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Vacation rentals in Chicago Loop

Vacation rentals in Chicago Loop

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Chicago Loop

Guests agree: these stays are highly rated for location, cleanliness, and more.

  • Metropolitan En Suite with Exceptional Loop Access
    SUPERHOSTPrivate room · 2 guests · 1 bed · 1 private bathroom
    Metropolitan En Suite with Exceptional Loop Access

    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 tourist- and conference-friendly destinations including McCormick Place (many 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:

    “The apartment was super well located, right in downtown Chicago. We were at a walking distance to all tourist points of interest. The bedroom was very comfortable, as was the bathroom. All the apartment was very clean. I never saw Anne, but her instructions were very clear for check in and check out, as well as for entering and leaving the apartment. I would definitely stay there again on some other trip to Chicago.”

  • 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”

  • Kasa | Chicago | Classy 2BD/2BA South Loop Apartment
    SUPERHOSTEntire flat · 6 guests · 3 beds · 2 bathrooms
    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.”

Holiday rentals for every style

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Popular amenities for Chicago Loop holiday rentals

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

Other great holiday rentals in Chicago Loop

Hidden downtown Gem
Entire flat
Hidden downtown Gem
Price:€75 / night
Studio across from The Bean and Grant Park!
Entire flat
Studio across from The Bean and Grant Park!
Price:€44 / night
Cute, clean 1 bedroom in shared apt (w cats!)
SUPERHOSTPrivate room
Cute, clean 1 bedroom in shared apt (w cats!)
Price:€16 / night
Sonder | Essex on the Park | Ideal 1BR + Pool
Entire flat
Sonder | Essex on the Park | Ideal 1BR + Pool
Price:€240 / night
Staypineapple Chicago, Deluxe King
SUPERHOSTRoom in boutique hotel
Staypineapple Chicago, Deluxe King
Price:€97 / night
Among Chicago's best known luxury high-rises
Entire flat
Among Chicago's best known luxury high-rises
Price:€72 / night
Cozy room off Chinatown - steps from the Line!
SUPERHOSTPrivate room
Cozy room off Chinatown - steps from the Line!
Price:€53 / night
Queen Room in River North Boutique Hotel
SUPERHOSTHotel room
Queen Room in River North Boutique Hotel
Price:€82 / night
Be Inspired in a Modernist, Creative, Light-Filled Loft
SUPERHOSTEntire loft
Be Inspired in a Modernist, Creative, Light-Filled Loft
Price:€86 / night
Kinzie Hotel, Deluxe King Non-Smoking
Room in boutique hotel
Kinzie Hotel, Deluxe King Non-Smoking
Price:€103 / night
Gritty Chic River North + ACME Hotel
SUPERHOSTHotel room
Gritty Chic River North + ACME Hotel
Price:€99 / night
LUX 1BR/1BA Top-Floor Unobstructed Downtown Views
SUPERHOSTEntire flat
LUX 1BR/1BA Top-Floor Unobstructed Downtown Views
Price:€156 / night
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