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Chicago Holiday Apartments & Accommodation

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Chicago
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Chicago
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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.

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Apartments and holiday lettings with a kitchen

Looking for self-catering accommodation in Chicago? Find the perfect letting for you with our selection of Chicago holiday rentals with kitchens. Well-appointed and equipped with plenty of cooking appliances, these holiday homes are great for self-catered stays.

House  Bronzeville
28 Apr - 5 May
£677 per night
House ∙ 8 guests ∙ 4 bedrooms

Holiday Home in Bronzeville with Terrace

4.8
Outstanding (13 ratings)
Bronzeville, Chicago, Illinois, United States
Kitchen
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Condo  River West
28 Apr - 5 May
-7%
£1,038
£964 per night
Condo ∙ 20 guests ∙ 5 bedrooms

Flat in River West with Barbecue & Terrace + Beautiful View

5.0
Outstanding (91 ratings)
River West, Chicago, Illinois, United States
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Apartment  Near West Side
28 Apr - 5 May
£333 per night
Apartment ∙ 8 guests ∙ 3 bedrooms

Flat in Near West Side with Barbecue & Terrace

5.0
Outstanding (19 ratings)
Near West Side, Chicago, Illinois, United States
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Holiday lettings and apartments with air conditioning

Good weather while on holiday is always great - and it's a plus to be able to control the temperature in your accommodation too. Find holiday homes and apartments in Chicago with air conditioning and cooling systems to ensure maximum comfort during your stay.

Condo  Wicker Park
28 Apr - 5 May
-5%
£816
£778 per night
Condo ∙ 14 guests ∙ 7 bedrooms

Flat in Wicker Park

4.8
Outstanding (8 ratings)
Wicker Park, Chicago, Illinois, United States
Air conditioning
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Condo  South Austin
28 Apr - 5 May
£203 per night
Condo ∙ 6 guests ∙ 3 bedrooms

Flat in South Austin with Terrace & Garden

South Austin, Chicago, Illinois, United States
Air conditioning
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Apartment  West Ridge
28 Apr - 5 May
-3%
£296
£286 per night
Apartment ∙ 8 guests ∙ 3 bedrooms

Pleasant Holiday Apartment in West Ridge

5.0
Outstanding (6 ratings)
West Ridge, Chicago, Illinois, United States
Air conditioning
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Holiday rentals with wifi

Whether it's for working remotely or streaming your favourite shows, internet access can be an indispensable amenity when it comes to choosing a holiday home. Check out HomeToGo's range of holiday lettings with WiFi in Chicago and enjoy a fast and reliable internet connection during your stay.

Apartment  Heart of Chicago
28 Apr - 5 May
£342 per night
Apartment ∙ 8 guests ∙ 3 bedrooms

Lovely Flat in Heart Of Chicago with Terrace

5.0
Outstanding (1 rating)
Heart of Chicago, Chicago, Illinois, United States
Internet
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Apartment  Park Manor
28 Apr - 5 May
-10%
£229
£205 per night
Apartment ∙ 8 guests ∙ 4 bedrooms

Holiday Apartment in Park Manor with Garden & Terrace

4.9
Outstanding (7 ratings)
Park Manor, Chicago, Illinois, United States
Internet
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House  Noble Square
28 Apr - 5 May
-3%
£967
£934 per night
House ∙ 12 guests ∙ 5 bedrooms

House in Noble Square with Terrace, Garden & Barbecue

5.0
Outstanding (95 ratings)
Noble Square, Chicago, Illinois, United States
Internet
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Best holiday rental deals in Chicago

Save up to 8%

House The Island
28 Apr - 5 May
-8%
£232
£213 per night
House ∙ 8 guests ∙ 3 bedrooms

Wonderful Holiday Home in The Island with Garden

4.6
Excellent (28 ratings)
The Island, Chicago, Illinois, United States
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Condo Near West Side
28 Apr - 5 May
-7%
£344
£320 per night
Condo ∙ 11 guests ∙ 3 bedrooms

Flat in Near West Side with Private Parking

4.8
Outstanding (39 ratings)
Near West Side, Chicago, Illinois, United States
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House East Village
28 Apr - 5 May
-7%
£354
£330 per night
House ∙ 5 guests ∙ 2 bedrooms

Holiday Home in East Village with Terrace & Barbecue

5.0
Outstanding (65 ratings)
East Village, Chicago, Illinois, United States
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Discover a letting matching your needs among the 9,674 unique lettings from different providers in Chicago. HomeToGo instantly sorts all of these holiday lettings to help you save up to 33%!

