Discover the ideal accommodation for your holiday in Chicago - Casamundo base64Hash Discover the ideal accommodation for your holiday in Chicago - Casamundo

Discover the ideal accommodation for your holiday in Chicago

Chicago
Anytime
Guests
Chicago
Anytime
Guests
If you are planning a trip to America and after an unforgettable trip to a large city, make sure you come to Chicago. In the Northern state of Illinois, you will not be disappointed about booking a Chicago vacation rental as there is so much to see and do here.
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Simple booking process - satisfied customers
Simple booking process - satisfied customers
Extensive customer support
Extensive customer support
Large variety and secure booking
Large variety and secure booking

Holiday rentals with wifi

Stay connected: Browse holiday rentals in Chicago with high-speed internet!

Apartment  Jefferson Park
15 Jun - 22 Jun
£117 per night
75 m² Apartment ∙ 4 guests ∙ 1 bedroom
Jefferson Park, Chicago, Illinois, United States
Free cancellation
Internet
Check availability
Apartment  Big Oaks
2 Nov - 9 Nov
-43%
£155
£89 per night
46 m² Apartment ∙ 3 guests ∙ 1 bedroom
Big Oaks, Chicago, Illinois, United States
Free cancellation
Internet
Check availability
Apartment  South Loop
7 Dec - 14 Dec
-8%
£288
£265 per night
129 m² Apartment ∙ 8 guests ∙ 3 bedrooms
South Loop, Chicago, Illinois, United States
Internet
Check availability
See all offers

Apartments and holiday lettings with a kitchen

Culinary bliss: Book a holiday rental on the beach in Chicago with a fully equipped kitchen today!

Apartment  Near North
14 Dec - 21 Dec
-8%
£182
£167 per night
69 m² Apartment ∙ 3 guests ∙ 1 bedroom
Near North, Chicago, Illinois, United States
Kitchen
Check availability
Apartment  South Loop
7 Dec - 14 Dec
-52%
£549
£266 per night
105 m² Apartment ∙ 5 guests ∙ 2 bedrooms
South Loop, Chicago, Illinois, United States
Free cancellation
Kitchen
Check availability
Apartment  Near North
14 Dec - 21 Dec
-8%
£258
£236 per night
108 m² Apartment ∙ 5 guests ∙ 2 bedrooms
Near North, Chicago, Illinois, United States
Kitchen
Check availability
See all offers

Holiday Homes with a Patio or Terrace

Sunset serenity: Book your Chicago holiday rental with a private terrace - relaxation awaits!

Apartment  Park West
6 Jan - 13 Jan
-66%
£465
£158 per night
51 m² Apartment ∙ 3 guests ∙ 1 bedroom
Park West, Chicago, Illinois, United States
Free cancellation
Balcony/Patio
Check availability
House  Marshall Square
11 Jan - 18 Jan
-49%
£250
£128 per night
House ∙ 6 guests ∙ 2 bedrooms
Marshall Square, Chicago, Illinois, United States
Free cancellation
Balcony/Patio
Check availability
Apartment  University Village / Little Italy
4 Jan - 11 Jan
-72%
£747
£207 per night
51 m² Apartment ∙ 4 guests ∙ 1 bedroom
University Village / Little Italy, Chicago, Illinois, United States
Free cancellation
Balcony/Patio
Check availability
See More Offers

Chicago: our recommendations

Discover the best offers in Chicago for your next holiday, starting at £90 per night.

