Chicago Holiday Apartments & Accommodation - HomeToGo base64Hash Chicago Holiday Apartments & Accommodation - HomeToGo

Chicago Holiday Apartments & Accommodation

Find 5,189 available offers from 28 partners
Chicago
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Choose the perfect holiday letting

Price per night
Up to £100
£100 - £199
From £200
Accommodation types
Apartment
Bed & Breakfast
Private room
Distance to center
Max. 1 km
Max. 2 km
Max. 5 km
Rating
Outstanding: 4.5+
Very Good: 4+
Good: 3.5+

Enjoy a fun and cultural trip with Chicago holiday accommodation

The historic city of Chicago boasts a fabulous skyline and a profusion of world-class museums, art galleries, jazz clubs, and playhouses. A walk through downtown Chicago will reveal some of the world's best architectural styles: Gothic, classic, modernist, and more.

The winds that blow across Lake Michigan have earned Chicago a nickname as the Windy City. Check in at your Chicago holiday apartment and find out what the fuss is all about.

Show all 5,189 properties
Save up to 60%

Best holiday rental deals in Chicago

Apartment South Loop
21 Jan - 28 Jan
-56%
£487
£212 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
South Loop, Chicago, Illinois, United States
Details
Kasa Living
View deal
Apartment South Loop
14 Jan - 21 Jan
-60%
£343
£139 per night
Apartment ∙ 3 guests ∙ 1 bedroom
South Loop, Chicago, Illinois, United States
Details
Kasa Living
View deal
Apartment Near North
14 Jan - 21 Jan
-38%
£247
£152 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Near North, Chicago, Illinois, United States
Details
Kasa Living
View deal

Compare 5,189 properties available in Chicago and discover a welcoming place to stay for a relaxing holiday. HomeToGo allows you to easily search and compare the prices for each rental from numerous providers to discover the best deal and save up to 60%.

Book Holiday Letting Offers with the Highest User Rating

Top-Rated Lettings and Properties in Chicago

Apartment New East Side
25 Jun - 2 Jul
-51%
£1,880
£926 per night
Apartment ∙ 8 guests ∙ 3 bedrooms
5.0
"Excellent" (2 ratings)
New East Side, Chicago, Illinois, United States
Details
travelstaytion
View deal

Recommended holiday lettings in Chicago

Rent a holiday home, apartment or cottage in Chicago from just £29 per night

House Gold Coast
14 Nov - 21 Nov
£530 per night
House ∙ 9 guests ∙ 4 bedrooms
Gold Coast, Chicago, Illinois, United States
Free cancellation
Details
UnderThe Doormat
View deal
Apartment South Loop
14 Jan - 21 Jan
-42%
£216
£125 per night
Apartment ∙ 2 guests ∙ 1 bedroom
South Loop, Chicago, Illinois, United States
Details
Kasa Living
View deal
Apartment South Loop
21 Jan - 28 Jan
-50%
£424
£212 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
South Loop, Chicago, Illinois, United States
Details
Kasa Living
View deal
Apartment South Loop
14 Jan - 21 Jan
-59%
£324
£132 per night
Apartment ∙ 2 guests ∙ 1 bedroom
South Loop, Chicago, Illinois, United States
Details
Kasa Living
View deal
Apartment South Loop
14 Jan - 21 Jan
-56%
£317
£139 per night
Apartment ∙ 3 guests ∙ 1 bedroom
South Loop, Chicago, Illinois, United States
Details
Kasa Living
View deal
Apartment Near North
21 Jan - 28 Jan
-50%
£305
£152 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Near North, Chicago, Illinois, United States
Details
Kasa Living
View deal
Apartment South Loop
14 Jan - 21 Jan
-50%
£516
£259 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
South Loop, Chicago, Illinois, United States
Details
Kasa Living
View deal
Apartment Near North
21 Jan - 28 Jan
-51%
£306
£151 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Near North, Chicago, Illinois, United States
Details
Kasa Living
View deal
Apartment Near North
4 Feb - 11 Feb
-49%
£398
£203 per night
Apartment ∙ 3 guests ∙ 1 bedroom
Near North, Chicago, Illinois, United States
Details
Kasa Living
View deal
See all offers

