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

Holiday lettings & accommodation in Chicago

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Choose from 5,600 holiday lettings and homes for your trip!

Best-rated holiday lettings in Chicago

Discover holiday rentals with top-notch guest ratings

Bed and breakfast Old Town
from £174 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed & breakfast with terrace | City view

5.0
Outstanding(539 ratings)
Old Town, Chicago, Illinois, United States
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Bed and breakfast Magnolia Glen
from £671 per night
Bed and breakfast ∙ 4 guests ∙ 1 bedroom

B&B with barbecue, garden & terrace | City view | Good for workation

4.6
Excellent(514 ratings)
Magnolia Glen, Chicago, Illinois, United States
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Bed and breakfast Bucktown
from £143 per night
Bed and breakfast ∙ 5 guests ∙ 1 bedroom

B&B with terrace & garden

4.9
Outstanding(412 ratings)
Bucktown, Chicago, Illinois, United States
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Pet-friendly rentals in Chicago

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

Bed and breakfast Bucktown
from £140 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Family-oriented wonderful bed and breakfast with terrace & garden | Suitable for remote work | Pets are welcome

4.9
Outstanding(412 ratings)
Bucktown, Chicago, Illinois, United States
Pet-friendly
View deal
Bed and breakfast Boystown
from £611 per night
Bed and breakfast ∙ 12 guests ∙ 5 bedrooms

B&B with 5 bedrooms for 12 persons

Boystown, Chicago, Illinois, United States
Pet-friendly
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Bed and breakfast Bucktown
from £143 per night
Bed and breakfast ∙ 3 guests ∙ 1 bedroom

Bed and breakfast with garden & terrace | Good for workation

4.9
Outstanding(412 ratings)
Bucktown, Chicago, Illinois, United States
Pet-friendly
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Best holiday rental offers in Chicago

Bed and breakfast Sheffield & DePaul
from £219 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Nice bed & breakfast with garden, terrace & barbeque | Good for workation

4.7
Excellent(122 ratings)
Sheffield & DePaul, Chicago, Illinois, United States
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Bed and breakfast Bucktown
from £149 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Family-oriented spacious B&B with garden & terrace | Good for workation | Pets allowed

4.9
Outstanding(412 ratings)
Bucktown, Chicago, Illinois, United States
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Bed and breakfast Fulton Market
from £256 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed & breakfast for 2 persons

4.9
Outstanding(211 ratings)
Fulton Market, Chicago, Illinois, United States
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Bed and breakfast Old Town
from £146 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

B&B with terrace

5.0
Outstanding(539 ratings)
Old Town, Chicago, Illinois, United States
View deal
Motel Rogers Park
from £83 per night
Motel ∙ 2 guests ∙ 1 bedroom

Motel with fast internet | Close to the beach

4.3
Very good(38 ratings)
Rogers Park, Chicago, Illinois, United States
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Bed and breakfast Humboldt Park
from £307 per night
Bed and breakfast ∙ 7 guests ∙ 3 bedrooms

Bed and breakfast | Perfect for remote work

Humboldt Park, Chicago, Illinois, United States
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Motel West Woodlawn
from £72 per night
Motel ∙ 2 guests ∙ 1 bedroom

Motel for 2 persons

West Woodlawn, Chicago, Illinois, United States
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Bed and breakfast Magnolia Glen
from £151 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed and breakfast with barbeque, terrace & garden | Garden view | Perfect for remote work

4.6
Excellent(514 ratings)
Magnolia Glen, Chicago, Illinois, United States
View deal
Bed and breakfast Roscoe Village
from £200 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Family-oriented charming B&B with terrace & garden

4.9
Outstanding(114 ratings)
Roscoe Village, Chicago, Illinois, United States
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Bed and breakfast Wicker Park
from £253 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed and breakfast with garden

4.5
Excellent(279 ratings)
Wicker Park, Chicago, Illinois, United States
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Motel River North
from £142 per night
Motel ∙ 2 guests ∙ 1 bedroom

Pleasant motel | Close to Magnificent Mile

4.5
Excellent(1180 ratings)
River North, Chicago, Illinois, United States
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Motel Washington Heights
from £64 per night
Motel ∙ 2 guests ∙ 1 bedroom

Pleasant motel for 2 persons

3.6
Good(437 ratings)
Washington Heights, Chicago, Illinois, United States
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Motel Archer Heights
from £95 per night
Motel ∙ 3 guests ∙ 1 bedroom

Motel for 3 persons

3.1
(1017 ratings)
Archer Heights, Chicago, Illinois, United States
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Motel North Park
from £69 per night
Motel ∙ 2 guests ∙ 1 bedroom

