Vacation rentals in Chicago

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Top-rated holiday rentals in Chicago

Guests agree: these stays are highly rated for location, cleanliness, and more.

SUPERHOST
  1. Private room
  2. Wicker Park
Spacious & Charming Private Room in Wicker Park

The apartment is wonderfully spacious, bright, and airy with soaring seven-foot windows. The place is kept clean, tidy, and organized. All the amenities for a comfortable stay are provided (see list). This “Shared Listing” is a value option where you save costs by sharing common area space with other guests staying in separate lockable bedrooms. Also, the building is conveniently located in a vibrant part of Wicker Park close to the train station giving easy access to other areas of Chicagoland.

  1. Entire rental unit
  2. East Rogers Park
Short-Term Sublet Near Lake Michigan

I used to be a live-in host, but since the pandemic I host visitors while I'm away traveling, so you will have the place all to yourself! The guestroom is SUNNY & peaceful, with balcony overlooking a lush yard, set back from street = QUIET. Available for 3-6 week stays. Equivalent to a large studio apartment + kitchen + bath. 1 block from Loyola U., 3 blocks to CTA Red Line train, 4 blocks to beaches! Second floor walk-up, bed is a full-sized FUTON (firm Japanese mattress).

SUPERHOST
  1. Private room
  2. West Town
Stylish & Ample 1PBR STAYCATION SPACE For You

The apartment is wonderfully spacious, bright, and airy with soaring seven-foot windows that have an amazing view of downtown. The place is kept clean, tidy, and organized. All the amenities for a comfortable stay are provided (see list). This “Shared Listing” is a value option where you save costs by sharing common area space with other guests staying in separate lockable bedrooms. Also, the building is conveniently located near the train station giving easy access to other areas of Chicagoland

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Other great holiday rentals in Chicago

SUPERHOST
  1. Private room
  2. Austin
Little Farm in the City Back Bedroom
SUPERHOST
  1. Private room
  2. McKinley Park
Downtown Chicago 8 minutes away SELF CHECK IN
  1. Entire rental unit
  2. Bridgeport
1 Bedroom Apartment by McCormick Place & Chinatown
SUPERHOST
  1. Private room
  2. Oak Park
warm comfortable home with lots to offer
SUPERHOST
  1. Private room
  2. River North
Restoring Chicago speakeasy of the 1920s room 3A
  1. Private room
  2. Woodlawn
Master Bedroom in Spacious and Comfy Chicago Condo
  1. Private room
  2. Lake View
Contemporary, private suite w fireplace
  1. Private room
  2. Near West Side
Cozy room in newly finished ultra modern aptmnt.
SUPERHOST
  1. Private room
  2. Wicker Park
Spacious & Bright Private Room in Wicker Park
SUPERHOST
  1. Private room
  2. West Town
Stylish & Bright 1PBR STAYCATION SPACE For You
SUPERHOST
  1. Private room
  2. Chinatown
Hotel quality private room near downtown RedLine
  1. Private room
  2. Little Italy
PRIVATE ROOM 5 minutes to the City