Holiday rentals with wifi

Apartment Internet South Loop
14 Jan - 21 Jan
-60%
£344
£139 per night
Apartment ∙ 3 guests ∙ 1 bedroom
South Loop, Chicago, Illinois, United States
Internet
Details
Kasa Living
View deal
Apartment Internet South Loop
14 Jan - 21 Jan
-50%
£425
£213 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
South Loop, Chicago, Illinois, United States
Internet
Details
Kasa Living
View deal
Apartment Internet South Loop
14 Jan - 21 Jan
-51%
£256
£125 per night
Apartment ∙ 2 guests ∙ 1 bedroom
South Loop, Chicago, Illinois, United States
Internet
Details
Kasa Living
View deal
See all offers

Apartments and holiday lettings with a kitchen

Apartment Kitchen South Loop
21 Jan - 28 Jan
-65%
£731
£258 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
South Loop, Chicago, Illinois, United States
Kitchen
Details
Kasa Living
View deal
Apartment Kitchen Near North
4 Feb - 11 Feb
-55%
£456
£204 per night
Apartment ∙ 3 guests ∙ 1 bedroom
Near North, Chicago, Illinois, United States
Kitchen
Details
Kasa Living
View deal
Apartment Kitchen Near North
14 Jan - 21 Jan
-50%
£331
£166 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Near North, Chicago, Illinois, United States
Kitchen
Details
Kasa Living
View deal
See all offers

Holiday lettings and apartments with air conditioning

Apartment Aircondition Near North
14 Jan - 21 Jan
-66%
£823
£281 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
Near North, Chicago, Illinois, United States
Aircondition
Details
Kasa Living
View deal
Apartment Aircondition South Loop
14 Jan - 21 Jan
-51%
£359
£175 per night
Apartment ∙ 3 guests ∙ 1 bedroom
South Loop, Chicago, Illinois, United States
Aircondition
Details
Kasa Living
View deal
Apartment Aircondition Near North
21 Jan - 28 Jan
-50%
£306
£152 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Near North, Chicago, Illinois, United States
Aircondition
Details
Kasa Living
View deal
See all offers

Popular holiday rental amenities in Chicago

  • Internet (5,551)
  • Air conditioning (4,773)
  • TV (4,494)
  • No smoking (2,998)
  • Microwave (2,241)
  • Pool (1,847)
  • Wheelchair access (1,674)
  • No pets (1,613)
  • Cot (1,466)
  • Kitchen (1,463)
  • Balcony/Patio (1,441)
  • Pet allowed (1,215)

Check above for our most commonly selected filters in Chicago and the number of rentals that include them. In Chicago, 5,553 rentals provide Internet. Consequently, if you can't imagine a holiday without internet, use the Internet filter to see this type of accommodation. You could even compare and find properties if you want a rental with a jacuzzi (120 rentals include Hot tub in Chicago) or you plan to go fishing (54 rentals with Fishing).

Price and Availability Index for Chicago

Holiday Letting Price Information in Chicago

We analysed price data and summarised them in this graph, which shows holiday letting prices for the next twelve months in Chicago. £397 is the highest price average in the next twelve months. On average, the most interesting prices are in one week in January (14/01 - 21/01), when the average price is only £166 per night.

Holiday Home Availability Information in Chicago

Our availability graph helps you identify the busiest months in Chicago. It is in June that you will find the week with the fewest available holiday lettings (04/06 - 11/06). Conversely, you will find the highest number of available rentals during one week in October (29/10 - 05/11).

The Weather in Chicago

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- Rainy days

Check out the climate diagram for Chicago. On average, the warmest month is July. However, temperatures can go lower than -7° in Chicago in February. The rainiest month is March, while the driest month is February.

7-Day Weather Forecast in Chicago

Sat, 21 May
15°
10°

15%

0 h

13 km/h

Sun, 22 May
15°

15%

4 h

11 km/h

Mon, 23 May
16°
10°

0%

11 h

11 km/h

Tue, 24 May
16°
12°

5%

1 h

10 km/h

Wed, 25 May
11°
11°

15%

0 h

13 km/h

Thu, 26 May
12°
12°

15%

0 h

9 km/h

Fri, 27 May
15°
12°

15%

1 h

15 km/h

Accommodation options for your holiday in Chicago

484 out of the 5,191 offers in Chicago are apartment rentals. In other words, they make up many of the properties in this destination (65.23%). The standard size of apartment rentals in Chicago is 78 m², with an average price of £269 a night. Furthermore, these rentals are perfect for couples and small groups, as that is the average number of guests that apartment rentals are able to accommodate in Chicago. If you're searching for another type of accommodation, you can find alternative accommodation types, such as bed & breakfast rentals, which are the second most typical property type in Chicago. The average size of bed & breakfast rentals in Chicago is 69 m² , and the average price is £265 per night.
Where to find the best food in Chicago?