Motel for 2 persons

3.6
Good(869 ratings)
North Park, Chicago, Illinois, United States
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Motel Peterson Park
from £66 per night
Motel ∙ 2 guests ∙ 1 bedroom

Nice motel for 2 persons

3.3
(831 ratings)
Peterson Park, Chicago, Illinois, United States
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Bed and breakfast East Village
from £3,050 per night
Bed and breakfast ∙ 16 guests ∙ 8 bedrooms

B&B with garden | Perfect for remote work

East Village, Chicago, Illinois, United States
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Bed and breakfast Sheffield & DePaul
from £222 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Charming B&B with terrace, BBQ & garden | Perfect for remote work

4.7
Excellent(122 ratings)
Sheffield & DePaul, Chicago, Illinois, United States
View deal
Bed and breakfast Old Town
from £161 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed & breakfast with terrace

5.0
Outstanding(539 ratings)
Old Town, Chicago, Illinois, United States
View deal
Bed and breakfast Fulton Market
from £220 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed & breakfast for 2 persons

4.9
Outstanding(211 ratings)
Fulton Market, Chicago, Illinois, United States
View deal
Motel Rogers Park
from £90 per night
Motel ∙ 2 guests ∙ 1 bedroom

Motel with fast internet | Close to the beach

4.3
Very good(38 ratings)
Rogers Park, Chicago, Illinois, United States
View deal
Bed and breakfast Magnolia Glen
from £146 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed and breakfast with garden, barbecue & terrace | City view | Perfect for remote work

4.6
Excellent(514 ratings)
Magnolia Glen, Chicago, Illinois, United States
View deal
Bed and breakfast Wicker Park
from £254 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

B&B with garden

4.5
Excellent(279 ratings)
Wicker Park, Chicago, Illinois, United States
View deal
Motel Archer Heights
from £95 per night
Motel ∙ 2 guests ∙ 1 bedroom

Motel for 2 persons

3.1
(1017 ratings)
Archer Heights, Chicago, Illinois, United States
View deal
Motel North Park
from £69 per night
Motel ∙ 2 guests ∙ 1 bedroom

Wonderful motel for 2 persons

3.6
Good(869 ratings)
North Park, Chicago, Illinois, United States
View deal
Motel River North
from £134 per night
Motel ∙ 4 guests ∙ 1 bedroom

Motel | Near Magnificent Mile

4.5
Excellent(1180 ratings)
River North, Chicago, Illinois, United States
View deal
Bed and breakfast Old Town
from £156 per night
Bed and breakfast ∙ 3 guests ∙ 1 bedroom

Charming bed and breakfast with terrace

5.0
Outstanding(539 ratings)
Old Town, Chicago, Illinois, United States
View deal
Bed and breakfast Fulton Market
from £220 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

B&B for 2 persons

4.9
Outstanding(211 ratings)
Fulton Market, Chicago, Illinois, United States
View deal
Motel Rogers Park
from £83 per night
Motel ∙ 3 guests ∙ 1 bedroom

Motel with fast internet

4.3
Very good(38 ratings)
Rogers Park, Chicago, Illinois, United States
View deal
Bed and breakfast Wicker Park
from £262 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed and breakfast with garden

4.5
Excellent(279 ratings)
Wicker Park, Chicago, Illinois, United States
View deal
Bed and breakfast Magnolia Glen
from £185 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

B&B with terrace, barbeque & garden | Garden view | Good for workation

4.6
Excellent(514 ratings)
Magnolia Glen, Chicago, Illinois, United States
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 (17/10 – 24/10). However, it's great if you plan to book an accommodation in december. In this period holiday rentals are comparatively cheap, with average prices of £299.

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 July (31/07 – 07/08). The week with the highest availability is in August (15/08 – 22/08) - 82 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.

7 reviews
Travellers who stayed in Chicago rated their holiday home 4.1/5 on average, based on 7 reviews.

And we love our apartments

Nice bed & breakfast with garden, terrace & barbeque | Good for workation
Family-oriented spacious B&B with garden & terrace | Good for workation | Pets allowed
Bed & breakfast for 2 persons
B&B with terrace
Motel with fast internet | Close to the beach
Show more in Chicago

Features of Chicago holiday rentals

💳 Discounts up to 61%
⭐ Popular amenities Kitchen, Internet and Pool
🏊  Holiday rentals with a pool 1,781 rentals
🌙 Minimum price starting at £64
🐾 Pet friendly holiday homes 2,427 rentals
🏡 Rentals available 5,600 rentals

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