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Vacation rentals in Downtown Chicago

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.

  • Queen Room in River North Boutique Hotel
    SUPERHOSTHotel room · 2 guests · 1 bed · 1 bath
    Queen Room in River North Boutique Hotel

    My place is close to Magnificent Mile, Water Tower Place, Museum of Contemporary Art, Signature Lounge, Signature Room At the 95th.. You’ll love my place because of the ambiance. My place is good for couples, solo adventurers, business travelers, families (with kids), and big groups.

    What guests are saying:

    “You can expect a clean room and well-maintained building. The building was quiet during my stay, which was helpful in getting a quality night’s sleep. Despite being located near elevated train tracks, I barely recognized the sound of trains speeding by. FieldHouse Jones is in an ideal location. It is near the Mag Mile, Gold Coast, Old Town, and a quick drive to Lincoln Park. Overall, I enjoyed my stay. I recommend anyone visiting Chicago who loves sports or trendy, modern spaces to consider booking a stay at FieldHouse Jones!”

  • Shared Artist Loft Own Private Room
    SUPERHOSTPrivate room · 3 guests · 2 beds · 1 private bath
    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:

    “Second time with Michael. This time I checked into his house speakeasy style. Art everywhere and everything you would expect from an artist.lookout..you might end up stepping into an old record.or piece of high historic value.here and there Clean and respectful of privacy Prepare to workout on the stairs up the loft ,but you will be rewarded by the rooftop view..and the many graceful plants everywhere. Will be back again”

  • LUX 1BR/1BA Top-Floor Unobstructed Downtown Views
    SUPERHOSTEntire apartment · 3 guests · 2 beds · 1 bath
    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:

    “Loved this location it was right in the heart of downtown ChiTown and very close to the water! The place is very stylist and you have an amazing view of the city. I appreciate the quick responses from our host and how easy the check in instructions were. I definitely recommend this Airbnb and the value was great!”

Vacation rentals for every style

Get the amount of space that is right for you.

  • Homes
  • Hotels
  • Unique stays

Popular amenities for Downtown Chicago vacation rentals

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

Other great vacation rentals in Downtown Chicago

Sonder | Essex on the Park | Ideal 1BR + Pool
Entire apartment
Sonder | Essex on the Park | Ideal 1BR + Pool
Price:$399 CAD/night
Cozy room off Chinatown - steps from the Line!
SUPERHOSTPrivate room
Cozy room off Chinatown - steps from the Line!
Price:$81 CAD/night
Enjoy city & lake views from this suite w/ shared pool, gym, sauna, & basketball
SUPERHOSTEntire condominium
Enjoy city & lake views from this suite w/ shared pool, gym, sauna, & basketball
Price:$253 CAD/night
Spacious Serene En Suite, Incredible Loop Location
SUPERHOSTPrivate room
Spacious Serene En Suite, Incredible Loop Location
Price:$69 CAD/night
River North's Finest - Monthly Bookings Only
SUPERHOSTEntire apartment
River North's Finest - Monthly Bookings Only
Price:$179 CAD/night
*COOL South Loop Loft 5 min to Downtown/McCormick
SUPERHOSTEntire loft
*COOL South Loop Loft 5 min to Downtown/McCormick
Price:$115 CAD/night
River North Grand Plaza suite w/ lake view, balcony! Shared pool, gym, game room
SUPERHOSTEntire condominium
River North Grand Plaza suite w/ lake view, balcony! Shared pool, gym, game room
Price:$399 CAD/night
Female Only  - 1 Bed in a Shared Bedroom
Hotel room
Female Only - 1 Bed in a Shared Bedroom
Price:$53 CAD/night
Kinzie Hotel, Deluxe, Two-Queens, Non-Smoking
Room in boutique hotel
Kinzie Hotel, Deluxe, Two-Queens, Non-Smoking
Price:$174 CAD/night
Kasa | Chicago | Premiere 2BD/2BA South Loop Apartment
SUPERHOSTEntire apartment
Kasa | Chicago | Premiere 2BD/2BA South Loop Apartment
Price:$286 CAD/night
Spectacular Downtown High Rise Extraordinary view
Private room
Spectacular Downtown High Rise Extraordinary view
Price:$126 CAD/night
Sonder | Essex on the Park | Sleek 1BR + View
Entire apartment
Sonder | Essex on the Park | Sleek 1BR + View
Price:$402 CAD/night
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