Cheap Apartments for Rent in the Uptown Neighborhood of Chicago, IL from $400 (127 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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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 Sheridan Park LLC priced from $1,095. Issel Building has the second lowest priced unit, which is a Studio apartment currently listed from $1,100. Here are the most affordable Uptown apartments for rent in Chicago, IL:

Apartment ListingModel NameBed/BathPriced From
Sheridan Park LLCStudio in UptownStudio,1BA$1,095
Issel BuildingStudio'sStudio,1BA$1,100
The Onyx on SheridanUpgraded Studio ApartmentStudio,1BA$1,125
3834 N SheffieldStudioStudio,1BA$1,145
The Annabelle ApartmentsStudio Floor Plan S3Studio,1BA$1,145

Best Value Apartments for Rent in Uptown, IL

As of November 15, 2025 the best value apartment in the Uptown area is the $1.75 price per square foot 5349 N Kenmore Ave Model at 5349 N Kenmore Ave, Unit 2 in the in the Edgewater neighborhood starting from $3,500. The second greatest value Uptown apartment is the 4101 N Kenmore Ave Model at 4101 N Kenmore Ave, Unit M01H starting at $2,995 with a $1.66 price per square foot in the Lakeview 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.
5349 N Kenmore Ave, Unit 25349 N Kenmore Ave3BR,2BA$1.75
4101 N Kenmore Ave, Unit M01H4101 N Kenmore Ave3BR,2BA$1.66
4318 N Sheridan Rd, Unit 24318 N Sheridan Rd2BR,2BA$1.75
1455 W Wilson Ave, Unit 21455 W Wilson Ave2BR,1BA$1.88
4452 N Sheridan Rd, Unit 34452 N Sheridan Rd2BR,2BA$1.80
1340 W Byron St, Unit 011340 W Byron St2BR,1BA$1.79
1940 W Wilson Ave, Unit 1954-2BB1940 W Wilson Ave2BR,1BA$1.77
900 W Montrose Ave906 Montrose - 2 Bed /1 bath2BR,1BA$1.80
4750 N Sheridan Rd, Unit 14750 N Sheridan Rd1BR,1BA$1.69
4036 N Ashland Ave, Unit E14036 N Ashland AveStudio ,1BA$1.87

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Pet Friendly Lifestyle
Uptown, Chicago, IL

Ranked #18

Among cities in Illinois for Apartment listings with Pet Friendly Amenities.

Pet Friendliness Lifestyle Score

4.0
Pet Friendly

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Best Local Schools in
Uptown, Chicago, IL

School data provided by Great Schools

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 the Cheapest Studio apartment in Uptown?

Currently the most affordable Cheap Studio Apartment in Uptown is at Sheridan Park LLC listed at $1,095.

How much is rent for a Cheap One Bedroom Uptown Apartment?

The lowest price for a Cheap One Bedroom Uptown Apartment is $1,250 at Times Square Apartments.

What is the lowest price for a Cheap Two Bedroom Uptown Apartment for rent?

Today's best deal for a Cheap Two Bedroom Apartment in Uptown is starting from $1,774 at Times Square Apartments.

What is the most affordable Uptown Three Bedroom Apartment?

The best deal on a cheap Uptown Three Bedroom Apartment rental is at Buena Shores and starts from $2,170.

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.

decorative image for A Local Expert’s Guide To 10 Budget-Friendly Neighborhoods to Rent in Chicago article

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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Apartment Common Area Rules: What Renters Need to Know

Written by: Christine Leonard, Esq.

Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.

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How to Negotiate Your Apartment Lease and Save Money

Written by: Christine Leonard, Esq.

Everything is a negotiation in real estate! 

decorative image for The Rental Move-In Inspection Checklist: A Guide for Renters article

The Rental Move-In Inspection Checklist: A Guide for Renters

Written by: Trey Huguley

The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.