Chicago’s ideal location on Lake Michigan provides the metropolis with a dramatic cityscape that visitors admire. Bold architecture dominates the bustling skyline, adding to the city’s beauty. One of the most iconic of them is the 100-story John Hancock Center in the Magnificent Mile district, which has an observation deck - offering the most magical view of the city. Willis Tower also affords panoramic city views from its 103rd-floor deck. For travelers with an interest in art and culture, exploring the renowned Art Institute of Chicago is a must. You can also enjoy a family day at Millennium Park. If you’re into fabulous, over-the-top vacation rentals that guarantee a luxurious stay, browse through this list of the top Airbnb mansions in Chicago, Illinois, for a memorable holiday.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on April 14, 2024.
1. Idyllic Victorian mansion in Irving Park neighborhood (from USD 1286)
If you wish to experience a luxurious holiday in Chicago, this 20th-century Victorian mansion is the perfect home away from home for you. Surrounded by lush greenery, it showcases an idyllic entrance that will make you feel connected with nature. This property in Irving Park neighborhood is perfect for big groups, and guests are allowed to bring one canine companion, as well. From a well-appointed kitchen with stainless appliances and stone countertops to bathrooms with bathtubs, functional and visually pleasing amenities are in store for guests. You’ll also love the dining room, equipped with a wooden dining set and a beautiful chandelier.
While the porch is perfect for morning coffee and people-watching, the backyard is ideal for cookouts.
Chicago, Illinois, United States
9.9 km (6.2 mi) from 875 North Michigan AvenueAccommodates: 14
Top guest reviews
Amenities & Room:
absolutely gorgeous kitchen with all the amenities you need to cook a big dinner with friendsCleanliness:
the house is beautiful and clean with a rich historyeasy street parking clean great decor very comfortablegreat stay the place was clean and cozy and nicoll was a great hostHost:
nicoll was a great hostRead more reviewsLocation:
great location and beautiful housegreat location-my kids walked to the blue line for a visit downtowna great place to stay very close to hot spots and in a nice neighborhoodnicoll's property is in the perfect location for any group visiting chicagothe place is huge and was well suited for our large family gathering
2. High-end Tudor property with alfresco dining
This upscale manor will truly make you feel like royalty. While it exudes an old-world charm from the outside, this Tudor home has undergone renovations to take its place in the modern world - with up-to-date pleasures. From the wooden floors (with underfloor heating) to gorgeous chandeliers, high-end details add luxury to the interiors. Besides being aesthetically pleasing, the kitchen is functional, with a breakfast counter, a dining set, and modern appliances. Bathrooms are spotless, and since they’re drenched in white, you can tell they’re sparklingly clean.
You’ll love having picnics in the premise’s outdoor space, with alfresco dining, a gas grill, and shady trees.
Chicago, Illinois, United States
11.25 km (7.0 mi) from 875 North Michigan AvenueSuperhost
Accommodates: 8
Top guest reviews
Amenities & Room:
we also appreciated that she stocked the kitchen with some foodliving room is comfortabletruly beautiful accommodations with spacious roomsCleanliness:
the house was super clean and bright and cheerythis home is so clean beautiful and invitingthe house was well stocked and clean and we all had lots of spaceclean comfortable stylish and very close to uchicago campusHost:
caryl is a great hostcaryl is a wonderful hosthost is host is very responsive and helpfulthis large home is great to host multiple generations of familycaryl is a pleasant and kind lady with a lovely home at a great neighborhoodRead more reviewsLocation:
beautiful home located in a quiet neighborhood near the university of chicago amazing restaurants and tourist locationseasy to walk to downtown area of hyde parkthe house is beautiful in a wonderful locationvery easy to park on the street out frontwe loved staying close to great restaurants on 53rd and 55th
3. Beautifully decorated abode with a formal dining room (from USD 850)
This stunning restored mansion showcases timeless beauty, appealing to Instagram-savvy vacationers and meticulous travelers. The luxurious abode showcases all-white furnishings, the perfect canvas sporting rustic touches, leather furniture, and vibrant decor. While the indoors provide a well-equipped kitchen, a formal dining area, and a family room, the backyard boasts a barbecue area and a fire pit that invites you to a night of stargazing and s'mores.
