The third-largest city of the United States is not only an important commercial and industrial hub–it is also rich in culture, art, and cuisine. Music is among the important facets of the city, with house music, electronic dance music, jazz, rock, and blues keeping the scene alive. The city hosts eccentric festivals, the majority of which are centered around music, and has wide-ranging places to visit, from art galleries to skateparks. The architecture of the city is most impressive, with glorious skyscrapers that have been designed most impressively. Imagine staying in one of the luxurious penthouses with a view of the charming Chicago skyline! Well, the dream is very easy to reach. Scroll down to find some of the best luxury Airbnb vacation rentals in Chicago, Illinois.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to luxury services and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on April 07, 2024.
1. The Bow (from USD 611)
Offering sweeping views of the stunning Chicago skyline, this luxurious property is located in the River West neighborhood. You also have easy access to the Chicago River from this penthouse. With an upscale design and opulent furnishings, this rental promises you a memorable and restful stay. There are several shared amenities available, including a gym, an outdoor pool, and a hot tub. The living area in this rental is spacious and has comfortable couches to lounge on.
The well-equipped kitchen with an island is another highlight of this beautiful Airbnb. Moreover, you can use the washer and dryer for your laundry needs.
Top guest reviews
Amenities & Room:
the cloud9 penthouse was absolutely spectacular it was comfortable had plenty of seating and the views were amazingCleanliness:
we have fantastic stay highly recommended beautiful apartment very clean covers all my expectationsHost:
the concierge at the front desk was beyond helpfulhost very easy to reach and went the extra milehad amazing access to cafes and restaurant and the host was so responsiveRead more reviewsLocation:
very comfortable and private locationamazing place the views are stunning great location in the middle of everythingthe subway was just around the corner for easily getting around townbest place to stay in chicagoabsolutely impressed by this place it was everything plus some
Superhost
2. Five-bedroom townhome with sauna (from USD 917)
For those who want to experience the luxury life in Chicago, this old townhome is the ideal choice. The five-bedroom rental is located close to The Second City, so feel free to catch a show with your family. The expansive living room inside is an inviting space, furnished with a white sofa and a large-screen TV. There is a wine rack underneath the stairs where you will find an exquisite collection of red and white wines.
The kitchen has a breakfast bar as well as a dining area, where you can enjoy your meals. The most attractive highlight of this rental is the private sauna available for your relaxation. Spend some time in the steam room and stay refreshed during your stay here.
Top guest reviews
Amenities & Room:
beds and furniture were all comfy and cleanthe beds were super comfortable and each room has its own bathroomthe beds were very comfortablethe kids loved the shuffle board videos games and movie room in the basementCleanliness:
spotless and greatHost:
the host and house manager were very responsive and accommodatingthe host was so great to work withthe host was very welcoming and was available at all timeshosts were phenomenal flexible and friendly would stay again in a heartbeathost was very quick to respond and helped assist us with an easy check inRead more reviewsLocation:
location in old town was awesomelocation is fabulous in old townazi's place is amazing excellent location and massive on the inside with a really nice rooftopeasy access to downtown lakefront lincoln park and west loopgreat spot for our family to come together in chicago amazing location with a great rooftop and grill
3. Upscale penthouse with hot tubs (from USD 564)
The grand Airbnb penthouse in Chicago with the rustic interior is located at the old town of Chicago. The high-ceiling complements the interior with a vintage French door connecting to a private balcony. This Chicago penthouse Airbnb has altogether five bedrooms with assorted beds which can accommodate a group of around 16 people. There are two fully-equipped kitchens and four bathrooms with hot tubs. The two living rooms are bright and beautiful, perfect to enjoy family time or fun with friends.
Top guest reviews
Amenities & Room:
wonderful space tons of sleeping roomplus there was a ton of extra space for production (the two kitchens were super clutch)a magnificent home that’s comfortable cozy and functional with all the necessary amenitiesthe roof terrace is a plus and the apartment has some stylish furniture and the showers are greatwe had a big group and there was definitely enough room for everyoneCleanliness:
bedrooms were clean and comfortableso nice so clean very stylisheverything was clean organized and in perfect working ordercasey's 5-bedroom penthouse is spacious clean and comfortablethe space was clean and beautiful and made our time in chicago all the more enjoyableHost:
the hosts were amazinghost was really helpful toogreat communications with the ownercasey had a great response time and was very accommodatingthe owner has a great taste in decor and designRead more reviewsLocation:
very good location and stylish apartmentgreat location in the city as well with the downtown shopping and riverwalk area within walking distancegreat location central to many things to doa great place in a super location with easy access to restaurants shopping and transportationgreat apartment in a great location
4. Designer loft at the heart of River West (from USD 1286)
The chic loft features excellent interior design and is located very close to the Chicago Blue Line. There is an open-plan grand living area with a spacious dining area and fully-equipped kitchen. There are three bedrooms on this penthouse, two with single queen-sized beds and one with a pair of queen-sized beds. Altogether, the penthouse can accommodate a group of 12 people. The guests are welcome to use huge semi-private rooftop terrace with an excellent view of the surrounding area.
