Choose the right place for you


  • Wi-Fi
  • Kitchen
  • Dishwasher


  • 9+ Exceptional
  • 8+ Fabulous
  • 7+ Very Good


  • Less than 1 km
  • Less than 3 km
  • Less than 5 km

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

  • G3. Next to Downtown! Best location & affordable!

    9 Exceptional (106)
    • 1 Guest · 1Bedroom
    Everybody is welcome! The location is just awesome! There is a bunch of restaurants and brunch places within 0.5miles all walkable. We are literally next to downtown, only 15-20minutes to the heart of
  • Heart of Chicago 2BD + Parking

    10 Exceptional (115)
    • 5 Guests · 2Bedrooms
    Comfortably fits 4-5Two private bedrooms and a queen foldout couch in living room. Impecable bathroom with great lighting. State of the art stainless steel appliances for a quick meal at home before a
  • Private Room/Bath Wicker Park, Free Street Parking

    10 Exceptional (90)
    • 2 Guests · 1Bedroom
    Welcome to West Wicker Park! Near public transportation for easy access to all Chicago has to offer. Easy arrival from O'hare Airport via the Blue Line. The Wicker Park scene has great restaurants, coffee
  • G1. Best location and most affordable! So much fun

    10 Exceptional (177)
    • 2 Guests · 1Bedroom
    Everybody is welcome! The location is just awesome! There is a bunch of restaurants and brunch places within 0.5miles all walkable. We are literally next to downtown, only 15-20minutes to the heart of
  • Cozy Bedroom in Spacious Duplex Apt

    10 Exceptional (193)
    • 2 Guests · 1Bedroom
    You will love your cozy bedroom in our spacious Duplex apartment. During your visit, take a nice stroll in beautiful Humboldt Park, go shopping in artsy Wicker Park or take a quick L ride to sight see
  • Chicago chinatown great location(B) (Chinese landlord)

    10 Exceptional (186)
    • 2 Guests · 1Bedroom
    want to leave room for tenants and tenants. If you have any questions or some situations, you can text me. I will answer you in time. Tell me when to check out or send a text message to me. Thanks

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

  • Sonder — Barry Apartments

    • Hotel
    Three-Bedroom on W Barry Avenue Apt 2F offers accommodation in Chicago, a 15-minute walk from Wrigley Field and 1.9 miles from Lincoln Park Zoo. The accommodation has free WiFi. The apartment is composed
  • Sonder — South State

    7.9 Very Good (12)
    • Hotel
    One of our bestsellers in Chicago! Sonder — South State is located in Chicago and offers a fitness centre. This property is a 13-minute walk from Field Museum of Natural History and has free WiFi. The
  • Sonder — 943 Crosby — Beautiful 1BR

    • Hotel
    Just a 19-minute walk from Water Tower Chicago and 1.1 miles from 360 Chicago and featuring free WiFi, One-Bedroom on N Crosby Street Apt 201 offers accommodation in Chicago. The property is 1.1 miles
  • HI Chicago Hostel

    8.8 Fabulous (4891)
    • Hotel
    Chicago Loop is a great choice for travellers interested in parks, architecture and museums.
  • Gritty Chic River North - ACME Hotel

    10 Exceptional (69)
    • Hotel
    If you've never been one for convention, ACME is the right choice for you. Located 2 ½ blocks from the Magnificent Mile in the River North neighborhood, ACME is downtown Chicago's lifestyle boutique hotel
  • Gritty Chic River North --- ACME Hotel

    10 Exceptional (63)
    • Hotel
    If you've never been one for convention, ACME is the right choice for you. Located 2 ½ blocks from the Magnificent Mile in the River North neighborhood, ACME is downtown Chicago's lifestyle boutique hotel

The best places to stay in Chicago

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

  • Last-Sec Booking 15 mins. to Center! Free Parking!

    10 Exceptional (471)
    • 2 Guests · 1Bedroom
    • 100% FREE 24-hour Street Parking! • 15 minutes to City Center! • Private Washroom! • Anytime check-in/check-out! • New construction apartment! • 1/2 Block from the Metro Train/El! • Highly private
  • H2. Unbeatable location! Right next to Downtown!

    9 Exceptional (87)
    • 3 Guests · 1Bedroom
    Only ONE BLOCK away to United Center. Best location and most affordable price! You can get to Untd Cntr in 5min walking. You have all the nice bars and restaurants of west loop 7min away by car.Hearth
  • Cozy room in Chicago style exposed brick apartment

    10 Exceptional (185)
    • 2 Guests · 1Bedroom
    Enjoy a quiet and peaceful home located in the epicenter of Chicago's hottest neighborhoods - Logan Square. Logan Square is a "locals" neighborhood, and about a 15-20 minute ride from the heart of downtown
  • Convenient location!

    10 Exceptional (123)
    • 2 Guests · 1Bedroom
    Our apartment has exposed brick which gives the place a unique feel. The room has drawers and a closet, Super close to many cute shops and good restaurants in Humboldt Park, and Wicker Park, a couple streets
  • Large Pet Friendly Room in Avondale/Logan Square

    10 Exceptional (95)
    • 2 Guests · 1Bedroom
    Large private room with tons of light located in the Avondale/Logan Square neighborhood of Chicago. Room features a queen size mattress, 32" TV with apple tv, and closet for storage. Guests will have access
  • Cute Brownstone in Lakeview

    10 Exceptional (286)
    • 2 Guests · 1Bedroom
    The apartment is vintage Chicago and cozy. Second floor with a lot of natural light. Convenient to the train, stores and neighborhood bars. 2 blocks from the brown line for easy access downtown. Walking

Farmhouse or Hotel? Choose from the best offers

Choose the accommodation tailor-made for you for your next vacation: sleep in a farmhouse or sleep in a hotel?

  • Farmstays in Chicago
    Farmstays in Chicago
  • Hotels in Chicago
    Hotels in Chicago

B&Bs and holiday homes Chicago: the best accommodation solutions

Chicago is a very appreciated destination by the world's tourists. The 589,173 reviews written for all the accommodation in the area are the proof: 11,942 reviews with a score of 10.0 Excellent and 698 reviews with a score of 8.0 Very Good. Reading these opinions you can learn which are the best accommodations with the best reviews in Chicago.
The best solutions for accommodation available in the area are many. 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. Amongst these you will be able to find the best offers for the best solution for your needs, wether you decide to go alone, for a romantic get-away, or with a group of friends. The end goal is an unforgettable holiday in Chicago.
Every type of accommodation at this destination displays a range of services that will adapt perfectrly to your necessity: Pets Allowed, Pool, Kitchen, Spa, Parking and much more. The choice is yours.

Chicago: How much does accommodation cost?

How much does holiday accommodation cost in Chicago? On average in Chicago it is possible to find accommodation solutions for 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: Which is the ideal month for a holiday?

Chicago: when to go? Whether you love the heat or the cold, if you're planning a trip here, it could be useful for you to know: July, has temperatures that can reach 27°C, it's the hottest month at this touristic destination. January instead is the coldest month, where temperatures can trop to -1°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.