Holiday homes and apartments in Chicago

Find your holiday rental in Chicago we have great deals on: houses, apartments, villas and any other accommodation

1233 holiday rentals in Chicago

Book your Chicago holiday rentals from 1233 short-term rentals listings. Compare top rentals sites such as Booking.com, HomeAway, TripAdvisor and more on Likibu, the world’s largest rentals Meta search.

  1. From
    £68/ night
    Apartment with wifi, 1 bedroom
    Booking.com
    • 22 guests
    • 1Bedrooms : 1
    • 1Bathrooms : 1
    •  
    4.65 / 5-
  2. Ad
    From
    £35/ night
    Live there. Book unique homes.
    Airbnb
    • Search on Airbnb - Chicago
  3. From
    £155/ night
    Apartment with jacuzzi, 2 bedrooms
    Booking.com
    • 55 guests
    • 2Bedrooms : 2
    • 2Bathrooms : 2
    •  
    4.45 / 5-
  4. From
    £98/ night
    Apartment with pool, 3 bedrooms
    HomeAway
    • 144 m²
    • 66 guests
    • 3Bedrooms : 3
    • 2Bathrooms : 2
    •  
    5 / 544 Reviews
  5. From
    £141/ night
    Apartment with jacuzzi, 1 bedroom
    Booking.com
    • 33 guests
    • 1Bedrooms : 1
    • 1Bathrooms : 1
    •  
    4.7 / 5-
  6. From
    £67/ night
    Apartment with garden, 2 bedrooms
    HomeAway
    • 111 m²
    • 55 guests
    • 2Bedrooms : 2
    • 2Bathrooms : 2
    •  
    4.89 / 546 Reviews
  7. From
    £69/ night
    Apartment with gym, 2 bedrooms
    TripAdvisor
    • 66 guests
    • 2Bedrooms : 2
    • 2Bathrooms : 2
    •  
    ? / 5 
  8. From
    £73/ night
    Apartment with air conditioning, 1 bedroom
    Booking.com
    • 44 guests
    • 1Bedrooms : 1
    • 1Bathrooms : 1
    •  
    4.5 / 5-
  9. From
    £117/ night
    Bed and breakfast with garden, 5 bedrooms
    HomeAway
    • 186 m²
    • 99 guests
    • 5Bedrooms : 5
    • 2Bathrooms : 2
    •  
    4.98 / 5113 Reviews
  10. From
    £117/ night
    Hotel with gym, 3 bedrooms
    Booking.com
    • 66 guests
    • 3Bedrooms : 3
    • 2Bathrooms : 2
    •  
    4.4 / 5-
  11. From
    £38/ night
    Apartment with air conditioning, 3 bedrooms
    TripAdvisor
    • 88 guests
    • 3Bedrooms : 3
    • 2Bathrooms : 2
    •  
    ? / 5 
  12. From
    £164/ night
    Apartment with garden, 3 bedrooms
    Booking.com
    • 66 guests
    • 3Bedrooms : 3
    • 3Bathrooms : 3
    •  
    5 / 5-
More results in Chicago

The striking lakeside city of Chicago is one of the largest in the US, meaning it's bursting with attractions which are perfect for every visitor. Whether you are drawn to The Windy City for its bold architecture, award-winning galleries or globally famous pizza scene, Likibu offers the ideal accommodation which is just waiting to be discovered. So, browse the extensive selection of the many holiday lettings, apartments and bed and breakfasts in Chicago online today.


Best holiday accommodation in Chicago

Holiday homes and apartments in Chicago with balcony or terrace

From
90 €/ night
Apartment with jacuzzi, 3 bedrooms
HomeAway
  • 121 m²
  • 88 guests
  • 3Bedrooms : 3
  • 2Bathrooms : 2
  •  
4.96 / 523 Reviews
From
116 €/ night
House with gym, 3 bedrooms
TripAdvisor
  • 66 guests
  • 3Bedrooms : 3
  • 1Bathrooms : 1
  •  
5 / 55 Reviews
From
135 €/ night
Apartment with garden, 3 bedrooms
HomeAway
  • 112 m²
  • 66 guests
  • 3Bedrooms : 3
  • 2Bathrooms : 2
  •  
4.97 / 562 Reviews
From
105 €/ night
Apartment with air conditioning, 1 bedroom
Booking.com
  • 11 guest
  • 1Bedrooms : 1
  • 1Bathrooms : 1
  •  
? / 5 

