Holiday lettings & accommodation in Chicago - Wimdu base64Hash Holiday lettings & accommodation in Chicago - Wimdu

Holiday lettings & accommodation in Chicago

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Best holiday rental offers in Chicago

Holiday park Near North
£58 per night
Holiday park ∙ 2 guests ∙ 1 bedroom
4.1/5.0 "Very good"
(2256 ratings)
Near North, Chicago, Illinois, United States
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Hostelworld
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Studio flat Chicago Loop
£74 per night
Studio flat ∙ 3 guests ∙ 1 bedroom
Chicago Loop, Chicago, Illinois, United States
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HomeToGo
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Apartment South Loop
£182 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
South Loop, Chicago, Illinois, United States
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HomeToGo
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Apartment South Loop
£263 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
South Loop, Chicago, Illinois, United States
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HomeToGo
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Apartment South Loop
£129 per night
Apartment ∙ 2 guests ∙ 1 bedroom
South Loop, Chicago, Illinois, United States
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HomeToGo
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Apartment Near North
£140 per night
Apartment ∙ 3 guests ∙ 1 bedroom
Near North, Chicago, Illinois, United States
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HomeToGo
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Apartment Near North
£380 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
Near North, Chicago, Illinois, United States
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HomeToGo
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Apartment South Loop
£130 per night
Apartment ∙ 2 guests ∙ 1 bedroom
South Loop, Chicago, Illinois, United States
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HomeToGo
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Apartment West Loop Gate
£102 per night
Apartment ∙ 2 guests ∙ 1 bedroom
West Loop Gate, Chicago, Illinois, United States
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HomeToGo
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Apartment West Loop Gate
£139 per night
Apartment ∙ 2 guests ∙ 1 bedroom
West Loop Gate, Chicago, Illinois, United States
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HomeToGo
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Apartment Near North
£115 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Near North, Chicago, Illinois, United States
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HomeToGo
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Apartment Near North
£109 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Near North, Chicago, Illinois, United States
Details
HomeToGo
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Apartment South Loop
£158 per night
Apartment ∙ 3 guests ∙ 1 bedroom
South Loop, Chicago, Illinois, United States
Details
HomeToGo
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Apartment South Loop
£146 per night
Apartment ∙ 3 guests ∙ 1 bedroom
South Loop, Chicago, Illinois, United States
Details
HomeToGo
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Apartment Goose Island
£114 per night
Apartment ∙ 4 guests ∙ 1 bedroom
Goose Island, Chicago, Illinois, United States
Details
Expedia
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Apartment Roscoe Village
£173 per night
Apartment ∙ 6 guests ∙ 1 bedroom
4.2/5.0 "Very good"
Roscoe Village, Chicago, Illinois, United States
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HomeToGo
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Apartment Wrigleyville
£401 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
5.0/5.0 "Excellent"
(293 ratings)
Wrigleyville, Chicago, Illinois, United States
Details
Expedia
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Resort Archer Heights
£152 per night
Resort ∙ 2 guests ∙ 1 bedroom
4.1/5.0 "Very good"
Archer Heights, Chicago, Illinois, United States
Details
HomeToGo
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Studio flat Printer's Row
£93 per night
Studio flat ∙ 2 guests ∙ 1 bedroom
Printer's Row, Chicago, Illinois, United States
Details
HomeToGo
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Apartment South Loop
£142 per night
Apartment ∙ 3 guests ∙ 1 bedroom
South Loop, Chicago, Illinois, United States
Details
HomeToGo
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Apartment Chicago Loop
£120 per night
Apartment ∙ 6 guests ∙ 1 bedroom
Chicago Loop, Chicago, Illinois, United States
Details
Get a Room
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Apartment Near North
£222 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
3.7/5.0 "Good"
(33 ratings)
Near North, Chicago, Illinois, United States
Details
HomeToGo
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Studio flat Printer's Row
£103 per night
Studio flat ∙ 2 guests ∙ 1 bedroom
Printer's Row, Chicago, Illinois, United States
Details
HomeToGo
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Apartment Near North
£113 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
3.7/5.0 "Good"
