Central Chicago Vacation Rentals & Ski-in/Ski-out Homes

Compare Vacation Rentals & Ski-in/Ski-out Homes in Central Chicago, Illinois, USA

New City Studio Escape Bright, Sleek & Modern
House
City Studio Escape Bright, Sleek & Modern
From US $251 per night
8.0 (1 Review)
1 Bedroom 4 Guests
GET THE BEST PRICE
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 US $107 per night
|
10.0 (10 Reviews)
3 Bedrooms 10 Guests
GET THE BEST PRICE
Chicago Avenue Inn
House
Chicago Avenue Inn
From US $132 per night
7.0 (90 Reviews)
1 Bedroom 2 Guests
GET THE BEST PRICE
New Boulevard Stays 5 mins to Riverwalk & Mag Mile 03
Apartment
Boulevard Stays 5 mins to Riverwalk & Mag Mile 03
From US $347 per night
New
2 Bedrooms 4 Guests
GET THE BEST PRICE
Lux Apts with Lake Views and Top Amenities
Apartment
Lux Apts with Lake Views and Top Amenities
From US $1,582 per night
|
10.0 (4 Reviews)
13 Bedrooms 32 Guests
GET THE BEST PRICE
4BR Corporate Suite Central and Modern
Hotel
4BR Corporate Suite Central and Modern
From US $486 per night
10.0 (3 Reviews)
4 Bedrooms 10 Guests
GET THE BEST PRICE
The Wheeler Mansion
Hotel
The Wheeler Mansion
From US $724 per night
|
10.0 (1 Review)
1 Bedroom 2 Guests
GET THE BEST PRICE
52nd Floor MagMile Penthouse VIEWS Fireplace Pool
Apartment
52nd Floor MagMile Penthouse VIEWS Fireplace Pool
From US $354 per night
10.0 (398 Reviews)
1 Bedroom 4 Guests
GET THE BEST PRICE
53 Floor MagMile Penthouse Views, Balcony, Pool
Apartment
53 Floor MagMile Penthouse Views, Balcony, Pool
From US $420 per night
10.0 (236 Reviews)
2 Bedrooms 6 Guests
GET THE BEST PRICE
Gold coast villa with free parking garage sleeps 10
Villa
Gold coast villa with free parking garage sleeps 10
From US $1,676 per night
|
10.0 (1 Review)
4 Bedrooms 10 Guests
GET THE BEST PRICE
51st Floor MagMile Penthouse Views Balcony Pool
Apartment
51st Floor MagMile Penthouse Views Balcony Pool
From US $375 per night
10.0 (224 Reviews)
1 Bedroom 4 Guests
GET THE BEST PRICE
53/54 Mag Mile Penthouse VIEWS, Fireplace, Pool
Apartment
53/54 Mag Mile Penthouse VIEWS, Fireplace, Pool
From US $901 per night
10.0 (203 Reviews)
2 Bedrooms 8 Guests
GET THE BEST PRICE
51/52nd Floor Penthouse-VIEWS, Fireplace, Pool
Apartment
51/52nd Floor Penthouse-VIEWS, Fireplace, Pool
From US $837 per night
10.0 (187 Reviews)
2 Bedrooms 7 Guests
GET THE BEST PRICE
52nd Floor, VIEWS, Pool, Balcony, Pool, Gym
Apartment
52nd Floor, VIEWS, Pool, Balcony, Pool, Gym
From US $375 per night
10.0 (61 Reviews)
1 Bedroom 4 Guests
GET THE BEST PRICE
Perfect Location Across from Park & Train Station
House
Perfect Location Across from Park & Train Station
From US $734 per night
|
10.0 (1 Review)
5 Bedrooms 13 Guests
GET THE BEST PRICE
50th Floor Mag Mile VIEWS, Balcony, Pool, Gym
Apartment
50th Floor Mag Mile VIEWS, Balcony, Pool, Gym
From US $296 per night
10.0 (24 Reviews)
1 Bedroom 2 Guests
GET THE BEST PRICE
MICH AVE #5|Safe DTown Grant Park, Museums 2bd/2ba
Condo
MICH AVE #5|Safe DTown Grant Park, Museums 2bd/2ba
From US $354 per night
10.0 (23 Reviews)
2 Bedrooms 6 Guests
GET THE BEST PRICE
Downtown Guild #3 | Mag Mile Gold Coast The Lake!
Condo
Downtown Guild #3 | Mag Mile Gold Coast The Lake!
From US $312 per night
10.0 (19 Reviews)
1 Bedroom 4 Guests
GET THE BEST PRICE
Tranquil Portage Park Stay
Apartment
Tranquil Portage Park Stay
From US $143 per night
10.0 (11 Reviews)
1 Bedroom 2 Guests
GET THE BEST PRICE
Downtown MICH AVE #20, Grant Park, Museums 2bd/2ba
Condo
Downtown MICH AVE #20, Grant Park, Museums 2bd/2ba
From US $380 per night
10.0 (8 Reviews)
2 Bedrooms 6 Guests
GET THE BEST PRICE
New Luxury 3 Bdr Apt in Chicago C9
Apartment
New Luxury 3 Bdr Apt in Chicago C9
From US $1,516 per night
10.0 (1 Review)
3 Bedrooms 6 Guests
GET THE BEST PRICE
Steps to Mag Mile, 2 BD, fast Wi-Fi, W&D
Apartment
