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

Holiday lettings & accommodation in Chicago

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Choose from 10,928 holiday lettings and homes for your trip!

Best-rated holiday lettings in Chicago

Discover holiday rentals with top-notch guest ratings

Condo Lincoln Park
from £168 per night
Condo ∙ 7 guests ∙ 4 bedrooms
4.8
Outstanding(33 ratings)
Lincoln Park, Chicago, Illinois, United States
Vrbo
View deal
Apartment Heart of Chicago
from £171 per night
Apartment ∙ 6 guests ∙ 4 bedrooms
5.0
Outstanding(7 ratings)
Heart of Chicago, Chicago, Illinois, United States
Vrbo
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Apartment Logan Square
from £57 per night
Apartment ∙ 4 guests ∙ 3 bedrooms
5.0
Outstanding(5 ratings)
Logan Square, Chicago, Illinois, United States
Vrbo
View deal

Pet-friendly rentals in Chicago

Explore best dog-friendly accommodation offers and enjoy holidays with your pet

House West Loop
from £165 per night
House ∙ 9 guests ∙ 3 bedrooms
4.6
Excellent(66 ratings)
West Loop, Chicago, Illinois, United States
Pet-friendly
Vrbo
View deal
Apartment Streeterville
from £190 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
4.8
Outstanding(36 ratings)
Streeterville, Chicago, Illinois, United States
Pet-friendly
Vrbo
View deal
Condo Old Town Triangle
from £146 per night
Condo ∙ 4 guests ∙ 2 bedrooms
4.4
Very good(34 ratings)
Old Town Triangle, Chicago, Illinois, United States
Pet-friendly
Vrbo
View deal
See all pet-friendly offers

Accommodation with Internet in Chicago

Choose your ideal cottage with Internet and WiFi in Chicago

House South Deering
from £116 per night
House ∙ 8 guests ∙ 4 bedrooms
South Deering, Chicago, Illinois, United States
Internet
Vrbo
View deal
Condo Roscoe Village
from £113 per night
Condo ∙ 10 guests ∙ 5 bedrooms
3.6
Good(49 ratings)
Roscoe Village, Chicago, Illinois, United States
Internet
Vrbo
View deal
Condo Lincoln Park
from £159 per night
Condo ∙ 7 guests ∙ 4 bedrooms
4.9
Outstanding(34 ratings)
Lincoln Park, Chicago, Illinois, United States
Internet
Vrbo
View deal
See all offers with internet

Holiday cottages with pool in Chicago

Discover best holiday homes and cottages with pool in Chicago

House Palmer Square
from £180 per night
House ∙ 16 guests ∙ 4 bedrooms
Palmer Square, Chicago, Illinois, United States
Pool
HomeToGo
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Condo Near North
from £171 per night
Condo ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding(21 ratings)
Near North, Chicago, Illinois, United States
Pool
Vrbo
View deal
Apartment Chicago Loop
from £199 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
4.9
Outstanding(49 ratings)
Chicago Loop, Chicago, Illinois, United States
Pool
Vrbo
View deal
See all offers with pool

