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

Prices and availability

Current Holiday letting prices in Chicago

£326for 23 Nov - 30 Nov
£286 annual average
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Average price per week

Current holiday letting availability in Chicago

9%for 23 Nov - 30 Nov
38% annual average
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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 amenities can you typically find at the holiday lettings in Chicago?

Out of all of the amenities you can find on Holidu, it appears that the holiday lettings in Chicago have everything that tourists need! Here, holiday lettings generally have a variety of amenities, the most popular being: Wi-Fi (98%), air conditioning (95%), and barbecue (26%)... Tempted?

How are the holiday lettings usually rated in Chicago?

On average, the holiday lettings here have rather positive reviews. Last year's information reveals that 28% of holiday lettings have a rating of 4.5 stars. This is a fairly high percentage which allows us to confirm that many are very enjoyable and will be the perfect choice for your next holiday.

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

For sure! In Chicago, 50% of the holiday lettings accept pets, and 12% even have a garden!

Do the holiday lettings in Chicago generally come with an internet connection?

Certainly! According to last year's data, 98% of holiday lettings in Chicago include 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 does it cost on average for holiday lettings in Chicago?

According to the information collected last year, there are fewer than 40% of the holiday lettings in Chicago that are less than £100 per night.

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

of course! Judging by information from Holidu, a large portion of holiday lettings in Chicago have access to a swimming pool. It's the ideal destination for you to spend the summer months! 26% even have a barbecue!

Are the holiday lettings in Chicago suitable for stays with the whole family or rather for a weekend break as a small group?

According to the information collected last year, 64% of holiday lettings are perfect for families with up to four guests. Approximately 52% of the holiday lettings here have at least two separate bedrooms. Chicago is the ideal destination for going in small groups, with family or friends!

When planning a luxurious weekend in Chicago, are holiday lettings a good option?

Sure! The holiday lettings in Chicago are ideal for spending a few days on holiday. However, if you are looking for unique accommodation, you shouldn't take long to make a reservation, since the holiday lettings here can fill up quickly. Out of all accommodations in Chicago, 20% have a pool, 12% have a garden and 3% have a sauna.

If you are dreaming of a trip to Chicago, what is the best time of the year?

Judging by the amenities in the holiday lettings in Chicago, it is the perfect destination both in summer and winter. This is because there are very varied options, with all the characteristics one can imagine. You can be sure that Chicago is an ideal place to enjoy both summer and winter.