Top guest reviews
Amenities & Room:
the apartment is great with lots of amenities good locationCleanliness:
the loft was clean and very well stocked for our staythe apartment is spotless beautifully decorated and extremely spaciouslaura's place was fantastic clean stylish and great amenitiesthe space is very inviting clean and just so much fun to stay inimmaculately clean conveniently located stylish well appointed and so much funHost:
she is very caring and a super hostan amazing host with an incredible propertylaura is a great host her place is beautifully decorated loved everything in her homelaura is attentive responsive and a superb hostlaura’s place was awesome she is an amazing host we can’t wait to come backRead more reviewsLocation:
laura's place is absolute perfection in every respectthe place is very safe and nearby eveything: transportation restaurants shoppingthe location is also perfect and accessible to all parts of the citylaura responded right away and had the place ready in short noticethe place has free street parking and is close to a lot of different activities bars and restaurants
5. Grand abode with a hot tub (from USD 492)
The luxurious home is located in one of the trendiest neighborhoods of the town, close to restaurants, shops, and bars. This rooftop Airbnb in Chicago has altogether five bedrooms with assorted beds for a group of 15 guests. There is a grand living room and a spacious dining room, especially fit to host a grand party. The charming entertainment corner comes with a huge flat-screen television for your entertainment, or you can soak in the hot tub in your leisure time. Guests can go up the roof deck to enjoy the fresh air.
Top guest reviews
Amenities & Room:
jenn-air kitchen was greatthe beds were really comfortable ac worked wonderfully and the location was idealCleanliness:
the house was sparkling clean comfortable and absolutely beautifully decoratedall beds were comfortable and cleaneverything was clean and ready to go when we arrivedac worked clean and the finishes were all amazing in this housegreat place clean plenty of space great technology touches with sonos throughout and big hdtvsHost:
highly responsive and accommodating hostwe were touched by a welcome note and top notch champagne left by the hostthe host should upload more pictures as the house is much nicer and inviting in persongreat host great house great neighborhood casey responded quickly as you'd hope a good host wouldcasey was a great host - very easy to communicate with and flexibleRead more reviewsLocation:
excellent location close to everythinggreat location and very updated housegood location (wicker park)immaculate great neighborhood with tons of restaurants and transportation close byvery nice house in a good location
6. Light-filled apartment best for families
This charming five-bedroom house is located very close to the lake, Foster Beach. This bright, luxury apartment in Chicago invites lots of natural light and has four bedrooms containing queen-sized beds. There is a huge game room to provide a good dose of entertainment or you can enjoy the sun in the lavish backyard of the property. Free parking is available with your stay.
Chicago, Illinois, United StatesAccommodates: 12
Top guest reviews
Amenities & Room:
john even brought an extra table and chairs so we could all sit comfortably on the deckthe second kitchen was a welcome surprise as were the stocked baths and kitchentvs in every room is a huge plus and the basement space is above and beyond greatthis place was great there were 5 bedrooms across 3 levels plenty of room to accommodate our 10 guestsbeds were insanely comfortable tooCleanliness:
very clean and beautifully decoratedclean well stocked with beautiful decorwonderful place very spacious clean and well decoratedsuper clean and well supplied place with room for our big groupit was a really comfortable spot clean and well keptHost:
amazing home and hosts were immediately accessiblejohn & amy were outstanding hosts in every wayamy and john were fantastic hostssuper friendly and thoughtful hostsperfect setup to host 10 friendsRead more reviewsLocation:
the location is fantasticgreat location as wellfantastic location in an amazing housethe location and accommodation were fantasticgreat location - close to downtown shopping and eateries
7. Well-located rental with lake views (from USD 349)
One of Chicago’s best areas is, no doubt, the Magnificent Mile. It’s your chance to live close to this prime location in the city when you book this two-bedroom condominium that can sleep up to six people. You will be a few steps away from the lake and all the popular things Chicago can offer. This home boasts an open-plan and bright layout, as well as a peaceful rooftop that overlooks the lake. There’s also a custom-made chef’s kitchen and free Wi-Fi at this upscale property.