What to eat during your Chicago holiday

The world comes to Chicago for gastronomical expertise, so indulge those tastebuds! Devon Avenue is the place for Indian delights, which you can eat in or take away to enjoy back at your Chicago holiday apartment. A mix of everything is served in Uptown, including American, Ghanaian, Nigerian, Japanese, and even Swedish delicacies.

Don't miss the world-famous Chicago-style deep-dish pizza, and devour some iconic Chicago hotdogs at Vienna Beef Factory Deli and Portillo's. Chicago is a drinking city that is home to a record number of dive bars, lounges, and breweries, the best of them found in the Logan Square and Bucktown areas.

What is the weather like in Chicago?

What weather to expect on your Chicago holiday

The best time to visit Chicago is in spring and fall, when the weather is pleasant and accommodation prices are reasonable. Moreover, plenty of cultural activities take place across this part of the calendar. If you intend to visit during summer, book your Chicago accommodation well in advance as this is the most popular visitng season. Chicago can be just as magical in winter, making it a true year-around city.

What are the top sights in Chicago?

What to do and see in Chicago

The city's most popular attraction is the Lincoln Park Zoo, which houses African Apes and other interesting species. Trivia lovers will be impressed to learn that Chicago is home to three out of America's five tallest buildings: the Sears Tower, Trump Tower, and the Aon Centre.

Chicago's ethnic neighborhoods are so true-to-life, you'd be forgiven for thinking you were genuinely in another country. There's Chinatown, the Korean community in Lawrence Avenue, the Swedish settlement at Andersonville, Little Italy, Greektown, and several other international pockets. The Polish Cathedrals of St. Mary of the Angels in Bucktown and St. Hyacinth Basilica in Avondale are exquisite. Experience the different facets of the city with guided architecture walks or a river boat tour.

What are the best places to discover the arts and culture of Chicago?

Art and culture in Chicago

Art and history enthusiasts will be spoilt for choice with the variety of art galleries and museums scattered across the city. The Art Institute of Chicago in the Loop district houses priceless Impressionist and Modernist works, and there's also the National Museum of Mexican Art in Pilsen, the Museum of Photography, the Polish Museum of America in Wicker Park, the International Museum of Surgical Science, and so on. Buy the Chicago CityPASS to save money if you plan on visiting several attractions in a short span of time.

For improvisational comedy and performance art, catch a show at The Annoyance Theatre, I.O., or the Playground. Steppenwolf in Lincoln Park is more serious, having hosted the likes of John Malkovich. Visit the Auditorium in the Loop for its architecture and brilliant use of performance space. For rock, blues, jazz, and spoken-word performances, the Chicago Theatre awaits.

What are the best activities for families in Chicago?

Family holidays in Chicago

Chicago has plenty to keep kids occupied. Right along the lake on Museum Campus lie three institutions in walking distance of each other. The Adler Planetarium has the coolest astronomy shows and exhibits, while the Shedd Aquarium features majestic sharks, dolphins, whales, and other superb marine life. The kids will love the giant Tyrannosaurus Rex skeleton in the Field Museum of Natural History. How about a picnic on the clean shores of Lake Michigan to finish up? The waters are safe and excellent for swimming.

What are the best events and festivals in Chicago?

Regular Events and Festivities

The year begins with colourful Chinese New Year celebrations and the highly-awaited Chicago Auto Show. April brings the Chicago Improv Festival and C2E2 Chicago Comic & Entertainemt Expo. The summer months are chock-full with events, including the Puerto Rican Parade & Festival, Chicago Blues Festival, and Chicago Pride Fest in June, followed by the Square Roots Festival in July, and Lollapalooza and the Chicago Jazz Festival in August.

