Apartment
10.0(418 Reviews)
1 Bedroom
4 Guests
Oceanfront
Parking
Pool
Ocean View
US $212/Night
7 Nights - US $1,485
Central Chicago Holiday Rentals
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Compare Villas, Resorts, & Rentals in Central Chicago
10.0
House
10.0(3 Reviews)
10 Bedrooms
10 Guests
Balcony/Terrace
Air Conditioner
Internet
Child Friendly
US $307/Night
7 Nights - US $2,147
US $109/Night
7 Nights - US $766
Apartment
10.0(234 Reviews)
1 Bedroom
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $253/Night
7 Nights - US $1,772
Apartment
10.0(2 Reviews)
4 Bedrooms
16 Guests
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $1,599/Night
7 Nights - US $11,193
Apartment
10.0(68 Reviews)
1 Bedroom
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $225/Night
7 Nights - US $1,576
New
Apartment
10.0(61 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
View
US $288/Night
7 Nights - US $2,013
Apartment
10.0(46 Reviews)
1 Bedroom
2 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $190/Night
7 Nights - US $1,327
Apartment
10.0(24 Reviews)
2 Bedrooms
4 Guests
Kitchen- Air Conditioner
- Internet
Laundry
US $273/Night
7 Nights - US $1,909
Luxury Holiday Rentals in Central Chicago
Over 3088+ Luxury Holiday Rentals in or Near Central Chicago
New
Apartment
6 Bedrooms
12 Guests
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $4,976/Night
7 Nights - US $34,831
New
Apartment
5 Bedrooms
12 Guests
EV Charge Station- Parking
- Balcony/Terrace
- Air Conditioner
US $4,545/Night
7 Nights - US $31,814
US $4,318/Night
7 Nights - US $30,226
House
10.0(39 Reviews)
5 Bedrooms
14 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $3,749/Night
7 Nights - US $26,240
Apartment
8 Bedrooms
16 Guests
- Parking
- View
- Air Conditioner
- Internet
US $3,579/Night
7 Nights - US $25,053
House
12 Bedrooms
24 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $3,573/Night
7 Nights - US $25,008
New
Apartment
10.0(1 Review)
7 Bedrooms
15 Guests
Hot Tub- Parking
- Pool
- Balcony/Terrace
US $3,565/Night
7 Nights - US $24,952
House
6 Bedrooms
26 Guests
Private Beach
Breakfast- EV Charge Station
- Parking
US $3,466/Night
7 Nights - US $24,260
Hotel
Private Pool- Parking
- Pool
- Kitchen
US $3,261/Night
7 Nights - US $22,829
Top-Rated Holiday Rentals with a Pool in Central Chicago
Over 931+ The Best Private Villas and Holiday Rentals in Central Chicago with a Pool
Apartment
10.0(15 Reviews)
2 Bedrooms
8 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $517/Night
7 Nights - US $3,622
Apartment
10.0(9 Reviews)
3 Bedrooms
10 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $478/Night
7 Nights - US $3,347
Apartment
10.0(9 Reviews)
2 Bedrooms
5 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $419/Night
7 Nights - US $2,930
Apartment
10.0(7 Reviews)
4 Bedrooms
9 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $1,627/Night
7 Nights - US $11,392
Apartment
10.0(6 Reviews)
3 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $663/Night
7 Nights - US $4,638
Apartment
10.0(5 Reviews)
3 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $643/Night
7 Nights - US $4,504
Apartment
10.0(5 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $445/Night
7 Nights - US $3,116
Apartment
10.0(5 Reviews)
2 Bedrooms
5 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $391/Night
7 Nights - US $2,740
Apartment
10.0(4 Reviews)
3 Bedrooms
7 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $780/Night
7 Nights - US $5,463
Pet-Friendly Holiday Rentals in Central Chicago
Over 1269+ Pet-Friendly Holiday Rentals in or Near Central Chicago
House
10.0(22 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $232/Night
7 Nights - US $1,624
House
10.0(2 Reviews)
1 Bedroom
8 Guests
- View
- Air Conditioner
- Internet
Pet Friendly
US $385/Night
7 Nights - US $2,692
Apartment
9.6(214 Reviews)
1 Bedroom
2 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $289/Night
7 Nights - US $2,020
New
Apartment
10.0(17 Reviews)
1 Bedroom
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $162/Night
7 Nights - US $1,133
Apartment
10.0(1 Review)
3 Bedrooms
8 Guests
- Oceanfront
- Pool
- Ocean View
- View
