Skip to content
Sign up
Log in
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.

  • 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:

    “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!”

  • Sonder | Essex on the Park | Ideal 1BR + Pool
    Entire flat · 4 guests · 2 beds · 1 bathroom
    Sonder | Essex on the Park | Ideal 1BR + Pool

    Whether you're traveling or staying locally, we want everyone to have a comfortable place to stay. Our contactless check-in and the ability to manage your stay from our app means you won't need to interact with anyone in person. Our cleaning professionals have been trained in proper disinfection techniques and will deep clean your Sonder before and after your stay. To protect your safety, building amenities are subject to availability and may be temporarily closed. Please check the “other things to note” section for specific updates about this building. If you need something, we can be reached 24/7 via text or phone. Named the most innovative travel company of 2019 by Fast Company, Sonder has hosted a million guests in 5,000+ spaces with an average rating of 4.6 stars. Each space is designed and run by us, so you’ll always know what to expect from your stay. - 24/7 virtual support via text, email, or phone - Self check-in - Private all-in-one living spaces - Coffee, fresh towels, and bathroom essentials provided - Enhanced cleaning before you arrive - Utilities included for short and long-term stays

    What guests are saying:

    “We had a terrific stay in this modern, open apartment. The interior is stylish and super clean and the views from the floor to ceiling windows were amazing, from sunrise to moon rise over the lake. The neighborhood has plenty to offer and was fairly quiet when we were there. It is a walk to the more central parts of the city but we did not mind that. Check in and out couldn't have been easier.”

  • 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”

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

Other great holiday rentals in Downtown Chicago

Metropolitan En Suite with Exceptional Loop Access
SUPERHOSTPrivate room
Metropolitan En Suite with Exceptional Loop Access
Price:€44 / night
Queen Room in River North Boutique Hotel
SUPERHOSTHotel room
Queen Room in River North Boutique Hotel
Price:€76 / night
Kasa | Chicago | Premiere 2BD/2BA South Loop Apartment
SUPERHOSTEntire flat
Kasa | Chicago | Premiere 2BD/2BA South Loop Apartment
Price:€102 / night
Spectacular Downtown High Rise Extraordinary view
Private room
Spectacular Downtown High Rise Extraordinary view
Price:€80 / night
Enjoy city & lake views from this suite w/ shared pool, gym, sauna, & basketball
SUPERHOSTEntire apartment
Enjoy city & lake views from this suite w/ shared pool, gym, sauna, & basketball
Price:€239 / night
*COOL South Loop Loft 5 min to Downtown/McCormick
SUPERHOSTEntire loft
*COOL South Loop Loft 5 min to Downtown/McCormick
Price:€84 / night
Gritty Chic River North + ACME Hotel
SUPERHOSTHotel room
Gritty Chic River North + ACME Hotel
Price:€97 / night
River North's Rock N Roll Airbnb
SUPERHOSTEntire flat
River North's Rock N Roll Airbnb
Price:€266 / night
Stunning Old Town Penthouse with Private Rooftop
SUPERHOSTEntire loft
Stunning Old Town Penthouse with Private Rooftop
Price:€776 / night
Chicago Chinatown great location(A)(中文房东)
SUPERHOSTPrivate room
Chicago Chinatown great location(A)(中文房东)
Price:€44 / night
Old Town Pied a Terre with Private Terrace!
SUPERHOSTEntire apartment
Old Town Pied a Terre with Private Terrace!
Price:€126 / night
Luxury Apartment 2BR 2BA Highrise/Millenimun Park
SUPERHOSTEntire flat
Luxury Apartment 2BR 2BA Highrise/Millenimun Park
Price:€311 / night
Show all