Steps to Mag Mile, 2 BD, fast Wi-Fi, W&D
From US $294 per night
10.0 (8 Reviews)
2 Bedrooms 4 Guests
GET THE BEST PRICE
53-54 Floor Penthouse
Apartment
53-54 Floor Penthouse
From US $601 per night
10.0 (7 Reviews)
2 Bedrooms 6 Guests
GET THE BEST PRICE
Historic Charm + Modern Comfort for Tourists
Apartment
Historic Charm + Modern Comfort for Tourists
From US $504 per night
10.0 (7 Reviews)
2 Bedrooms 5 Guests
GET THE BEST PRICE
The Loop 2BR: Historic, Modern Luxury, Amenities
Apartment
The Loop 2BR: Historic, Modern Luxury, Amenities
From US $640 per night
10.0 (5 Reviews)
2 Bedrooms 5 Guests
GET THE BEST PRICE
Beautiful Chicago 2BD 1BA, minutes from Downtown!
Apartment
Beautiful Chicago 2BD 1BA, minutes from Downtown!
From US $236 per night
10.0 (5 Reviews)
2 Bedrooms 4 Guests
GET THE BEST PRICE
Luxéry Stay "Chicago" Downtown/McCormick/Wintrust Area
Apartment
Luxéry Stay "Chicago" Downtown/McCormick/Wintrust Area
From US $823 per night
10.0 (4 Reviews)
1 Bedroom 4 Guests
GET THE BEST PRICE
5-Star Gold Coast Experience in a Luxe 2BR Retreat
Apartment
5-Star Gold Coast Experience in a Luxe 2BR Retreat
From US $606 per night
10.0 (1 Review)
2 Bedrooms 5 Guests
GET THE BEST PRICE
Historic luxury Townhouse in Downtown Chicago
House
Historic luxury Townhouse in Downtown Chicago
From US $1,961 per night
|
9.8 (7 Reviews)
5 Bedrooms 10 Guests
GET THE BEST PRICE
New & Modern Lux City Escape
Hotel
New & Modern Lux City Escape
From US $453 per night
10.0 (1 Review)
3 Bedrooms 8 Guests
GET THE BEST PRICE
2BR City Escape
Hotel
2BR City Escape
From US $399 per night
10.0 (1 Review)
1 Bedroom 2 Guests
GET THE BEST PRICE
Modern & Furnished 2BR Apt with In-unit Laundry - Sunnyside 2E
Apartment
Modern & Furnished 2BR Apt with In-unit Laundry - Sunnyside 2E
From US $350 per night
9.5 (4 Reviews)
2 Bedrooms 4 Guests
GET THE BEST PRICE
The Peninsula Chicago
Hotel
The Peninsula Chicago
From US $734 per night
|
9.8 (1012 Reviews)
1 Bedroom 2 Guests
GET THE BEST PRICE
Chic Studio with WiFi and AC in Beautiful Chicago
Apartment
Chic Studio with WiFi and AC in Beautiful Chicago
From US $418 per night
10.0 (1 Review)
1 Bedroom 3 Guests
GET THE BEST PRICE
Spacious 2BR Group Stay near McCormick & Wintrust
House
Spacious 2BR Group Stay near McCormick & Wintrust
From US $394 per night
10.0 (1 Review)
2 Bedrooms 8 Guests
GET THE BEST PRICE
Foundry Unmatched Skyline Views at Lincoln Park
Apartment
Foundry Unmatched Skyline Views at Lincoln Park
From US $376 per night
|
9.4 (11 Reviews)
4 Bedrooms 8 Guests
GET THE BEST PRICE
The Bernardin Gold Coast Luxury Apartments Near Magnificent Mile
Apartment
The Bernardin Gold Coast Luxury Apartments Near Magnificent Mile
From US $1,103 per night
|
9.2 (28 Reviews)
9 Bedrooms 24 Guests
GET THE BEST PRICE
K2 Sky High Apartments with Stunning Chicago Views in West Loop
Apartment
K2 Sky High Apartments with Stunning Chicago Views in West Loop
From US $531 per night
|
9.2 (17 Reviews)
17 Bedrooms 43 Guests
GET THE BEST PRICE
ENVITAE 3BR Luxury Corner Loft with Navy Pier Views
Apartment
ENVITAE 3BR Luxury Corner Loft with Navy Pier Views
From US $180 per night
|
9.2 (17 Reviews)
3 Bedrooms 6 Guests
GET THE BEST PRICE
Post Chicago Getaway Ideal 4BR for Groups
Apartment
Post Chicago Getaway Ideal 4BR for Groups
From US $751 per night
|
9.2 (15 Reviews)
24 Bedrooms 48 Guests
GET THE BEST PRICE
Cozy Casa by OHare Airport
Apartment
Cozy Casa by OHare Airport
From US $118 per night
9.2 (6 Reviews)
1 Bedroom 9 Guests
GET THE BEST PRICE
River North | Rooftop With In & Out Parking | 5
Apartment
River North | Rooftop With In & Out Parking | 5
From US $344 per night
10.0 (1 Review)
2 Bedrooms 6 Guests
GET THE BEST PRICE
UrbanEden Loft Apartment
Apartment
UrbanEden Loft Apartment
From US $103 per night
9.2 (5 Reviews)
2 Bedrooms 4 Guests
GET THE BEST PRICE
See More Properties

