6795+ Rental Villas and Private Getaways in Chicago |
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Chicago Vacation Rentals & One Degree Stays Homes

About Chicago Vacation Rentals

There are more than 6795 vacation rentals that are available in Chicago. These rentals, including vacation rentals, One Degree Stays Homes (ODSs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an ODS property in Chicago.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With OneDegreeStays Chicago, you have the flexibility of comparing different options of various deals with a single click. Looking for an ODS with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (ODSs), and other popular Airbnb-style properties in Chicago. Places to stay near Chicago are 742.91 ft² on average, with prices averaging US $397 a night.

OneDegreeStays makes it easy and safe to find and compare vacation rentals in Chicago with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

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Top Rental Accommodation Types in Chicago

Type Count
Holiday Apartments 4351
Vacation Homes 1063
Villas 9
Cottages 4

Use these Quick Filters to Find a Vacation Rental in Chicago

★ Pro Tip: OneDegreeStays makes it easy to compare the best listings on ODS homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between ODS homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect 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.

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

OneDegreeStays 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


Chicago 7,265 Properties
Central Chicago 1,799 Properties
Downtown Chicago 1,640 Properties
The Loop 749 Properties
West Side 743 Properties
Near North Side 691 Properties
North Side 619 Properties
Far North Side 379 Properties
South Side 375 Properties
South Loop 368 Properties
Near South Side 357 Properties
River North 356 Properties

Frequently Asked Questions About Chicago?

What are the top vacation rentals in Chicago?

There are a lot of options in Chicago. If you plan on staying in the Chicago area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Chicago:

How many vacation rentals have private pools in Chicago?

There are 94 vacation rentals with private pools near Chicago. Top-rated ODS homes that have access to a swimming pool include:

Which vacation homes in Chicago are best for families?

If you are looking for a family-friendly vacation home in Chicago, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Chicago:

How many onedegreestays vacation rentals are available in Chicago?

Currently, the total number of properties listed by One Degree Stays in 2025 is over 6795 in the Chicago area, and still counting. By aggregating listings from multiple websites, One Degree Stays offers an immense amount of choice of the best ODS properties in Chicago. 

Nearby Neighborhood (16) 
Neighborhood Property Count
Downtown Chicago Vacation Rentals in Chicago, Illinois 1640
The Loop Vacation Rentals in Chicago, Illinois 749
Near North Side Vacation Rentals in Chicago, Illinois 691
South Loop Vacation Rentals in Chicago, Illinois 368
Near South Side Vacation Rentals in Chicago, Illinois 357
River North Vacation Rentals in Chicago, Illinois 356
Lakeview Vacation Rentals in Chicago, Illinois 264
West Loop Vacation Rentals in Chicago, Illinois 200
Lincoln Park Vacation Rentals in Chicago, Illinois 153
Hyde Park Vacation Rentals in Chicago, Illinois 107
Logan Square Vacation Rentals in Chicago, Illinois 78
Rogers Park Vacation Rentals in Chicago, Illinois 72
O'Hare Vacation Rentals in Chicago, Illinois 67
Edgewater Vacation Rentals in Chicago, Illinois 59
Wrigleyville Vacation Rentals in Chicago, Illinois 46
Gold Coast Vacation Rentals in Chicago, Illinois 42

People Also Ask

There are 6795 Chicago, IL Vacation Rentals

Recently Booked Vacation Rentals in Chicago