Top guest reviews
Amenities & Room:
the view from the living room is stunningthe view from the living room and bedrooms are absolutely stunningthe rooms are nice and some amenities are provided; hand towels bath towels etcthe place is spacious clean cozy and loved the view of the laketwo nice and cozy rooms to accommodate you for a nice nights sleepCleanliness:
well worth it clean comfortable beds and pillowssuper easy check in and the apartment was very clean and spaciousthe property is beautiful and very cleanthis place is outstanding checking-in was a breeze it’s clean and comfortablethe place was easy to find easy to access and wonderfully cleanHost:
thank you for being such wonderful hosts :)hosts are very responsivewonderful hosts and even better citythey were very informative made me feel really comfortablereally nice and even a better hostRead more reviewsLocation:
the location was greatwalking distance to all sorts of restaurants and magnificent mileall of my favorite downtown chicago places are walking distancegreat location exactly like the picturesgreat location to walk around shop and see the city
8. Downtown duplex penthouse with city skyline views (from USD 856)
The upscale luxurious penthouse is located in the chic River West neighborhood of downtown Chicago. The newly rehabilitated penthouse has a modern interior, five bedrooms with queen-sized beds, a single bed, couches, and air mattresses. The penthouse is fit to accommodate a large group, up to 16 people. Two large living areas are spread through the penthouse with a very large equipped kitchen. Apart from the facility like a Sonos sound system, there is a game room with poker table, Xbox, board games, foosball, and a shuffleboard table. The rooftop can be accessed upon request and offers an excellent view of the Chicago skyline.
Top guest reviews
Amenities & Room:
the wifi was flawless with an amazing sonos sound systemthe furniture is cozy and the beds are very comfortableour team had a comfortable staygreat for large parties of people looking for a large space that’s comfortableCleanliness:
clean great communication great spacethe space is huge and it was as clean as can bethe space was also very clean i would definitely recommend staying herethe space was beautiful and clean and the location was perfecthe is very responsive and the place is very cleanHost:
sameer & mike were amazing hostsowners very responsive to all requeststhe hosts were very courteous and professionalsameer was an incredible host quick and easy to respond and answer any questions we hadsameer is a fantastic host he was consistently available to answer questions and his responsiveness was top notchRead more reviewsLocation:
nicely located downtown and close to river north areagreat place and location to visit chicagothis location is perfect for any groupthe location is nestled between two of the best neighborhoods in a chicago (fulton market and river north)a short walk from the loop makes it easy to find the best food in chicago
9. Fully furnished penthouse with a gallery (from USD 155)
You can’t go wrong with this designer penthouse with three bedrooms if you’re looking for luxurious Airbnbs in the city. This spacious home can accommodate eight people and it is even its own art gallery. Gorgeous pieces of art, along with art installations, fill this place up. The open-concept living, kitchen, and dining spaces are bright and airy, while the rooms are cozy when it needs to be. Other features of this home include the balcony with a grill, perfect for barbecue and ice-cold beer nights!
Top guest reviews
Amenities & Room:
this is a beautiful apartment full of art and so many amenitiesthe apartment itself had an abundance of natural light which makes every home betterthe apartment is filled with paintings and art installations on every corner which is very fascinatingthis was a beautiful apartment it’s spacious the decor is perfect and it was full of amenitiesthe designer penthouse was perfect the space is thoughtfully designed and it was nice to have two full bathroomsCleanliness:
super clean and plenty of roomsparkling clean tasteful and great record collectionthe unit was clean and very niceHost:
matthew was a fantastic hostmatthew is an excellent hostmatthew is a great guy and hostmatthew was an amazing host very communicative and kindmathew is a great hostRead more reviewsLocation:
the location is greatbeautiful apartment in a central locationwe loved the location as welland also very close if you’re going to the magnificent milethe location was great it was only a block from the blue line
10. Laid-back contemporary home (from USD 1500)
This spacious three-level contemporary home is located very close to McCormick Place. Neighborhoods like Hyde Park, Chinatown, and University Village are easily accessible. This bright home is full of natural lights and decorated with handcrafted home accessories. It has four bedrooms with king-sized, queen-sized, and double beds to accommodate a group of eight. The spacious living room has a fireplace and connected to the dining area and eat-in kitchen. The French doors open to the private roof deck with an excellent view of the surrounding area.
Top guest reviews
Amenities & Room:
very nice rooms plenty of amenities and responsive hostCleanliness:
clean classy and roomythe house is very clean and hygienic with super clean bathroomspam's place is gorgeous it is clean spacious and stylishit was spacious clean and modern with lovely decorvery clean extremely responsive host impeccable instructions for check inHost:
amazing place with an awesome responsive hostshe was extremely responsive flexible and sweetpam was ridiculously responsive and made everything so easy for uspam was a fantastic host and responded to inquiries in a matter of seconds in most instancescheck-in and check-out were a breeze and communication with the host was excellentRead more reviewsLocation:
there was a shopping center in walking distance and was super easy to get whatever the house neededonly and only positive to talk about this placebeautiful home quiet walking to grocery a plus and central to chicago sightsgreat location house is ultra spacious and very cleanwhat a great place to stay
11. Gorgeous two-bedroom penthouse (from USD 180)
This two-bedroom penthouse is located in a very convenient location, close to some famous bars and restaurants. The charming penthouse offers you three private decks to enjoy the sun and fresh air. The two bedrooms come with queen-sized beds each and there is a couch in the living area. Overall, the penthouse can accommodate a group of five. This penthouse is located on the top floor of the building and boasts a brand-new kitchen and a master bathroom. Free parking is available in this quiet neighborhood.
