Holiday Homes & Rentals in Chicago

Holiday Homes & Rentals in Chicago

Start comparing over 312 rentals in Chicago and book at the best price!

Search millions of holiday rentals
+
Compare over 1500 websites
=
Find your perfect holiday rental at the best price

Find offers

Free cancellation
Holiday home
Holiday apartment
Pool
Internet
Pets allowed
4.0
& higher
4.5
& higher

Popular Holiday Homes & Rentals in Chicago

from
€169
per night
Holiday rental for 6 people, with pets
6 pers.3 bedrooms129m²800m to city center
FREE cancellation
4.5
(9 reviews)
from
€444
per night
Holiday rental for 8 people, child-friendly
8 pers.4 bedrooms750m to city center
FREE cancellation
4.3
(7 reviews)
from
€95
per night
Holiday rental for 2 people, child-friendly
2 pers.56m²400m to city center
FREE cancellation
4.5
(130 reviews)
show all

Holiday homes with free cancellation

from
€346
per night
Holiday rental for 6 people
6 pers.3 bedrooms3.7km to city center
FREE cancellation
from
€233
per night
Holiday rental for 4 people, child-friendly
4 pers.1 bedroom92m²2km to city center
FREE cancellation
5.0
(2 reviews)
from
€82
per night
Holiday rental for 7 people, with balcony
7 pers.3 bedrooms4.4km to city center
FREE cancellation
4.6
(12 reviews)
show all

Holiday Homes & Rentals in Chicago

from
€104
per night
Holiday rental for 2 people, child-friendly
2 pers.47m²800m to city center
FREE cancellation
4.4
(304 reviews)
from
€120
per night
Holiday rental for 3 people, child-friendly
3 pers.1 bedroom68m²800m to city center
FREE cancellation
from
€362
per night
Holiday rental for 4 people, child-friendly
4 pers.1 bedroom65m²5.2km to city center
FREE cancellation
from
€203
per night
Holiday rental for 3 people, with pool
3 pers.1 bedroom2.6km to city center
FREE cancellation
from
€40
per night
Holiday rental for 2 people, with garden, child-friendly
2 pers.1 bedroom3.6km to city center
FREE cancellation
4.6
(3 reviews)
from
€241
per night
Holiday rental for 5 people, with balcony, child-friendly
5 pers.2 bedrooms1.2km to city center
FREE cancellation
5.0
(5 reviews)
show all

Holiday Homes & Rentals with Pool

from
€125
per night
Holiday rental for 2 people, with pool
2 pers.1 bedroom51m²3km to city center
FREE cancellation
from
€138
per night
Holiday rental for 4 people, with pool
4 pers.2 bedrooms88m²450m to city center
FREE cancellation
from
€192
per night
Holiday rental for 6 people, child-friendly
6 pers.2 bedrooms1km to city center
FREE cancellation
show all

Holiday Homes & Rentals with Internet

from
€86
per night
Holiday rental for 2 people, with pets
2 pers.55m²950m to city center
FREE cancellation
from
€172
per night
Holiday rental for 6 people, child-friendly
6 pers.2 bedrooms1.8km to city center
FREE cancellation
from
€89
per night
Holiday rental for 4 people, child-friendly
4 pers.1 bedroom1.8km to city center
FREE cancellation
5.0
show all

Pet-Friendly Holiday Homes & Rentals

from
€252
per night
Holiday rental for 4 people, child-friendly
4 pers.2 bedrooms1.4km to city center
FREE cancellation
from
€108
per night
Holiday rental for 6 people, child-friendly
6 pers.3 bedrooms2km to city center
FREE cancellation
5.0
(3 reviews)
from
€207
per night
Holiday rental for 8 people, child-friendly
8 pers.3 bedrooms2.3km to city center
FREE cancellation
show all

Find Holiday Homes & Rentals in Chicago

Map

Most popular in Chicago

Pool 110
Internet 474
Pets allowed 134
Balcony/Terrace 54
TV 439
Air conditioning 355

Prices and availability

Prices

November
December
January
February
March
April
€437
Average price per week

Availabilities

November
December
January
February
March
April
34 %
Percentage of available rentals

FAQs: Holiday Homes & Rentals in Chicago

What is the average price of holiday homes in Chicago?

As indicated by its annual average price of €271.17, Chicago is not a city that stands out for being the most expensive or the cheapest in the USA.

What time of year offers, on average, the best holiday rental prices in Chicago?

If you want to save the maximum amount during your visit to Chicago, book to go there in February (€227.46 per night on average), March (€231.31), or January (€237.08) to find the lowest prices for the whole year.

In which months is it more expensive to rent a holiday letting in Chicago?

When you look at renting a holiday letting in Chicago, the highest prices are usually seen in the month of August (with an average of €319.7 per night), followed by July (€317.06), and September (€304.23).

Is Chicago a good location for a last-minute getaway?

It's better to book sooner than later in Chicago as only 27% of the properties are free, according to our 2020 data.

Which months offer the highest availability?

June, December, and January are, in order of highest to lowest, the months that present the largest number of properties free, with respective average availability figures of 34.75%, 31.75% and 30.4%.

During which months are there fewer rentals available in Chicago?

The month with the highest average booked rental figures is April (only 19.25% of properties were available on average in 2020). Followed by March (22.25%), and October (22.4%).

How many homes are available in Chicago?

In Chicago we offer you an extensive catalogue of approximately 320 properties, with options to suit everyone, thanks to our 7 local and international partners.

Holidu compares hundreds of websites to find your perfect holiday rental for the best price.

Booking.com Holiday Homes & Rentals in ChicagoBooking.com Holiday Homes & Rentals in ChicagoHomeAway Holiday Homes & Rentals in ChicagoHomeAway Holiday Homes & Rentals in ChicagoFeWo-direkt Holiday Homes & Rentals in ChicagoFeWo-direkt Holiday Homes & Rentals in ChicagoVrbo Holiday Homes & Rentals in ChicagoVrbo Holiday Homes & Rentals in ChicagoHRS Holiday Homes & Rentals in ChicagoHRS Holiday Homes & Rentals in ChicagoAbritel Holiday Homes & Rentals in ChicagoAbritel Holiday Homes & Rentals in ChicagoAirbnb Holiday Homes & Rentals in ChicagoAirbnb Holiday Homes & Rentals in Chicago
  1. Holiday rentals
  2. USA
  3. Chicago