Central Chicago Luxury Rental
20 Guests
1 Bedroom
6 Bathrooms
Free Cancellation
Apartment
- Air Conditioner
- Internet
- Child Friendly
US $5,000/Night
For 7 Nights US $35,000
7000 ft²
14 Guests
5 Bedrooms
5 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $4,178/Night
For 7 Nights US $29,244
4585 ft²
16 Guests
9 Bedrooms
9 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $4,049/Night
For 7 Nights US $28,343
4800.7 ft²
16 Guests
8 Bedrooms
6 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- View
- Parking
US $3,579/Night
For 7 Nights US $25,053
3337 ft²
16 Guests
10 Bedrooms
9 Bathrooms
Family Friendly
Condo
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $3,523/Night
For 7 Nights US $24,659
4294.8 ft²
26 Guests
6 Bedrooms
5 Bathrooms
House
- Private Beach
- Fireplace/Heating
- Ocean View
US $3,466/Night
For 7 Nights US $24,260
1515 ft²
3 Bathrooms
Family Friendly
Hotel
- Spa
- Fireplace/Heating
- Pool
US $3,330/Night
For 7 Nights US $23,310
7500 ft²
42 Guests
9 Bedrooms
9 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $3,262/Night
For 7 Nights US $22,836
4800 ft²
16 Guests
8 Bedrooms
6 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $3,117/Night
For 7 Nights US $21,820
2831 ft²
16 Guests
9 Bedrooms
5 Bathrooms
Family Friendly
Condo
- Fireplace/Heating
- Kitchen
- Air Conditioner
US $2,784/Night
For 7 Nights US $19,485
7200 ft²
16 Guests
11 Bedrooms
10 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $2,676/Night
For 7 Nights US $18,735
1001.04 ft²
13 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Parking
- Air Conditioner
US $2,671/Night
For 7 Nights US $18,695
Why Choose Rent By Owner for your Central Chicago Luxury Rental?
What makes our Luxury Rental special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Weekly Weather Forecast for Central Chicago
How to Book Your Central Chicago Luxury Rental
What's our booking process?
Our platform allows you to browse a curated selection of luxury rental. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Central Chicago
Common Luxury Rental Amenities
What amenities can you expect?
Our Luxury Rental are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Other Places to Stay in Central Chicago, IL
Chicago
Chicago
Downtown Chicago
The Loop
Near North Side
South Loop
South Side
River North
Near South Side
Prairie District
Streeterville
Rush and Division
Central Chicago Luxury Rental Frequently Asked Questions
1. What are the top Luxury Rentals in Central Chicago?
There are a lot of options in Central Chicago. If you plan on staying in the Central Chicago area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Luxury Rentals in Central Chicago:
- 52nd Floor MagMile Penthouse Views Fireplace Pool
- 55th Floor Penthouse with Award-Winning Views
- 53 Floor MagMile Penthouse Views, Balcony, Pool
- 51st Floor MagMile Penthouse Views Balcony Pool
- 2-Story Penthouse Views, Fireplace, Pool, Gym
- Magic Factory Loft 2West
- 4BR Old Town Chicago Loft | Walk to Wells St
- Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!
- Magic Factory Loft 3East 4 Bd/4 Ba Families Groups
- 52nd Floor Penthouse with Skyline Views and Pool
2. How many Luxury Rentals are available in Central Chicago?
Currently, the total number of properties listed by RBO in 2026 is over 3028 in the Central Chicago area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Luxury Rentals in Central Chicago.
More Rentals You May Like Near Central Chicago
1575 ft²
2 Bathrooms
Family Friendly
Hotel
- Private Pool
- Fireplace/Heating
- Pool
US $2,569/Night
For 7 Nights US $17,985
3000 ft²
20 Guests
6 Bedrooms
4 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $2,558/Night
For 7 Nights US $17,904
3000 ft²
20 Guests
6 Bedrooms
4 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $2,558/Night
For 7 Nights US $17,904
12 Guests
1 Bedroom
4 Bathrooms
Free Cancellation
Apartment
- Pool
- Pet Friendly
- Parking
US $2,500/Night
For 7 Nights US $17,500
6000 ft²
22 Guests
6 Bedrooms
6 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $2,481/Night
For 7 Nights US $17,369
5000 ft²
22 Guests
6 Bedrooms
6 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $2,479/Night
For 7 Nights US $17,355
5000 ft²
24 Guests
6 Bedrooms
6 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $2,417/Night
For 7 Nights US $16,920
1463.89 ft²
7 Guests
1 Bedroom
2 Bathrooms
Free Cancellation
Apartment
- Private Pool
- Hot Tub
- Fireplace/Heating
US $2,400/Night
For 7 Nights US $16,798
3165 ft²
16 Guests
5 Bedrooms
6 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $2,368/Night
For 7 Nights US $16,579
3660 ft²
16 Guests
6 Bedrooms
6 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Air Conditioner
US $2,349/Night
For 7 Nights US $16,444
3600 ft²
20 Guests
6 Bedrooms
5 Bathrooms
Ocean View
Apartment
- Oceanfront
- Fireplace/Heating
- Ocean View
US $2,262/Night
For 7 Nights US $15,832
1575.84 ft²
5 Bathrooms
Family Friendly
Hotel
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $2,250/Night
For 7 Nights US $15,750