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Holiday homes and chalets with fireplace in Chicago

From
90 €/ night
Apartment with jacuzzi, 2 bedrooms
HomeAway
  • 102 m²
  • 44 guests
  • 2Bedrooms : 2
  • 1Bathrooms : 1
  •  
4.9 / 521 Reviews
From
114 €/ night
Apartment with air conditioning, 3 bedrooms
HomeAway
  • 111 m²
  • 66 guests
  • 3Bedrooms : 3
  • 1Bathrooms : 1
  •  
4.9 / 599 Reviews
From
137 €/ night
House with air conditioning, 4 bedrooms
HomeAway
  • 99 guests
  • 4Bedrooms : 4
  • 3Bathrooms : 3
  •  
4.93 / 528 Reviews
From
91 €/ night
Apartment with air conditioning, 3 bedrooms
HomeAway
  • 130 m²
  • 88 guests
  • 3Bedrooms : 3
  • 2Bathrooms : 2
  •  
4.82 / 511 Reviews

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Holiday Homes and Apartments with wifi in Chicago

From
91 €/ night
Apartment with garden, 2 bedrooms
HomeAway
  • 111 m²
  • 66 guests
  • 2Bedrooms : 2
  • 1Bathrooms : 1
  •  
4.96 / 570 Reviews
From
82 €/ night
Apartment with air conditioning, 1 bedroom
Booking.com
  • 11 guest
  • 1Bedrooms : 1
  • 1Bathrooms : 1
  •  
3.95 / 5-
From
117 €/ night
Apartment with gym, 2 bedrooms
Booking.com
  • 44 guests
  • 2Bedrooms : 2
  • 1Bathrooms : 1
  •  
3.95 / 5-
From
145 €/ night
Apartment with air conditioning, 2 bedrooms
HomeAway
  • 74 m²
  • 55 guests
  • 2Bedrooms : 2
  • 1Bathrooms : 1
  •  
4.93 / 529 Reviews

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FInd and book your dream apartment or holiday home in Chicago

Visit Chicago and be blown away by the sights of the Windy City

The spectacular skyline which towers at the fringe of Lake Michigan is instantly recognisable as one of the most daring in America, with iconic structures such as the Willis Tower enticing visitors to the country's third biggest city. There is even more to Chicago than meets the eye, however, as this Midwestern city offers a diverse cultural scene and of course, globally renowned deep-dish pizza.  Find your place in this amazing destination and reserve your perfect holiday apartment or home right here and choose accommodation which puts you in the heart of the city's dining, music and prestigious art scene.

When to go?

The late spring months of April to June, and the autumn months of September and early October are the best time to visit Chicago, as you can enjoy a pleasant climate, without the summer holiday crowds. St Patrick's Day weekend in mid-March similarly attracts crowds from around the US, as the river is dyed green in celebration.

How to get there?

Found in the Midwestern region of the US, on the banks of Lake Michigan, the city happens to be home to the sixth busiest airport in the world, with over 79 million passengers using O'Hare International Airport to pass through Chicago annually. With direct flights to 218 destinations, flying non-stop to O' Hare is the quickest and most convenient option for visitors who are travelling from the UK. A selection of airlines including British Airways, United and American Airlines offer direct flights to London Heathrow, with a flight duration of just under 9 hours. The most cost-effective way of reaching the centre from O' Hare is on the Rapid Transit Train system, by taking the blue line for around 40 minutes from the terminal, straight to your holiday rental or bed and breakfast.

Where to stay in Chicago

The Loop

This high-rise studded district is the beating heart of Chicago's renowned cultural scene, with countless restaurants, shops, theatres and bars to lose yourself amongst when the day turns into night in the Windy City. You do not necessarily need to be a night owl to enjoy a holiday apartment in this thrilling area, as choosing accommodation here will leave you just a stone's throw away from enjoying some of the most famous icons in the city, including the Willis Tower and the Cloud Gate structure, which is otherwise recognised as ‘The Bean'.