Recommended holiday lettings in Chicago

Rent a holiday home, apartment or cottage in Chicago from just £47 per night

House West Town
5 May - 12 May
£658 per night
House ∙ 10 guests ∙ 5 bedrooms

Holiday Home in West Town with Pool & Barbecue

West Town, Chicago, Illinois, United States
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Villa Douglas
28 Apr - 5 May
£151 per night
Villa ∙ 2 guests ∙ 1 bedroom

Villa in Douglas with Garden

Douglas, Chicago, Illinois, United States
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Apartment Cragin
28 Apr - 5 May
£148 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Holiday Apartment in Cragin with Garden

Cragin, Chicago, Illinois, United States
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Condo Washington Park
28 Apr - 5 May
£459 per night
Condo ∙ 7 guests ∙ 3 bedrooms

Flat in Washington Park with Terrace

Washington Park, Chicago, Illinois, United States
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House Near North Side
28 Apr - 5 May
£323 per night
House ∙ 11 guests ∙ 3 bedrooms

House in Near North Side with Free Garage + City View

Near North Side, Chicago, Illinois, United States
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House Pullman
28 Apr - 5 May
£183 per night
House ∙ 7 guests ∙ 4 bedrooms

Pleasant House in Pullman with Garden, Terrace & Barbecue

4.6
Excellent (31 ratings)
Pullman, Chicago, Illinois, United States
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Apartment Old Town
28 Apr - 5 May
£241 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Flat in Old Town with Barbecue

4.9
Outstanding (12 ratings)
Old Town, Chicago, Illinois, United States
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Apartment South Loop
28 Apr - 5 May
£391 per night
Apartment ∙ 8 guests ∙ 3 bedrooms

Lovely Flat in South Loop with Optional Parking

5.0
Outstanding (6 ratings)
South Loop, Chicago, Illinois, United States
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Apartment Heart of Chicago
28 Apr - 5 May
£189 per night
Apartment ∙ 6 guests ∙ 2 bedrooms

Flat in Heart Of Chicago with Free Parking

4.4
Very good (20 ratings)
Heart of Chicago, Chicago, Illinois, United States
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Budget-friendly Holiday Homes in Chicago

Find Fantastic yet Cheap Lettings

House East Village
28 Apr - 5 May
-7%
£1,272
£1,179 per night
House ∙ 12 guests ∙ 4 bedrooms

House in East Village with Barbecue & Terrace

4.9
Outstanding (26 ratings)
East Village, Chicago, Illinois, United States
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House River West
28 Apr - 5 May
£1,130 per night
House ∙ 11 guests ∙ 4 bedrooms

House in River West with Garden, Terrace & Barbecue

5.0
Outstanding (103 ratings)
River West, Chicago, Illinois, United States
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House Fifth City
28 Apr - 5 May
£222 per night
House ∙ 5 guests ∙ 3 bedrooms

Charming House in Fifth City with Barbecue, Garden & Terrace

4.9
Outstanding (11 ratings)
Fifth City, Chicago, Illinois, United States
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Top-Rated Lettings and Properties in Chicago

Book Holiday Letting Offers with the Highest User Rating

Apartment South Loop
28 Apr - 5 May
£391 per night
Apartment ∙ 8 guests ∙ 3 bedrooms

Holiday Apartment in South Loop with Terrace

5.0
Outstanding (4 ratings)
South Loop, Chicago, Illinois, United States
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Apartment West Loop Gate
28 Apr - 5 May
£605 per night
Apartment ∙ 6 guests ∙ 3 bedrooms

Entire Flat in West Loop Gate with Terrace, Pool & Barbecue, Near Willis Tower + Skyline Views

5.0
Outstanding (129 ratings)
West Loop Gate, Chicago, Illinois, United States
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Apartment Avondale
28 Apr - 5 May
-3%
£187
£180 per night
Apartment ∙ 6 guests ∙ 3 bedrooms

Holiday Apartment in Avondale with Pool, Terrace & Garden

5.0
Outstanding (19 ratings)
Avondale, Chicago, Illinois, United States
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Popular holiday rental amenities in Chicago

  • Pool (2,377)
  • WiFi (9,322)
  • Kitchen (5,328)
  • Air conditioning (9,399)
  • Washing machine (5,142)
  • TV (8,962)
  • Parking (1,561)
  • Balcony/patio (2,436)
  • Pet-friendly (2,303)
  • Microwave (5,052)
  • No smoking (9,043)
  • Dishwasher (3,463)

Chicago is an ideal holiday destination if you want to rent a property with a pool. Nearly a quarter of the accommodation options here have this amenity. Hotel room with pools in Chicago are a good choice for groups of 7 and have an average cost of £387 per night. In Chicago, two-thirds of the holiday rentals offering a pool are located near the water.

