8 Best Luxurious Airbnbs in Chicago, IL - Curated 2024

8 Best Luxurious Airbnbs in Chicago, IL – Curated 2024

Experience Luxury of the highest level with these mind blowing Airbnbs

Chicago, Illinois is popular for its rich history, vibrant cultural scene, and exquisite architecture. The city has a plethora of famous museums. These include the Art Institute of Chicago and the Museum of Science and Industry. Skylines are another specialty of the city, such as the Willis Tower and John Hancock Center. It’s also conveniently located near restaurants, nightlife, and shopping centers, which are just a few of the many attractions. The city boasts an exquisite food culture, diverse neighborhoods, beautiful lakefronts, and a legendary music scene.

Let us take a look on our selection of top 8 luxurious Airbnbs in Chicago, Illinois

Also read: 10 Family-Friendly Airbnbs in Margaret River, Australia for a Family Vacation!

Best Airbnbs in Chicago, Illinois that epitomise luxury

1. This stunning ultra-modern loft located in Fulton Market

high class Airbnbs in Chicago

quality guest room of Airbnbs in Chicago

Listing name: Beautiful Luxury Loft in Fulton Market, Sleeps 12
Listing Type: Entire rental unit
Max. No. of guests:
Attractions nearby:
Fulton Market, Magnificent Mile, Wicker Park

This Airbnb is a newly renovated designer 2,500 square foot brick-and-timber loft with 15 foot ceilings. It is set up in the heart of the vibrant West Loop neighbourhood. The Airbnb is suitable for groups who prioritise Chicago’s best dining and nightlife spots. 

A top quality living room and fully-equipped Kitchen is available too. Pets are also allowed here, for travellers who want to bring their furry friends. 

This is one of the best Airbnbs in Chicago for groups.


2. This vintage loft at convenient location

classy hall of Airbnbs in Chicago

aesthetically pleasing view of Airbnbs in Chicago

Listing name: Stunning Old Town Penthouse with Private Rooftop
Listing Type: Entire loft
Max. No. of guests:
Attractions nearby:
Michigan Avenue, Oak Street Beach, Red Line El train

This is one of the oldest Airbnbs in Chicago. It was built in 1897 and completely renovated in 2016. The 4,000 sq. ft penthouse loft is present in the heart of downtown Chicago. With 5 bedrooms, 4 bathrooms, and 2 kitchens, it is the apt spot for large groups. Location is another major positive, as this stay is near to amazing restaurants, comedy clubs, theatres, and more. 

A spot for travellers who prefer vintage Airbnbs in Chicago that epitomize luxury and convenience.


3. This aesthetic tropical penthouse

elegant living room of Airbnbs in Chicago

colorfully eye-catching hall of Airbnbs in Chicago

Listing name: Tropical penthouse in Wicker Park Sleeps 14
Listing Type: 14
Max. No. of guests: Entire home
Attractions nearby:
Jeni’s ice cream, Sweetgreen, Violet Hour

A penthouse that screams luxury all the way. This Penthouse can accommodate over 14 guests with its 4 bedrooms and an extra common area. Built in the heart of  Wicker Park, the home provides first-class facilities as well. These include a City skyline view, 65-inch HDTV, Central heating, and many more. 

Luxury doesn’t get bigger than this.


4. This modern Airbnb with spacious loft

simplistic hall of Airbnbs in Chicago

huge open space of Airbnbs in Chicago

Listing name: Designer loft in the heart of River West
Listing Type: Entire loft
Max. No. of guests:
Attractions nearby:
Divvy bike rental station, Chicago blue line stop, River West

This Chicago Airbnb is an epitome of designing excellence. The humongous living area boasts of a chef’s kitchen, dining room, and living room all together. Another highlight feature is a huge semi private rooftop terrace. Services include Washing machine, Air conditioning, Coffee maker, and more.

A top recommendation for travellers who prefer Airbnbs in Chicago with huge spaces with excellent architecture.


5. This multi-purpose dream home

modern living room of Airbnb in Chicago

classy interior of Airbnbs in Chicago

Listing name: Hyde Park Haven: Exquisite Airbnb
Listing Type: Entire home
Max. No. of guests:
Attractions nearby: Hyde Park, University of Chicago, Lake Michigan

For travels who are workaholics and gym freaks, this is the go-to choice. The Hyde Park Haven has  4 bedrooms, 3.5 bathrooms, and a gym. Additionally, several desks and multiple monitors are installed for those who want to work. This Airbnb thus serves the purposes of luxury, fitness, and work. A private garage and beautiful outdoor space are other highlight facilities. 

A top choice for multipurpose travellers.


6. This charming Airbnb apartment with beautiful views

exquisite room with view of Airbnbs in Chicago

elegant hall with beautiful outside view of Airbnbs in Chicago

Listing name: 2BD/2BA MAG MILE MASTERPIECE (+Rooftop)
Listing Type: Entire apartment
Max. No. of guests:
Attractions nearby:
John Hancock Center, Navy Pier, John Hancock Observatory

For tourists who want to combine luxury with visual excellence, this is the top Airbnb choice. This apartment offers you a Tranquil rooftop, and an excellent view of Lake Michigan. It has remodeled interiors, and is near to popular attractions in Chicago. A custom chef kitchen is present as well with SS appliances and granite counter tops.

An Airbnb that’s recommended for convenience and aesthetic views.


7. This eco-friendly classy loft

majestic room view

old-school yet stylish setup

Listing name: Walk to Oak Park from a Bright Madison Street Loft
Listing Type: Entire loft
Max. No. of guests:
Attractions nearby:
Brookfield Zoo, Chicago Architecture Foundation, Ernest Hemmingway Museum and Birthplace

This loft has two full bedrooms and two full bathrooms and the master bathroom has a Jacuzzi too. With in-room plants, central air conditioning, and a working fireplace, guests are bound to be calm and peaceful here. You also get a Smart TV with cable and Netflix access. Another highlight of this Airbnb is its Balcony with a view of downtown Chicago’s skyline. 

A top choice for travelers who want a stay that personifies luxury and positivity. 


8. This five-bedroom trendy house

white classy interior

simplistic hall

Listing name: Spacious Five Bedroom Home in Trendy Chicago Neighborhood
Listing Type: 15
Max. No. of guests: Entire home
Attractions nearby:
Divvy bike station, O’Hare International Airport, Wicker Park

This massive Airbnb with 5 bedrooms can accommodate upto 15 guests. The house screams luxury, as you can unwind on the rooftop deck, or even soak in the jacuzzi tub.  Several living rooms and a gourmet kitchen are part of this home as well. The basement is massive, with an entertainment area that has a wine fridge, popcorn machine and 75 inch TV.

In short, one of those luxurious Airbnbs in Chicago to celebrate life.


About Author

Febin M

A deep lover of travel destinations, movies, games, and football. Believes in enjoying life to the fullest.