Vacation Rentals & accomodation in Chicago

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

• from

  50€

  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

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• from

  42€

  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

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• from

  40€

  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

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• from

  43€

  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,

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• from

  28€

  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

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• from

  36€

  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,

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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

• from

  175€

  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

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• from

  17€

  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

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• from

  60€

  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.

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• from

  208€

  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

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• from

  345€

  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

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• from

  18€

  HI Chicago Hostel

  8.8 Fabulous (4891)

  • Hotel

  Chicago Loop is a great choice for travellers interested in parks, architecture and museums.

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The best places to stay in Chicago

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

• from

  45€

  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

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• from

  35€

  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

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• from

  45€

  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

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• from

  40€

  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

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• from

  45€

  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

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• from

  35€

  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

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Nearby cities

• Carlyle
• Algonquin
• Savoy
• Woodland Hills
• Highland Park
• Naperville