Central Chicago Holiday Rentals

Compare Villas, Resorts, & Rentals in Central Chicago, Illinois, USA

New Boulevard Stays 5 mins to Riverwalk & Mag Mile 03
Apartment
Boulevard Stays 5 mins to Riverwalk & Mag Mile 03
From ZA R6,012 per night
New
2 Bedrooms 4 Guests
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Well-Appointed Cozy Portage Park Apt, Dogs, Kids, Free Parking, 420 Compliant
Apartment
Well-Appointed Cozy Portage Park Apt, Dogs, Kids, Free Parking, 420 Compliant
From ZA R1,856 per night
|
10.0 (10 Reviews)
3 Bedrooms 10 Guests
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Chicago Avenue Inn
House
Chicago Avenue Inn
From ZA R2,296 per night
7.0 (90 Reviews)
1 Bedroom 2 Guests
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Lux Apts with Lake Views and Top Amenities
Apartment
Lux Apts with Lake Views and Top Amenities
From ZA R27,441 per night
|
10.0 (3 Reviews)
13 Bedrooms 32 Guests
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4BR Corporate Suite Central and Modern
Hotel
4BR Corporate Suite Central and Modern
From ZA R8,425 per night
10.0 (3 Reviews)
4 Bedrooms 10 Guests
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New City Studio Escape Bright, Sleek & Modern
House
City Studio Escape Bright, Sleek & Modern
From ZA R4,690 per night
New
1 Bedroom 4 Guests
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The Wheeler Mansion
Hotel
The Wheeler Mansion
From ZA R12,555 per night
|
10.0 (1 Review)
1 Bedroom 2 Guests
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52nd Floor MagMile Penthouse VIEWS Fireplace Pool
Apartment
52nd Floor MagMile Penthouse VIEWS Fireplace Pool
From ZA R6,136 per night
10.0 (398 Reviews)
1 Bedroom 4 Guests
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53 Floor MagMile Penthouse Views, Balcony, Pool
Apartment
53 Floor MagMile Penthouse Views, Balcony, Pool
From ZA R7,290 per night
10.0 (236 Reviews)
2 Bedrooms 6 Guests
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Gold coast villa with free parking garage sleeps 10
Villa
Gold coast villa with free parking garage sleeps 10
From ZA R29,066 per night
|
10.0 (1 Review)
4 Bedrooms 10 Guests
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51st Floor MagMile Penthouse Views Balcony Pool
Apartment
51st Floor MagMile Penthouse Views Balcony Pool
From ZA R6,505 per night
10.0 (224 Reviews)
1 Bedroom 4 Guests
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53/54 Mag Mile Penthouse VIEWS, Fireplace, Pool
Apartment
53/54 Mag Mile Penthouse VIEWS, Fireplace, Pool
From ZA R15,618 per night
10.0 (203 Reviews)
2 Bedrooms 8 Guests
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51/52nd Floor Penthouse-VIEWS, Fireplace, Pool
Apartment
51/52nd Floor Penthouse-VIEWS, Fireplace, Pool
From ZA R14,524 per night
10.0 (187 Reviews)
2 Bedrooms 7 Guests
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52nd Floor, VIEWS, Pool, Balcony, Pool, Gym
Apartment
52nd Floor, VIEWS, Pool, Balcony, Pool, Gym
From ZA R6,497 per night
10.0 (61 Reviews)
1 Bedroom 4 Guests
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Perfect Location Across from Park & Train Station
House
Perfect Location Across from Park & Train Station
From ZA R12,736 per night
|
10.0 (1 Review)
5 Bedrooms 13 Guests
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50th Floor Mag Mile VIEWS, Balcony, Pool, Gym
Apartment
50th Floor Mag Mile VIEWS, Balcony, Pool, Gym
From ZA R5,126 per night
10.0 (24 Reviews)
1 Bedroom 2 Guests
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MICH AVE #5|Safe DTown Grant Park, Museums 2bd/2ba
Condo
MICH AVE #5|Safe DTown Grant Park, Museums 2bd/2ba
From ZA R6,139 per night
10.0 (23 Reviews)
2 Bedrooms 6 Guests
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Downtown Guild #3 | Mag Mile Gold Coast The Lake!
Condo
Downtown Guild #3 | Mag Mile Gold Coast The Lake!
From ZA R5,402 per night
10.0 (19 Reviews)
1 Bedroom 4 Guests
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Downtown MICH AVE #20, Grant Park, Museums 2bd/2ba
Condo
Downtown MICH AVE #20, Grant Park, Museums 2bd/2ba
From ZA R6,584 per night
10.0 (8 Reviews)
2 Bedrooms 6 Guests
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53-54 Floor Penthouse
Apartment
53-54 Floor Penthouse
From ZA R10,422 per night
10.0 (7 Reviews)
2 Bedrooms 6 Guests
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New Luxury 3 Bdr Apt in Chicago C9
Apartment
New Luxury 3 Bdr Apt in Chicago C9
From ZA R26,291 per night
10.0 (1 Review)
3 Bedrooms 6 Guests
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Downtown Charm: 2BR, Comfort, Great Amenities
Apartment
Downtown Charm: 2BR, Comfort, Great Amenities
From ZA R9,161 per night
10.0 (7 Reviews)
2 Bedrooms 5 Guests
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Steps to Mag Mile, 2 BD, fast Wi-Fi, W&D
Apartment
Steps to Mag Mile, 2 BD, fast Wi-Fi, W&D
From ZA R5,093 per night
10.0 (6 Reviews)
2 Bedrooms 4 Guests
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The Loop 2BR: Historic, Modern Luxury, Amenities
Apartment
The Loop 2BR: Historic, Modern Luxury, Amenities
From ZA R11,095 per night
10.0 (5 Reviews)
2 Bedrooms 5 Guests
