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/night
Check availability
Property
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/night
Check availability
Property
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/night
Check availability
Property
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/night
Check availability
Property
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/night
Check availability
Property
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/night
Check availability
Property
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/night
Min 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/night
Min 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/night
Min 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/night
Min 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/night
Min 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/night
Min 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/night
Min 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/night
Check availability
Property
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/night
Min 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/night
Check availability
Property
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/night
Min stay: 30 nights
Property
Apartment · Studio
Farwell dream
6.3

Good

·
Rogers Park
·
1 br
·
Sleeps 4
·
Oven · Workspace · Dishwasher ·
From
$26/night
Check availability
Property
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/night
Check availability
Property
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/night
Check availability
Property
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/night
Check availability
Property
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.
Home > Illinois Vacation Rentals > Chicago Vacation Rentals
Updated: September 26, 2023