Estia Villas - Vacation Rentals in Downtown Chicago
Villa
9.0
(
2 Reviews
)
5 Bedrooms
4 Bathrooms
14 Guests
4004.17 ft²
-
Parking -
Balcony/Terrace -
Air Conditioner -
Internet
US $1,620
/Night
7 Nights - $11,340
See More Downtown Chicago Vacation Rentals
Luxury Places to Stay in Downtown Chicago
Over 2842+
Luxury Places to Stay in or Near Downtown Chicago
New
Apartment
10.0
(
1 Review
)
4 Bedrooms
3 Bathrooms
10 Guests
1076.39 ft²
-
Parking
-
Pool -
Air Conditioner
-
Internet
US $10,000
/Night
7 Nights - $70,000
US $3,761
/Night
7 Nights - $26,327
Apartment
8 Bedrooms
6 Bathrooms
16 Guests
4800.7 ft²
-
Parking
-
View -
Air Conditioner
-
Internet
US $3,579
/Night
7 Nights - $25,053
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
House
10.0
(
38 Reviews
)
5 Bedrooms
5 Bathrooms
14 Guests
7000 ft²
-
Oceanfront -
Parking
-
Ocean View -
Balcony/Terrace
US $3,090
/Night
7 Nights - $21,633
Hotel
1575 ft²
-
Private Pool -
Parking
-
Pool
-
Kitchen
US $3,064
/Night
7 Nights - $21,450
New
House
12 Bedrooms
7 Bathrooms
23 Guests
5005.22 ft²
-
Parking
-
Balcony/Terrace
-
Air Conditioner
-
Internet
US $3,043
/Night
7 Nights - $21,299
Apartment
10.0
(
1 Review
)
7 Bedrooms
7 Bathrooms
15 Guests
-
Hot Tub -
Parking
-
Pool
-
Balcony/Terrace
US $2,882
/Night
7 Nights - $20,176
Find More Downtown Chicago Villas, Resorts, & Rentals on BedroomVillas
Top-Rated Vacation Rentals with a Pool in Downtown Chicago
Over 1043+
Top-Rated Vacation Rentals with a Pool in or Near Downtown 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
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
(
11 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $507
/Night
7 Nights - $3,552
Apartment
10.0
(
9 Reviews
)
2 Bedrooms
2 Bathrooms
5 Guests
-
Parking
-
Pool
-
Kitchen
-
Air Conditioner
US $478
/Night
7 Nights - $3,349
Apartment
10.0
(
7 Reviews
)
4 Bedrooms
3 Bathrooms
9 Guests
3000 ft²
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $1,494
/Night
7 Nights - $10,455
Pet-Friendly Vacation Rentals in Downtown Chicago
Over 1312+
Pet-Friendly Vacation Rentals in or Near Downtown Chicago
Apartment
10.0
(
1 Review
)
3 Bedrooms
3 Bathrooms
8 Guests
1603.82 ft²
-
Oceanfront
-
Pool
-
Ocean View
-
View
US $454
/Night
7 Nights - $3,178
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
9.4
(
834 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
-
Oceanfront
-
Parking
-
Ocean View
-
View
US $303
/Night
7 Nights - $2,120
Apartment
10.0
(
31 Reviews
)
3 Bedrooms
3 Bathrooms
10 Guests
2300 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $605
/Night
7 Nights - $4,238
Apartment
10.0
(
31 Reviews
)
4 Bedrooms
3 Bathrooms
10 Guests
1250 ft²
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Internet
US $401
/Night
7 Nights - $2,809
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
Apartment
10.0
(
19 Reviews
)
3 Bedrooms
2 Bathrooms
12 Guests
1800 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
View
US $517
/Night
7 Nights - $3,619
Apartment
10.0
(
16 Reviews
)
3 Bedrooms
3 Bathrooms
8 Guests
1800 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $542
/Night
7 Nights - $3,796
See More Pet-Friendly Vacation Rentals in Downtown Chicago on PetFriendly.io
Large Vacation Homes & Villas in Downtown Chicago
Over 305+
Large Vacation Homes & Villas in or Near Downtown Chicago
House
10.0
(
3 Reviews
)
10 Bedrooms
3 Bathrooms
10 Guests
1205.56 ft²
-
Balcony/Terrace
-
Air Conditioner
-
Internet
-
Child Friendly
US $307
/Night
7 Nights - $2,147
Apartment
10.0
(
125 Reviews
)
4 Bedrooms
3 Bathrooms
15 Guests
1850 ft²
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Internet
US $940
/Night
7 Nights - $6,578
US $857
/Night
7 Nights - $6,001
