Holiday rentals and lettings in Chicago

Holiday rentals and lettings in Chicago

Start comparing over 440 rentals in Chicago and book at the best price!

Find offers

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

Holiday Rentals & Lettings in Chicago

Holiday rental for 2 people, with pets in Chicago
Holiday rental for 2 people, with pets
1 bedroom
from £142 / nightFREE cancellation
Holiday rental for 2 people in Chicago
Holiday rental for 2 people
from £162 / nightFREE cancellation
Holiday rental for 2 people in Chicago
Holiday rental for 2 people
1 bedroom
3.6
(164 reviews)
from £13 / night
Holiday rental for 3 people, with pets in Chicago
Holiday rental for 3 people, with pets
1 bedroom
from £108 / nightFREE cancellation

Popular Holiday Rentals & Lettings in Chicago

Holiday rental for 2 people in Chicago
Holiday rental for 2 people
from £108 / nightFREE cancellation
Holiday rental for 4 people in Chicago
Holiday rental for 4 people
1 bedroom
4.7
(61 reviews)
from £97 / nightFREE cancellation
Holiday rental for 2 people, with view and garden in Chicago
Holiday rental for 2 people, with view and garden
1 bedroom
3.8
(138 reviews)
from £34 / night
Holiday rental for 2 people, with pets in Chicago
Holiday rental for 2 people, with pets
from £108 / nightFREE cancellation

Holiday Rentals with Free Cancellation

Holiday rental for 2 people, with terrace, child-friendly in Chicago
Holiday rental for 2 people, with terrace, child-friendly
1 bedroom
3.3
(299 reviews)
from £52 / nightFREE cancellation
Holiday rental for 2 people in Chicago
Holiday rental for 2 people
2.5
(5 reviews)
from £62 / nightFREE cancellation
Holiday rental for 2 people in Chicago
Holiday rental for 2 people
0.5
from £55 / nightFREE cancellation
Holiday rental for 2 people in Chicago
Holiday rental for 2 people
1 bedroom
3.9
(12 reviews)
from £56 / nightFREE cancellation

Pet-friendly Holiday Rentals & Lettings

Holiday rental for 6 people, with pets in Chicago
Holiday rental for 6 people, with pets
3 bedrooms
from £163 / nightFREE cancellation
Holiday rental for 9 people, child-friendly in Chicago
Holiday rental for 9 people, child-friendly
4 bedrooms
3.5
(2 reviews)
from £425 / nightFREE cancellation
Holiday rental for 2 people in Chicago
Holiday rental for 2 people
1 bedroom
4.5
(4 reviews)
from £76 / night
Holiday rental for 5 people, with terrace, with pets in Chicago
Holiday rental for 5 people, with terrace, with pets
2 bedrooms
4.2
(15 reviews)
from £165 / nightFREE cancellation

Holiday Rentals & Lettings with Pool

Holiday rental for 4 people, with hot tub and sauna as well as terrace and pool in Chicago
Holiday rental for 4 people, with hot tub and sauna as well as terrace and pool
1 bedroom
4.4
(217 reviews)
from £113 / night
Holiday rental for 2 people, with pool and sauna as well as view in Chicago
Holiday rental for 2 people, with pool and sauna as well as view
1 bedroom
4.2
(369 reviews)
from £118 / night
Holiday letting for 2 people, with pool in Chicago
Holiday letting for 2 people, with pool
1 bedroom
3.2
(42 reviews)
from £39 / night
Holiday rental for 2 people, with terrace and pool, with pets in Chicago
Holiday rental for 2 people, with terrace and pool, with pets
1 bedroom
4.0
(217 reviews)
from £80 / night

Holiday Rentals & Lettings with Internet

Holiday letting for 2 people, with terrace in Chicago
Holiday letting for 2 people, with terrace
1 bedroom
4.8
(132 reviews)
from £122 / nightFREE cancellation
Holiday letting for 2 people, with hot tub and garden in Chicago
Holiday letting for 2 people, with hot tub and garden
1 bedroom
4.5
(68 reviews)
from £108 / night
Holiday rental for 2 people in Chicago
Holiday rental for 2 people
1 bedroom
3.4
(139 reviews)
from £22 / night
Holiday letting for 2 people in Chicago
Holiday letting for 2 people
1 bedroom
2.5
(59 reviews)
from £14 / night

Find Holiday Rentals & Lettings in Chicago

Map

Highlights in Chicago

  • Cultural city
  • Amazing museums
  • Delicious food
  • Urban cycling

Most popular in Chicago

Pool 3
Internet 367
Pets allowed 187
Balcony/Terrace 50
TV 301
Air conditioning 310

Prices and availability

Holiday lettings prices in Chicago

£304for 20 Aug - 27 Aug
£299 annual average
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Average price per week

Holiday lettings availability in Chicago

1%for 20 Aug - 27 Aug
33% annual average
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Percentage of available lettings

Holiday rentals and lettings in Chicago

Lettings in a vibrant and cultural city

Boasting world-class museums, vibrant shopping districts and countless nightlife venues, Chicago is one of the world’s most fascinating cities, which we should all visit at least once! So, let’s look for a holiday rental for your city break. You can get stuck in and stay right in the heart of downtown, a wonderful option for those looking to get a taste of Chicago’s 24/7 lifestyle. Holiday rentals in the suburbs are also popular, especially for families and larger groups. Lakeside rentals both north (look around Edgewater Beach) and south of the centre (see Hyde Park) come highly recommended!