Price and Availability Index for Chicago

Click on any bar to see price and availability information

Holiday Letting Price Information in Chicago

This graph displays average prices of the holiday cottages and holiday apartments located in Chicago. It is during one week in October (05/10 – 12/10) that you will find the highest prices in Chicago. On average, the most interesting prices are in one week in March (08/03 – 15/03), when the average price is only £99 per night.

Rental availability information in Chicago

Check out the graph above to find out how many holiday rentals are available in Chicago (in %). It is in February that you will find the week with the fewest available holiday lettings (22/02 – 01/03). People tend to travel to Chicago least during a week in June (01/06 – 08/06) when only 31% of the rentals are booked.

The Weather in Chicago

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- Rainy days

Check out the weather diagram for Chicago. July is the hottest month in Chicago, with average daily maximum temperatures of 29°. January is the coolest month, with the average minimum temperature falling to -8°. February is the driest month of the year in Chicago.

7-Day Weather Forecast in Chicago

Sat, 13 Apr
18°
16°

0%

6 h

14 km/h

Sun, 14 Apr
15°
10°

0%

4 h

20 km/h

Mon, 15 Apr
18°
15°

10%

6 h

13 km/h

Tue, 16 Apr
19°
14°

15%

0 h

18 km/h

Wed, 17 Apr
20°
15°

15%

0 h

28 km/h

Thu, 18 Apr

15%

0 h

15 km/h

Fri, 19 Apr

10%

1 h

22 km/h

Accommodation options for your holiday in Chicago

Travellers interested in apartment rental in Chicago have many alternatives, since this is the most prevalent accomodation type on offer there. The standard size of apartment rental in Chicago is 85 m², with a median price of £270 per night. Moreover, the majority of apartment rental in Chicago are able to welcome 4 people, which makes Chicago a great destination for medium-sized groups and families. Travellers who would prefer an alternative to a apartment rental can, with HomeToGo's fantastic range, also find an ideal house rentals for them. This property type is the second most popular kind of accommodation in Chicago. These properties cost £521 per night, on average, and have an average size of 146 m².
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.

Information about holiday rentals in Chicago

🏡 Holiday homes available 9,674 rentals
💳 Discounts available up to 33%
🌙 Nightly prices from £47
⭐ Popular amenities Pool, Internet and Kitchen
🐾 Pet friendly rentals 2,301 properties
🏊 Holiday rentals with pools 2,365 properties
8 reviews
Chicago holiday rentals have an average rating of 4.6/5 across 8 reviews left by travellers.

Frequently Asked Questions

How many accommodation are available to rent in Chicago?

There are currently 9,674 holiday rentals from 27 providers on offer in Chicago.

What is the most popular holiday home amenity in Chicago?

When choosing a holiday home in Chicago, consider looking for a place with Pool, Internet, or Kitchen, which are the three most popular amenities for this destination.

How many holiday rentals with a pool there are on offer in Chicago?

Holiday homes with pools are 24 of all offers in Chicago for an average price of £387 per night.

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

August and July are the warmest months in Chicago, while October and February have the least rain.

How do I find deals on holiday rentals in Chicago?

You can get great value holiday homes in Chicago with the nightly price of accommodation beginning at £47 - and HomeToGo has created plenty of features that make it a piece of cake to uncover the best offers. When considering different dates for your holiday, you can use HomeToGo's flexible dates technology to scan for low-price date options and see discounts of up to 33%. In addition, HomeToGo's 'distance from' filter enables you to find hidden gem holiday homes in great value, lesser-known locales which are still near to the area of your choice, whether that's the coastline, a swimming lake, winter sports area or town centre. Book early to get the best of good availability and top discounts - and do so without worries by clicking on HomeToGo's 'free cancellation' filter when you search.

What are the pros of finding a holiday rental in Chicago with HomeToGo?

From increased privacy away from the crowds to plenty of room to enjoy with your travel companions, holiday lets in Chicago provide a variety of benefits. HomeToGo surfaces real reviews written by previous guests, and searching is secure, simple, and hassle-free - so with 9,674 lets from 27 providers in the area, you're sure to discover the ideal place to stay with the amenities and features you need in Chicago.

Find the perfect Chicago home to match your style

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