Film lovers and athletes should watch out for the Chicago International Film Festival and the Chicago Marathon in October. The year ends on a whimsical note with Christkindlmarket, the Magnificent Mile Lights Festival, and the Winter WonderFest at Navy Pier, where the entire city is adorned with lights.

Book a Chicago holiday home for an unforgettable time in the Windy City!

What are the must-see attractions in Chicago?

Chicago: Culture in the Windy City

360 Chicago Observation Deck

What better to way to see the city than from above? Travel up to the 94th floor of the John Hancock Centre for stunning views of the city and over Lake Michigan.

Museum of Science and Industry

At this interactive museum you'll find a life-size replica coal mine and recreated historic Chicago streets with functional shops.

Cloud Gate

One of the most iconic pieces of art in the United States, Cloud Gate was created by Anish Kapoor. This beautiful reflective sculpture is nicknamed 'The Bean' due to its shape.

Millennium Park

This urban park in the centre of Chicago is a great place to wile away an afternoon amidst a tranquil backdrop. Concerts, local fairs and fun events are held regularly at the park.

Art Institute of Chicago

As one of the oldest and largest galleries in the country, this impressive museum showcases over 300,000 artworks. Modern art, photography, ancient sculptures and more feature.

Frequently Asked Questions

How much does it cost to rent a holiday home in Chicago?

On average, a Apartment rentals or Bed & Breakfast rentals in Chicago costs £29 per night.

How many holiday homes are available to book in Chicago?

August is the time of year with the highest amount of Apartment rentals and Bed & Breakfast rentals available in Chicago, so you'll find plenty of great holiday deals during this month.

What is the most popular holiday home amenity in Chicago?

The top three amenities our customers choose for holiday rentals in Chicago are Internet, TV and Pool.

How many holiday homes are on offer in Chicago?

Holidaymakers looking for accommodation in Chicago will be pleased to know that there are 5,191 options on offer, with prices starting from just £29 per night.

Am I allowed to bring my pet when staying in a Chicago holiday home?

Finding accommodation in Chicago for you and your dog is definitely possible, with 1,327 pet-friendly holiday homes available.

What's the best time of year to travel to Chicago?

Sun lovers should visit Chicago in July and August to enjoy the warmest weather.

Can you get discounts on holiday lettings in Chicago?

You can find great value holiday lets in Chicago with the nightly price of a let beginning at £29 - and HomeToGo has introduced plenty of features that mean it's easy to see the best deals. When considering different dates for a trip, try a search using HomeToGo's flexible dates technology to easily look for low-price timings and see savings of up to 60%. In addition, HomeToGo's 'distance from' filter makes it easy to locate top quality accommodation offers in great value, under-the-radar locales that are just as close to your desired destination, whether that's a beach, lake, ski region or city centre. Start your search as soon as possible to get the benefits of the greatest variety of options and top discounts - and do so without worries by ticking HomeToGo's 'free cancellation' filter when you search.

What are the pros of booking a holiday letting in Chicago with HomeToGo?

From serenity away from the crowds to more space to enjoy with your loved ones, holiday homes in Chicago bring a variety of benefits. HomeToGo surfaces real reviews from verified visitors, and searching is secure, simple, and stress-free - so with 5,191 lets from 27 providers in the area, you're guaranteed to uncover the ideal type of accommodation with all of the amenities to suit you in Chicago.

We list offers from thousands of providers, including:

Booking.com Holiday Rentals in Chicago Novasol Holiday Rentals in Chicago TripAdvisor Holiday Rentals in Chicago Airbnb Holiday Rentals in Chicago Inter Chalet Holiday Rentals in Chicago HomeAway Holiday Rentals in Chicago EveryStay Holiday Rentals in Chicago Interhome Holiday Rentals in Chicago 9flats.com Holiday Rentals in Chicago HouseTrip Holiday Rentals in Chicago Belvilla Holiday Rentals in Chicago Sykes Cottages Holiday Rentals in Chicago Homestay.com Holiday Rentals in Chicago Ski Planet Holiday Rentals in Chicago Only-apartments Holiday Rentals in Chicago James Villa Holidays Holiday Rentals in Chicago

Travel tips, inspiration and ideas for your holiday in Chicago

Top holiday destinations near Chicago

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