Vacation rental deals in Chicago

We have selected the best vacation rentals in Chicago. Save money with Bluepillow by comparing the best deals from major travel websites in Chicago

Save on Bed & Breakfast in Chicago

Are you looking for an accommodation in Chicago and do you want to save money? Choose from 56 Bed & Breakfasts in Chicago

The best places to stay in Chicago

Book an apartment in Chicago and choose the right accommodation for your needs

Where to stay in Chicago

In a destination like Chicago it will be possible to stay charming. Accommodations? Chicago offers various accommodation alternatives, that meet everyone's needs: for who travels in a group, as a couple, with the family or alone.
Over a total of 5,396 accommodation, it is possible to distinguish 4,962 apartments, 407 hotels, 25 b&bs, 700 independent homes, 10 villas, 12 hostels and much more. Every alternative is equipped with a large range of services that wil allow for a more alluring stay between your choices. The best features in Chicago are: Pets Allowed, Pool, Kitchen, Spa and Parking.
The world's tourists appreciate Chicago. Would you like to know which is the best accommodation with the best reviws in Chicago? The best types of accommodation according to the tourists are Accommodations. Proof is the multitude of reviews that each of them has written. 11,942 reviews with a score of 10.0 Excellent and 698 reviews with a score of 8.0 Verry Good, over a total of 589,173 reviews.

Chicago: Organize a holiday and find the best accommodation deals

In Chicago it will be possible to find accommodation solutions at an average cost of 274 pounds per night.

The main interest points and what to see in Chicago during your stay

The best accommodation in Chicago can be found near the main interest points.

Not far from the centre you can find 5,396 accommodation available with the best offers: 4,962 Apartments, 25 B&Bs, 407 Hotels, and much more.
Below you can find the best apartments near the centre.

Chicago and the time with the best weather for a holiday

Chicago: do you want to know which is the hottest month: the hottest month of the year is July where temperatures can reach 27°C.
If instead you are cold lovers the best month with the coldes temperatures is January, where the temperature can drop to -1°C.
On average in Chicago you will find an average temperature of 13°C.


There is just something great about this city. In many instances it goes head to head to head with New York City but this city has its own charm. Chicago is home to a diverse population and different ethnicities; it has a busy financial district, one of the best shopping malls in the country. It is home to some of the best universities including the top ranked North Western University and who can forget to count pizza. Not just any pizza, but classic Chicago style pizza in which you can dig into and enjoy the cheesy goodness of life.
Home of the Chicago bulls (Basketball) and Chicago Cubs (Baseball) don’t be surprised if everyone is game crazy there. Oprah Winfrey used to air her show from this great city so it has been a regular place for all the celebrities.
Like any big city, Chicago has a thriving Downtown where one can find the best clubs, restaurants, malls and stores. There is the famous Sears Tower where you can go and have a full view of the city from the top or you can relax on the beaches of Lakeshore. So have a short stay in Chicago and enjoy all of these places. You can even have some great last minute offers for vacation rentals in Chicago.


Lincoln Park
This is a great community area in Chicago and has people hailing from various nationalities living here. It has an amazing parks, shops and restaurants to enjoy food at. Chicago is famous for its deep dish style pizza, so you won’t have to search for it much in this area. If you want to find some place to stay at, you can find some great deals on apartments in Chicago in this area a well.

Hyde Park
This is one best neighbourhood to view some classic architecture buildings and cathedrals. It has a museum of science and history, Chicago University and the Rockefeller Chapel. This area is a delight of its own during your short stay in Chicago.

Wicker Park
All the best places are called Park in Chicago it seems. Another great place in the city is Wicker Park. This is one of the busiest and liveliest neighbourhoods of the city and has many restaurants, cafes, and clubs to go to. It’s a hip and happening place for businessmen, party goers and shoppers alike.


Sears Tower

Lincoln Park Zoo

Lakeshore Drive

Navy Pier

John Hancock Centre

Chicago River walk


The weather of Chicago is continental and experiences all the seasons. It is generally humid and very hot during the summers and very cold during the winters. Temperatures dropping to below freezing are a norm every winter.

So for your next vacation to the USA, plan a short stay in Chicago and experience all the unique things this great city has to offer. From the food and architecture to sports and shopping, Chicago has it all. There are many vacation rentals in Chicago that you can get. Its best to book early on but sometimes you can get some amazing deals on last minute offers as well.