Chicago Holiday Rentals
About Casai's Private Villas and Holiday Rentals in Chicago
Discover more than 12397 vacation rentals available in Chicago. 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 Chicago.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Chicago, 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 Chicago. On average, places to stay near Chicago offer 735.33 ft², with nightly prices averaging US $374.
With Casai, finding and comparing holiday rentals in Chicago is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Top Accommodation Types in Chicago
| Type | Count |
|---|---|
| Holiday Apartments | 6081 |
| Vacation Homes | 3449 |
| Cottages | 50 |
| Villas | 23 |
Use these Quick Filters to Find a Holiday Rental in Chicago
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Chicago.
Weather in Chicago, IL
View the weather forecast for Chicago before booking your Chicago Vacation Rentals to confirm your best time to go.
Top Attractions Around Chicago, IL
Casai offers a large selection of top attractions around Chicago . Research things to do on your vacation before you visit Chicago.
Other Places to Stay in Chicago, IL
Frequently Asked Questions About Chicago?
What are the top holiday rentals in Chicago?
With numerous options available in Chicago, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Chicago:
- The Sono Chicago
- 52nd Floor MagMile Penthouse Views Fireplace Pool
- Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC
- 3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
- Remodeled, spacious and bright apartment — near Loyola, beach & subway
- 51st Floor MagMile Penthouse Views Balcony Pool
- NEW LUXURY PENTHOUSE CONDO
- Full Bed | Non Smoking
- Great Location-Beautiful Friendly Andersonville Neighborhood
- NEW LUXURY CONDO WITH PATIO DECK
How many holiday rentals have private pools in Chicago?
Discover a selection of holiday rentals with private pools near Chicago with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
- Spacious 1 bd sleeps 4 quiet and near Michigan Ave. free gift
- Lux Apts with Lake Views and Top Amenities
- Stay One Chicago
- Stylish River North Suites: Luxury Living Near Chicago’s Best Shopping&Nightlife
Which holiday homes in Chicago are best for families?
If you're searching for a family-friendly holiday home in Chicago, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Chicago:
- Best Lincoln Square Location - Spacious 2 bedroom
- The Brown House - A luxurious UChicago Campus stay
- Wrigleyville Inn
How many Casai.com holiday rentals are available in Chicago?
As of 2026, Casai boasts over 12397 properties listed in the Chicago area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Chicago.
Nearby Neighborhood (16)
| Neighborhood | Property Count |
|---|---|
| Downtown Chicago Vacation Rentals in Chicago, Illinois | 1367 |
| The Loop Vacation Rentals in Chicago, Illinois | 626 |
| Near North Side Vacation Rentals in Chicago, Illinois | 561 |
| River North Vacation Rentals in Chicago, Illinois | 333 |
| South Loop Vacation Rentals in Chicago, Illinois | 267 |
| Near South Side Vacation Rentals in Chicago, Illinois | 248 |
| Lakeview Vacation Rentals in Chicago, Illinois | 213 |
| West Loop Vacation Rentals in Chicago, Illinois | 180 |
| Lincoln Park Vacation Rentals in Chicago, Illinois | 132 |
| O'Hare Vacation Rentals in Chicago, Illinois | 60 |
| Logan Square Vacation Rentals in Chicago, Illinois | 52 |
| Wrigleyville Vacation Rentals in Chicago, Illinois | 52 |
| Edgewater Vacation Rentals in Chicago, Illinois | 50 |
| Hyde Park Vacation Rentals in Chicago, Illinois | 49 |
| Rogers Park Vacation Rentals in Chicago, Illinois | 48 |
| Wicker Park Vacation Rentals in Chicago, Illinois | 39 |
