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Discover the ideal accommodation for your holiday in Chicago

Chicago
Anytime
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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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Chicago: Our recommendations

Apartment South Loop 6
129 m² Apartment
6 3
South Loop, Chicago, Illinois, United States
from £915
for 7 nights
Apartment South Loop 5
105 m² Apartment
5 2
South Loop, Chicago, Illinois, United States
from £668
for 7 nights
Studio flat Chicago Loop 3
50 m² Studio flat
3 1
Chicago Loop, Chicago, Illinois, United States
from £446
for 7 nights
See all offers

Holiday rentals with wifi

Apartment Internet South Loop
Internet
67 m² Apartment
3 1
South Loop, Chicago, Illinois, United States
from £548
for 7 nights
Apartment Internet South Loop
Internet
Apartment
3 1
South Loop, Chicago, Illinois, United States
from £542
for 7 nights
Apartment Internet South Loop
Internet
73 m² Apartment
2 1
South Loop, Chicago, Illinois, United States
from £512
for 7 nights
See all offers

Apartments and holiday lettings with a kitchen

Apartment Kitchen South Loop
Kitchen
47 m² Apartment
2 1
South Loop, Chicago, Illinois, United States
from £536
for 7 nights
Apartment Kitchen South Loop
Kitchen
68 m² Apartment
3 2
South Loop, Chicago, Illinois, United States
from £542
for 7 nights
Apartment Kitchen Near North
Kitchen
57 m² Apartment
3 1
Near North, Chicago, Illinois, United States
from £530
for 7 nights
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Holiday lettings and apartments with air conditioning

Apartment Aircondition Streeterville
Aircondition
Apartment
6 2
Streeterville, Chicago, Illinois, United States
from £873
for 7 nights
Apartment Aircondition Near North
Aircondition
56 m² Apartment
2 1
Near North, Chicago, Illinois, United States
from £632
for 7 nights
Apartment Aircondition Near North
Aircondition
56 m² Apartment
2 1
Near North, Chicago, Illinois, United States
from £530
for 7 nights
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.

What are the most popular accommodations in Chicago?

The most booked accommodations in Chicago are hotel rooms and apartment rentals. We search from more than 2,865 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 £60. On average, properties in Chicago will have a size of 85 m² (Apartment rentals) and 41 m² (Hotel rooms).

Do you offer pet-friendly hotel rooms in Chicago?

When travelling with your dog in Chicago, hotel rooms are recommended. These are the most common type of pet-friendly accommodations and cost an average of £286 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 hotel rooms has space for 3 guests.

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