Estia Villas - Vacation Rentals in Chicago
Villa
9.8
(
22 Reviews
)
3 Bedrooms
2 Bathrooms
12 Guests
1700 ft²
-
Hot Tub -
Parking -
Balcony/Terrace -
Kitchen
US $527
/Night
7 Nights - $3,688
Apartment
9.4
(
19 Reviews
)
4 Bedrooms
2 Bathrooms
20 Guests
2497.23 ft²
-
Parking
-
Balcony/Terrace
-
View -
Air Conditioner
US $316
/Night
7 Nights - $2,210
Villa
9.6
(
12 Reviews
)
1 Bedroom
6 Bathrooms
16 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $628
/Night
7 Nights - $4,395
Bed & Breakfast
9.2
(
36 Reviews
)
8 Bedrooms
8 Bathrooms
24 Guests
502.83 ft²
-
Hot Tub
-
Breakfast -
Parking
-
Balcony/Terrace
US $271
/Night
7 Nights - $1,900
Villa
9 Bedrooms
5 Bathrooms
12 Guests
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $1,711
/Night
7 Nights - $11,980
Villa
9.0
(
21 Reviews
)
8 Bedrooms
4 Bathrooms
19 Guests
1496.18 ft²
-
Breakfast
-
Parking
-
Balcony/Terrace
-
View
US $849
/Night
7 Nights - $5,942
Villa
3 Bedrooms
2 Bathrooms
9 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $617
/Night
7 Nights - $4,320
US $1,442
/Night
7 Nights - $10,094
See More Chicago Vacation Rentals
Luxury Places to Stay in Chicago
Over 7914+
Luxury Places to Stay in or Near Chicago
New
Apartment
4 Bedrooms
3 Bathrooms
10 Guests
1076.39 ft²
-
Parking
-
Pool -
Air Conditioner
-
Internet
US $10,000
/Night
7 Nights - $70,000
Bed & Breakfast
8 Bedrooms
8 Bathrooms
16 Guests
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Internet
US $4,197
/Night
7 Nights - $29,376
House
4 Bedrooms
2 Bathrooms
10 Guests
2497.23 ft²
-
Parking
-
Internet
-
Child Friendly -
Security/Safety
US $3,786
/Night
7 Nights - $26,500
US $3,761
/Night
7 Nights - $26,327
New
House
6 Bedrooms
4 Bathrooms
6000 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $3,640
/Night
7 Nights - $25,481
Apartment
8 Bedrooms
6 Bathrooms
16 Guests
4800.7 ft²
-
Parking
-
View
-
Air Conditioner
-
Internet
US $3,579
/Night
7 Nights - $25,053
Apartment
3 Bedrooms
2 Bathrooms
1 Guest
-
Hot Tub
-
Kitchen
-
Internet
-
Pet Friendly
US $3,482
/Night
7 Nights - $24,371
House
6 Bedrooms
5 Bathrooms
26 Guests
4294.8 ft²
-
Private Beach -
Breakfast
-
EV Charge Station -
Parking
US $3,466
/Night
7 Nights - $24,260
See More Chicago Luxury Vacation Rentals
Find More Chicago Villas, Resorts, & Rentals on BedroomVillas
Top-Rated Vacation Rentals with a Pool in Chicago
Over 1301+
Top-Rated Vacation Rentals with a Pool in or Near Chicago
Apartment
10.0
(
416 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
-
Oceanfront -
Parking
-
Pool
-
Ocean View
US $277
/Night
7 Nights - $1,941
Apartment
10.0
(
233 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
-
Oceanfront
-
Parking
-
Pool
-
Ocean View
US $277
/Night
7 Nights - $1,941
Apartment
10.0
(
67 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
-
Oceanfront
-
Parking
-
Pool
-
Ocean View
US $293
/Night
7 Nights - $2,053
House
10.0
(
44 Reviews
)
3 Bedrooms
2 Bathrooms
7 Guests
1200 ft²
-
Parking
-
Pool
-
Ocean View
-
Balcony/Terrace
US $681
/Night
7 Nights - $4,764
Apartment
10.0
(
43 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
735 ft²
-
Oceanfront
-
Parking
-
Pool
-
Ocean View
US $210
/Night
7 Nights - $1,468
Apartment
10.0
(
13 Reviews
)
2 Bedrooms
3 Bathrooms
8 Guests
2600 ft²
-
Oceanfront
-
Parking
-
Pool
-
Ocean View
US $647
/Night
7 Nights - $4,528
Apartment
10.0
(
12 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
452.08 ft²
-
Private Pool -
Oceanfront
-
Breakfast
-
Parking
US $117
/Night
7 Nights - $819
Apartment
10.0
(
11 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $507