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Beautiful Chicago 2BD 1BA, minutes from Downtown!
Apartment
Beautiful Chicago 2BD 1BA, minutes from Downtown!
From ZA R4,092 per night
10.0 (5 Reviews)
2 Bedrooms 4 Guests
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Luxéry Stay "Chicago" Downtown/McCormick/Wintrust Area
Apartment
Luxéry Stay "Chicago" Downtown/McCormick/Wintrust Area
From ZA R14,274 per night
10.0 (4 Reviews)
1 Bedroom 4 Guests
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Luxéry Stay South Loop - McCormick/Wintrust Area
Apartment
Luxéry Stay South Loop - McCormick/Wintrust Area
From ZA R13,168 per night
10.0 (4 Reviews)
1 Bedroom 4 Guests
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Chic Studio with WiFi and AC in Beautiful Chicago
Apartment
Chic Studio with WiFi and AC in Beautiful Chicago
From ZA R7,241 per night
10.0 (1 Review)
1 Bedroom 3 Guests
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Historic luxury Townhouse in Downtown Chicago
House
Historic luxury Townhouse in Downtown Chicago
From ZA R34,008 per night
|
9.8 (7 Reviews)
5 Bedrooms 10 Guests
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2BR City Escape
Hotel
2BR City Escape
From ZA R6,926 per night
10.0 (1 Review)
1 Bedroom 2 Guests
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The Langham, Chicago
Hotel
The Langham, Chicago
From ZA R10,627 per night
|
9.8 (1007 Reviews)
1 Bedroom 2 Guests
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Spacious 2BR Group Stay near McCormick & Wintrust
House
Spacious 2BR Group Stay near McCormick & Wintrust
From ZA R6,831 per night
10.0 (1 Review)
2 Bedrooms 8 Guests
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Modern & Furnished 2BR Apt with In-unit Laundry - Sunnyside 2E
Apartment
Modern & Furnished 2BR Apt with In-unit Laundry - Sunnyside 2E
From ZA R6,070 per night
9.5 (4 Reviews)
2 Bedrooms 4 Guests
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The Peninsula Chicago
Hotel
The Peninsula Chicago
From ZA R12,724 per night
|
9.8 (1005 Reviews)
1 Bedroom 2 Guests
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420 friendly 2br/2ba with optional parking/sleeps 6
Apartment
420 friendly 2br/2ba with optional parking/sleeps 6
From ZA R6,649 per night
10.0 (1 Review)
2 Bedrooms 6 Guests
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Walk Everywhere! 5 mins to Magnificent Mile, River
Apartment
Walk Everywhere! 5 mins to Magnificent Mile, River
From ZA R6,309 per night
10.0 (1 Review)
2 Bedrooms 4 Guests
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Foundry Unmatched Skyline Views at Lincoln Park
Apartment
Foundry Unmatched Skyline Views at Lincoln Park
From ZA R6,521 per night
|
9.4 (11 Reviews)
4 Bedrooms 8 Guests
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The Bernardin Gold Coast Luxury Apartments Near Magnificent Mile
Apartment
The Bernardin Gold Coast Luxury Apartments Near Magnificent Mile
From ZA R19,129 per night
|
9.2 (28 Reviews)
9 Bedrooms 24 Guests
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McCormick Place 2br/2ba with Optional Parking/Patio/Gym/sleeps 6
Apartment
McCormick Place 2br/2ba with Optional Parking/Patio/Gym/sleeps 6
From ZA R6,163 per night
10.0 (1 Review)
2 Bedrooms 6 Guests
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K2 Sky High Apartments with Stunning Chicago Views in West Loop
Apartment
K2 Sky High Apartments with Stunning Chicago Views in West Loop
From ZA R9,205 per night
|
9.2 (17 Reviews)
17 Bedrooms 43 Guests
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ENVITAE 3BR Luxury Corner Loft with Navy Pier Views
Apartment
ENVITAE 3BR Luxury Corner Loft with Navy Pier Views
From ZA R3,122 per night
|
9.2 (17 Reviews)
3 Bedrooms 6 Guests
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Bright Streeterville 2BR w/Gym, Pool, near Navy Pier, by Blueground
Apartment
Bright Streeterville 2BR w/Gym, Pool, near Navy Pier, by Blueground
From ZA R6,050 per night
10.0 (1 Review)
2 Bedrooms 4 Guests
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Post Chicago Getaway Ideal 4BR for Groups
Apartment
Post Chicago Getaway Ideal 4BR for Groups
From ZA R13,022 per night
|
9.2 (15 Reviews)
24 Bedrooms 48 Guests
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River North | Rooftop With In & Out Parking | 5
Apartment
River North | Rooftop With In & Out Parking | 5
From ZA R5,960 per night
10.0 (1 Review)
2 Bedrooms 6 Guests
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Cozy Casa by OHare Airport
Apartment
Cozy Casa by OHare Airport
From ZA R2,052 per night
9.2 (6 Reviews)
1 Bedroom 9 Guests
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Spacious 1 bd sleeps 4 quiet and near Michigan Ave
Apartment
Spacious 1 bd sleeps 4 quiet and near Michigan Ave
From ZA R5,522 per night
10.0 (1 Review)
1 Bedroom 5 Guests
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UrbanEden Loft Apartment
Apartment
UrbanEden Loft Apartment
From ZA R1,791 per night
9.2 (5 Reviews)
2 Bedrooms 4 Guests
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About Casai's Private Villas and Holiday Rentals in Central Chicago