US $442/Night
7 Nights - US $3,092
Condo
10.0(15 Reviews)
2 Bedrooms
4 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $371/Night
7 Nights - US $2,596
Apartment
10.0(11 Reviews)
2 Bedrooms
7 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $677/Night
7 Nights - US $4,741
Apartment
10.0(3 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $371/Night
7 Nights - US $2,594
Apartment
10.0(1 Review)
2 Bedrooms
4 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $302/Night
7 Nights - US $2,115
Large Holiday Rentals and Private Villas in Central Chicago
Over 353+ Large Holiday Rentals and Private Villas in or Near Central Chicago
Apartment
9.6(35 Reviews)
2 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $353/Night
7 Nights - US $2,471
Apartment
10.0(2 Reviews)
3 Bedrooms
10 Guests
- EV Charge Station
- Parking
Spa- Air Conditioner
US $278/Night
7 Nights - US $1,949
US $857/Night
7 Nights - US $6,001
Apartment
9.6(18 Reviews)
2 Bedrooms
10 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $206/Night
7 Nights - US $1,442
New
Apartment
10.0(2 Reviews)
4 Bedrooms
10 Guests
- Parking
- Pool
- Air Conditioner
- Internet
US $463/Night
7 Nights - US $3,243
Apartment
9.4(30 Reviews)
2 Bedrooms
13 Guests
- Kitchen
- Air Conditioner
- Internet
- Laundry
US $171/Night
7 Nights - US $1,200
Apartment
9.2(34 Reviews)
2 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $280/Night
7 Nights - US $1,957
Apartment
9.2(10 Reviews)
2 Bedrooms
14 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $434/Night
7 Nights - US $3,036
Apartment
8.2(11 Reviews)
2 Bedrooms
10 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $206/Night
7 Nights - US $1,442
Wheelchair Accessible Holiday Homes in Central Chicago
Over 2130+ Wheelchair Accessible Holiday Homes in or Near Central Chicago
Apartment
10.0(12 Reviews)
2 Bedrooms
4 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $415/Night
7 Nights - US $2,903
Apartment
10.0(1 Review)
3 Bedrooms
6 Guests
- Parking
- Pool
- Air Conditioner
- Internet
US $1,516/Night
7 Nights - US $10,612
Hotel
10.0(4 Reviews)
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $399/Night
7 Nights - US $2,796
Apartment
10.0(6 Reviews)
2 Bedrooms
5 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $481/Night
7 Nights - US $3,365
Apartment
10.0(1 Review)
2 Bedrooms
6 Guests
- Air Conditioner
- Internet
- Child Friendly
Wheelchair Accessible
US $307/Night
7 Nights - US $2,151
Condo
10.0(6 Reviews)
2 Bedrooms
5 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $377/Night
7 Nights - US $2,642
Condo
10.0(5 Reviews)
2 Bedrooms
5 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $373/Night
7 Nights - US $2,610
Apartment
10.0(5 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $174/Night
7 Nights - US $1,219
Apartment
10.0(5 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $160/Night
7 Nights - US $1,117
Central Chicago Private Villas and Holiday Homes Under $200
Over 1082+ Central Chicago Private Villas and Holiday Homes Under $200
Apartment
10.0(5 Reviews)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $138/Night
7 Nights - US $969
Apartment
10.0(1 Review)
1 Bedroom
2 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $185/Night
7 Nights - US $1,295
Apartment
9.4(534 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $186/Night
7 Nights - US $1,302
Apartment
10.0(4 Reviews)
2 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $157/Night
7 Nights - US $1,102
Apartment
10.0(1 Review)
1 Bedroom
2 Guests
- Hot Tub
- Pool
- Air Conditioner
- Internet
US $74/Night
7 Nights - US $518
Apartment
10.0(2 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $187/Night
7 Nights - US $1,308
Apartment
10.0(2 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $174/Night
7 Nights - US $1,219
Condo
10.0(2 Reviews)
1 Bedroom
3 Guests
- Pool
- Kitchen
- Air Conditioner
- Internet
US $123/Night
7 Nights - US $861
Apartment
10.0(1 Review)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $188/Night
7 Nights - US $1,318
Instantly Bookable Holiday Homes in Central Chicago
Over 2017+ Instantly Bookable Holiday Homes in or Near Central Chicago
House