/Night
7 Nights - $3,552
See More Chicago Vacation Rentals with a Pool
Pet-Friendly Vacation Rentals in Chicago
Over 3186+
Pet-Friendly Vacation Rentals in or Near Chicago
Apartment
9.7
(
18 Reviews
)
2 Bedrooms
2 Bathrooms
8 Guests
1001.04 ft²
-
Parking
-
Air Conditioner
-
Internet
-
Pet Friendly
US $299
/Night
7 Nights - $2,093
Apartment
10.0
(
175 Reviews
)
2 Bedrooms
1 Bathroom
6 Guests
1000 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $525
/Night
7 Nights - $3,678
Condo
2 Bedrooms
1 Bathroom
6 Guests
-
Hot Tub
-
Ocean View
-
Balcony/Terrace
-
View
US $100
/Night
7 Nights - $699
Condo
10.0
(
131 Reviews
)
3 Bedrooms
3 Bathrooms
10 Guests
2200 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $414
/Night
7 Nights - $2,898
House
9.8
(
54 Reviews
)
4 Bedrooms
3 Bathrooms
16 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $656
/Night
7 Nights - $4,593
Apartment
10.0
(
103 Reviews
)
2 Bedrooms
1 Bathroom
6 Guests
1200 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $348
/Night
7 Nights - $2,433
New
Apartment
9.6
(
63 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
1000 ft²
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $256
/Night
7 Nights - $1,791
House
9.8
(
103 Reviews
)
3 Bedrooms
3 Bathrooms
20 Guests
2000 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $776
/Night
7 Nights - $5,433
See More Pet-Friendly Vacation Rentals in Chicago on PetFriendly.io
Large Vacation Homes & Villas in Chicago
Over 1027+
Large Vacation Homes & Villas in or Near Chicago
Apartment
10.0
(
124 Reviews
)
4 Bedrooms
3 Bathrooms
15 Guests
1850 ft²
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Internet
US $940
/Night
7 Nights - $6,578
House
3.0
(
193 Reviews
)
9 Bedrooms
27 Bathrooms
23 Guests
-
Parking
-
Internet
-
Child Friendly
US $7
/Night
7 Nights - $49
US $857
/Night
7 Nights - $6,001
Apartment
10.0
(
136 Reviews
)
3 Bedrooms
1 Bathroom
10 Guests
1000 ft²
-
Breakfast
-
Parking
-
Balcony/Terrace
-
Kitchen
US $211
/Night
7 Nights - $1,480
Apartment
10.0
(
117 Reviews
)
4 Bedrooms
3 Bathrooms
16 Guests
2300 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $768
/Night
7 Nights - $5,377
Apartment
10.0
(
68 Reviews
)
5 Bedrooms
2 Bathrooms
11 Guests
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $1,138
/Night
7 Nights - $7,964
House
10.0
(
62 Reviews
)
5 Bedrooms
7 Bathrooms
12 Guests
6200 ft²
-
Parking
-
Spa -
Ocean View
-
Balcony/Terrace
US $1,995
/Night
7 Nights - $13,967
House
10.0
(
61 Reviews
)
6 Bedrooms
5 Bathrooms
17 Guests
5000 ft²
-
Oceanfront
-
Hot Tub
-
Parking
-
Spa
US $2,170
/Night
7 Nights - $15,189
See More Family Vacation Rentals in Chicago on FVR
Wheelchair Accessible Vacation Homes in Chicago
Over 3046+
Wheelchair Accessible Vacation Homes in or Near Chicago
Apartment
10.0
(
58 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
441 ft²
-
Oceanfront
-
Ocean View
-
Balcony/Terrace
-
View
US $266
/Night
7 Nights - $1,862
Apartment
10.0
(
1 Review
)
3 Bedrooms
2 Bathrooms
6 Guests
-
Parking
-
Pool
-
Air Conditioner
-
Internet
US $1,516
/Night
7 Nights - $10,612
Bed & Breakfast
9.8
(
212 Reviews
)
1 Bedroom
1 Bathroom
-
Breakfast
-
Kitchen
-
Air Conditioner
-
Internet
US $324
/Night
7 Nights - $2,269
Apartment
10.0
(
30 Reviews
)
4 Bedrooms
3 Bathrooms
10 Guests
1250 ft²
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Internet
US $453
/Night
7 Nights - $3,170
Apartment
10.0
(
29 Reviews
)
3 Bedrooms
3 Bathrooms
10 Guests
2300 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $685
/Night
7 Nights - $4,794
Apartment
10.0
(
24 Reviews
)