About Central Chicago Vacation Rentals

Explore over 2658 vacation rentals in Central 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 Central 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 Central Chicago. Discover rentals with desirable amenities like swimming pools, hot tubs, and pet-friendly options. Find the ideal vacation rental in Central Chicago tailored to your preferences. On average, these rentals offer 740.65 ft² of space, and are priced at an average of US $440 per night.

SunSki Resorts simplifies and secures the process of finding and comparing vacation rentals in Central Chicago at prices typically 30-40% lower than hotels. Discover your perfect vacation rental and book now.

Other Places to Stay in Central Chicago, IL


Chicago 7,264 Properties
Chicago 4,202 Properties
Downtown Chicago 1,639 Properties
The Loop 749 Properties
Near North Side 690 Properties
South Side 375 Properties
South Loop 368 Properties
Near South Side 357 Properties
River North 355 Properties
Prairie District 267 Properties
Streeterville 203 Properties
Rush and Division 74 Properties

Frequently Asked Questions About Central Chicago?

What are the top vacation rentals in Central Chicago?

How many SunSkiResorts vacation rentals or resorts are available in Central Chicago?

Discover the ideal vacation rental in Central Chicago with SunSki Resorts™. We provide an extensive selection of over 2658 properties, encompassing vacation homes, private villas, cottages, and more. Explore our listings to find the perfect place to stay for your upcoming trip to Central Chicago.

Nearby Neighborhood (16)

Neighborhood Property Count
Downtown Chicago Vacation Rentals in Chicago, Illinois 1639
The Loop Vacation Rentals in Chicago, Illinois 749
Near North Side Vacation Rentals in Chicago, Illinois 690
South Loop Vacation Rentals in Chicago, Illinois 368
Near South Side Vacation Rentals in Chicago, Illinois 357
River North Vacation Rentals in Chicago, Illinois 355
Near West Side Vacation Rentals in Chicago, Illinois 332
West Town Vacation Rentals in Chicago, Illinois 296
Streeterville Vacation Rentals in Chicago, Illinois 203
West Loop Vacation Rentals in Chicago, Illinois 200
Lincoln Park Vacation Rentals in Chicago, Illinois 154
Bronzeville Vacation Rentals in Chicago, Illinois 95
Old Town Vacation Rentals in Chicago, Illinois 54
River West Vacation Rentals in Chicago, Illinois 50
Gold Coast Vacation Rentals in Chicago, Illinois 42
Chinatown Vacation Rentals in Chicago, Illinois 3053

There are 2658 Central Chicago, IL Vacation Rentals

Recently Booked Hotels, Resorts, or Rentals in Central Chicago