Skip to content

Vacation rentals in Downtown Chicago

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Downtown Chicago

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

Private room in Chicago
Remote Workers Dream - Private Bath and Workspace
Are you a professional remote worker or a digital nomad looking to explore Chicago? If so I made this listing for you! Welcome to my home one block from the Blue Line which runs 24/7 downtown and to O'Hare and a straight shot to Wrigley Field. You will have a clean cozy room, a private renovated bathroom, and a SECOND light-filled room to work or relax with a desk, chair, and TV. I live across from a beautiful park and have a backyard for BBQs and chilling. High-speed WIFI for your work!
$61 per night
SUPERHOST
Private room in Chicago
Logan Square Vintage Deluxe Private Suite & Bath
A private vintage haven - bedroom, bath and living space - in the heart of Logan Square. Surrounded by great shopping, food, cafes and bars, with easy travel to downtown. We follow the Airbnb guidelines for enhanced cleaning, and expect you are vaccinated, to ensure a safe visit for all. Kitschy and cool, cozy and comfortable - a walk up, second floor, private suite in a classic Chicago Victorian frame house on a quiet neighborhood street. A small, separate entry space that's all yours.
$91 per night
SUPERHOST
Private room in Chicago
A+ location by Mag Mile, views, large sunny room
Unbeatable location next to Water Tower Place, with lots of natural light and partial lake view in a quiet vintage building with lots of character. Walk to nearly any attraction in central Chicago. Apartment is shared with single host (covid-vaccinated), happy to help with sightseeing advice and discounts on popular tourist attractions. (Guests love: Location, View, Comfortable room and bed, Friendly/respectful host, Flexible luggage policy, fast wifi)
$89 per night
SUPERHOST

Other great vacation rentals in Downtown Chicago

Private room in Chicago
Private BR in Condo close to Chicago Dwtwn!
$91 per night
SUPERHOST
Private room in Chicago
British Themed Room in the Middle of Boystown
$78 per night
SUPERHOST
Private room in Chicago
Spacious & Relaxing Loft in Awesome Andersonville!
$81 per night
SUPERHOST
Private room in Chicago
⭐️ Master Bedroom near Train, Grocery & Nightlife ⭐️
$53 per night
SUPERHOST
Private room in Chicago
Great room, private bathroom, awesome location!
$54 per night
SUPERHOST
Private room in Chicago
ChicagoRiver Double Room (+Complimentary BIKES)
$75 per night
SUPERHOST
Private room in Chicago
The Sweet!
$76 per night
SUPERHOST
Private room in Chicago
⭐️ Comfy Bedroom by Downtown, Train; Rooftop! ⭐️
$53 per night
SUPERHOST
Private room in Chicago
#4 Historic Chicago Home - Private Single Bedroom
$55 per night
Private room in Chicago
Modern, Super-CLEAN, Garden Level Bedroom 3
$39 per night
SUPERHOST
Rental unit in Chicago
*CHI-City Getaway- Expanding Views!*
$191 per night
SUPERHOST
Private room in Chicago
Private Bathroom. XL Top Floor. Ideal Location!
$120 per night
SUPERHOST
  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Downtown Chicago