Compare Villas, Resorts, & Rentals in Uptown, Chicago, Illinois, USA
About Casai's Private Villas and Holiday Rentals in Uptown
Discover more than 83 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 892.15 ft², with nightly prices averaging US $246.
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?
- Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!
- Family Friendly 2BD/2BA Near Wrigley, Lincoln Square
- ❤️ Spacious and Airy Apartment With Parking On Site!
- Spacious 2-BR Condo + Free On-Site Parking
- Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
- Stunning, Spacious, & Sun-soaked 2BR Uptown Condo by AllSet Turnover
- Newly Renovated 1 BR in Art Deco Architectural Gem, Steps to L & Free Parking
- Uptown Gem
- Chic apartment in marvelous Chicago with WiFi, AC
- Spacious 4-bedroom apartment with WiFi, AC in brilliant Chicago
How many Casai.nz holiday rentals are available in Uptown?
As of 2026, Casai boasts over 83 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 | 267 |
| Edgewater Vacation Rentals in Chicago, Illinois | 77 |
| Ravenswood Vacation Rentals in Chicago, Illinois | 32 |
| Edgewater Beach Vacation Rentals in Chicago, Illinois | 30 |
| Andersonville Vacation Rentals in Chicago, Illinois | 1089 |
| Lakewood-Balmoral Vacation Rentals in Chicago, Illinois | 1059 |
| Buena Park Vacation Rentals in Chicago, Illinois | 1182 |
| Sheridan Park Vacation Rentals in Chicago, Illinois | 1230 |
