Find Holiday Homes & Rentals in Chicago

Highlights in Chicago

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

Best Holiday Homes & Rentals in Chicago

Guests agree: these stays are highly rated for location, cleanliness, and more.
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Chicago, Cook County
Holiday Rental • 72 m² • 1 Bedroom
4.7
(11 reviews)
Summary:Come relax in one of our South Loop apartments professionally managed by Kasa. These apartments are well-connected to the Chicago scene you're seeking. Close to large companies and a short distance from Grant Park, a number of fantastic local restaurants, bars, and shopping options can also be found nearby. The property is within a 20 minute walk to McCormick Place and the Museum Campus.The Space:Check-in is quick and easy, each person in your group 18 and older will need to present a photo ID upon check-in with the Kasa Concierge. We'll send check-in instructions via email before y...
from €146 / night
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Chicago, Cook County
Holiday Rental • 68 m² • 1 Bedroom
4.9
(12 reviews)
Come relax in one of our South Loop apartments professionally managed by Kasa. These spaces are well-connected to the Chicago South Loop scene you're seeking. Wander to Museum Campus, featuring contemporary art and architecture - you will always have something new to see. Take a short, 10 minute walk to Grant Park and experience a number of fantastic local restaurants and bars with spectacular views of Lake Michigan. Kasa offers everything you need for a quick trip or an extended stay.The Space:Each of our apartments have their own unique layout and decor. Pictures above are a sampling of K...
from €151 / night
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Chicago, Cook County
Holiday Rental • 120 m² • 3 Bedrooms
4.2
(27 reviews)
Walk to everything Chicago has to offer- downtown, beach, park, restaurants and bars; bring family or friends to this spacious house on a quiet neighborhood street in historic Old Town.This amazing space has 3 bedrooms (important: one of the bedrooms is a walk through- please see description), 2.5 bath, outdoor space, parking on property, washer, dryer, fully stocked kitchen with stainless steel appliances and granite countertops. Pets are welcome too! What else can you possible need?CLEANING PRACTICESWith cornavirus being a constant in the news, I would like to comment on our cleaning prac...
from €226 / night

Prices and availability

Holiday lettings prices in Chicago

€368for 10 Dec - 17 Dec
€371 annual average
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Average price per week

Holiday lettings availability in Chicago

32%for 10 Dec - 17 Dec
38% annual average
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Percentage of available rentals

Holiday homes and rentals in Chicago

Homes 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 home 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 homes 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!

Homes 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 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.

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