3 Bedrooms
3 Bathrooms
12 Guests
2200 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $642
/Night
7 Nights - $4,491
Condo
10.0
(
14 Reviews
)
2 Bedrooms
2 Bathrooms
5 Guests
689 ft²
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Internet
US $347
/Night
7 Nights - $2,432
Condo
10.0
(
13 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1292 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $740
/Night
7 Nights - $5,182
Chicago Vacation Rentals and Airbnb Places to Stay Under $200
Over 2932+
Chicago Vacation Rentals and Airbnb Places to Stay Under $200
Apartment
10.0
(
83 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $177
/Night
7 Nights - $1,241
Apartment
1 Bedroom
1 Bathroom
4 Guests
645.83 ft²
-
Air Conditioner
-
Internet
-
Pet Friendly
-
Child Friendly
US $112
/Night
7 Nights - $784
Bed & Breakfast
10.0
(
545 Reviews
)
1 Bedroom
1 Bathroom
-
Parking
-
Balcony/Terrace
-
Air Conditioner
-
Internet
US $176
/Night
7 Nights - $1,233
Apartment
10.0
(
64 Reviews
)
1 Bedroom
1 Bathroom
3 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $189
/Night
7 Nights - $1,321
Apartment
10.0
(
57 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
850 ft²
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Internet
US $199
/Night
7 Nights - $1,394
Apartment
10.0
(
49 Reviews
)
1 Bedroom
1 Bathroom
3 Guests
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $189
/Night
7 Nights - $1,321
Apartment
10.0
(
31 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
750 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $183
/Night
7 Nights - $1,284
Apartment
10.0
(
24 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Internet
US $191
/Night
7 Nights - $1,336
See More Chicago Vacation Rental Deals
Instantly Bookable Vacation Homes in Chicago
Over 4644+
Instantly Bookable Vacation Homes in or Near Chicago
Apartment
10.0
(
258 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
1500 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $288
/Night
7 Nights - $2,017
Apartment
10.0
(
6 Reviews
)
1 Bedroom
1 Bathroom
5 Guests
-
Oceanfront
-
Parking
-
Ocean View
-
View
US $190
/Night
7 Nights - $1,330
Bed & Breakfast
9.8
(
105 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
650 ft²
-
Pool
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $435
/Night
7 Nights - $3,046
Apartment
9.6
(
27 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
2400 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $356
/Night
7 Nights - $2,495
Condo
10.0
(
38 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
1200 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $664
/Night
7 Nights - $4,651
Apartment
9.6
(
22 Reviews
)
2 Bedrooms
1 Bathroom
6 Guests
900 ft²
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $268
/Night
7 Nights - $1,877
Condo
9.6
(
20 Reviews
)
4 Bedrooms
2 Bathrooms
9 Guests
2094 ft²
-
Balcony/Terrace
-
Laundry -
Security/Safety
US $1,219
/Night
7 Nights - $8,534
Apartment
10.0
(
122 Reviews
)
2 Bedrooms
2 Bathrooms
5 Guests
1650 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $601
/Night
7 Nights - $4,209
See More Chicago Short-Term Vacation Rentals
About Chicago Vacation Rentals
With more than 13 Chicago vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Estiavillas and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Chicago.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Estiavillas Chicago, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Chicago. Places to stay near Chicago are 2133.43 ft² on average, with prices averaging US $689 a night.
