2876+ Rental Villas and Private Getaways in Downtown Chicago |
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Downtown Chicago Villa Rentals

About Downtown Chicago Vacation Rentals

There are more than 2876 incredible getaway rentals that are available in Downtown Chicago. These choices include villas, hotels, and other rental options. Browse from a massive selection of luxury amenities at great prices, providing you with the dream spot to base your next vacation. Relax with BedroomVillas and uncover great stays in Downtown Chicago.

BedroomVillas features numerous last-minute deals on villas, hotels, and rentals, in locations near you or across the globe. If you need a place for a group or event, be it a hotel or vacation rental (as well as cabins and private luxury villas), let us help. With BedroomVillas in Downtown Chicago, you can compare options from multiple suppliers with a single click to find the price point, amenities, and style of stay that works for you. Group deals, private pools, hot tubs, allows pets, or even huge master suite bedrooms with open-air showers? You can find it all with the BedroomVillas vacation rentals, resorts, and Airbnb-style properties in Downtown Chicago. Places to stay near Downtown Chicago are 751.54 ft² on average, with prices averaging $433 a night.

BedroomVillas helps you find the ideal holiday rental to create lifetime travel memories in Downtown Chicago. Prices listed are often found to be discounted versus the rack rates. Just search for your destination and secure your perfect place to stay today.

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Top Private Villas, Resorts, and Rentals in Downtown Chicago

Type Count
Holiday Apartments 1867
Vacation Homes 540
Hostels 9
Villas 7
B&B 4
Cabin Rentals 2

Use these Quick Filters to Find a Vacation Rental in Downtown Chicago

★ Pro Tip: BedroomVillas is a luxury vacation rental website, pulling some of the top private villas and exclusive holiday stays from sources across the web. We supply you with a huge list of incredible beach houses and holiday rentals from trusted, reliable suppliers, helping you to compare prices and locations to find the best fit for your getaway. Create lifelong memories in Downtown Chicago with BedroomVillas.

Weather in Downtown Chicago, IL

View the weather forecast for Downtown Chicago before booking your Downtown 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

Find Hotels, Resorts, and Rentals Nearby in these Cities & Neighborhoods


Chicago 9,118 Properties
Chicago 5,682 Properties
Central Chicago 2,510 Properties
Near North Side 1,092 Properties
The Loop 892 Properties
River North 671 Properties
West Loop 254 Properties
Streeterville 253 Properties
Rush and Division 79 Properties
Gold Coast 73 Properties
Killgubbin 43 Properties
West Loop Gate 31 Properties

Complexes around Downtown Chicago, IL


Wells Apartments St Chicago 132 Properties
Kasa River North 25 Properties
Accommodation Schaumburg 26 Properties
Gold Coast Doorman Blocks 9 Properties
Naperville Inn 10 Properties
Town 9 Properties
South Loop Grant Park 10 Properties
Claridge 3 Properties
Courtyard 3 Properties
Flat 3 Properties
Mccormick Place 3 Properties
The Blackstone Autograph 3 Properties
Travelodge 3 Properties
The Whitehall Hotel 2 Properties
Sonder Cros 1 Properties
See More Complexes

Frequently Asked Questions About Downtown Chicago?

What are the top hotels or resorts in Downtown Chicago?

We provide an array of great vacation destinations in Downtown Chicago. If you are looking to stay in or around the Downtown Chicago area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Downtown Chicago:

How many vacation rentals have private pools in Downtown Chicago?

We have 67 luxury villas and vacation rentals featuriung a private pool in and near Downtown Chicago. Some of the best destinations to stay that feature or have access to a swimming pool are:

Which hotel or resort in Downtown Chicago is best for families?

Searching for a family-friendly getaway in Downtown Chicago? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.

How many hotels, resorts, or rentals are available in Downtown Chicago?

BedroomVillas offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by BedroomVillas in 2025 is over 2876 in the Downtown Chicago area, and that number rises every day. By combining listings from multiple websites and travel providers, BedroomVillas can provide you with a diverse amount of choices of the best luxury stays in Downtown Chicago. 

Nearby Neighborhood (16) 
Neighborhood Property Count
Near North Side Rental Villas and Private Getaways in Chicago, Illinois 1092
The Loop Rental Villas and Private Getaways in Chicago, Illinois 892
River North Rental Villas and Private Getaways in Chicago, Illinois 671
South Loop Rental Villas and Private Getaways in Chicago, Illinois 533
Near South Side Rental Villas and Private Getaways in Chicago, Illinois 524
Near West Side Rental Villas and Private Getaways in Chicago, Illinois 488
West Town Rental Villas and Private Getaways in Chicago, Illinois 428
West Loop Rental Villas and Private Getaways in Chicago, Illinois 254
Streeterville Rental Villas and Private Getaways in Chicago, Illinois 253
Lincoln Park Rental Villas and Private Getaways in Chicago, Illinois 223
University Village / Little Italy Rental Villas and Private Getaways in Chicago, Illinois 175
River West Rental Villas and Private Getaways in Chicago, Illinois 80
Old Town Rental Villas and Private Getaways in Chicago, Illinois 78
Gold Coast Rental Villas and Private Getaways in Chicago, Illinois 73
Lakeshore East Rental Villas and Private Getaways in Chicago, Illinois 735
Near East Side Rental Villas and Private Getaways in Chicago, Illinois 735

People Also Ask

There are 324 hotels in Downtown Chicago 31 resorts, and 2416 rentals

Recently Booked Hotels, Resorts, or Rentals in Downtown Chicago