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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 bathroom
    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!”

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

    “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”

  • Chicago chinatown great location(B) (中文房东)
    SUPERHOSTPrivate room · 2 guests · 1 bed · 1 shared bathroom
    Chicago chinatown great location(B) (中文房东)
    What guests are saying:

    “Ming's house is great to stay while visiting Chicago. She is super friendly and her family too. The bed is very comfortable and you have access to everything, including the washer and dryer. A 7-minute walk is the "Red line" train station that will leave you downtown in a few stops. Patch to anyone staying here”

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

Queen Room in River North Boutique Hotel
SUPERHOSTHotel room
Queen Room in River North Boutique Hotel
Price:₹6,664 / night
Guest Bedroom at White Walls
SUPERHOSTPrivate room
Guest Bedroom at White Walls
Price:₹2,307 / night
Gritty Chic River North + ACME Hotel
SUPERHOSTHotel room
Gritty Chic River North + ACME Hotel
Price:₹8,281 / night
LUX 1BR/1BA Top-Floor Unobstructed Downtown Views
SUPERHOSTEntire flat
LUX 1BR/1BA Top-Floor Unobstructed Downtown Views
Price:₹12,181 / night
Cozy room off Chinatown - steps from the Line!
SUPERHOSTPrivate room
Cozy room off Chinatown - steps from the Line!
Price:₹4,464 / night
Cute, clean 1 bedroom in shared apt (w cats!)
SUPERHOSTPrivate room
Cute, clean 1 bedroom in shared apt (w cats!)
Price:₹1,595 / night
*COOL South Loop Loft 5 min to Downtown/McCormick
SUPERHOSTEntire loft
*COOL South Loop Loft 5 min to Downtown/McCormick
Price:₹6,590 / night
Great Location Studio in the Gold Coast!!
SUPERHOSTEntire flat
Great Location Studio in the Gold Coast!!
Price:₹4,496 / night
Spectacular Downtown High Rise Extraordinary view
Private room
Spectacular Downtown High Rise Extraordinary view
Price:₹7,334 / night
River North's Finest - Monthly Bookings Only
SUPERHOSTEntire flat
River North's Finest - Monthly Bookings Only
Price:₹9,821 / night
Kasa | Chicago | Premiere 2BD/2BA South Loop Apartment
SUPERHOSTEntire flat
Kasa | Chicago | Premiere 2BD/2BA South Loop Apartment
Price:₹12,978 / night
Staypineapple Chicago, Deluxe King
SUPERHOSTRoom in boutique hotel
Staypineapple Chicago, Deluxe King
Price:₹8,110 / night
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