(56 ratings)
Near North, Chicago, Illinois, United States
Details
HomeToGo
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Apartment Near North
£102 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
3.7/5.0 "Good"
(89 ratings)
Near North, Chicago, Illinois, United States
Details
HomeToGo
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Apartment New East Side
£165 per night
Apartment ∙ 8 guests ∙ 3 bedrooms
New East Side, Chicago, Illinois, United States
Details
HomeToGo
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Apartment Streeterville
£125 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
Streeterville, Chicago, Illinois, United States
Details
HomeToGo
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House Douglas
£82 per night
House ∙ 2 guests ∙ 1 bedroom
4.2/5.0 "Very good"
(210 ratings)
Douglas, Chicago, Illinois, United States
Details
Expedia
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Apartment South Loop
£112 per night
Apartment ∙ 2 guests ∙ 1 bedroom
4.7/5.0 "Outstanding"
(96 ratings)
South Loop, Chicago, Illinois, United States
Details
Expedia
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Apartment Greektown
£114 per night
Apartment ∙ 2 guests ∙ 1 bedroom
5.0/5.0 "Excellent"
(1 rating)
Greektown, Chicago, Illinois, United States
Details
Expedia
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Apartment Near North
£112 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
3.7/5.0 "Good"
(13 ratings)
Near North, Chicago, Illinois, United States
Details
HomeToGo
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House Douglas
£68 per night
House ∙ 2 guests ∙ 1 bedroom
3.8/5.0 "Good"
(86 ratings)
Douglas, Chicago, Illinois, United States
Details
Expedia
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Apartment Near North
£91 per night
Apartment ∙ 2 guests ∙ 1 bedroom
3.7/5.0 "Good"
(100 ratings)
Near North, Chicago, Illinois, United States
Details
HomeToGo
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Apartment New East Side
£192 per night
Apartment ∙ 8 guests ∙ 2 bedrooms
New East Side, Chicago, Illinois, United States
Details
HomeToGo
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Apartment New East Side
£187 per night
Apartment ∙ 8 guests ∙ 3 bedrooms
New East Side, Chicago, Illinois, United States
Details
HomeToGo
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Apartment New East Side
£181 per night
Apartment ∙ 8 guests ∙ 3 bedrooms
New East Side, Chicago, Illinois, United States
Details
HomeToGo
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Condo Central Station
£132 per night
Condo ∙ 2 guests ∙ 1 bedroom
3.6/5.0 "Good"
(10 ratings)
Central Station, Chicago, Illinois, United States
Details
Expedia
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Resort Chicago Loop
£210 per night
Resort ∙ 4 guests ∙ 1 bedroom
Chicago Loop, Chicago, Illinois, United States
Details
HomeToGo
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Resort Chicago Loop
£161 per night
Resort ∙ 3 guests ∙ 1 bedroom
Chicago Loop, Chicago, Illinois, United States
Details
HomeToGo
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House Lake View
£290 per night
House ∙ 2 guests ∙ 2 bedrooms
4.9/5.0 "Excellent"
(8 ratings)
Lake View, Chicago, Illinois, United States
Details
Expedia
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Apartment Streeterville
£1,031 per night
Apartment ∙ 8 guests ∙ 3 bedrooms
Streeterville, Chicago, Illinois, United States
Details
HomeToGo
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Apartment Old Town Triangle
£218 per night
Apartment ∙ 2 guests ∙ 1 bedroom
5.0/5.0 "Excellent"
(2 ratings)
Old Town Triangle, Chicago, Illinois, United States
Details
Expedia
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Apartment Wrightwood Neighbors
£209 per night
Apartment ∙ 2 guests ∙ 1 bedroom
5.0/5.0 "Excellent"
(1 rating)
Wrightwood Neighbors, Chicago, Illinois, United States
Details
Expedia
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Resort Chicago Loop
£161 per night
Resort ∙ 4 guests ∙ 1 bedroom
Chicago Loop, Chicago, Illinois, United States
Details
HomeToGo
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Aparthotel Near North Side
£77 per night
Aparthotel ∙ 4 guests ∙ 1 bedroom
Near North Side, Chicago, Illinois, United States
Details
HomeToGo
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Apartment Lake View
£279 per night
Apartment ∙ 4 guests ∙ 1 bedroom
Lake View, Chicago, Illinois, United States
Details
HomeToGo
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Aparthotel South Loop
£104 per night
Aparthotel ∙ 4 guests ∙ 1 bedroom
South Loop, Chicago, Illinois, United States
Details
HomeToGo
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Apartment Streeterville
£183 per night
Apartment ∙ 8 guests ∙ 3 bedrooms
Streeterville, Chicago, Illinois, United States
Details
HomeToGo
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Apartment Streeterville
£962 per night
Apartment ∙ 8 guests ∙ 3 bedrooms
Streeterville, Chicago, Illinois, United States
Details
HomeToGo
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Apartment New East Side
£936 per night
Apartment ∙ 8 guests ∙ 3 bedrooms
5.0/5.0 "Excellent"
(2 ratings)
New East Side, Chicago, Illinois, United States
Details
HomeToGo
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Price and Availability Index for Chicago