Pilsen

If you have chosen to visit Chicago for its diverse art scene, look no further than an apartment in the vibrant district of Pilsen. Wake up alongside some of the city's most exotic street art, colourful murals, and exciting museum exhibitions, including a homage to Mexican Art, and book a holiday home in this unique neighbourhood.

Gold Coast

The historic Gold Coast district is the epitome of everything that is so unique about Chicago, rolled into one golden neighbourhood. This waterside coast is where you can find some of the most distinguished luxury apartment rentals and glamorous holiday homes in the entire city, but this is unsurprising when you consider the esteemed position of these properties. Wake up in a room with a view of Lake Michigan from a high-rise accommodation, spend your days bathing on the beach which runs parallel to the district, and your nights in the Gold Coast's open-air restaurants for a whole new dining experience.

Wicker Park 

For convenience to O' Hare airport, Wicker Park and Bucktown is the ideal district to secure a holiday apartment which is a home away from home. The easy airport access is not the only bonus to choosing accommodation in Wicker Park, however, as it is another hip neighbourhood which attracts art lovers who can almost certainly immerse themselves in all the indie music, European inspired coffee shops and rooftop parties which this area offers.

Old Town

Whoever says the Chicago architecture exclusively consists of skyscrapers must have never explored the Victorian Old Town. With its nineteenth-century winding streets, all of which survived the great fire in 1871, the Old Town Triangle is the perfect place to choose a self-catered apartment, as it remains a tranquil escape whilst being just a short Transit ride away from the famous attractions and museums.

Logan Square

As one of the most upcoming neighbourhoods in the city, the bohemian district of Logan Square is the ideal place to secure a holiday letting if you want to immerse yourself in the independent eateries and shopping experiences of the city. Choosing a reasonably priced self-catered apartment, home-stay or youth hostel here will allow you to spend your savings in its fairy-light lit bars, vintage and vinyl stores along Logan Square's boulevards.

What is there to do and see in Chicago?

Art Institute of Chicago

One of the greatest and oldest museums in the United States, the Art Institute of Chicago is home to works from some of the biggest names in the art world, including Edward Hopper's ‘Nighthawks', Picasso's ‘The Old Guitarist' amongst other works from the likes of Grant Wood and Georges Seurat. The museum is a staple in the American art canon and houses the second largest collection outside the Metropolitan Museum of Art. 

Millennium Park

Chicago's skyscrapers tower above a park which attracts millions of tourists, artists and locals every year, making it the most popular attraction in the entire Midwest. There is even more to this green space than a traditional park, however, as here is where you can find the ultimate Chicago icon, the Cloud Gate structure, or ‘The Bean' as it is more commonly referred to as.

Take in the views from the Willis Tower Sky Deck

There is no better way to take the extent of this city's glory than from 1,353 feet in the air, from the deck of the Willis Tower, which also happens to be the tallest building in the Western Hemisphere. Complete with interactive exhibitions and a glass walkway which extends 4 feet beyond the tower, this Sky Deck offers a way of experiencing Chicago like no other.

Walk along the Chicago Riverwalk

The path along the Chicago River has been cleverly designed to showcase the very best of Chicago's architecture at your leisure, with areas to lounge, drink and dine at almost every bend. There is nothing quite like seeing The Windy City from the river, so whether you choose to walk along the path, or opt for a luxury river cruise, this Chicago staple must not be missed.

Sample some deep-dish pizza from The Art of Pizza

You cannot leave the city without sampling at least one slice of deep-dish pizza; whether you are a pizza lover or not, nobody does a deep dish like Chicago. Though the best place to grab a slice remains a debate for every visitor and locals alike, many would agree that the Lakeview establishment is a great place to start.

Garfield Park Conservatory

For an alternative to exploring the city's art scene in its streets and museums, visit the Garfield Park Conservatory, which has been described as "landscape art under glass" and is entirely free of charge. With its green goodness stretching over 180 acres, most of which include a swimming pool, a lagoon and an impressive greenhouse, this conservatory is the ideal place to escape the bustle of the city streets for visitors of every age.