Apartments for Rent in Chicago, IL Under $2,000 with Swimming Pool (73 Rentals)

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Apartment Common Area Rules: What Renters Need to Know

From the lounge to the laundry room, understand your rights and responsibilities in shared apartment spaces. Get tips on pet rules, noise, and security.

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1133 N. Dearborn
$1,869 - $4,064
Total Monthly Price

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$1,869 - $4,064
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Studio to 2 Bedroom Apartments Available Aug 1

1133 N. Dearborn

1133 N Dearborn StChicago, IL 60610
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1120 N. LaSalle
$1,615 - $3,616
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$1,615 - $3,616
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Studio to 2 Bedroom Apartments Available Aug 1

1120 N. LaSalle

1120 LaSalle DrChicago, IL 60610
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Understanding Amenity Fees: Know Where You Might Be Able to Save Money

What are amenity fees and are they optional? This guide breaks down everything you need to know about apartment amenity fees, including when you can opt out and how you might be able to lower your rent.

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1111 N. Dearborn
$1,824 - $4,902
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$1,824 - $4,902
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Studio to 3 Bedroom Apartments Available Now

1111 N. Dearborn

1111 N Dearborn StChicago, IL 60610
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It's time to soak up some sun!

One of the easiest and more obvious ways of enjoying the summer sun is to lounge out by your community pool. Learn a Few Rules to Keep in Mind while at the pool.

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211 E. Ohio St.
Studio to 2 Bedroom Apartments

211 E. Ohio St.

205-215 E Ohio StChicago, IL 60611
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Hollywood Towers
1 Bedroom Apartments

Hollywood Towers

5701 N Sheridan RdChicago, IL 60660
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R+D659
Studio to 4 Bedroom Apartments

R+D659

645-659 W Randolph StChicago, IL 60661
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55 E Erie St
Studio to 3 Bedroom Apartments

55 E Erie St

55 E Erie StChicago, IL 60611
Corporate Housing
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600 N Lake Shore Dr
Studio to 3 Bedroom Apartments

600 N Lake Shore Dr

600 N Lake Shore DrChicago, IL 60611
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Coronado
Studio to 2 Bedroom Apartments

Coronado

3900 N Pine Grove AveChicago, IL 60613
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1636 N Wells St
Studio Apartments

1636 N Wells St

1636 N Wells StChicago, IL 60614
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Luxury condo unit
Studio to 3 Bedroom Apartments

Luxury condo unit

333 N CanalChicago, IL 60606
Corporate Housing
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Renters Insurance 101: What It Is, What It Covers, and Why You Need It

From theft to fire to water damage, the unexpected can happen to any renter. Discover why renters insurance is one of the smartest and most affordable investments you can make as a tenant.

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1850 N. Clark St.
Studio to 1 Bedroom Apartments

1850 N. Clark St.

1850-1856 N Clark StChicago, IL 60614
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Albion Oak Park
$1,871 - $4,844
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$1,871 - $4,844
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Studio to 3 Bedroom Apartments Available Now

Albion Oak Park

1000 Lake StOak Park, IL 60301
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District 1860
Rent Specials
$1,992 - $4,494
Total Monthly Price

Total Monthly Price

Base Rent
$1,992 - $4,494
Total Monthly Price
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Studio to 3 Bedroom Apartments Available Now

District 1860

7215 N District AveLincolnwood, IL 60712
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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.

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Showing Results 1-50, Page 1 of 2

Chicago, IL Local Guide

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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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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Remember the 3 Rules of Real Estate:
Location, Location, Location!

Explore Chicago, IL Rentals by Map

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Chicago, IL Area Reviews

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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 Chicago Apartments with Swimming Pool

What is the Cheapest Swimming Pool apartment in Chicago?

Currently the most affordable Apartment in Chicago with Swimming Pool is at Courts of the Fountains listed at $1,180.

How much is the average rent for Chicago Apartments with Swimming Pool?

The average rent for a Apartment in Chicago with Swimming Pool is $4,219.

What is the largest Chicago Apartment for rent with Swimming Pool?

Today's Apartment with Swimming Pool and the most square footage in Chicago is a 4,425 square feet unit starting from $2,258 at 369 Grand by Onni.

What is the average size for Chicago Apartments for rent with Swimming Pool?

The average size for a rental with Swimming Pool in Chicago is currently at 599 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

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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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Renters Insurance 101: What It Is, What It Covers, and Why You Need It

Written by: Robin Stewart

Insurance seems to be a part of life. In some states, having insurance is the law, as is the case for automobile insurance. Renters are no exception.

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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.

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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.

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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.