
Luxury Apartments for Rent in Chicago, IL with Swimming Pool (243 Rentals) Page 4 of 5
The most luxurious Apartments in Chicago with high-end amenities, features, and finishes.


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601 N State St

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619 W Randolph St

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912 N State St

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942 W Huron St

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215 N Clinton St

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158 W Division St

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1415 W Randolph St

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2219 W Wellington Ave, Unit CH

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3018 N Sheridan Rd, Unit 14A

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400 N State St, Unit 1-3303

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1833 N Leavitt St, Unit 212

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900 W Washington Blvd, Unit 32E

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502 E Illinois St, Unit 1812

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4315 N Hazel St, Unit 104

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1436 W Randolph St, Unit 619

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17 N Ada St, Unit 701

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1150 S Michigan Ave

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316 W Erie St, Unit 807

715 S Clark St, Unit 2801

190 E Illinois St, Unit 2102

617 N Wells St, Unit 1003

1356 W Randolph St, Unit 1802

145 N Desplaines St, Unit 1003

461 W Chicago Ave, Unit 2003

347 W Chestnut St, Unit 1313

181 E Illinois St, Unit 220EI

461 W Chicago Ave, Unit 1502

1356 W Randolph St, Unit 2003

501 N State St, Unit 2203

525 N State St, Unit 2

200 N Wells St, Unit 2201

190 E Illinois St, Unit 3005

513 S Damen Ave, Unit 916

513 S Damen Ave, Unit 809

513 S Damen Ave, Unit 1312

513 S Damen Ave, Unit 2009

513 S Damen Ave, Unit 1205

513 S Damen Ave, Unit 1416

513 S Damen Ave, Unit 702

513 S Damen Ave, Unit 1906

513 S Damen Ave, Unit 401

347 W Chestnut St, Unit 2112

740 N Aberdeen St, Unit 321

915 W Washington St, Unit 1807

347 W Chestnut St, Unit 911

450 N State St, Unit 1509

14 N Peoria St, Unit 506

1637 W Chicago Ave

Luxury spectacular view
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 | $2,022 | $595 | $4,964 |
| Chicago 1 Bedroom Apartments | $2,461 | $640 | $9,987 |
| Chicago 2 Bedroom Apartments | $3,030 | $500 | $10,000+ |
| Chicago 3 Bedroom Apartments | $3,646 | $883 | $10,000+ |
| Chicago 4 Bedroom Apartments | $3,690 | $924 | $10,000+ |
| Chicago 5 Bedroom Apartments | $5,854 | $2,695 | $10,000+ |
| Chicago 6 Bedroom Apartments | $10,532 | $6,790 | $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 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 $4,220.
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 607 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

Best Places to Live Near Chicago: 5 Cities That Keep the Windy City Accessible
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I’m Nicole, you’re ApartmentHomeLiving.com Local Expert for Chicago. There’s no denying I love the Windy City. Yet there’s also no denying that rental homes in Chicago can be pricy, small, and hard to find.

Chicago Relocation 101: Mastering Utilities, Registration, and the CTA
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Moving to a new city is always an exciting time, especially one as vibrant and diverse as Chicago. With world-class museums, a breathtaking lakefront, and numerous employment opportunities, there’s much to love about this city.

Explore the Windy City (But Watch for Falling Ice) - An Insider's Guide to Renting in Chicago
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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.
Articles, How-To's, and Tips

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.

Apartment Occupancy Rates: Renter Attraction vs Renter Retention
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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.

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

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.