Holiday rentals and lettings in Chicago

Holiday rentals and lettings in Chicago

Start comparing over 1,596 rentals in Chicago and book at the best price!

Find Holiday Rentals & Lettings in Chicago

Highlights in Chicago

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

Best Holiday Rentals & Lettings in Chicago

Guests agree: these stays are highly rated for location, cleanliness, and more.
Holiday Rental for 6 People in Chicago, Cook County
Holiday Rental for 6 People in Chicago, Cook County, Photo 1
Holiday Rental for 6 People in Chicago, Cook County, Photo 2
Holiday Rental for 6 People in Chicago, Cook County, Photo 3
Holiday Rental for 6 People in Chicago, Cook County, Photo 4
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Chicago, Cook County
Holiday Rental • 6 Guests • 2 Bedrooms
10.0
(5 reviews)
This top-floor residence presents an open layout with high ceilings and floor-to-ceiling windows. The master bedroom includes a private en-suite bathroom and walk-in closet, while the second bedroom also features its own attached private bathroom. The full kitchen is impeccably equipped with top brands, and the living area ensures entertainment with a 75" TV and Sonos sound system. For additional guests, a futon and a rollaway bed are included, and a Pack & Play is available upon request. - For the safety of all our guests, we handle a $1000 security deposit via credit card and a simple...
from £159 / night
Holiday Rental for 5 People in Chicago, Cook County
Holiday Rental for 5 People in Chicago, Cook County, Photo 1
Holiday Rental for 5 People in Chicago, Cook County, Photo 2
Holiday Rental for 5 People in Chicago, Cook County, Photo 3
Holiday Rental for 5 People in Chicago, Cook County, Photo 4
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Chicago, Cook County
Holiday Rental • 5 Guests • 2 Bedrooms
The main bedroom features a comfortable queen bed and a private bathroom with a walking closet. The second bedroom offers a comfortable queen bed with a closet and a conveniently located hall bathroom. The spacious living area, filled with natural light, features a Sonos sound system. We enhance your mornings with Nespresso coffee from our fully equipped kitchen and ensure a restful sleep with complimentary earplugs and an eye mask. A single rollaway bed is available in the unit for an additional guest, and a Pack & Play can be arranged upon request. - For the safety of all our guests, ...
from £167 / night
Holiday Rental for 5 People in Chicago, Cook County
Holiday Rental for 5 People in Chicago, Cook County, Photo 1
Holiday Rental for 5 People in Chicago, Cook County, Photo 2
Holiday Rental for 5 People in Chicago, Cook County, Photo 3
Holiday Rental for 5 People in Chicago, Cook County, Photo 4
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Chicago, Cook County
Holiday Rental • 5 Guests • 2 Bedrooms
10.0
(3 reviews)
The main bedroom provides a comfortable queen bed, TV, walk-in closet, and private bathroom. The second bedroom offers a comfortable queen bed with a closet and hall bathroom. The spacious living area, bathed in natural light from oversize windows, is enhanced by a Sonos sound system. For your comfort, we provide high-quality coffee and tea, earplugs and an eye mask for better sleep, and a fully equipped kitchen with top-brand appliances. A single rollaway bed is available for an extra guest, and a Pack 'n Play can be requested. - For the safety of all our guests, we handle a $1000 security...
from £167 / night

Prices and availability

Current Holiday letting prices in Chicago

£338for 6 Sep - 13 Sep
£298 annual average
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Average price per week

Current holiday letting availability in Chicago

11%for 6 Sep - 13 Sep
31% annual average
Oct
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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.

Information about holiday lettings in Chicago

🏡 Holiday lettings available: 1373 properties.
💳 Discount available: up to -46%.
🌙 Minimum price per night: from £36.
⭐ Most popular amenities: Wi-Fi, air conditioning and barbecue.
🐾 Pet-friendly: 716 properties.
📶 For workation: 99% of the properties.
🏊 With pool: 340 properties.

FAQs: Holiday Rentals & Lettings in Chicago

Which facilities are available at the holiday lettings in Chicago?

Out of all the facilities offered by Holidu, it appears that the holiday lettings in Chicago offer everything that holiday-makers want! Here, holiday lettings generally have a variety of amenities, the most popular being: Wi-Fi (100%), air conditioning (98%), and barbecue (43%)... Not bad, right?

How are the holiday lettings usually rated in Chicago?

The holiday lettings here often have a lot of positive reviews. 51% of the holiday lettings in Chicago have an average rating of 4.5 stars!

Are the holiday lettings in Chicago suitable for families with children?

Judging by information from Holidu, less than 10% of holiday lettings in Chicago are child-friendly. Here, it will most likely be easier to stay as a couple or with friends.

Are the holiday lettings in Chicago suitable for holiday-makers and their pets?

Of course! In Chicago, 51% of the holiday lettings are pet-friendly, and 21% also have a garden!

Do the holiday lettings in Chicago mostly offer an internet connection?

Of course! According to last year's data, 100% of holiday lettings in Chicago offer an internet connection. So no need to panic, you will be able to access your emails and favourite social media sites throughout your stay!

How much do guests usually expect to pay for holiday lettings in Chicago?

Most of the holiday lettings in Chicago (47%) cost less than £100 per night. This is the perfect destination for booking an affordable holiday letting!

Do the holiday lettings in Chicago often have a swimming pool?

Definitely! According to Holidu's data, a large portion of holiday lettings in Chicago are equipped with a swimming pool. It is therefore an ideal destination for hot summer days! In addition,43% even have a barbecue!

Are the holiday lettings in Chicago suitable for trips with friends or better for an escape as a small group?

According to Holidu's information, 64% of holiday lettings welcome small groups of up to four guests. Approximately 62% of the holiday lettings here have at least two separate bedrooms. Chicago is the perfect destination for families of four!

Are you able to enjoy a beautiful view and spend time outside at the holiday lettings in Chicago?

42% of holiday lettings have a balcony or terrace, and 0% have a view. However, this does not represent the majority of properties here, so availability can be limited. If this is important to you, you should start your holiday planning early. Also, don't forget to use the filters that suit you the best to be sure to find what you are looking for. However, 21% of holiday lettings in Chicago have gardens, where you can enjoy the outdoors. If you like to have lunch or dinner outside, and especially if you like barbecues, 43% of the holiday lettings have them.

When is the best time of the year to travel to Chicago?

Judging by the amenities in the holiday lettings in Chicago, it is an ideal destination to enjoy at any time of the year. This is because there are properties with swimming pools, air conditioning and even fireplaces. You can be sure that Chicago is an ideal place to enjoy both summer and winter.