
Luxury Apartments for Rent in Chicago, IL with Swimming Pool (231 Rentals) Page 5 of 5
The most luxurious Apartments in Chicago with high-end amenities, features, and finishes.


Total Monthly Price
District 1860

Elmhurst 255

The Henry at Harms Woods

Total Monthly Price
Albion Evanston

Total Monthly Price
Park 205 Apartments

Ovaltine

Top of The Mount Apartments

The Emerson

Total Monthly Price
Optima Old Orchard Woods

Park Ridge Commons

The Element

Arbor House

Total Monthly Price
Uptown La Grange

The Residences at Hamilton Lakes

Total Monthly Price
Orion Prospect

Ellison

Total Monthly Price
Vyne on Haven

Novu Apartments

The Monarch

Ashton Arlington Heights

The Park Evanston

Total Monthly Price
Avidor Evanston 55+ Active Adult Apartment Homes

Total Monthly Price
The Marke

The Residences at Sawmill Station

Welkin Apartments

Valley Lo Towers

Central Park East

Total Monthly Price
1717 Evanston

Legacy Crossings

The Bennington
Chicago, IL Local Guide

How much does it cost to rent an apartment in Chicago?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Chicago Studio Apartments | $1,988 | $600 | $9,940 |
| Chicago 1 Bedroom Apartments | $2,490 | $650 | $10,000+ |
| Chicago 2 Bedroom Apartments | $3,091 | $850 | $10,000+ |
| Chicago 3 Bedroom Apartments | $3,854 | $883 | $10,000+ |
| Chicago 4 Bedroom Apartments | $3,443 | $970 | $10,000+ |
| Chicago 5 Bedroom Apartments | $7,474 | $2,600 | $10,000+ |
| Chicago 6 Bedroom Apartments | $6,142 | $750 | $10,000+ |
Explore Chicago
Chicago, IL Area Reviews
Nicole • 4+ years in Chicago
April 10, 2026Big 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 Midpointe listed at $1,081.
How much is the average rent for Chicago Apartments with Swimming Pool?
The average rent for a Apartment in Chicago with Swimming Pool is $4,245.
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 584 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

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.

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.

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.

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

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.

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.

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.

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.