11562+ Vacation Home Rentals in Chicago |
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Chicago Vacation Rentals & Ski-in/Ski-out Homes

About Chicago Vacation Rentals

Explore over 11562 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 739.9 ft² of space, and are priced at an average of US $339 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.

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Top Types of Ski Accommodations in Chicago

Type Count
Holiday Apartments 5656
Vacation Homes 3180
B&B 58
Cottages 48
Villas 22
Cabin Rentals 15
Others 11
Unique Vacation Rentals 2
Unique Vacation Rentals 1
Ski Chalet Rentals 1

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.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

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.


Navy Pier
Wrigley Field
McCormick Place
Millennium Park
Union Station
Soldier Field
Willis Tower
Art Institute of Chicago
Naval Base Great Lakes
United Center
Grant Park
John G. Shedd Aquarium
Chicago Museum of Science and Industry
Chicago Theatre
Chicago Riverwalk
Field Museum of Natural History
Six Flags Great America
University of Chicago
Brookfield Zoo
Northwestern University

Other Places to Stay in Chicago, IL


Cook County 5,408 Properties
Chicago 4,189 Properties
Central Chicago 1,686 Properties
Downtown Chicago 1,548 Properties
West Side 806 Properties
The Loop 717 Properties
North Side 654 Properties
Near North Side 617 Properties
Lake County 574 Properties
DuPage County 473 Properties
Far North Side 381 Properties
Near West Side 371 Properties

Complexes around Chicago, IL


Wells Apartments St Chicago 132 Properties
Naperville Inn 18 Properties
Town 16 Properties
South Loop Grant Park 28 Properties
Wrigley 35 Properties
Lakeview 20 Properties
Mccormick Place 6 Properties
Kasa River North 12 Properties
Transit Dt 13 Properties
Doubletree 3 Properties
Hilton 6 Properties
Breakfast 17 Properties
Gold Coast Doorman Blocks 9 Properties
Courtyard 3 Properties
Lofts 12 Properties
See More Complexes

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.

How many vacation rentals have private pools in Chicago?

Uncover 319 vacation rentals boasting private pools near Chicago. Explore top-rated RBO homes offering access to a swimming pool:

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.™

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 11562 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

People Also Ask

There are 11562 Chicago, IL Vacation Rentals

Recently Booked Vacation Rentals in Chicago