Apartment Near North
14 Dec - 21 Dec
-8%
£182
£167 per night
69 m² Apartment ∙ 3 guests ∙ 1 bedroom
Near North, Chicago, Illinois, United States
Check availability
Apartment South Loop
7 Dec - 14 Dec
-8%
£288
£265 per night
129 m² Apartment ∙ 8 guests ∙ 3 bedrooms
South Loop, Chicago, Illinois, United States
Check availability
Apartment Near North
14 Dec - 21 Dec
-8%
£153
£141 per night
56 m² Apartment ∙ 2 guests ∙ 1 bedroom
Near North, Chicago, Illinois, United States
Check availability
Condo Old Town
2 Dec - 9 Dec
-55%
£2,218
£995 per night
Condo ∙ 16 guests ∙ 8 bedrooms
Old Town, Chicago, Illinois, United States
Free cancellation
Check availability
Apartment Near North
14 Dec - 21 Dec
-8%
£258
£236 per night
108 m² Apartment ∙ 5 guests ∙ 2 bedrooms
Near North, Chicago, Illinois, United States
Check availability
Apartment South Loop
7 Dec - 14 Dec
-8%
£235
£215 per night
107 m² Apartment ∙ 5 guests ∙ 2 bedrooms
South Loop, Chicago, Illinois, United States
Check availability
Apartment Near North
14 Dec - 21 Dec
-8%
£143
£132 per night
56 m² Apartment ∙ 2 guests ∙ 1 bedroom
Near North, Chicago, Illinois, United States
Check availability
Apartment South Loop
7 Dec - 14 Dec
-8%
£174
£159 per night
73 m² Apartment ∙ 2 guests ∙ 1 bedroom
South Loop, Chicago, Illinois, United States
Check availability
Apartment West Town
1 Feb - 8 Feb
-60%
£647
£260 per night
Apartment ∙ 8 guests ∙ 4 bedrooms
West Town, Chicago, Illinois, United States
Free cancellation
Check availability
See all offers

Plan a City Break To Chicago

Although Springfield is the capital of the state, it is the 6th largest city in Illinois. Chicago is however the 3rd largest city in the whole of the country, after New York and L.A. and has one of the largest economies in the world. This can be seen demonstrated in the breathtaking skyline here, found in the Downtown District. Across the city, you can see fantastic skyscrapers from all sorts of shapes and heights! If you are wanting to get a great overview of the city, head to the Willis Tower which has a great observation deck. At a height of 1,353 feet, it is definitely not suitable for those with a fear of heights! The views over the city are breathtaking and you can see the port of Chicago in the distance.

Accommodation Chicago – The must see sights of the city

For the art fans, make sure you hit the Art Institute of Chicago whilst staying in a Chicago vacation rental. It is a famous art exhibit known for its impressionist pieces, Asian arts and modern and contemporary art. There are over 260,000 pieces in the exhibit from across 5,000 years of history split into many different wings. This exhibition is second largest in the US after the Metropolitan Museum of Art in New York. If you fancy going outdoors during the day, head to one of the many beaches along the coastline, such as the Ohio Street Beach or the Montrose Avenue Beach. With the backdrop of the skyscrapers, it is a truly unique experience while sitting on the beach, looking up at such fine architecture! Head to the famous Lake Michigan whilst staying in Chicago accommodation. It is one of the most famous lakes and is a beautiful area to walk around or to sit back and relax during the summer. This famous lake can also be visited during a stay in Michigan so if you fancy exploring whilst staying in Chicago, you have the opportunity to do so. If you want to a visit with many great outdoor activities, head to Santa Fe in New Mexico as the hot temperatures during the summer means it is ideal to sit out in many of the parks scattered throughout the city.

In the evenings, you will not be bored whilst staying in apartments in Chicago. There is plenty of entertainment for those seeking parties – but only suitable for those over 21. From various nightclubs to swanky bars and lounges to envy those in South Beach, Miami, in the state of Florida, you are bound to find something to keep you entertained till the early hours! There are also plenty of comedy nights throughout the city in Chicago so make sure you research beforehand to make sure you see and do everything! Enjoy your holiday.

10 reviews
We collected 10 reviews from travellers who stayed in Chicago. Holiday homes in this destination received an average rating of 4.5/5.

Frequently asked questions

What are the most popular accommodations in Chicago?

The most booked accommodations in Chicago are apartment rental and bed and breakfast rental. We search from more than 472 accommodations in Chicago to help you find the perfect place to stay during your trip.

What does it cost to rent a holiday home in Chicago?

With Casamundo, you will find holiday rentals in Chicago starting from as little as £90. On average, properties in Chicago will have a size of 65 m² (Bed and breakfast rental) and 75 m² (Apartment rental).

Do you offer pet-friendly apartment rental in Chicago?

When travelling with your dog in Chicago, apartment rental are recommended. These are the most common type of pet-friendly accommodations and cost an average of £279 per night.

Do you also offer accommodations that are suitable for groups in Chicago ?

For your holiday in Chicago, we have a great selection of accommodations for groups. The typical apartment rental has space for 4 guests.

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