Condo
10.0
(
37 Reviews
)
3 Bedrooms
2 Bathrooms
10 Guests
1800 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $856
/Night
7 Nights - $5,990
Apartment
10.0
(
27 Reviews
)
4 Bedrooms
4 Bathrooms
10 Guests
1350 ft²
-
Kitchen
-
Air Conditioner
-
Internet
-
Child Friendly
US $523
/Night
7 Nights - $3,659
House
10.0
(
26 Reviews
)
4 Bedrooms
2 Bathrooms
10 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $390
/Night
7 Nights - $2,733
Apartment
10.0
(
21 Reviews
)
3 Bedrooms
2 Bathrooms
10 Guests
2500 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $433
/Night
7 Nights - $3,030
House
10.0
(
9 Reviews
)
5 Bedrooms
4 Bathrooms
14 Guests
3000 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $846
/Night
7 Nights - $5,921
See More Family Vacation Rentals in Downtown Chicago on FVR
Wheelchair Accessible Vacation Homes in Downtown Chicago
Over 2022+
Wheelchair Accessible Vacation Homes in or Near Downtown Chicago
Apartment
10.0
(
1 Review
)
3 Bedrooms
2 Bathrooms
6 Guests
-
Parking
-
Pool
-
Air Conditioner
-
Internet
US $1,516
/Night
7 Nights - $10,612
Apartment
10.0
(
12 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1000 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
View
US $432
/Night
7 Nights - $3,023
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
(
11 Reviews
)
2 Bedrooms
2 Bathrooms
7 Guests
1109 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $530
/Night
7 Nights - $3,712
Apartment
10.0
(
10 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
848 ft²
-
Kitchen
-
Air Conditioner
-
Internet
-
Child Friendly
US $657
/Night
7 Nights - $4,596
Condo
10.0
(
9 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
807 ft²
-
Kitchen
-
Air Conditioner
-
Internet
-
Child Friendly
US $759
/Night
7 Nights - $5,310
New
Apartment
10.0
(
8 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
915 ft²
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Internet
US $356
/Night
7 Nights - $2,493
Apartment
10.0
(
7 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1000 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
View
US $486
/Night
7 Nights - $3,399
Downtown Chicago Vacation Rentals and Airbnb Places to Stay Under $200
Over 1050+
Downtown Chicago Vacation Rentals and Airbnb Places to Stay Under $200
Apartment
10.0
(
1 Review
)
1 Bedroom
1 Bathroom
2 Guests
592.02 ft²
-
Hot Tub
-
Pool
-
Air Conditioner
-
Internet
US $74
/Night
7 Nights - $518
Condo
10.0
(
2 Reviews
)
1 Bedroom
1 Bathroom
3 Guests
784 ft²
-
Pool
-
Kitchen
-
Air Conditioner
-
Internet
US $123
/Night
7 Nights - $861
Hostel
9.0
(
1349 Reviews
)
1 Bedroom
1 Bathroom
-
Air Conditioner
-
Internet
-
Wheelchair Accessible -
Accessibility
US $136
/Night
7 Nights - $953
Condo
10.0
(
1 Review
)
2 Bedrooms
1 Bathroom
4 Guests
-
Air Conditioner
-
Internet
-
Pet Friendly -
Child Friendly
US $150
/Night
7 Nights - $1,047
Apartment
10.0
(
1 Review
)
1 Bedroom
1 Bathroom
2 Guests
625 ft²
-
Parking
-
Pool
-
Kitchen
-
Air Conditioner
US $146
/Night
7 Nights - $1,023
Apartment
10.0
(
1 Review
)
2 Bedrooms
2 Bathrooms
4 Guests
950 ft²
-
Pool
-
Kitchen
-
Air Conditioner
-
Internet
US $142
/Night
7 Nights - $991
Apartment
10.0
(
1 Review
)
1 Bedroom
1 Bathroom
2 Guests
518 ft²
-
Parking
-
Pool
-
Kitchen
-
Air Conditioner
US $108
/Night
7 Nights - $753
Apartment
10.0
(
1 Review
)
1 Bedroom
1 Bathroom
2 Guests
650 ft²
-
Pool
-
Kitchen
-
Air Conditioner
-
Internet
US $105
/Night
7 Nights - $737
Instantly Bookable Vacation Homes in Downtown Chicago
Over 1825+
Instantly Bookable Vacation Homes in or Near Downtown Chicago
Condo
10.0
(
59 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1507 ft²
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Internet
