14 Best Luxury Airbnb Vacation Rentals In Chicago, Illinois - Updated 2024

| 5 min read

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 May 18, 2024.

1. The Bow (from USD 598)

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.

Stayed at this property?
Chicago, Illinois, United States
48 reviews   Superhost Wifi Available
ENTIRE RENTAL UNIT 3 Beds 7 Guests 3 Bedrooms 3 Bathrooms

Accommodates: 7

Top guest reviews
Amenities & Room:
the cloud9 penthouse was absolutely spectacular it was comfortable had plenty of seating and the views were amazing
we have fantastic stay highly recommended beautiful apartment very clean covers all my expectations
the concierge at the front desk was beyond helpful
host very easy to reach and went the extra mile
had amazing access to cafes and restaurant and the host was so responsive
very comfortable and private location
amazing place the views are stunning great location in the middle of everything
the subway was just around the corner for easily getting around town
best place to stay in chicago
absolutely impressed by this place it was everything plus some
Read more reviews

2. Five-bedroom townhome with sauna (from USD 1193)

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.

Stayed at this property?
Chicago, Illinois, United States
35 reviews   Superhost Wifi Available
ENTIRE HOME 5 Beds 12 Guests 5 Bedrooms 7 Bathrooms

Accommodates: 12

Top guest reviews
Amenities & Room:
beds and furniture were all comfy and clean
the beds were super comfortable and each room has its own bathroom
the beds were very comfortable
the kids loved the shuffle board videos games and movie room in the basement
spotless and great
the host and house manager were very responsive and accommodating
the host was so great to work with
the host was very welcoming and was available at all times
hosts were phenomenal flexible and friendly would stay again in a heartbeat
host was very quick to respond and helped assist us with an easy check in
location in old town was awesome
location is fabulous in old town
azi's place is amazing excellent location and massive on the inside with a really nice rooftop
easy access to downtown lakefront lincoln park and west loop
great spot for our family to come together in chicago amazing location with a great rooftop and grill
Read more reviews

3. Upscale penthouse with hot tubs (from USD 488)

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.

Stayed at this property?
Chicago, Illinois, United States
213 reviews   Wifi Available
Entire loft 8 Beds 10 Guests 5 Bedrooms 4 Bathrooms

Accommodates: 10

Top guest reviews
Amenities & Room:
wonderful space tons of sleeping room
plus 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 amenities
the roof terrace is a plus and the apartment has some stylish furniture and the showers are great
we had a big group and there was definitely enough room for everyone
bedrooms were clean and comfortable
so nice so clean very stylish
everything was clean organized and in perfect working order
casey's 5-bedroom penthouse is spacious clean and comfortable
the space was clean and beautiful and made our time in chicago all the more enjoyable
the hosts were amazing
host was really helpful too
great communications with the owner
casey had a great response time and was very accommodating
the owner has a great taste in decor and design
very good location and stylish apartment
great location in the city as well with the downtown shopping and riverwalk area within walking distance
great location central to many things to do
a great place in a super location with easy access to restaurants shopping and transportation
great apartment in a great location
Read more reviews

4. Designer loft at the heart of River West (from USD 5551)

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.

Stayed at this property?
Chicago, Illinois, United States
37 reviews   Wifi Available
Entire loft 4 Beds 8 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 8

Top guest reviews
Amenities & Room:
the apartment is great with lots of amenities good location
the loft was clean and very well stocked for our stay
the apartment is spotless beautifully decorated and extremely spacious
laura's place was fantastic clean stylish and great amenities
the space is very inviting clean and just so much fun to stay in
immaculately clean conveniently located stylish well appointed and so much fun
she is very caring and a super host
an amazing host with an incredible property
laura is a great host her place is beautifully decorated loved everything in her home
laura is attentive responsive and a superb host
laura’s place was awesome she is an amazing host we can’t wait to come back
laura's place is absolute perfection in every respect
the place is very safe and nearby eveything: transportation restaurants shopping
the location is also perfect and accessible to all parts of the city
laura responded right away and had the place ready in short notice
the place has free street parking and is close to a lot of different activities bars and restaurants
Read more reviews

5. Grand abode with a hot tub (from USD 619)

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.

