Choose the right place for you


  • 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

  • Cozy room in a Charming Coach House

    10 Exceptional (93)
    • 2 Guests · 1Bedroom
    This apartment is actually a small house that sits behind an apartment building. With high ceilings, modern appliances, & an open floor plan, this newly renovated space has a cozy and chic feeling, thoughtfully
  • Master Suite and Bathroom in Wicker Park

    10 Exceptional (200)
    • 3 Guests · 1Bedroom
    Enjoy your home away from home in this spacious 3 bedroom 2 bath condo at the crossroads of Bucktown and Wicker Park. Close to bars, restaurants, boutiques, cafes, and grocery stores, as well as public
  • Cozy private room on Chicago's west side

    10 Exceptional (163)
    • 2 Guests · 1Bedroom
    Come stay in a budding west side neighborhood! The place is close to the beautiful Humbolt Park and within walking distance of dozens of bars, cafes and restaurants like, Sportsman's Club, The California
  • Vintage Logan Square Bedroom

    10 Exceptional (181)
    • 2 Guests · 1Bedroom
    We are located in the heart of Logan Square, two blocks from the California Blue Line train station. This is the first of two rooms listed on airbnb at this property. Your humble hosts are an artist couple,
  • Trendy. Safe. Convenient to CTA

    10 Exceptional (111)
    • 1 Guest · 1Bedroom
    I'm lucky to live in a fantastic Lincoln Park location that is central to everything Chicago has to offer. Shopping, check. Dining, check. Nightlife, check. Bed, check. I live next door to the train. You
  • In the heart of Pilsen's art community.

    10 Exceptional (81)
    • 2 Guests · 1Bedroom
    My place is very close to downtown and the Lakefront. Uber and Lyft cab service arrives within 5 minutes, Divvy bikes 1 block away. My neighborhood is the new hot spot, A mix of artists Mexican's and hipsters,

Save on Bed & Breakfast in Chicago

Are you looking for an accommodation in Chicago and do you want to save money? Choose from 57 Bed & Breakfasts in Chicago

  • Sonder — Armitage Suite

    9.4 Exceptional (11)
    • Hotel
    Three-Bedroom on W Armitage Avenue Apt B offers accommodation in Chicago, 0.9 miles from Lincoln Park Zoo and 2.5 miles from Wrigley Field. The accommodation is 2.5 miles from the 360 Chicago and features
  • Holiday Jones

    8.5 Fabulous (731)
    • Hotel
    Located on Division Street in the heart of Chicago's Wicker Park neighborhood, this hostel offers rooms with free WiFi and an on-site lounge. Offering a true Chicago experience, the hostel is located near
  • Private Queen Room in a Boutique Hotel

    10 Exceptional (15)
    • Hotel
    Sleeping one or two guests, this spacious room offers one Queen bed, free Wi-Fi, complimentary toiletries, cable TV, iron and ironing board, hairdryer, and in-room safe.
  • 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
  • HI Chicago Hostel

    8.8 Fabulous (4891)
    • Hotel
    Chicago Loop is a great choice for travellers interested in parks, architecture and museums.

The best places to stay in Chicago

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

  • 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
  • Master Bedroom, Heart of Wicker Park

    10 Exceptional (171)
    • 2 Guests · 1Bedroom
    Large 4 bedroom located on Milwaukee Ave., half a block from Wicker Park's Six Corners. Live music, art, night life, amazing food all outside your door. Blue line stop half a block away. Shared unit with
  • Private Rm in Artist Apartment near Wicker Park

    10 Exceptional (108)
    • 2 Guests · 1Bedroom
    Our place is a recently rehabbed, fully updated 2 bedroom flat in a 3 floor grey stone with secure entry. Nice new wood floors throughout unit, kitchen includes marble counter tops, a breakfast nook, and
  • Historic Brownstone in Lincoln Park

    10 Exceptional (130)
    • 6 Guests · 2Bedrooms
    Prime Location! Brownstone in North Lincoln Park / South Lakeview, 2nd floor unit with high ceilings and tons of sunlight. Two bedrooms with queen beds, living room with pull out couch/queen size with
  • Private Studio in Bridgeport, Chicago

    10 Exceptional (84)
    • 2 Guests · 0Bedroom
    A bright studio guesthouse, perfect for business travelers, a couples getaway, personal retreat, or a solo adventurer. Equipped with a kitchenette that includes cabinet space for your non-perishable
  • 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

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