Lettings to get the best out of your Chicago holiday

Downtown Chicago offers fortuitous visitors to the city myriad flats with fully-equipped gourmet kitchens, large balconies and amazing views. Out in the suburbs, spacious terraces and detached homes dominate with well-kept gardens, tons of natural light and parking.

Holidays in Chicago

The area and getting around

A huge city full of little worlds to explore

Sprawling Chicago in the far north of the US is the country’s third largest city, boasting one of the world’s busiest airports. The city is a hodgepodge of diverse neighbourhoods to explore, each of which maintains its own personality and culture. Step into Andersonville and you will feel like you have teleported into a small town, with a laid-back vibe and colourful streets lined with beautiful homes and unique local businesses.

A cool neighbourhood around every corner

Pilsen is a predominantly Mexican-American community with an awesome food and art scene. West Loop is a former industrial zone transformed into a chic foodie paradise replete with contemporary upscale bars and restaurants. Boystown is the gay capital of the city, with a high street packed with queer-focused bars and businesses.

Travellers and activities

Chicago for museum lovers

The Chicago Loop’s major museums are among the largest of their kind in the country, housing collections that are unique to the city. Whether you are in love with all things arty or hopelessly devoted to science, museum lovers are in for a massive treat in this most cultural of cities. The Art Institute of Chicago has been voted one of the top museums in the world by TripAdvisor. It features an enormous collection of Impressionist and Post-Impressionist art, second only to the Louvre in Paris. Need we say more about the Art Institute of Chicago? Adler Planetarium on Chicago's Museum Campus is an out-of-this world attraction! Explore the origins of the universe through state-of-the-art exhibits, peer through ancient telescopes, and view the stars in the Western Hemisphere’s oldest planetarium.

Chicago for urban cyclists

Chicago is a cyclist's paradise with more than 160 kilometres of cycle lanes criss-crossing the city. Follow the path that runs along the shore of Lake Michigan, passing many of Chicago’s most popular attractions and providing sensational views of that awesome skyline. Or take the popular trail through woods, leafy suburbs and golf courses to Chicago Botanic Garden, a 32-kilometre route that follows the Chicago River. Don’t miss the unique park trail along Bloomingdale Avenue which was built on an old elevated train track!

Chicago has 18.5 miles of lakefront to explore with 26 beaches!

Top 5 travel tips in Chicago

1. Get your photo taken at The Bean

The mirrored sculpture The Bean by the Indo-British artist Anish Kapoor, located in Millennium Park in the heart of Chicago, has become the city’s most renowned landmark. Get your photo taken at The Bean and participate in one of the most iconic activities in Chicago!

2. Stroll the Lakefront Trail at sunset

The Lakefront Trail is a 28-kilometre paved walk that runs along the shore of Lake Michigan. For an easy afternoon walk, start in the museum area and finish at the beach on North Avenue. Watching the urban panorama shift and unveil new treasures as you walk along the shore is highly gratifying!

3. Be entertained at Navy Pier

Navy Pier is a rare delight. With immaculate parks and gardens, top-quality restaurants, wonderful shopping, an IMAX theatre, the Chicago Children's Museum, Chinese acrobats and myriad places to relax right in front of the lake, it is like an amusement park with the vertigo.

4. Visit the world’s most artistic park

Millennium Park, also called the “Garden of the Arts”, is a recreational and artistic urban development that occupies ten hectares of the city centre. The park has won several awards, fusing works of art and architecture from international celebrated virtuosos. The most renowned work is the gorgeous Jay Pritzker Concert Pavilion, designed by Canadian architect Frank Gehry, which can accommodate seven thousand people.

5. Step into a different world in Chinatown

Like any big North American city, Chicago has a Chinatown. As soon as you pass under the arch that leads into the neighbourhood on Wentworth Avenue, you will feel like you have entered another city, another country, with its corresponding exotic sights, sounds and smells. Don’t miss the mural that tells the story of Chinese immigration in the United States or the wall of the nine dragons, a typical element in Chinese imperial gardens and palaces.

FAQs: Holiday Rentals & Lettings in Chicago

How much do the holiday lettings in Chicago cost on average?

By looking at an annual average price of £263, Chicago is not a city that stands out as the most expensive or the cheapest in the USA.

When are holiday rentals cheaper in Chicago?

If you want to save the maximum amount during your visit to Chicago, you should travel in February (£218 per night on average), April (£221), or March (£222) to find the lowest prices for the whole year.

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

When it comes to looking for a holiday letting in Chicago, the months when it is most expensive are, in descending order, September, August and October with average prices per night of £307, £294, and £291, respectively.

Are there usually many holiday rentals available in Chicago?

It's worthwhile to be proactive in Chicago as only 18% of the properties remain free, following the data observed last year.

Which months offer the highest availability?

In the previous year, the months with the largest number of accommodations available in Chicago were February, May, and January with average availabilities of 27%, 26% and 24%, respectively. However, even during the time when availability is the highest, the average is 25%. Due to this, it is better to always book a little in advance to be sure to find the rental of your dreams.

During which months are there fewer rentals available in Chicago?

The months with the lowest properties available in Chicago are, in order, September, November and October, with respective average availability figures of 8%, 10%, and 10%, based on data collected from last year. During these three months, availability is really low (9%). Due to this, it is better to book as soon as possible.

How many holiday lettings are there in Chicago?

We have grouped together the offers from 6 different partners in Chicago, so we can offer you around 700 properties. You're going to have a hard time choosing your favourite!

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

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