Since WiFi is available here, you can easily stay connected with your colleagues if need be.
Chicago, Illinois, United States
7.82 km (4.9 mi) from 875 North Michigan AvenueAccommodates: 16
Top guest reviews
Amenities & Room:
it had everything we could ever need including some welcome snacks (and air conditioning )all the rooms were warm and invitingwe used 7 of the 9 bedrooms and it was perfectly comfortableour 4 children happily played in the game room on 3rd floorwe were able to cook a huge meal for our reunion to enjoy around the grand dining tableCleanliness:
it was immaculately clean and there was plenty of space for everyone to stretch outthe space is definitely historic but has been updated to make it comfortable and cleanHost:
loved the host and spaceana is an amazing and accommodating host appreciate her hospitalityana was so responsivehosts were a joy to work withher response time was super fast she's very friendly and you can tell she cares about her guestsRead more reviewsLocation:
the location is also great- plenty of restaurants bars and groceries within walking distancegreat place for our group of friends running the chicago marathonlocation offered great access to chicago lakefront restaurants museums and other venuesana was clear with instructions and provided thoughtful suggetions of locations in the area (groceries restaurants suggestions)we walked to the lakeshore and enjoyed pho at the best vietnamese restaurant (tank) in chicago
4. Historic mansion with a spacious deck
A gorgeous foyer will greet you upon entry into this tastefully furnished Gold Coast mansion. The wooden floors, ornamental plants, and generally extravagant design will also mesmerize you. An open kitchen, a master bathroom with a spa bath, and a living space with a Netflix-ready TV are some of the indoor’s key features. Since WiFi is accessible here, you can flood your Pinterest with the house’s museum-like aesthetics.
As soon as you step out onto the private deck, a fully furnished space with delight you. There’s plenty of outdoor seating, where you can relax while appreciating fresh air and skyline views.
Chicago, Illinois, United States
966 meters (0.7 ft) from 875 North Michigan AvenueAccommodates: 12
Top guest reviews
Cleanliness:
enough room for everyone - very spacious & cleanHost:
host very helpfulRead more reviewsLocation:
we loved our stay in chicago thanks to this beautiful locationgreat location great communication and lovely place would definitely stay here again
5. Custom-built guesthouse with two full kitchens
This custom-built vacation rental screams luxury from every corner. From the elegant wooden finishes to the chic furniture, well-curated fittings dominate its interiors. The state-of-the-art (main) kitchen is a paradise for culinary enthusiasts, outfitted with stainless steel appliances and brick details for added visuals. Know that there is another well-appointed kitchen in the house, so multiple cooks can work easily to create culinary masterpieces.
While the adults enjoy unleashing their cooking skills, the kids will have a field day playing air hockey and board games in the game room.
Chicago, Illinois, United States
6.71 km (4.2 mi) from 875 North Michigan AvenueAccommodates: 16
Top guest reviews
Cleanliness:
instructions were easy to follow and the airbnb was cleanHost:
overall my stay was great host responded quickly to all my inquiriesbut for the most part it was a great stay and neda was very responsiveRead more reviewsLocation:
the location is ideal for public transportation really close to the train/busthere’s a train station about a 10 minute walk away making it fairly easily accessible to downtownspace was great and very close to so much in downtown chicagothat being said we had a great time and located close to everythingthe communication was excellent and the accommodation was an ideal location for business travel
Have a luxurious holiday in Chicago
Chicago is a highly urbanized metropolis with iconic architectural wonders and luxurious offerings. Here, you can book a stay that can make you feel like a celebrity! If you’re interested, choose from this list of the top Airbnb mansions in Chicago, Illinois, and have a luxurious holiday!
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