Estiavillas makes it easy and safe to find and compare vacation rentals in Chicago with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Use these Quick Filters to Find a Vacation Rental in Chicago
★ Pro Tip: Estiavillas makes it easy to compare the best listings on Estiavillas homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Estiavillas homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Chicago.
Weather in Chicago
View the weather forecast for Chicago before booking your 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
Top Attractions Around Chicago, IL
Estiavillas offers a large selection of top attractions around Chicago. Research things to do on your vacation before you visit Chicago.
Navy Pier
Wrigley Field
McCormick Place
Millennium Park
Union Station
Soldier Field
Willis Tower
Art Institute of Chicago
Naval Base Great Lakes
United Center
Grant Park
John G. Shedd Aquarium
Chicago Museum of Science and Industry
Chicago Theatre
Chicago Riverwalk
Field Museum of Natural History
Six Flags Great America
University of Chicago
Brookfield Zoo
Northwestern University
Other Places to Stay Near Chicago, IL
Chicago
6,245 Properties
Central Chicago
1,462 Properties
Downtown Chicago
1,386 Properties
West Side
753 Properties
The Loop
635 Properties
Near North Side
568 Properties
North Side
513 Properties
River North
333 Properties
Far North Side
319 Properties
Near West Side
313 Properties
West Town
307 Properties
South Loop
277 Properties
Complexes around Chicago, IL
Wells Apartments St Chicago
132 Properties
Town
17 Properties
South Loop Grant Park
28 Properties
Wrigley
32 Properties
Lakeview
17 Properties
Kasa River North
12 Properties
Transit Dt
14 Properties
Naperville Inn
9 Properties
Gold Coast Doorman Blocks
9 Properties
Lofts
14 Properties
Belmont
7 Properties
Mccormick Place
5 Properties
District Block
10 Properties
Sonder South Wabash
10 Properties
Accommodation Schaumburg
5 Properties
Chicago Vacation Rental Frequently Asked Questions
What are the top vacation rentals in Chicago?
There are a lot of options in Chicago. If you plan on staying in the Chicago area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Chicago:
- HUGE! 3BR Private Home+Garage+360° Roof Deck+Hot Tub+EV+Sleeps 12
- Spacious 8 BDR + 2 Kitchens + Garage! Sleeps 16!
- City Villa Sleeps 10-20 Free TV & Parking
- Villa D' Citta
- The Twin Lions: Bespoke Travel Lodge w/Speakeasy*
- Beautiful 5br home for 14 guests with free parking
- The Villa Toscana
- Hamaline Luxury Guest House
- Lakefront Rooftop Parking
- Luxury 9 BR, Villa Mins from Downtown and the Lake.
How many vacation rentals have private pools in Chicago?
There are 101 vacation rentals with private pools near Chicago. Top-rated homes that have access to a swimming pool include:
Which vacation homes in Chicago are best for families?
If you are looking for a family-friendly vacation home in Chicago, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Chicago:
How many vacation rentals are available in Chicago?
Currently, the total number of properties listed in 2026 is over 13 in the Chicago area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Chicago.
