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Vacation rentals in Chicago

Vacation rentals in Chicago

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Chicago

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

Modern Chicago Loft with a Complimentary Garage Spot
SUPERHOSTEntire apartment · 2 guests · 1 bed · 1 bath
Modern Chicago Loft with a Complimentary Garage Spot

Dine by the natural wood breakfast bar or on the rooftop deck. This classy loft boasts open-plan living, exposed brickwork and stunning artwork. Check out our other available listings within the same building by clicking below on our host profile.

What guests are saying:

“The place was super clean. Literally the cleanest airbnb I’ve ever stayed at. Super easy to check in and out. The hosts were also easy to get in contact with and they made sure to check in to see if everything was fine after we arrived. Would definitely stay again!”

Best in Chicago, private, amazing garden space
SUPERHOSTEntire apartment · 5 guests · 3 beds · 1 bath
Best in Chicago, private, amazing garden space

We offer the highest standards of cleanliness during the Covid-19 pandemic. Excellent workspace with fast wifi and beautiful outdoor deck and garden space to relax. The most popular Airbnb in Illinois (Buzzfeed, Aug. 2017). After 10 years hosting we still enjoy making our space a special place…as one reviewer commented, "The pictures don't really do justice to how beautiful the apartment is. I will miss having my morning coffee while overlooking the tranquil garden."

What guests are saying:

“Upon arrival we had no problem getting a parking space, out front and center which made it super easy to bring our luggage in. Checking in was a breeze, she does have recommendations for food grocery stores etc. if you don’t know the area. We ended up getting delivery from my pi pizza. ( it was decent but was kind of bummed they didn’t deliver the cheesecake and still charged me for it. ) We did stop at Kuma’s corner in Belmont say on the patio and enjoyed a brew with amazing burgers and Mac and cheese. Love this place ! The apartment was cleaned top notch. If you didn’t bring much on your stay there is pretty much everything you need, just bring drinks and snacks. The decor was eclectic and tastefully done. Also being Chicago the fact that they had a nice sitting area amongst their plants and fountain was nice. Several places to sit to enjoy coffee or wine. ( front window, kitchen nook outside on the patio or down low in their yard by the fountain) The yard is shared but they give you privacy if you are enjoying the outside area. The only downside of our trip was the timing, due to covid and some of the recent news happenings we didn’t experience the town as much as wanted, places being closed and safety measures. With that being said no reflection on their place if you plan to visit the area it’s a great apartment. Thank you for the stay best wishes to you.”

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

“Michael was an amazing host! The place was absolutely gorgeous, comfortable, and stylish. The rooftop deck was breathtaking. Michael was incredibly responsive, courteous, and had a lot of little details in the room. He also let us leave our luggage after check out so that we can continue exploring the city without having to take our luggage. Thank you!”

Holiday rentals for every style

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Popular amenities for Chicago holiday rentals

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

Other great holiday rentals in Chicago

Industrial Style Chicago Loft with FREE parking
SUPERHOSTEntire loft
Industrial Style Chicago Loft with FREE parking
Price:$119 NZD / night
Hip Chicago Apartment - FREE Parking Spot Included
SUPERHOSTEntire apartment
Hip Chicago Apartment - FREE Parking Spot Included
Price:$101 NZD / night
LUX 1BR/1BA Top-Floor Unobstructed Downtown Views
SUPERHOSTEntire apartment
LUX 1BR/1BA Top-Floor Unobstructed Downtown Views
Price:$236 NZD / night
Luxury Chicago Loft, 1 blk to train w/ 2 pkg spots
SUPERHOSTEntire loft
Luxury Chicago Loft, 1 blk to train w/ 2 pkg spots
Price:$216 NZD / night
Explore Chicago from an Urban Sanctuary with Free Parking
SUPERHOSTEntire apartment
Explore Chicago from an Urban Sanctuary with Free Parking
Price:$93 NZD / night
Enjoy Chicago’s Nightlife from Studio Apartment
SUPERHOSTEntire apartment
Enjoy Chicago’s Nightlife from Studio Apartment
Price:$93 NZD / night
Cozy and Stylish Studio with Free Parking in Irving Park
SUPERHOSTEntire apartment
Cozy and Stylish Studio with Free Parking in Irving Park
Price:$84 NZD / night
Walk to Lake Michigan From a Contemporary Uptown Haven
SUPERHOSTEntire apartment
Walk to Lake Michigan From a Contemporary Uptown Haven
Price:$75 NZD / night
Stunning Retro Apartment in Andersonville
SUPERHOSTEntire apartment
Stunning Retro Apartment in Andersonville
Price:$140 NZD / night
Traveler's Dream - 1 bed in a shared bedroom
Hotel room
Traveler's Dream - 1 bed in a shared bedroom
Price:$53 NZD / night
Great Place Garfield Park 3 Bedroom
SUPERHOSTEntire apartment
Great Place Garfield Park 3 Bedroom
Price:$53 NZD / night
Feel at Home in Chicago, with Parking, Steps from Evanston
SUPERHOSTEntire house
Feel at Home in Chicago, with Parking, Steps from Evanston
Price:$131 NZD / night
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