
Luxury Homes for Rent in the Uptown Neighborhood of Chicago, IL (130 Rentals) Page 3 of 3
The most luxurious Homes in the Uptown area of Chicago with high-end amenities, features, and finishes.


909 W Dakin St, Unit 302

3923 N Ashland Ave, Unit 6B

3923 N Ashland Ave, Unit 6C
4717 N Beacon St

906 W Sunnyside Ave

950 W Dakin St

733 W Bittersweet Pl

5024 N Winthrop Ave

5158 N Ashland Ave
The Art of the Rental Viewing: What to look for during a property tour
Touring a rental? This guide helps you know exactly what to look for, from safety features to hidden flaws, so you can confidently sign your lease or keep searching.

1451 W Berwyn Ave

819 W Eastwood Ave

4943 N Winthrop Ave

3950 N Lake Shore Dr

4212 N Ashland Ave

4103 N Kenmore Ave

1056 W Lawrence Ave

904 W Dakin St

1512 W Wilson Ave

954 W Cuyler Ave
Smart Renter's Guide: Calculating Affordable Rent & Housing Costs
Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.

4610 N Ashland Ave

1350 W Byron St

1318 W Winnemac Ave

1507 W Carmen Ave

4819 N Ashland Ave

4113 N Southport Ave

4350 N Broadway

5039 N Winthrop Ave

3951 N Wayne Ave

3928 N Greenview Ave
Uptown, Chicago, IL Local Guide

How much does it cost to rent a home in Uptown?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Uptown 2 Bedroom Homes for Rent | $2,950 | $1,950 | $4,450 |
| Uptown 3 Bedroom Homes for Rent | $6,455 | $2,100 | $10,000+ |
| Uptown 4 Bedroom Homes for Rent | $4,228 | $2,799 | $7,900 |
Browse Homes for Rent in this Neighborhood
There are currently 130 rentals with your search options within a 2 mile radius of the Uptown Neighborhood of Chicago, IL.
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Frequently Asked Questions about Uptown
What type of rentals are currently available in Uptown?
There are currently 1088 Apartments for Rent in Uptown, IL with pricing that ranges from $1,095 to $6,500. There are also 368 Single Family Homes for rent, Condos, and Townhome rentals currently available in Uptown ranging from $1,050 to $40,000.
What is the current price range for Rental Homes in Uptown?
Today's rental pricing for Homes for Rent, Condos and Townhomes in Uptown ranges from $1,050 to $40,000 with an average monthly rent of $2,740.
How much are larger Three and Four Bedroom Rentals in Uptown?
For those who are looking for larger living arrangements, Three Bedroom Apartments in Uptown range from $2,550 to $5,200, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,100 to $40,000. Four Bedroom Single-Family rentals are also available starting from $2,799 and Four Bedroom Apartments start at $3,795.
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

The Windy City Price Tag: Your Complete Guide to the Cost of Living in Chicago
Written by: Nicole Harms
When choosing a place to live, there are many things you must consider. Your employer, your shopping preferences, and even schools are all important to think about. Yet cost of living is also important to know and plan for.

Best Places to Live Near Chicago: 5 Cities That Keep the Windy City Accessible
Written by: Nicole Harms
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
Written by: Nicole Harms
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
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

Exploring Rental Options: Apartments, Townhomes, and Lofts - Oh My!
Written by: Robin Stewart
Where do you see yourself? When you think of home, sweet home, are you in a 3/2 apartment? Dreaming of a tall townhome? Maybe an industrial loft heavy on cool vibes is on your visioning board.

Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags
Written by: Robin Stewart
Renters want to find a great apartment, the right place for them, one that checks all the boxes of location, rental cost, amenities, safety, and more.

First Apartment Regrets: Real Renters Share What They'd Do Differently
Written by: Robin Stewart
Hindsight is 20/20. Live and Learn. With age comes wisdom. We’re familiar with all those expressions, and all of them apply to lessons first-time renters learn.

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.