Cheap Apartments for Rent in the Uptown Neighborhood of Chicago, IL from $400 (111 Rentals)

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

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The Annabelle Apartments
$888 - $2,181
Total Monthly Price

Total Monthly Price

Base Rent
$838 - $2,131
Required Monthly Fees
$50

Total Monthly Price
$888 - $2,181
Studio to 1 Bedroom Apartments Available Now

The Annabelle Apartments

661 W Sheridan AveChicago, IL 60613
Affordability
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  • Customer Reviewed
  • 3D Tour

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Wyndham Apartments
Rent Specials
$1,209 - $2,166
Total Monthly Price

Total Monthly Price

Base Rent
$1,159 - $2,116
Required Monthly Fees
$50

Total Monthly Price
$1,209 - $2,166
Studio to 2 Bedroom Apartments Available Now

Wyndham Apartments

5240 N Sheridan RdChicago, IL 60640
Affordability
  • Verified
  • Customer Reviewed
  • 3D Tour

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4635 N Paulina St
$1,250 - $1,350
Total Monthly Price

Total Monthly Price

Base Rent
$1,250 - $1,350

Total Monthly Price
$1,250 - $1,350
Studio Apartment Available Now

4635 N Paulina St

4635 N Paulina StChicago, IL 60640
Affordability
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Times Square Apartments
$1,279 - $2,574
Total Monthly Price

Total Monthly Price

Base Rent
$1,229 - $2,524
Required Monthly Fees
$50

Total Monthly Price
$1,279 - $2,574
Studio to 2 Bedroom Apartments Available Now

Times Square Apartments

869 W Buena AveChicago, IL 60613
Affordability
  • Verified
  • Customer Reviewed
  • 3D Tour

Explore the Windy City (But Watch for Falling Ice) - An Insider's Guide to Renting in Chicago

Learn about the best things about living in Chicago from a local in the Insiders Guide to Renting in Chicago. Find your perfect Chicago apartment today!

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4614 Paulina N St
$1,295 - $1,795
Total Monthly Price

Total Monthly Price

Base Rent
$1,295 - $1,795

Total Monthly Price
$1,295 - $1,795
Studio to 1 Bedroom Apartment Available Now

4614 Paulina N St

4614 Paulina N StChicago, IL 60640
Affordability
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4871 N Magnolia Ave
$1,300 - $2,300
Total Monthly Price

Total Monthly Price

Base Rent
$1,300 - $2,300

Total Monthly Price
$1,300 - $2,300
Studio to 2 Bedroom Apartment Available Now

4871 N Magnolia Ave

4871 N Magnolia AveChicago, IL 60640
Affordability
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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.

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4616 N Paulina St
$1,350 - $1,795
Total Monthly Price

Total Monthly Price

Base Rent
$1,350 - $1,795

Total Monthly Price
$1,350 - $1,795
Studio to 1 Bedroom Apartment Available Now

4616 N Paulina St

4616 N Paulina StChicago, IL 60640
Affordability
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Chatelaine Apartments
Studio to 1 Bedroom Apartments

Chatelaine Apartments

4911 N Winthrop AveChicago, IL 60640
  • Utilities Included

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.

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 The Annabelle Apartments priced from $888. 4735 Beacon has the second lowest priced unit, which is a Studio apartment currently listed from $1,050. Here are the most affordable Uptown apartments for rent in Chicago, IL:

Apartment ListingModel NameBed/BathPriced From
The Annabelle ApartmentsStudio Floor Plan S3Studio,1BA$888
4735 BeaconStudio - New RehabStudio,1BA$1,050
The EdisonStudio | 1 bath - EFFRStudio,1BA$1,071
Sheridan Park LLCStudio in UptownStudio,1BA$1,075
4600 BeaconStudioStudio,1BA$1,095
3838 N. BroadwayStudioStudio,1BA$1,145

Best Value Apartments for Rent in Uptown, IL

As of March 03, 2026 the best value apartment in the Uptown area is the $1.94 price per square foot 1454 W Winnemac Ave Model at 1454 W Winnemac Ave, Unit 3 in the in the Uptown Chicago neighborhood starting from $3,295. The second greatest value Uptown apartment is the 1455 W Wilson Ave Model at 1455 W Wilson Ave, Unit 2 starting at $3,000 with a $1.88 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.
1454 W Winnemac Ave, Unit 31454 W Winnemac Ave2BR,1BA$1.94
1455 W Wilson Ave, Unit 21455 W Wilson Ave2BR,1BA$1.88
4318 N Sheridan Rd, Unit 24318 N Sheridan Rd2BR,2BA$1.75
900 W Montrose Ave901 Agatite - 2 bed 2 bath2BR,2BA$1.93
4443 N Sheridan Rd, Unit 34443 N Sheridan Rd2BR,2BA$2.00
1012 W Sunnyside Ave, Unit 31012 W Sunnyside Ave2BR,1BA$2.00
4537 N Greenview Ave, Unit Garden R4537 N Greenview Ave1BR,1BA$1.82
902 W Montrose Ave, Unit A00C902 W Montrose Ave2BR,1BA$2.00
4750 N Sheridan Rd, Unit 14750 N Sheridan Rd1BR,1BA$1.99
911 W Lawrence Ave, Unit #407911 W Lawrence Ave1BR,1BA$2.00

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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The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro

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

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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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Lifestyle Ratings

ApartmentHomeLiving brings you our detailed rental search system called 'Lifestyle ratings', composed of rentals and neighborhoods across the USA, including Chicago. LifeStyle Ratings are a useful tool for comparing and sorting apartments and neighborhoods when choosing your rental home. This takes in many factors including rankings of the best places for the best proximity to parks and outdoor amenities, luxury amenities, kid and pet-friendly communities, availability of transit options, walking, and biking. These search options are in the site filters at the top of this page.

Frequently Asked Questions about Cheap Uptown Apartments

What is a cheap apartment in Uptown?

A cheap apartment is any apartment up to the 30% percentile of cost for the area, which in Uptown is under $1,145.

What is the price of a cheap apartment in Uptown?

The cheapest apartment in Uptown is Wyndham Apartments which is listed at $1,341, while the average apartment in Uptown costs $5,795.

What types of apartments are the cheapest in Uptown?

Student, low-income, and by-the-bed apartments are typically the cheapest rentals in most cities, though they require qualifying criteria to rent. There are 6 regular apartments in Uptown that we think qualify as ‘cheap apartments’ that do not have special requirements to apply to rent.

How do the prices of cheap apartments compare to the average apartment in Uptown?

Cheap apartments in Uptown have an average cost of $130 which is $5,665 cheaper than the average rent for all rentals in Uptown.

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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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.

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18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property

Written by: Lauren Harrington

Renting your next home can feel thrilling and overwhelming at the same time.

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A Renters Guide for Tips on Writing Your Notice for Not Renewing Your Apartment

Written by: Bob Mallory

Packing up everything you own to move is so stressful for many that ending your apartment lease can feel like a small or unimportant task. Ending your lease involves more than simply turning over your keys on the last day.

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Renting with Roommates: Realistic Expectations for Shared Lease

Written by: Christine Leonard, Esq.

Given the high costs for housing, I have found that many people are looking for a roommate to share expenses. These arrangements can increase opportunities for more desirable and larger spaces.