Compare Vacation Rentals & Rent By Owner Homes in Uptown, Chicago, Illinois, USA
About Uptown Vacation Rentals
With more than 93 Uptown vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rent By Owner Homes (RBOs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an RBO property in Uptown.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Uptown, you have the flexibility of comparing different options of various deals with a single click. Looking for an RBO with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (RBOs), and other popular Airbnb-style properties in Uptown. Places to stay near Uptown are 876.86 ft² on average, with prices averaging R4,940 a night.
RentByOwner makes it easy and safe to find and compare vacation rentals in Uptown with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Other Places to Stay in Uptown, IL
Frequently Asked Questions About Uptown?
What are the top vacation rentals in Uptown?
- W3 - Spacious 2BR Apt + Free On-site Parking
- W2 - ❤️ New and Clean! Big Apartment with Parking
- Family Friendly 2BD/2BA Near Wrigley, Lincoln Square
- Newly Renovated 1 BR in Art Deco Architectural Gem, Steps to L & Free Parking
- Uptown Gem
- Spacious 4-bedroom apartment with WiFi, AC in brilliant Chicago
- -Lovely 5BD/3BR/3Parking on premises/Sleeps 14 guests/Andersonville
- Music-Inspired 2BR Garden Flat in Historic Uptown Near Legendary Music Venues
- Ultra-modern 4BR/2.5BA Uptown/Edgewater duplex, featuring a rooftop deck with fire pit and easy access to the lake, dining, shopping, and Chicago’s cultural highlights.
- Chic Vintage Stay w/Private Balcony – Walk to Argyle Redline, Lake, Dining
How many Rentbyowner vacation rentals are available in Uptown?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 93 in the Uptown area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Uptown.
Nearby Neighborhood (8)
| Neighborhood | Property Count |
|---|---|
| Lakeview Vacation Rentals in Chicago, Illinois | 186 |
| Edgewater Vacation Rentals in Chicago, Illinois | 46 |
| Ravenswood Vacation Rentals in Chicago, Illinois | 1335 |
| Edgewater Beach Vacation Rentals in Chicago, Illinois | 924 |
| Andersonville Vacation Rentals in Chicago, Illinois | 1161 |
| Sheridan Park Vacation Rentals in Chicago, Illinois | 1303 |
| Lakewood-Balmoral Vacation Rentals in Chicago, Illinois | 1121 |
| Buena Park Vacation Rentals in Chicago, Illinois | 1255 |
