Vacation Rentals in Chicago, IL
PRICE PER NIGHT
ACCOMMODATION TYPES
Top-Rated Vacation Rentals in Chicago, IL
Book a vacation rental in Chicago that has the highest visitor rating. Here are 6 of the best vacation rentals in Chicago.
Price drop
La Villita - Gateway to Chicago
10
Excellent
·
South Lawndale
·
2 br
·
Sleeps 5
·
Furnished · In Unit Laundry · On Site Laundry ·
From
$191/nightProperty
Apartment · 2 Beds · 1 bath
Amenities
Furnished
In Unit Laundry
On Site Laundry
Smoking Allowed
Free Parking
Air Conditioning
Wifi
Assigned Parking
Other spaces
Workspace, Kitchen
Price drop
Modern Vintage 2BR Walkable To Dining & Lakefront
10
Excellent
·
Edgewater
·
2 br
·
Sleeps 4
·
Hardwood Floor · Oven · In Unit Laundry ·
From
$145/nightProperty
Apartment · 2 Beds · 1 bath
Amenities
Hardwood Floor
Oven
In Unit Laundry
Dishwasher
Furnished
Wifi
Air Conditioning
Other spaces
Kitchen
Family Apartment with Deck and Yard Near Northwestern
9.4
Excellent
·
Evanston
·
2 br
·
Sleeps 6
·
Free Parking · Oven · In Unit Laundry ·
From
$300/nightProperty
Apartment · 2 Beds · 2 baths
Amenities
Free Parking
Oven
In Unit Laundry
Dishwasher
Air Conditioning
Furnished
Wifi
Other spaces
Balcony, Kitchen
Price drop
Chicago Family Apartment - Kids and Pets Welcome!
9
Excellent
·
Evanston
·
2 br
·
Sleeps 6
·
Workspace · Furnished · In Unit Laundry ·
From
$294/nightProperty
Apartment · 2 Beds · 2 baths
Amenities
Furnished
In Unit Laundry
Free Parking
Wifi
Air Conditioning
Other spaces
Workspace, Kitchen
Price drop
Luxurious classic Gold coast villa for 12 guests
9
Excellent
·
Near North Side
·
4 br
·
Sleeps 12
·
Furnished · Fireplace · Dishwasher ·
From
$2,293/nightProperty
Apartment · 4 Beds · 3 baths
Amenities
Furnished
Fireplace
Dishwasher
Assigned Parking
Air Conditioning
Hardwood Floor
Free Parking
In Unit Laundry
Other spaces
Balcony, Workspace, Kitchen
Price drop
2-Story Modern Apt about 5 Mi to Dtwn Chicago!
8
Very good
·
Grand Boulevard
·
4 br
·
Sleeps 8
·
Furnished · Free Parking · Air Conditioning ·
From
$507/nightProperty
Apartment · 4 Beds · 3 baths
Amenities
Furnished
Free Parking
Air Conditioning
Wifi
In Unit Laundry
Dishwasher
Other spaces
Kitchen
Our Recommended Vacation Rentals in Chicago, IL
We analyzed vacation rentals in Chicago from many property providers including but not limited to VRBO, Booking.com, Evolve, Blueground and more. We're providing our top recommended offers on the best vacation rentals in Chicago to help you find a deal for your next trip.
Online tours
3 bedroom in East Ukrainian Village on a flexible lease #1422
No rating
·
West Town
·
3 br
·
In Unit Laundry · Microwave · On Site Laundry ·
From
$90/nightMin stay: 30 nights
Property
Apartment · 3 Beds · 1 bath
Amenities
In Unit Laundry
Microwave
On Site Laundry
Price drop
450 W Belmont Ave #986
No rating
·
Lakeview
·
1 br
·
Furnished · Wheelchair Accessible · In Unit Laundry ·
From
$97/nightMin stay: 30 nights
Property
Apartment · 1 Bed · 1 bath
Amenities
Furnished
Wheelchair Accessible
In Unit Laundry
Microwave
Oven
Residents Lounge
Assigned Parking
Central Heat
Other spaces
Balcony
Online tours
750 N Rush St #165
No rating
·
Near North Side
·
1 br
·
Dishwasher · Concierge Service · Furnished ·
From
$90/nightMin stay: 30 nights
Property
Apartment · 1 Bed · 1 bath
Amenities
Dishwasher
Concierge Service
Furnished
Fitness Center
Business Center
Microwave
Oven
Swimming Pool
911 W School St #458
No rating
·
Lakeview
·
1 br
·
Oven · Wifi · Wheelchair Accessible ·
From
$80/nightMin stay: 30 nights
Property
Apartment · 1 Bed · 1 bath
Amenities
Oven
Wifi
Wheelchair Accessible
In Unit Laundry
Tv
Air Conditioning
Furnished
Central Heat
Other spaces
Balcony
Price drop
3450 N Lake Shore Dr #376
No rating
·
Lakeview
·
Studio
·
Dishwasher · Oven · Swimming Pool ·
From
$61/nightMin stay: 30 nights
Property
Apartment · Studio · 1 bath
Amenities
Dishwasher
Oven
Swimming Pool
Tv
Furnished
Business Center
Wheelchair Accessible
Elevator
1210 S Indiana Ave #353
No rating
·
South Loop
·
1 br
·
Residents Lounge · Private Pool · Wifi ·
From
$115/nightMin stay: 30 nights
Property
Apartment · 1 Bed · 1 bath
Amenities
Residents Lounge
Private Pool
Wifi
Fitness Center
Oven
Tv
In Unit Laundry
Elevator
Budget-Friendly Vacation Rentals in Chicago, IL
Traveling on a budget? We've got you covered. Find a great deal on a vacation rental in Chicago starting at $12. Use the price filter at the top of the page to search for more specific prices.