Discover more than 2652 vacation rentals available in Central 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 Central Chicago.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Central 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 Central Chicago. On average, places to stay near Central Chicago offer 743.85 ft², with nightly prices averaging ZA R7,688.

With Casai, finding and comparing holiday rentals in Central 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.

Other Places to Stay in Central Chicago, IL


Chicago 7,039 Properties
Chicago 4,014 Properties
Downtown Chicago 1,585 Properties
The Loop 738 Properties
Near North Side 649 Properties
South Side 369 Properties
South Loop 363 Properties
Near South Side 351 Properties
River North 327 Properties
Prairie District 246 Properties
Streeterville 197 Properties
Rush and Division 72 Properties

Frequently Asked Questions About Central Chicago?

What are the top holiday rentals in Central Chicago?

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

As of 2025, Casai boasts over 2652 properties listed in the Central Chicago area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Central Chicago.

Nearby Neighborhood (16)

Neighborhood Property Count
Downtown Chicago Vacation Rentals in Chicago, Illinois 1585
The Loop Vacation Rentals in Chicago, Illinois 738
Near North Side Vacation Rentals in Chicago, Illinois 649
South Loop Vacation Rentals in Chicago, Illinois 363
Near South Side Vacation Rentals in Chicago, Illinois 351
Near West Side Vacation Rentals in Chicago, Illinois 329
River North Vacation Rentals in Chicago, Illinois 327
West Town Vacation Rentals in Chicago, Illinois 293
West Loop Vacation Rentals in Chicago, Illinois 198
Streeterville Vacation Rentals in Chicago, Illinois 197
Lincoln Park Vacation Rentals in Chicago, Illinois 145
Bronzeville Vacation Rentals in Chicago, Illinois 101
Old Town Vacation Rentals in Chicago, Illinois 51
River West Vacation Rentals in Chicago, Illinois 51
Gold Coast Vacation Rentals in Chicago, Illinois 39
Chinatown Vacation Rentals in Chicago, Illinois 3053

There are 2652 Central Chicago, IL Vacation Rentals

Recently Booked Hotels, Resorts, or Rentals in Central Chicago