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Vacation rentals in Downtown Chicago

Vacation rentals in Downtown Chicago

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Downtown Chicago

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

Shared Artist Loft Own Private Room
SUPERHOSTPrivate room · 3 guests · 2 beds · 1 shared bathroom
Shared Artist Loft Own Private Room

Note: Check-in is at noon. Note: we have upgraded our Wi-Fi to the very best. Our Wi-Fi now reaches all rooms at the highest speeds. Thank you. NOTE: If the date your looking for is already booked i have another beautiful room listed under, SHARED artist loft very unique. you may be able to book the date you need under that listing so look for it. Also we have an authentic Chicago speakeasy being restored just around the corner, listed as authentic Chicago speakeasy. Thank you. There is an additional $50 fee per person for the third and fourth person staying in the room. SUNNY 4th floor artist loft. In the Middle of River North Chicago. Minutes from everything. 60 ft outdoor deck, kitchen, private bedroom with king bed and a twin bed in the room, a full bed can be added WiFi. IT IS A 4 floor WALK UP. You must be able to WALK UP. Enjoy.

What guests are saying:

“Michael was an amazing host! The place was absolutely gorgeous, comfortable, and stylish. The rooftop deck was breathtaking. Michael was incredibly responsive, courteous, and had a lot of little details in the room. He also let us leave our luggage after check out so that we can continue exploring the city without having to take our luggage. Thank you!”

LUX 1BR/1BA Top-Floor Unobstructed Downtown Views
SUPERHOSTEntire flat · 3 guests · 2 beds · 1 bathroom
LUX 1BR/1BA Top-Floor Unobstructed Downtown Views

AIRBNB SUPERHOST W/ OVER 600 REVIEWS (PLEASE SEE OTHER LISTINGS) Better views than any hotel! Top-floor, high-rise Apt above the clouds in the heart of Downtown blocks from Michigan Ave (Magnificent Mile), Navy Pier, The Bean, & ALL of Downtown's Top Hotels, Bars, & Restaurants. RIVER NORTH/STREETERVILLE/GOLD COAST considered one of safest & most beautiful in Chicago Condo over 800 sq. ft feat. Luxury Jr. 1 bedroom, open space & unique character. 3rd guest has twin daybed in living area.

What guests are saying:

“This place is awesome! The location is an obvious perk, but the space itself is also beautifully decorated and cozy. The view was breathtaking at night, but I loved the bright sunlight coming into the apartment in the morning as well. Coming back to such a homey and clean apartment after a full day of Chicago activities was so relaxing. Definitely will be booking this spot again for our next trip to Chicago!”

Traveler's Dream - 1 bed in a shared bedroom
Hotel room · 1 guest · 4 beds · 1 bathroom
Traveler's Dream - 1 bed in a shared bedroom

Join us at Freehand Chicago Hotel for your travels in Chicago. Perfect for travelers here too long for a traditional hotel or for just 1 night; make us your home away from home. This listing is for one bunk for one person in a shared mixed/co-ed room with 4 bunks (up to 3 roommates). We have many options such as private standard rooms and private quad rooms. Please send us a message with any questions. $2 nightly resort fee

What guests are saying:

“Freehand is great for the price and location. Literally in the heart of Chicago. Stylish lobby, very kind staff. Clean, organized. I was a little upset to find out there wasn’t going to be a kitchen available to guests because of renovation, but that’s understandable. Will book again when I come back.”

Holiday rentals for every style

Get the amount of space that is right for you.

  • Homes
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  • Unique stays

Popular amenities for Downtown Chicago holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Downtown Chicago

Sonder | Spacious 1BR in South Loop Near Trader Joe's
Entire flat
Sonder | Spacious 1BR in South Loop Near Trader Joe's
Price:$ 545 SGD / night
Stunning Old Town Penthouse with Private Rooftop
PLUSEntire loft
Stunning Old Town Penthouse with Private Rooftop
Price:$ 1,305 SGD / night
Hotel Perks - Private Bedroom | Private Bathroom
Hotel room
Hotel Perks - Private Bedroom | Private Bathroom
Price:$ 135 SGD / night
Metropolitan En Suite with Exceptional Loop Access
SUPERHOSTPrivate room
Metropolitan En Suite with Exceptional Loop Access
Price:$ 81 SGD / night
Great location.
SUPERHOSTEntire flat
Great location.
Price:$ 117 SGD / night
Zen Loft Downtown Chicago
SUPERHOSTEntire flat
Zen Loft Downtown Chicago
Price:$ 786 SGD / night
Unique Lincoln Park Duplex Apt
SUPERHOSTEntire apartment
Unique Lincoln Park Duplex Apt
Price:$ 162 SGD / night
Great Location Studio III
SUPERHOSTEntire flat
Great Location Studio III
Price:$ 81 SGD / night
Cozy 2BR-2BA a block away from Millenium Park
Entire flat
Cozy 2BR-2BA a block away from Millenium Park
Price:$ 157 SGD / night
Spectacular Downtown High Rise Extraordinary view
Private room
Spectacular Downtown High Rise Extraordinary view
Price:$ 126 SGD / night
*COOL South Loop Loft 5 min to Downtown/McCormick
SUPERHOSTEntire loft
*COOL South Loop Loft 5 min to Downtown/McCormick
Price:$ 129 SGD / night
SHARED Artist Loft . Very Unique
SUPERHOSTPrivate room
SHARED Artist Loft . Very Unique
Price:$ 130 SGD / night
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