US $442
/Night
7 Nights - $3,097
Apartment
9.0
(
2 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
-
Kitchen
-
Air Conditioner
-
Internet
-
Pet Friendly
US $266
/Night
7 Nights - $1,861
Condo
10.0
(
39 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
-
Kitchen
-
Air Conditioner
-
Internet
-
Child Friendly
US $617
/Night
7 Nights - $4,318
Apartment
10.0
(
19 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
-
Kitchen
-
Air Conditioner
-
Internet
-
Laundry
US $323
/Night
7 Nights - $2,263
Condo
10.0
(
9 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $671
/Night
7 Nights - $4,694
Apartment
10.0
(
7 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
350 ft²
-
Kitchen
-
Air Conditioner
-
Internet
-
Child Friendly
US $208
/Night
7 Nights - $1,455
Apartment
10.0
(
6 Reviews
)
2 Bedrooms
2 Bathrooms
7 Guests
1261 ft²
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $482
/Night
7 Nights - $3,371
House
10.0
(
5 Reviews
)
8 Bedrooms
3 Bathrooms
18 Guests
-
Kitchen
-
Air Conditioner
-
Internet
-
Pet Friendly
US $1,017
/Night
7 Nights - $7,118
About Downtown Chicago Vacation Rentals
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Estiavillas Downtown 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 Downtown Chicago. Places to stay near Downtown Chicago are 4004.17 ft² on average, with prices averaging US $1,620 a night.
Estiavillas makes it easy and safe to find and compare vacation rentals in Downtown 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.
Top Rental Accommodation Types in Downtown Chicago
| Type | Count |
|---|---|
| Villas | 1 |
Use these Quick Filters to Find a Vacation Rental in Downtown 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 Downtown Chicago.
Weather in Downtown Chicago
View the weather forecast for Downtown Chicago before booking your Downtown 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
Other Places to Stay Near Downtown Chicago, IL
Chicago
6,261 Properties
Chicago
3,647 Properties
Central Chicago
1,468 Properties
The Loop
640 Properties
Near North Side
566 Properties
River North
331 Properties
West Loop
181 Properties
Streeterville
125 Properties
Rush and Division
68 Properties
West Loop Gate
39 Properties
Gold Coast
34 Properties
Killgubbin
30 Properties
Complexes around Downtown Chicago, IL
Wells Apartments St Chicago
132 Properties
Kasa River North
12 Properties
Gold Coast Doorman Blocks
9 Properties
Naperville Inn
9 Properties
Town
9 Properties
South Loop Grant Park
10 Properties
Accommodation Schaumburg
4 Properties
Claridge
3 Properties
Courtyard
3 Properties
Flat
3 Properties
Mccormick Place
3 Properties
The Blackstone Autograph
3 Properties
Travelodge
3 Properties
The Whitehall Hotel
2 Properties
Sonder Cros
1 Properties
Downtown Chicago Vacation Rental Frequently Asked Questions
What are the top vacation rentals in Downtown Chicago?
There are a lot of options in Downtown Chicago. If you plan on staying in the Downtown 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 Downtown Chicago:
How many vacation rentals have private pools in Downtown Chicago?
There are 73 vacation rentals with private pools near Downtown Chicago. Top-rated homes that have access to a swimming pool include:
Which vacation homes in Downtown Chicago are best for families?
If you are looking for a family-friendly vacation home in Downtown 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 Downtown Chicago:
How many vacation rentals are available in Downtown Chicago?
Currently, the total number of properties listed in 2026 is over 1 in the Downtown Chicago area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Downtown Chicago.