Holiday Letting Price Information in Chicago

The graph above shows the average prices of holiday rentals in Chicago throughout the year. Holiday rental prices are the highest in july (24/07 - 31/07). However, it's great if you plan to book an accommodation in january. In this period holiday rentals are comparatively cheap, with average prices of £141.

Holiday Home Availability Information in Chicago

Above, you can see what percentage of the holiday rentals in Chicago are available at different times of year. The busiest week of the year is in July (31/07 - 07/08). The week with the highest availability is in November (06/11 - 13/11) - 97 of the holiday rentals are still available.

Apartment, Accommodation & Bed and Breakfast in Chicago

Chicago SkylineChicago is the third largest city in the United States and has been nicknamed the “Windy City”. With a population of over three million people Chicago has a lot to offer all types of visitors and tourists, and has plenty of accommodation to suit every budget. The city is well-known for its fabulous architecture, including skyscrapers and brick bungalows that influenced other buildings throughout the country. Walking architecture tours are available to make visitors aware of the works of intriguing architects such as Frank Lloyd Wright, Daniel Burnham, and Mies van der Rohe. Teeming with activity, the Art Institute, the Museum of Science and Industry and the Natural History Museum each provide beautiful experiences that can't be forgotten. In Downtown Chicago lies the great Millennium Park featuring a band shell and the famous oval Cloud Gate Sculpture where you can see your reflection as you stand close to it. Restaurants are large and plentiful in Hyde Park and Lincoln Park. Chicago is a city of jazz and blues and hosts impressive theaters. It's a city known for people working, building and enjoying life.

Apartments & Bed and Breakfasts in Chicago

Although Chicago is host to many forms of accommodation, there are many parts of the city that are strictly residential, where you won’t find any hotels. But don’t worry, Wimdu has you covered no matter where you would like to rest your hat. We offer holiday apartments, private apartments and bed and breakfasts all over the city in both Downtown Chicago and the residential areas. Downtown Chicago is relatively big area that encompasses more than one neighbourhood. These neighbourhoods include; River North, Streetville, Loop, South Loop and West Loop. These areas are central but you will still need to make travel arrangements to make your way around the city. Here you can find a range of accommodation from high rise apartments, infamous bungalow apartments and plenty of bed and breakfasts. Apartments in these areas are all the heart of the city with each area encompassing their very own unique character, be sure to do some research into what area would suit you the most. If you would prefer to stay a little out of the city and in a more quiet residential area, then we also offer a great range of accommodation in the surrounding neighbourhood’s. Renting an apartment here will give you a real insight into how the people of Chicago live day to day, it can also be an excellent way to discover the city as a local would. Likewise we offer bed and breakfast rentals around these areas.

Fun Facts!

  • Chicago is home to more than 200 theaters
  • There are 15 miles of bathing beach’s, 26 miles of lakefront and 552 parks in Chicago
  • An average of 35 million people visit the city of Chicago each year!
  • Chicago is where U.S President Barak Obama’s home is located.
  • Chicago hosts more than 36 annual parades.
  • There are more than 7’300 restaurants, and 200 art galleries in Chicago.

What to Do and See

Chicago is a bustling city with plenty of things to do and see, because the city is so big it is hard to know where to begin. We suggest starting off by visiting “360Chicago” observation deck. 360Chicago soars more than 1000 feet about lake Michigan where you can view the city’s majestic skyline, it offers visitor’s the most breathtaking views of downtown Chicago, the lakefront and four neighboring states. You might even spot you apartment if you’re lucky! If it is the kids you want to entertain then why not take a trip to Shedd Aquarium, with more than two million visitors per year it is an attraction not to be missed. Here you will have a chance to see beluga whales, Pacific white-sided dolphins, Alaska sea otters and California sea lions up close. Shedd Aquarium is enjoyed by both young and old alike. If history is more your thing, then visit The Field Museum, this is your passport to travel back 4.5 billion years ago under one roof. You can journey through 4 billion years of life on earth in the Evolving Planet exhibit and marvel over precious stones from their rough beginnings to sparkling jewelry. You can also see the most complete and best-preserved Tyrannosaurus-Rex fossil known to man. Nay Pier is Chicago’s number one attraction, encompassing more than 50 acres of prime Chicago lakefront territory, Navy Pier is a city with in a city. Here you can find restaurants, parks, museums, gardens and shopping centre’s. Fireworks light up the Chicago Skyline twice a week during the summer months.

Getting Around

As big as the city of Chicago is, it is not too difficult to make your way around the city. Chicago has one of the world’s simplest street patterns and numbering systems. One way to get around the city is to have a local show you around and the City of Chicago Department of Cultural Affairs has a service that does that for free. Chicago buses run over 100 routes that lace the city; buses stop every few blocks and several lines operate 24 hours a day. Be aware that exact change is needed for the fare. “L” trains connect the city via above-ground, street-level and subway trains and serve 144 rail stations all over town, making the “L” one og the most efficient and affordable methods of transportation available. Two lines operate 24 hours a day. Taxis are plentiful and easy to hail down, they offer a convenient way of getting around the city. Credit cards are accepted in all cabs and it is standard to tip the driver 15-20% of the fare. If you would like a more alternative way to make your way around the city then why not try one of Chicago’s water taxis, they are the perfect combination of sightseeing and convenient transportation. The taxis service most popular tourist destinations such as Chinatown, Museum Campus, Michigan Avenue and Union Station. A single ride can cost you from $3-$8 and a day pass can cost from $11-$29. If you would prefer to rent a car, there is an interactive parking map of downtown Chicago to search for public and multistoried parking by address and point of interest. We suggest that it is always a good idea to find your accommodation whether it be an apartment or bed and breakfast close to what you would most like to see and do. Make sure you check out our map to see what area would best suit you.

And we love our apartments

Holiday park
50 m² Studio flat
105 m² Apartment
Apartment
47 m² Apartment
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Wimdu is Europe's largest marketplace for private accommodation. With over 300,000 lettings in more than 150 countries, you're sure to find the perfect place to stay.

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