10.0(13 Reviews)
2 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $884/Night
7 Nights - US $6,185
Apartment
9.0(2 Reviews)
2 Bedrooms
4 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $266/Night
7 Nights - US $1,861
Apartment
10.0(5 Reviews)
1 Bedroom
5 Guests
- Child Friendly
US $300/Night
7 Nights - US $2,102
Apartment
10.0(4 Reviews)
2 Bedrooms
5 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $413/Night
7 Nights - US $2,891
Apartment
10.0(3 Reviews)
2 Bedrooms
6 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $623/Night
7 Nights - US $4,362
Apartment
10.0(3 Reviews)
2 Bedrooms
7 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $477/Night
7 Nights - US $3,340
Apartment
10.0(3 Reviews)
2 Bedrooms
4 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $469/Night
7 Nights - US $3,280
Apartment
10.0(3 Reviews)
1 Bedroom
2 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $366/Night
7 Nights - US $2,563
Apartment
10.0(3 Reviews)
2 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $224/Night
7 Nights - US $1,570
Book a Last Minute Place to Stay in Central Chicago
About Casai's Private Villas and Holiday Rentals in Central Chicago
Discover more than 3097 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 775.8 ft², with nightly prices averaging US $412.
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 near the Central Chicago, IL
There are 3097 Central Chicago, IL Holiday Rentals
- Prices for a holiday home in Central Chicago start at US $68
- Top rated vacation home in Central Chicago is 52nd Floor MagMile Penthouse Views Fireplace Pool
- Most popular short term in Central Chicago is Riu Plaza Chicago
- Cheapest place to stay in Central Chicago is Ideal Lincoln Park Studio w/W/D & Lounge, 2 blocks from L, by Blueground
- Most expensive holiday rental in Central Chicago is McCormick 6B/4Ba Luxury Suite w Jacuzzi/Group stay
Recently Booked Holiday Rentals in Central Chicago
Frequently Asked Questions About Central Chicago?
What are the top holiday rentals in Central Chicago?
With numerous options available in Central Chicago, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Central Chicago:
- 52nd Floor MagMile Penthouse Views Fireplace Pool
- 51st Floor MagMile Penthouse Views Balcony Pool
- 4BR Old Town Chicago Loft | Walk to Wells St
- 52nd Floor Penthouse with Skyline Views and Pool
- Brilliant Downtown Chicago 3-Bedroom Condominium
- Modern Corner 2BR in Streeterville | Roof Deck | Lake Views
- 50th Floor Mag Mile Views, Balcony, Pool, Gym
- Gorgeous 3BR River North Condo - Free Parking
- Private Historical Mansion,Luxury Home in Chicago’s Gold Coast, Event-Capable.
- City Center, River North Condo HUGE 3BR, Patio, Parking(2x)
How many holiday rentals have private pools in Central Chicago?
Discover a selection of holiday rentals with private pools near Central 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 Central Chicago are best for families?
If you're searching for a family-friendly holiday home in Central Chicago, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Central Chicago:
How many Casai.com holiday rentals are available in Central Chicago?
As of 2026, Casai boasts over 3097 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 | 1386 |
| The Loop Vacation Rentals in Chicago, Illinois | 620 |
| Near North Side Vacation Rentals in Chicago, Illinois | 584 |
| River North Vacation Rentals in Chicago, Illinois | 348 |
| Near West Side Vacation Rentals in Chicago, Illinois | 312 |
| West Town Vacation Rentals in Chicago, Illinois | 307 |
| South Loop Vacation Rentals in Chicago, Illinois | 295 |
| Near South Side Vacation Rentals in Chicago, Illinois | 277 |
| West Loop Vacation Rentals in Chicago, Illinois | 182 |
| Lincoln Park Vacation Rentals in Chicago, Illinois | 128 |
| Streeterville Vacation Rentals in Chicago, Illinois | 123 |
| Bronzeville Vacation Rentals in Chicago, Illinois | 78 |
| River West Vacation Rentals in Chicago, Illinois | 44 |
| Old Town Vacation Rentals in Chicago, Illinois | 40 |
| Gold Coast Vacation Rentals in Chicago, Illinois | 38 |
| Printers Row Vacation Rentals in Chicago, Illinois | 4161 |
