Holiday rentals and lettings in Chicago

Holiday rentals and lettings in Chicago

Start comparing over 134 rentals in Chicago and book at the best price!

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

Popular Holiday Rentals & Lettings in Chicago

from
£143
per night
Holiday rental for 6 people, with pets
6 pers.3 bedrooms129m²800m to city center
FREE cancellation
4.5
(9 reviews)
from
£375
per night
Holiday rental for 8 people, child-friendly
8 pers.4 bedrooms750m to city center
FREE cancellation
4.3
(7 reviews)
from
£80
per night
Holiday rental for 2 people, child-friendly
2 pers.56m²400m to city center
FREE cancellation
4.5
(130 reviews)
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Holiday Rentals with Free Cancellation

from
£79
per night
Holiday rental for 4 people
4 pers.2 bedrooms83m²1.8km to city center
FREE cancellation
from
£81
per night
Holiday rental for 4 people, child-friendly
4 pers.2 bedrooms2.8km to city center
FREE cancellation
from
£90
per night
Holiday rental for 2 people
2 pers.1 bedroom60m²1.5km to city center
FREE cancellation
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Holiday Rentals & Lettings in Chicago

from
£88
per night
Holiday rental for 2 people, child-friendly
2 pers.47m²800m to city center
FREE cancellation
4.4
(304 reviews)
from
£101
per night
Holiday rental for 3 people, child-friendly
3 pers.1 bedroom68m²800m to city center
FREE cancellation
from
£306
per night
Holiday rental for 4 people, child-friendly
4 pers.1 bedroom65m²5.2km to city center
FREE cancellation
from
£213
per night
Holiday rental for 4 people, child-friendly
4 pers.2 bedrooms1.4km to city center
FREE cancellation
from
£69
per night
Holiday rental for 7 people, with balcony
7 pers.3 bedrooms4.4km to city center
FREE cancellation
4.6
(12 reviews)
from
£172
per night
Holiday rental for 3 people, with pool
3 pers.1 bedroom2.6km to city center
FREE cancellation
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Pet-friendly Holiday Rentals & Lettings

from
£68
per night
Holiday rental for 2 people, with pets
2 pers.1 bedroom65m²950m to city center
FREE cancellation
from
£75
per night
Holiday rental for 2 people
2 pers.64m²400m to city center
FREE cancellation
from
£83
per night
Holiday rental for 2 people, with pets
2 pers.1 bedroom57m²3.7km to city center
FREE cancellation
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Holiday Rentals & Lettings with Pool

from
£117
per night
Holiday rental for 4 people, with pool
4 pers.2 bedrooms88m²450m to city center
FREE cancellation
from
£106
per night
Holiday rental for 2 people, with pool
2 pers.1 bedroom51m²3km to city center
FREE cancellation
from
£162
per night
Holiday rental for 6 people, child-friendly
6 pers.2 bedrooms1km to city center
FREE cancellation
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Holiday Rentals & Lettings with Internet

from
£34
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
£204
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)
from
£73
per night
Holiday rental for 2 people, with pets
2 pers.55m²950m to city center
FREE cancellation
show all

Find Holiday Rentals & Lettings in Chicago

Map

Highlights in Chicago

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

Most popular in Chicago

Pool 109
Internet 476
Pets allowed 134
Balcony/Terrace 54
TV 440
Air conditioning 356

Prices and availability

Prices

November
December
January
February
March
£355
Average price per week

Availabilities

November
December
January
February
March
34 %
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 you pay on average for holiday rentals in Chicago?

Based on its annual average price of £242.24, Chicago is not a city that stands out for being the most expensive or the cheapest in the USA.

Which months allow you to save the most on holiday rentals?

If you are looking to get the most out of your money, the cheapest months to visit Chicago are January (£194.78 per night for accommodation, on average), December (£205.14), and February (£213.65).

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, August, July and September with average prices per night of £278.14, £275.84, and £264.68, respectively.

Is Chicago a good location for a spontaneous getaway?

If you decide to discover Chicago, we recommend planning your travels in advance because it tends to be very high in demand, with an annual average occupation of 69% in the year 2020.

What time of the year can I find more available holiday rentals?

January, April, and June are, in order of highest to lowest, the months offering the largest number of properties free, with respective average availability figures of 43%, 42% and 34.75%.

During which months are there fewer rentals available in Chicago?

The month with the highest average booked rental figures is October (only 22.4% of properties were available on average in 2019). Followed by August (26.8%), and July (27.25%).

How many holiday lettings does Holidu have in Chicago?

Holidu offers around 1200 accommodations in Chicago from 8 different partners, so you will find the perfect type of accommodation you are looking for. We have everything you need!

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

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