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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.

  • Spacious Serene En Suite, Incredible Loop Location
    SUPERHOSTPrivate room · 2 guests · 1 bed · 1 private bath
    Spacious Serene En Suite, Incredible Loop Location

    Located in the heart of everything, in a location guests rave about. Enjoy your own private bed/bath en suite in this shared apartment. Easy access to many tourist and conference destinations including McCormick Place (many are within walking distance or a short cab ride), restaurants, all train stops and many buses, both airports, salon/spas, coffee shops, convenience store, independent bookstore, night life, Millenium Park, Navy Pier, gas station, pay parking lot close by, and so much more.

    What guests are saying:

    “Anne was extremely helpful and hospitable. Any question or clarification we had was quickly responded to. This was one of the best equipped Airbnb’s I’ve been at, she had everything a guest could need. The apartment is kept very clean. The area is nice—walking distance from grocery stores, restaurants, and not even 15 minutes away from downtown. It was a great stay!”

  • 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!”

  • 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”

Holiday rentals for every style

Get the amount of space that is right for you.

  • Homes
  • Hotels
  • Unique stays

Popular amenities for Downtown Chicago holiday rentals

  • Kitchen
  • Wi-Fi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Downtown Chicago

Kasa | Chicago | Premiere 2BD/2BA South Loop Apartment
SUPERHOSTEntire apartment
Kasa | Chicago | Premiere 2BD/2BA South Loop Apartment
Price:$150 NZD / night
Sonder | Essex on the Park | Ideal 1BR + Pool
Entire apartment
Sonder | Essex on the Park | Ideal 1BR + Pool
Price:$237 NZD / night
Queen Room in River North Boutique Hotel
SUPERHOSTHotel room
Queen Room in River North Boutique Hotel
Price:$131 NZD / night
Gritty Chic River North + ACME Hotel
SUPERHOSTHotel room
Gritty Chic River North + ACME Hotel
Price:$166 NZD / night
Kinzie Hotel, Deluxe King Non-Smoking
Room in boutique hotel
Kinzie Hotel, Deluxe King Non-Smoking
Price:$148 NZD / night
Studio across from The Bean and Grant Park!
Entire apartment
Studio across from The Bean and Grant Park!
Price:$76 NZD / night
Chicago Chinatown great location(A)(中文房东)
SUPERHOSTPrivate room
Chicago Chinatown great location(A)(中文房东)
Price:$75 NZD / night
Spectacular Downtown High Rise Extraordinary view
Private room
Spectacular Downtown High Rise Extraordinary view
Price:$137 NZD / night
River North's Finest - Monthly Bookings Only
SUPERHOSTEntire apartment
River North's Finest - Monthly Bookings Only
Price:$202 NZD / night
Among Chicago's best known luxury high-rises
Entire apartment
Among Chicago's best known luxury high-rises
Price:$116 NZD / 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:$325 NZD / night
Old Town Pied a Terre with Private Terrace!
SUPERHOSTEntire condominium
Old Town Pied a Terre with Private Terrace!
Price:$214 NZD / night
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