6328 N Cicero Ave Unit 109
No rating
·
Forest Glen
·
Studio
·
Storage ·
From
$12/nightMin stay: 30 nights
Property
Apartment · Studio
Amenities
Storage
Hollywood Rentals LLC
6.9
Good
·
Edgewater
·
1 br
·
Sleeps 2
·
On Site Laundry · Air Conditioning · Workspace ·
From
$16/nightProperty
Apartment · 1 Bed · 1 bath
Amenities
On Site Laundry
Air Conditioning
Oven
Furnished
Wifi
Other spaces
Workspace, Kitchen
Price drop
$550 - shared 3 Bedroom 2 Bathroom Apartment, 1 room is available In Chicago With Great Amenities
No rating
·
New City
·
3 br
·
Central Heat · Air Conditioning · On Site Laundry ·
From
$18/nightMin stay: 30 nights
Property
Apartment · 3 Beds · 2 baths
Amenities
Central Heat
Air Conditioning
On Site Laundry
Hardwood Floor
5430 Happy Home
8.4
Very good
·
Washington Park
·
1 br
·
Sleeps 7
·
Furnished · Kitchen · Air Conditioning ·
From
$21/nightProperty
Apartment · 1 Bed · 2 baths
Amenities
Furnished
Air Conditioning
Wifi
Oven
Carpet
On Site Laundry
Free Parking
Other spaces
Kitchen, Workspace
6326 N Cicero Ave Ste 107
No rating
·
Forest Glen
·
Studio
·
From
$23/nightMin stay: 30 nights
Property
Apartment · Studio
Farwell dream
6.3
Good
·
Rogers Park
·
1 br
·
Sleeps 4
·
Oven · Workspace · Dishwasher ·
From
$26/nightProperty
Apartment · 1 Bed · 1 bath
Amenities
Oven
Dishwasher
Wheelchair Accessible
Furnished
Hardwood Floor
Wifi
Air Conditioning
Other spaces
Workspace, Kitchen
Vacation Rentals With A Pool in Chicago, IL
Want to relax by the pool? Book one of these Chicago vacation rentals with a pool.
Price drop
The Chicago by Cloud9-365
10
Excellent
·
Near West Side
·
3 br
·
Sleeps 7
·
Pool · Swimming Pool · Assigned Parking ·
From
$794/nightProperty
Apartment · 3 Beds · 2 baths
Amenities
Pool
Swimming Pool
Assigned Parking
Furnished
Wifi
Air Conditioning
In Unit Laundry
Other spaces
Balcony, Kitchen
The Musical by Cloud9-833
10
Excellent
·
Near North Side
·
2 br
·
Sleeps 6
·
Swimming Pool · Wifi · Fireplace ·
From
$1,292/nightProperty
Apartment · 2 Beds · 2 baths
Amenities
Swimming Pool
Wifi
Fireplace
Garage Parking
Oven
Pool
Assigned Parking
Business Center
Other spaces
Workspace
Price drop
Cloud9 - Penthouse with heated POOL - The Windy
1
Poor
·
Near West Side
·
2 br
·
Sleeps 6
·
Balcony · Business Center · Swimming Pool ·
From
$1,355/nightProperty
Apartment · 2 Beds · 2 baths
Amenities
Business Center
Swimming Pool
Wifi
Private Pool
Assigned Parking
Air Conditioning
Pool
Fitness Center
Other spaces
Balcony, Workspace, Kitchen
Expand your search criteria to see more vacation rentals near Chicago.
Updated: September 26, 2023
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