Top guest reviews
Amenities & Room:
nice amenities (entertainment system wi-fi laundry barbeque sun deck) adds to the appealhe is also very helpful with details for getting in and making your stay comfortable (wifi amenities etcthe second bathroom has a large washer/dryer that we put to good usebig flat with all the amenities comfortable and very good and easy comunication with chadthere's a wonderful roof deck and chad's apartment is perfect for a day week or monthCleanliness:
it is super clean and stylishchad's place was clean and tastefully furnishedthe apartment is wonderful- nicely decorated and very clean and comfortablethe penthouse is very clean and invitingthe apartment was clean and on a quiet street with ample parkingHost:
chad is a great hostchad was an awesome hostchad was an awesome hostchad was a great hostchad was a great hostRead more reviewsLocation:
great location in lincoln park area and close to citythe location was fantasticwe loved the locationmany shops within walking distance easy street parkingthis was an ideal rental-nestled in the heart of a quaint neighborhood within walking distance to everything
12. Charming loft with brick and wood interiors
The charming loft with hardwood floors and modern furnishing is located on the Wicker Park locality. The hardwood floor complements the brick and wooden rustic interior. It is quite large, with four bedrooms with queen-sized beds. The loft can accommodate a group of up to 16 people. There is a professional chef’s kitchen and three bathrooms with large walk-in showers. The living area is huge as well, with separate private dining space for a large group. The add-on facilities are cigar parlour, pool table, and dart board for your entertainment.
Chicago, Illinois, United StatesTop guest reviews
Amenities & Room:
there were so many compliments on the place highly recommend the most comfortable beds everthe living space offered ample seating pool/ping pong great flat screen xbox and gamesthe large bedrooms and bathrooms were amazing it helped a lot with out of town familyCleanliness:
the place was clean when i arrivedreally beautiful place it was very clean and spaciousthe space was very clean and check in was easyabsolutely beautiful spacious impeccably cleanthe bedrooms are clean and comfortableHost:
mike was a awesome hostmike was a great host the whole wayit was able to host our family of 12 people perfectlyfantastic home and experience mike was an incredible host for our grouphe was so helpful and thoughtful and helped with any questions i hadRead more reviewsLocation:
great location so many stores and food options within walking distancegreat location great for hosting eventsamazing location and touches through out the residencewould recommend this location for large groups or gatheringsthis place was the best ever great location
13. Bright home at the heart of Gold Coast
This grand home is located in a most convenient location of the Chicago city in the middle of Michigan Avenue and Rush Street, in the heart of the historic district of Chicago. The shopping and dining facilities are located close, with walking distance from Magnificent Mile and Oak Street Beach. The house is very bright and cheerful, with whitewash walls complementing the hardwood floors. The house comes with five bedrooms, a sleek interior, and plush furnishing. The rooms have mostly king-sized beds and one with a queen-sized bed–overall perfect to fit a group of 10. The spacious living area has dining facilities with a fully-equipped kitchen to prepare your meals.
Chicago, Illinois, United StatesTop guest reviews
Read more reviewsCleanliness:
the space is beautiful clean and exactly how it looks it pictures
14. Historic row-house in the Gold Coast area
This historic row-house defines luxury in the Gold Coast area, Chicago’s classiest neighborhood. Its charming interior, fitted with antiques, chandeliers, and gleaming cherry wood floors create a royal ambiance. This luxury vacation rental in Chicago has four bedrooms with assorted beds, set to accommodate a group of seven. The excellently decorated living area is huge. The kitchen is attached to the huge dining area, set up to host dinner parties. There is a rooftop garden deck with an antique fountain attached to the master suite. Another backyard garden is located on the first floor. The house is located close to downtown, near the designer boutiques, shops, restaurants, and bars.
Chicago, Illinois, United StatesTop guest reviews
Cleanliness:
stunning clean home at a great location and fabulous hostsHost:
the hosts take care of everything you could possibly need with speed accuracy and a wonderful attitudechris is the most thoughtful helpful and responsible hostRead more reviewsLocation:
wonderful neighborhood with many great cafes bars and amazing shopping in walking distance host is very accomodatingfantastic home in a great location
Luxurious stays in the city of rich culture
The windy city is the finest blend of modernism featuring rich art, culture, and music. A lavish way of exploring this city must include staying in the Airbnb rentals which redefines the word luxury. So, what are you thinking of? Choose one out of the best luxury vacation rentals in Chicago and make the reservation immediately.
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