Short Term Lease Apartments for Rent in Chicago, IL Under $5,500 (400 Rentals) Page 2 of 8

How Many Bedrooms?Done
Select your price rangeDone
to
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Lifestyle Matching SearchDone
Learn more about Lifestyle Search
By AmenitiesDone
By Community TypeDone
Features and AvailabilityDone
Done

Rental terms in Chicago as short as a month! Perfect when you can't commit to a full year of renting.

Navigating the Rental Market: Tips for First-Time Renters

Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.

Read Article
property at 109 S Paulina St

$5,379

Total Monthly Price

Total Monthly Price

Base Rent
$5,379
Total Monthly Price
$5,379

2 Bedroom, 1 Bath Home for Rent

Available Aug 7

109 S Paulina St

ChicagoIL60612
property at 2207 W 18th St

$2,908 - $5,180

Total Monthly Price

Total Monthly Price

Base Rent
$5,180
Total Monthly Price
$5,180

2 Bedroom Rentals

Available Aug 29

2207 W 18th St

ChicagoIL60608

The Rise of Digital Nomads: Remote Work Tips for Apartment Renters

As a digital nomad you work from your own apartment or home or enjoy the spectacular views of amazing locations throughout the nation and globally as you travel, all while maintaining a connection to your team digitally. Learn How this Trend is on the Rise.

Read Article
property at 2316 W Estes Ave

$5,016

Total Monthly Price

Total Monthly Price

Base Rent
$5,016
Total Monthly Price
$5,016

2 Bedroom, 2 Bath Home for Rent

Available Mar 1, 2027

2316 W Estes Ave

ChicagoIL60645

How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide

Finding the right apartment starts with three things: location, cost, and amenities. Get the insider perspective from a real estate professional on how to nail all three.

Read Article

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!

Read Article
property at 2337 W Touhy Ave

$4,393

Total Monthly Price

Total Monthly Price

Base Rent
$4,393
Total Monthly Price
$4,393

2 Bedroom, 2 Bath Home for Rent

Available Aug 4

2337 W Touhy Ave

ChicagoIL60645
property at 318 W Grand Ave

$4,355 - $9,396

Total Monthly Price

Total Monthly Price

Base Rent
$4,355
Total Monthly Price
$4,355

2 Bedroom Rentals

Available Aug 1

318 W Grand Ave

ChicagoIL60654

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.

Read Article
Showing Results 51-100, Page 2 of 8

Chicago, IL Area Reviews

  • Parks
  • Entertainment
  • Local Vibes
  • Restaurants
  • Location
  • Traffic
  • Public Transportation
  • Outdoor Access
  • Cost of Living
  • Safety

Nicole • 4+ years in Chicago

April 10, 2026

Big city challenges with traffic but also provides the amenities of the city you can't find elsewhere

Frequently Asked Questions about Short-term Chicago Apartments

What is the Cheapest Short-term apartment in Chicago?

Currently the most affordable Short-term Apartment in Chicago is at 5445 Ingleside By 3L Living listed at $684.

How much is the average rent for a Short-term Chicago Apartment?

The average rent for a Short-term Apartment in Chicago is $2,911.

What is the largest Short-term Chicago Apartment for rent?

Today's Short-term apartment with the most square footage in Chicago is a 2,267 square feet unit starting from $2,894 at State and Grand.

What is the average size for Chicago Short-term Apartments for rent?

The average size for a Short-term rental in Chicago is currently at 571 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

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.

decorative image for Top Student Friendly Neighborhoods to Rent Near Colleges in Chicago article

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.

decorative image for Best Neighborhoods to Rent in Near Chicago's Top Employers article

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.

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

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

decorative image for Apartment Occupancy Rates: Renter Attraction vs Renter Retention article

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.

decorative image for How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide article

How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide

Written by: Robin Stewart

Evaluating rental properties for clients draws many parallels to house-hunting. Whether an apartment, loft, townhouse, or other rental, finding the right place means finding “home” for your client.

decorative image for Pet-Friendly Renting: Everything You Need to Know Before You Move article

Pet-Friendly Renting: Everything You Need to Know Before You Move

Written by: Christine Leonard, Esq.

For so many of us, pets are the best companions and a big part of our lives. For this reason, a pet-friendly house or apartment is often a very important - and nonnegotiable - part of a move.

decorative image for Creative Ways Developers Reimagine Retail Spaces as Residential Units article

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.