Wilson Ave2BR,1BA$1.88
4318 N Sheridan Rd, Unit 24318 N Sheridan Rd2BR,2BA$1.75
4452 N Sheridan Rd, Unit 24452 N Sheridan Rd2BR,2BA$1.93
4443 N Sheridan Rd, Unit 34443 N Sheridan Rd2BR,2BA$2.00
1012 W Sunnyside Ave, Unit 21012 W Sunnyside Ave2BR,1BA$2.09
4875 N Paulina St4875 N Paulina St1BR,1BA$1.88
1256 W Montrose Ave, Unit 1F1256 W Montrose AveStudio ,1BA$2.08

Don't Settle: How to Negotiate Your Apartment Lease and Save Money

Discover the insider tips from an attorney and real estate agent on how to negotiate your next apartment lease. Find out what's on the table and what's not, so you can save money and get the best terms possible.

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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

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A 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

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Real 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.

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Quick 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.

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Best Local Schools in
Uptown, Chicago, IL

School data provided by Great Schools

Frequently Asked Questions about Uptown

What type of rentals are currently available in Uptown?

There are currently 1119 Apartments for Rent in Uptown, IL with pricing that ranges from $1,050 to $8,645. There are also 349 Single Family Homes for rent, Condos, and Townhome rentals currently available in Uptown ranging from $1,095 to $40,000.

What is the current price range for Rental Homes in Uptown?

Today's rental pricing for Homes for Rent, Condos and Townhomes in Uptown ranges from $1,095 to $40,000 with an average monthly rent of $5,445.

How much are larger Three and Four Bedroom Rentals in Uptown?

For those who are looking for larger living arrangements, Three Bedroom Apartments in Uptown range from $1,871 to $8,645, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,000 to $40,000. Four Bedroom Single-Family rentals are also available starting from $4,200 and Four Bedroom Apartments start at $4,200.

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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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.

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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.

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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.

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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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Creative Ways Developers Reimagine Retail Spaces as Residential Units

Written by: Robin Stewart

Adaptive reuse is when a commercial property is converted and repurposed. The real estate industry has embraced a growing number of these projects.

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Neighborhood and Market Insights: How to Choose the Right Area to Rent

Written by: Robin Stewart

Apartment-hunting can be a gargantuan task. Renters have a wish list of items—some luxuries, some necessities—but finding what you seek in the right place is perhaps the most important part of the journey.

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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.

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Expert Solutions for Creating the Perfect Work-From-Home Apartment Layouts

Written by: Lauren Harrington

This article is based on first-hand experience managing apartment communities and helping renters adapt to their spaces after moving in.