Chicago Vacation Rentals & Ski-in/Ski-out Homes
About Chicago Vacation Rentals
Explore over 7394 vacation rentals in Chicago with SunSki Resorts. These accommodations, comprising vacation homes, cottages, cabins, and condos, boast excellent amenities at great value, ensuring comfort and luxury. Enhance your stay with SunSki Resorts in Chicago for more space and value.
In search of last-minute deals or the best bargains on vacation rentals? With SunSki Resorts, you can conveniently compare various options and deals in Chicago. Discover rentals with desirable amenities like swimming pools, hot tubs, and pet-friendly options. Find the ideal vacation rental in Chicago tailored to your preferences. On average, these rentals offer 740.48 ft² of space, and are priced at an average of US $380 per night.
SunSki Resorts simplifies and secures the process of finding and comparing vacation rentals in Chicago at prices typically 30-40% lower than hotels. Discover your perfect vacation rental and book now.
Top Types of Ski Accommodations in Chicago
| Type | Count |
|---|---|
| Holiday Apartments | 4813 |
| Vacation Homes | 1134 |
| B&B | 50 |
| Villas | 7 |
| Cottages | 5 |
| Others | 3 |
| Cabin Rentals | 2 |
Use these Quick Filters to Find a Vacation Rental in Chicago
★ Pro Tip: Discover Your Ideal Vacation Rental in Chicago with SunSki Resorts™. Compare a diverse array of properties, including RBO homes, vacation rentals, cottages, cabins, and more. Utilize our advanced filters to search by location, amenities, and price. Book with confidence and enjoy savings of up to 40-60% compared to a hotel stay. Create unforgettable memories with SunSki Resorts™.
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
Sunski 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
Complexes around Chicago, IL
Frequently Asked Questions About Chicago?
What are the top vacation rentals in Chicago?
When organizing your trip to Chicago, don't miss the chance to explore the top-rated vacation rentals in the vicinity. With a plethora of options available, you're bound to discover the ideal accommodation for your stay in Chicago. Peruse our collection of highly-rated properties and secure your reservation today.
- 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
- 55th Floor Penthouse with Award-Winning Views
- 3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
- 53 Floor MagMile Penthouse Views, Balcony, Pool
- Luxury Loyola 3 Bedroom, 2 Bath, Near Subway and Beach
- 51st Floor MagMile Penthouse Views Balcony Pool
- 2-Story Penthouse Views, Fireplace, Pool, Gym
- NEW LUXURY PENTHOUSE CONDO
How many vacation rentals have private pools in Chicago?
Uncover 93 vacation rentals boasting private pools near Chicago. Explore top-rated RBO homes offering access to a swimming pool:
- Stylish River North Suites Luxe Comfort Near Chicago’s Best Shopping & Nightlife
- ENVITAE 3BR Luxury Corner Loft with Navy Pier Views
- Stay One Chicago
- Spacious 1 bd sleeps 4 quiet and near Michigan Ave. free gift
Which vacation homes or resorts in Chicago are best for families?
Choose SunSki for a wide variety of vacation rentals, including family-friendly homes, ski cabins, cottages, and more in Chicago. Enjoy great views, locations and save money with SunSki Resorts.™
- Spacious 3BD Penthouse Retreat Near Wrigley Field
- Modern 3BR Apt in Boystown, 12-min walk to Wrigley - Stratford 1S
- Wrigleyville Inn
How many SunSkiResorts vacation rentals or resorts are available in Chicago?
Discover the ideal vacation rental in Chicago with SunSki Resorts™. We provide an extensive selection of over 7394 properties, encompassing vacation homes, private villas, cottages, and more. Explore our listings to find the perfect place to stay for your upcoming trip to Chicago.
Nearby Neighborhood (16)
| Neighborhood | Property Count |
|---|---|
| Downtown Chicago Vacation Rentals in Chicago, Illinois | 1548 |
| The Loop Vacation Rentals in Chicago, Illinois | 717 |
| Near North Side Vacation Rentals in Chicago, Illinois | 617 |
| South Loop Vacation Rentals in Chicago, Illinois | 366 |
| Near South Side Vacation Rentals in Chicago, Illinois | 351 |
| River North Vacation Rentals in Chicago, Illinois | 332 |
| Lakeview Vacation Rentals in Chicago, Illinois | 266 |
| West Loop Vacation Rentals in Chicago, Illinois | 214 |
| Lincoln Park Vacation Rentals in Chicago, Illinois | 154 |
| Hyde Park Vacation Rentals in Chicago, Illinois | 103 |
| Logan Square Vacation Rentals in Chicago, Illinois | 87 |
| Edgewater Vacation Rentals in Chicago, Illinois | 78 |
| Rogers Park Vacation Rentals in Chicago, Illinois | 74 |
| O'Hare Vacation Rentals in Chicago, Illinois | 50 |
| Wrigleyville Vacation Rentals in Chicago, Illinois | 49 |
| Wicker Park Vacation Rentals in Chicago, Illinois | 46 |