Stayed at this property?
Chicago, Illinois, United States
128 reviews   Wifi Available
ENTIRE HOME 8 Beds 15 Guests 5 Bedrooms 3 Bathrooms

Accommodates: 15

Top guest reviews
Amenities & Room:
jenn-air kitchen was great
the beds were really comfortable ac worked wonderfully and the location was ideal
the house was sparkling clean comfortable and absolutely beautifully decorated
all beds were comfortable and clean
everything was clean and ready to go when we arrived
ac worked clean and the finishes were all amazing in this house
great place clean plenty of space great technology touches with sonos throughout and big hdtvs
highly responsive and accommodating host
we were touched by a welcome note and top notch champagne left by the host
the host should upload more pictures as the house is much nicer and inviting in person
great host great house great neighborhood casey responded quickly as you'd hope a good host would
casey was a great host - very easy to communicate with and flexible
excellent location close to everything
great location and very updated house
good location (wicker park)
immaculate great neighborhood with tons of restaurants and transportation close by
very nice house in a good location
Read more reviews

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.

Stayed at this property?
Chicago, Illinois, United States
52 reviews   Wifi Available
ENTIRE HOME 5 Beds 12 Guests 5 Bedrooms 3 Bathrooms

Accommodates: 12

Top guest reviews
Amenities & Room:
john even brought an extra table and chairs so we could all sit comfortably on the deck
the second kitchen was a welcome surprise as were the stocked baths and kitchen
tvs in every room is a huge plus and the basement space is above and beyond great
this place was great there were 5 bedrooms across 3 levels plenty of room to accommodate our 10 guests
beds were insanely comfortable too
very clean and beautifully decorated
clean well stocked with beautiful decor
wonderful place very spacious clean and well decorated
super clean and well supplied place with room for our big group
it was a really comfortable spot clean and well kept
amazing home and hosts were immediately accessible
john & amy were outstanding hosts in every way
amy and john were fantastic hosts
super friendly and thoughtful hosts
perfect setup to host 10 friends
the location is fantastic
great location as well
fantastic location in an amazing house
the location and accommodation were fantastic
great location - close to downtown shopping and eateries
Read more reviews

7. Well-located rental with lake views (from USD 399)

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.

Stayed at this property?
Chicago, Illinois, United States
170 reviews   Superhost Wifi Available
ENTIRE CONDO 2 Beds 6 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 6

Top guest reviews
Amenities & Room:
the view from the living room is stunning
the view from the living room and bedrooms are absolutely stunning
the rooms are nice and some amenities are provided; hand towels bath towels etc
the place is spacious clean cozy and loved the view of the lake
two nice and cozy rooms to accommodate you for a nice nights sleep
well worth it clean comfortable beds and pillows
super easy check in and the apartment was very clean and spacious
the property is beautiful and very clean
this place is outstanding checking-in was a breeze it’s clean and comfortable
the place was easy to find easy to access and wonderfully clean
thank you for being such wonderful hosts :)
hosts are very responsive
wonderful hosts and even better city
they were very informative made me feel really comfortable
really nice and even a better host
the location was great
walking distance to all sorts of restaurants and magnificent mile
all of my favorite downtown chicago places are walking distance
great location exactly like the pictures
great location to walk around shop and see the city
Read more reviews

8. Downtown duplex penthouse with city skyline views (from USD 799)

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.

Stayed at this property?
Chicago, Illinois, United States
125 reviews   Superhost Wifi Available
ENTIRE CONDO 7 Beds 16 Guests 5 Bedrooms 2 Bathrooms

Accommodates: 16

Top guest reviews
Amenities & Room:
the wifi was flawless with an amazing sonos sound system
the furniture is cozy and the beds are very comfortable
our team had a comfortable stay
great for large parties of people looking for a large space that’s comfortable
clean great communication great space
the space is huge and it was as clean as can be
the space was also very clean i would definitely recommend staying here
the space was beautiful and clean and the location was perfect
he is very responsive and the place is very clean
sameer & mike were amazing hosts
owners very responsive to all requests
the hosts were very courteous and professional
sameer was an incredible host quick and easy to respond and answer any questions we had
sameer is a fantastic host he was consistently available to answer questions and his responsiveness was top notch
nicely located downtown and close to river north area
great place and location to visit chicago
this location is perfect for any group
the 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
Read more reviews

9. Fully furnished penthouse with a gallery (from USD 424)

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!

Stayed at this property?
Chicago, Illinois, United States
433 reviews   Superhost Wifi Available
ENTIRE CONDO 3 Beds 6 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 6

Top guest reviews
Amenities & Room:
this is a beautiful apartment full of art and so many amenities
the apartment itself had an abundance of natural light which makes every home better
the apartment is filled with paintings and art installations on every corner which is very fascinating
this was a beautiful apartment it’s spacious the decor is perfect and it was full of amenities
the designer penthouse was perfect the space is thoughtfully designed and it was nice to have two full bathrooms
super clean and plenty of room
sparkling clean tasteful and great record collection
the unit was clean and very nice
matthew was a fantastic host
matthew is an excellent host
matthew is a great guy and host
matthew was an amazing host very communicative and kind
mathew is a great host
the location is great
beautiful apartment in a central location
we loved the location as well
and also very close if you’re going to the magnificent mile
the location was great it was only a block from the blue line
Read more reviews

10. Laid-back contemporary home (from USD 23333)

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.

