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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.

  • Sonder | Essex on the Park | Ideal 1BR + Pool
    Entire apartment · 4 guests · 2 beds · 1 bath
    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.”

  • 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!”

  • Kasa | Chicago | Classy 2BD/2BA South Loop Apartment
    SUPERHOSTEntire apartment · 6 guests · 3 beds · 2 baths
    Kasa | Chicago | Classy 2BD/2BA South Loop Apartment

    Come relax in this luxury apartment professionally managed by Kasa. This apartment is well-connected to the Chicago scene you're seeking. Close to large companies and a short distance from Grant Park, a number of fantastic local restaurants, bars, and shopping options can also be found nearby. The property is fewer than two miles from McCormick Place and the Museum Campus. Key features include: • Luxurious king-size beds with memory foam mattresses • Queen-size sleeper sofa in living room • Modern, high-end kitchen where you can cook and enjoy wonderful cuisine • Ultra high-speed Internet • 24-hour health and fitness center • Gourmet coffee bar in the building • Controlled access • Night patrol for extra security • Outdoor lounges • Pet friendly — Enjoy your Kasa with your furry friend! • On-site dog park and designated dog walking areas Note: Pet fee of $15 per day will apply with a one-pet limit (dogs or cats only).

    What guests are saying:

    “Perfect stay! Clean, well designed and detailed. The views are incredible. You will watch the sun rise and set from immaculate windows. Walking distance to everything. We walked to dinner, breakfast, coffee and nightlife. If we didn’t walk, everything was a 10 minute Uber ride for about $8-$10. There is a target right next door, a dog park outside and a Trader Joe’s a 10 min walk away. Make sure to check out the pool room and balcony at sunset! We will be back.”

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

Amazing River and City Views 2+2 W/Balcony
SUPERHOSTEntire apartment
Amazing River and City Views 2+2 W/Balcony
Price:$399 / night
Zen Loft Downtown Chicago
SUPERHOSTEntire apartment
Zen Loft Downtown Chicago
Price:$667 / night
Stunning Old Town Penthouse with Private Rooftop
Entire loft
Stunning Old Town Penthouse with Private Rooftop
Price:$1,041 / 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:$367 / night
River North's Rock N Roll Airbnb
SUPERHOSTEntire apartment
River North's Rock N Roll Airbnb
Price:$304 / night
Luxury Apartment 2BR 2BA Highrise/Millenimun Park
SUPERHOSTEntire apartment
Luxury Apartment 2BR 2BA Highrise/Millenimun Park
Price:$400 / night
Domio | Navy Pier | Grand 3BR/2BA Apt + Fitness Center
SUPERHOSTEntire apartment
Domio | Navy Pier | Grand 3BR/2BA Apt + Fitness Center
Price:$492 / night
Luxury 2 Bedroom in the Heart of Chicago
SUPERHOSTEntire apartment
Luxury 2 Bedroom in the Heart of Chicago
Price:$201 / night
PENTHOUSE-3❤️Huge Downtown Loft (CDC Clean!)
SUPERHOSTEntire loft
PENTHOUSE-3❤️Huge Downtown Loft (CDC Clean!)
Price:$91 / night
Spacious Serene En Suite, Incredible Loop Location
SUPERHOSTPrivate room
Spacious Serene En Suite, Incredible Loop Location
Price:$52 / night
*COOL South Loop Loft 5 min to Downtown/McCormick
SUPERHOSTEntire loft
*COOL South Loop Loft 5 min to Downtown/McCormick
Price:$89 / night
Unwind in Style Steps from the Magnificent Mile
SUPERHOSTEntire apartment
Unwind in Style Steps from the Magnificent Mile
Price:$250 / night
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