Best holiday rental offers in Chicago

Villa South Shore
from £262 per night
Villa ∙ 16 guests ∙ 3 bedrooms
South Shore, Chicago, Illinois, United States
Agoda
View deal
Apartment Lake View East
from £290 per night
Apartment ∙ 16 guests ∙ 4 bedrooms
5.0
Outstanding(108 ratings)
Lake View East, Chicago, Illinois, United States
Vrbo
View deal
Apartment River North
from £57 per night
Apartment ∙ 2 guests ∙ 1 bedroom
4.4
Very good(22 ratings)
River North, Chicago, Illinois, United States
Vrbo
View deal
Apartment Lake View East
from £324 per night
Apartment ∙ 20 guests ∙ 5 bedrooms
5.0
Outstanding(60 ratings)
Lake View East, Chicago, Illinois, United States
Vrbo
View deal
Apartment Gage Park
from £60 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Gage Park, Chicago, Illinois, United States
Vrbo
View deal
Apartment Grand Boulevard
from £102 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
Grand Boulevard, Chicago, Illinois, United States
Vrbo
View deal
House West Town
from £218 per night
House ∙ 13 guests ∙ 5 bedrooms
4.4
Very good(15 ratings)
West Town, Chicago, Illinois, United States
Vrbo
View deal
House Douglas
from £110 per night
House ∙ 9 guests ∙ 4 bedrooms
4.1
Very good(27 ratings)
Douglas, Chicago, Illinois, United States
Vrbo
View deal
Apartment Streeterville
from £253 per night
Apartment ∙ 6 guests ∙ 4 bedrooms
4.8
Outstanding(25 ratings)
Streeterville, Chicago, Illinois, United States
Vrbo
View deal
Apartment North Kenwood
from £206 per night
Apartment ∙ 10 guests ∙ 4 bedrooms
4.7
Excellent(50 ratings)
North Kenwood, Chicago, Illinois, United States
Vrbo
View deal
House Smith Park
from £152 per night
House ∙ 10 guests ∙ 4 bedrooms
Smith Park, Chicago, Illinois, United States
HomeToGo
View deal
House Grand Boulevard
from £154 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding(1 rating)
Grand Boulevard, Chicago, Illinois, United States
Vrbo
View deal
Apartment South Loop
from £94 per night
Apartment ∙ 9 guests ∙ 5 bedrooms
South Loop, Chicago, Illinois, United States
Vrbo
View deal
Apartment Grand Boulevard
from £144 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
4.0
Very good(15 ratings)
Grand Boulevard, Chicago, Illinois, United States
Vrbo
View deal
Apartment Near North
from £191 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding(2 ratings)
Near North, Chicago, Illinois, United States
Vrbo
View deal
Apartment West Town
from £159 per night
Apartment ∙ 5 guests ∙ 3 bedrooms
5.0
Outstanding(4 ratings)
West Town, Chicago, Illinois, United States
Vrbo
View deal
Apartment Grand Crossing
from £185 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding(3 ratings)
Grand Crossing, Chicago, Illinois, United States
Vrbo
View deal
House Edgewater Beach
from £245 per night
House ∙ 12 guests ∙ 6 bedrooms
5.0
Outstanding(2 ratings)
Edgewater Beach, Chicago, Illinois, United States
Vrbo
View deal
Apartment Bucktown
from £135 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding(16 ratings)
Bucktown, Chicago, Illinois, United States
Vrbo
View deal
House Goose Island
from £159 per night
House ∙ 14 guests ∙ 3 bedrooms
4.9
Outstanding(50 ratings)
Goose Island, Chicago, Illinois, United States
Vrbo
View deal
House Lincoln Park
from £304 per night
House ∙ 24 guests ∙ 4 bedrooms
5.0
Outstanding(183 ratings)
Lincoln Park, Chicago, Illinois, United States
Vrbo
View deal
Apartment West Town
from £86 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding(22 ratings)
West Town, Chicago, Illinois, United States
Vrbo
View deal
House Grand Boulevard
from £274 per night
House ∙ 8 guests ∙ 4 bedrooms
Grand Boulevard, Chicago, Illinois, United States
Agoda
View deal
House Streeterville
from £162 per night
House ∙ 8 guests ∙ 2 bedrooms
4.0
Very good(3 ratings)
Streeterville, Chicago, Illinois, United States
Vrbo
View deal
Apartment Grand Boulevard
from £143 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
4.4
Very good
Grand Boulevard, Chicago, Illinois, United States
Agoda
View deal
House Avondale
from £393 per night
House ∙ 16 guests ∙ 8 bedrooms
4.7
Excellent(3 ratings)
Avondale, Chicago, Illinois, United States
Vrbo
View deal
Apartment Near West Side
from £280 per night
Apartment ∙ 10 guests ∙ 4 bedrooms
5.0
Outstanding(11 ratings)
Near West Side, Chicago, Illinois, United States
Vrbo
View deal
House Grand Boulevard
from £190 per night
House ∙ 8 guests ∙ 3 bedrooms
5.0
Outstanding(2 ratings)
Grand Boulevard, Chicago, Illinois, United States
Vrbo
View deal
Apartment South Shore
from £122 per night
Apartment ∙ 7 guests ∙ 4 bedrooms
5.0
Outstanding(1 rating)
South Shore, Chicago, Illinois, United States
Vrbo
View deal
Condo East Village
from £184 per night
Condo ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding(3 ratings)
East Village, Chicago, Illinois, United States
Vrbo
View deal
Apartment West Loop
from £93 per night
Apartment ∙ 10 guests ∙ 4 bedrooms
4.4
Very good(26 ratings)
West Loop, Chicago, Illinois, United States
Vrbo
View deal
House Near North
from £130 per night
House ∙ 4 guests ∙ 1 bedroom
5.0
Outstanding(3 ratings)
Near North, Chicago, Illinois, United States
Vrbo
View deal
Condo West Town
from £154 per night
Condo ∙ 7 guests ∙ 3 bedrooms
5.0
Outstanding(48 ratings)
West Town, Chicago, Illinois, United States
Vrbo
View deal
Apartment West Loop
from £414 per night
Apartment ∙ 16 guests ∙ 5 bedrooms
4.9
Outstanding(35 ratings)
West Loop, Chicago, Illinois, United States
Vrbo
View deal
Condo Noble Square
from £238 per night
Condo ∙ 7 guests ∙ 3 bedrooms
5.0
Outstanding(52 ratings)
Noble Square, Chicago, Illinois, United States
Vrbo
View deal
House Old Irving Park
from £294 per night
House ∙ 14 guests ∙ 6 bedrooms
4.6
Excellent(24 ratings)
Old Irving Park, Chicago, Illinois, United States
Vrbo
View deal
Apartment Gold Coast
from £74 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
5.0
Outstanding(3 ratings)
Gold Coast, Chicago, Illinois, United States
Vrbo
View deal
House Lake View
from £394 per night
House ∙ 12 guests ∙ 4 bedrooms
5.0
Outstanding(53 ratings)
Lake View, Chicago, Illinois, United States
Vrbo
View deal
Apartment Logan Square
from £241 per night
Apartment ∙ 6 guests ∙ 4 bedrooms
5.0
Outstanding(9 ratings)
Logan Square, Chicago, Illinois, United States
Vrbo
View deal
Show more in Chicago

Price and Availability Index for Chicago

Click on any bar to see price and availability information

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 october (04/10 – 11/10). 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 £108.

Rental 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 November (15/11 – 22/11). The week with the highest availability is in March (29/03 – 05/04) - 71 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.

5,839,306 reviews
Travellers who stayed in Chicago rated their holiday home 4.3/5 on average, based on 5,839,306 reviews.

And we love our apartments

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214 m² Apartment
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Features of Chicago holiday rentals

💳 Discounts up to 61%
⭐ Popular amenities Kitchen, Internet and Pool
🏊  Holiday rentals with a pool 2,471 rentals
🌙 Minimum price starting at £57
🐾 Pet friendly holiday homes 4,574 rentals
🏡 Rentals available 10,928 rentals

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