Stayed at this property?
Chicago, Illinois, United States
38 reviews   Wifi Available
ENTIRE HOME 4 Beds 8 Guests 4 Bedrooms 3 Bathrooms

Accommodates: 8

Top guest reviews
Amenities & Room:
very nice rooms plenty of amenities and responsive host
clean classy and roomy
the house is very clean and hygienic with super clean bathrooms
pam's place is gorgeous it is clean spacious and stylish
it was spacious clean and modern with lovely decor
very clean extremely responsive host impeccable instructions for check in
amazing place with an awesome responsive host
she was extremely responsive flexible and sweet
pam was ridiculously responsive and made everything so easy for us
pam was a fantastic host and responded to inquiries in a matter of seconds in most instances
check-in and check-out were a breeze and communication with the host was excellent
there was a shopping center in walking distance and was super easy to get whatever the house needed
only and only positive to talk about this place
beautiful home quiet walking to grocery a plus and central to chicago sights
great location house is ultra spacious and very clean
what a great place to stay
Read more reviews

11. Gorgeous two-bedroom penthouse (from USD 5521)

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.

Stayed at this property?
Chicago, Illinois, United States
190 reviews   Superhost Wifi Available
ENTIRE RENTAL UNIT 2 Beds 4 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 4

Top guest reviews
Amenities & Room:
nice amenities (entertainment system wi-fi laundry barbeque sun deck) adds to the appeal
he is also very helpful with details for getting in and making your stay comfortable (wifi amenities etc
the second bathroom has a large washer/dryer that we put to good use
big flat with all the amenities comfortable and very good and easy comunication with chad
there's a wonderful roof deck and chad's apartment is perfect for a day week or month
it is super clean and stylish
chad's place was clean and tastefully furnished
the apartment is wonderful- nicely decorated and very clean and comfortable
the penthouse is very clean and inviting
the apartment was clean and on a quiet street with ample parking
chad is a great host
chad was an awesome host
chad was an awesome host
chad was a great host
chad was a great host
great location in lincoln park area and close to city
the location was fantastic
we loved the location
many shops within walking distance easy street parking
this was an ideal rental-nestled in the heart of a quaint neighborhood within walking distance to everything
Read more reviews

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.

Stayed at this property?
Chicago, Illinois, United States
87 reviews  
Entire loft 9 Beds 4 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
there were so many compliments on the place highly recommend the most comfortable beds ever
the living space offered ample seating pool/ping pong great flat screen xbox and games
the large bedrooms and bathrooms were amazing it helped a lot with out of town family
the place was clean when i arrived
really beautiful place it was very clean and spacious
the space was very clean and check in was easy
absolutely beautiful spacious impeccably clean
the bedrooms are clean and comfortable
mike was a awesome host
mike was a great host the whole way
it was able to host our family of 12 people perfectly
fantastic home and experience mike was an incredible host for our group
he was so helpful and thoughtful and helped with any questions i had
great location so many stores and food options within walking distance
great location great for hosting events
amazing location and touches through out the residence
would recommend this location for large groups or gatherings
this place was the best ever great location
Read more reviews

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.

Stayed at this property?
Chicago, Illinois, United States
10 reviews  
Entire house 5 Beds 5 Bedrooms 5 Bathrooms
Top guest reviews
the space is beautiful clean and exactly how it looks it pictures
great location and beautiful home
great place to stay
Read more reviews

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.

Stayed at this property?
Chicago, Illinois, United States
5 reviews  
Entire house 0 Beds 4 Bedrooms 4 Bathrooms
Top guest reviews
stunning clean home at a great location and fabulous hosts
the hosts take care of everything you could possibly need with speed accuracy and a wonderful attitude
chris is the most thoughtful helpful and responsible host
wonderful neighborhood with many great cafes bars and amazing shopping in walking distance host is very accomodating
fantastic home in a great location
Read more reviews

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.

Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.


Get Trip101 in your inbox

Unsubscribe in one click. See our Privacy Policy for more information on how we use your data

Saptami's primary life mission revolves around the exploration of the uncharted. Following the completion of her MBA, she steered clear of the conventional 9-to-5 career path, prioritizing the...Read more

 Want to contribute as a Local Expert?
Explore Chicago
Good things are meant to be shared!
Back to top
Visited any of these places? Click this button to activate our "Add a Tip" feature to share your experience.