Compare Villas, Resorts, & Rentals in Uptown, Chicago, Illinois, USA
About Casai's Private Villas and Holiday Rentals in Uptown
Discover more than 94 vacation rentals available in Uptown. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Uptown.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Uptown, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Uptown. On average, places to stay near Uptown offer 875.96 ft², with nightly prices averaging US $292.
With Casai, finding and comparing holiday rentals in Uptown is easy and secure, often at a 30-40% discount compared to hotel prices. Simply 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 holiday rentals in Uptown?
- W2 - ❤️ New and Clean! Big Apartment with Parking
- W3 - Spacious 2BR Apt + Free On-site Parking
- Family Friendly 2BD/2BA Near Wrigley, Lincoln Square
- Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
- 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
- Massive Queen Anne Mansion for your whole family to stay!
- Music-Inspired 2BR Garden Flat in Historic Uptown Near Legendary Music Venues
How many Casai.com holiday rentals are available in Uptown?
As of 2026, Casai boasts over 94 properties listed in the Uptown area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Uptown.
Nearby Neighborhood (8)
| Neighborhood | Property Count |
|---|---|
| Lakeview Vacation Rentals in Chicago, Illinois | 214 |
| Edgewater Vacation Rentals in Chicago, Illinois | 55 |
| Ravenswood Vacation Rentals in Chicago, Illinois | 1335 |
| Edgewater Beach Vacation Rentals in Chicago, Illinois | 906 |
| Andersonville Vacation Rentals in Chicago, Illinois | 1162 |
| Sheridan Park Vacation Rentals in Chicago, Illinois | 1303 |
| Buena Park Vacation Rentals in Chicago, Illinois | 1255 |
| Lakewood-Balmoral Vacation Rentals in Chicago, Illinois | 1131 |
