2397+ Private Villas and Holiday Rentals in Downtown Chicago |
  1. USA
  2. Illinois
  3. Chicago
  4. Downtown Chicago

Downtown Chicago Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Downtown Chicago

Discover more than 2397 vacation rentals available in Downtown 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 Downtown Chicago.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Downtown 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 Downtown Chicago. On average, places to stay near Downtown Chicago offer 717.48 ft², with nightly prices averaging ZA R7,821.

With Casai, finding and comparing holiday rentals in Downtown 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.

Show more
Show less

Top Accommodation Types in Downtown Chicago

Type Count
Holiday Apartments 1432
Vacation Homes 370
Villas 4

Use these Quick Filters to Find a Holiday Rental in Downtown 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 Downtown Chicago.

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

Other Places to Stay in Downtown Chicago, IL


Chicago 7,244 Properties
Chicago 4,211 Properties
Central Chicago 1,955 Properties
Near North Side 818 Properties
The Loop 775 Properties
River North 484 Properties
Streeterville 202 Properties
West Loop 198 Properties
Rush and Division 77 Properties
Gold Coast 39 Properties
Killgubbin 37 Properties
West Loop Gate 24 Properties

Frequently Asked Questions About Downtown Chicago?

What are the top holiday rentals in Downtown Chicago?

With numerous options available in Downtown Chicago, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Downtown Chicago:

How many holiday rentals have private pools in Downtown Chicago?

Discover a selection of holiday rentals with private pools near Downtown 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.

Which holiday homes in Downtown Chicago are best for families?

If you're searching for a family-friendly holiday home in Downtown Chicago, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Downtown Chicago:

How many Casai.co.za holiday rentals are available in Downtown Chicago?

As of 2025, Casai boasts over 2397 properties listed in the Downtown Chicago area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Downtown Chicago.

Nearby Neighborhood (16) 
Neighborhood Property Count
Near North Side Vacation Rentals in Chicago, Illinois 818
The Loop Vacation Rentals in Chicago, Illinois 775
River North Vacation Rentals in Chicago, Illinois 484
South Loop Vacation Rentals in Chicago, Illinois 372
Near South Side Vacation Rentals in Chicago, Illinois 360
Near West Side Vacation Rentals in Chicago, Illinois 331
West Town Vacation Rentals in Chicago, Illinois 283
Streeterville Vacation Rentals in Chicago, Illinois 202
West Loop Vacation Rentals in Chicago, Illinois 198
Lincoln Park Vacation Rentals in Chicago, Illinois 143
University Village / Little Italy Vacation Rentals in Chicago, Illinois 89
Old Town Vacation Rentals in Chicago, Illinois 53
River West Vacation Rentals in Chicago, Illinois 52
Gold Coast Vacation Rentals in Chicago, Illinois 39
Magnificent Mile Vacation Rentals in Chicago, Illinois 4128
Lakeshore East Vacation Rentals in Chicago, Illinois 735

People Also Ask

There are 2397 Downtown Chicago, IL Holiday Rentals

Recently Booked Holiday Rentals in Downtown Chicago