Holiday rentals in Chicago

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Top-rated holiday rentals in Chicago

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Superhost

Private room in River North

Artist Loft, Private Room

Beautiful shared artist loft space with private room. Located on the top floor of a building built in the early 1900s, enjoy a unique experience in the heart of River North/downtown Chicago. Our One-of-a-kind rooftop garden is a must-see during Summer/early Fall. This space is ideal for socializing. NOTE: Includes 4.5-story walkup, NO ELEVATOR. No exterior window in bedroom, interior window only. ALREADY BOOKED??? If room is unavailable, check out my profile to see our other listings!

$164 SGD per night

Superhost

Private room in River North

Chicago Speakeasy-Style Loft Space (Room 3A)

Welcome to our Chicago Speakeasy-style loft space. Built in the early 1900s, our two-floor loft provides a unique experience in the heart of River North/downtown Chicago. Centrally located River North Chicago is a go-to district with lively night scene, and a wide variety of restaurants, bars and clubs. There are many public transit stations within walking distance. ALREADY BOOKED??? If this room is unavailable, check out my profile to see our other listings! Feel free to message me!

$154 SGD per night

Superhost

Private room in Lake View

Bright Room with a Garden View

This room is bright, cozy and offers a view of the garden and off the main street in Boystown, Chicago. The room has a queen bed, tv and small closet. This is a shared bathroom with two other rooms, there is a shared refrigerator on the floor and coffee just outside the room. On the main floor is a shared kitchen, living room and dining room. Wifi all throughout the house. Complimentary continental breakfast is provided in the morning. Parking info below

$114 SGD per night