Chicago is a great city if you want to experience the great nightlife, the exceptional dining scene, or just to explore a city that has a lot to offer, whether that is for a weekend trip or a week-long getaway.
With Millennium Park, lakefront trails, a river, a lake, and of course the famous Bean, Chicago has something for everyone.
We’ve put together a list of our 12 favorite AirBnBs in Chicago that you can book for yourself.
Whether you are traveling to the Windy City by yourself, as a couple, with a large group of girlfriends, or for a bachelorette party, you can find the perfect Chicago AirBnB to stay in no matter what the season!
The 10 Best Things To Do In Chicago, Illinois
- Walk along the 2.7 mile 606 elevated railway track, to travel between Logan Square, Wicker Park, Humboldt Park, and Bucktown.
- Walk or bike along the Lakefront Trail, an 18-mile path from Hollywood Avenue to 71st Street.
- Explore Millennium Park, a 24.5-acre park downtown, which hosts special events throughout the year. And see the world-famous Cloud Gate (the Bean).
- Take a walk through Jackson Park.
- Have a cocktail at a rooftop bar and admire the cities skyline.
- Sample Chicago’s world-famous deep-dish pizza at local mainstays like Lou Malnati’s and Giordano’s.
- Visit Garfield Park Conservatory, with flora and fauna from wet and dry environments.
- Learn something new at one of Chicago’s museums – Museum of Contemporary Art, Art Institute of Chicago, or the International Museum of Surgical Science.
- Take a cruise along the Chicago River or take a boat trip on Lake Michigan.
- See the panoramic views from the 442-meter Willis Tower at the Chicago Skydeck, formally the world’s highest building.
Best AirBnBs for Bachelorette Parties and Large Groups
Designer Penthouse
If you are looking for a great place to stay in Chicago with easy access to the city’s attractions, look no further than this designer penthouse.
Located just half a block away from a subway line and close to the Magnificent Mile with ample shopping and dining options.
This gorgeous penthouse is ideal for a group getaway with friends or family, or to celebrate a special occasion such as a bachelorette party or birthday.
There are three bedrooms sleeping up to 8 guests comfortably in queen and double beds.
With lots of natural light thanks to the huge windows, this penthouse has a neutral and cozy feel, while also being modern and contemporary.
The living area has plenty of room for all the guests to sit comfortably, and even has a balcony, a rarity in Chicago!
The kitchen and dining area are located within the same room as the living room giving the penthouse lots of space for entertaining and relaxing.
- Location: River West
- Sleeps: 8 guests
- Size: 3 bedrooms / 3 beds / 2 baths
- Price: Check Latest Prices
Featured Guest Review: “If you’re thinking about booking here, do it now! Loved everything about this space! It’s so artful, unique and Matthew was insanely thoughtful, polite, and kind. Check-in and out was a breeze.” – Brittney
Art Gallery Condo
Live alongside Open House Contemporary exhibition, with artwork by emerging artists and while also being in modern luxury.
This unique apartment has lots of natural light and a big open plan living, dining, and fully equipped kitchen.
The apartment has lots of plants for decoration and a fireplace. The living area has a balcony with a BBQ grill and large patio glass doors.
There are three bedrooms and is fit for 8 guests, one with two single beds, one with a double bed, and one with a queen bed.
Located in the heart of River West, this apartment is half a block from the subway, close to some of the cities best restaurants and top attractions.
- Location: River West
- Sleeps: 8 guests
- Size: 3 bedrooms / 4 beds / 2 baths
- Price: Check Latest Prices
Featured Guest Review: “The place is just as pictured! Local displayed art was a trip! Kitchen is equipped with everything one needs. All the beds are super comfortable, and bathrooms stocked with all your needs. Would love to stay there again.” – Shimaa
5-Bedroom Home
Ideal for a bachelorette party, girls’ getaway, or family trip, this apartment sleeps up to 15 in five bedrooms.
One bedroom has a king bed, one has a single bed, the third bedroom has a queen bed and single bed, the fourth has a bunk bed, and the fifth bedroom has a bunk bed and king bed.
Whether you are looking for somewhere to cook great meals, have a movie night, or hit the town, this home is perfect for every occasion.
With grand features and furniture, there is a large living area, a full kitchen with a breakfast bar, a formal dining room, and three and a half bathrooms.
In addition to the typical rooms, this house has a recreation room with a popcorn machine, sofas, and bean bags.
This house also has a rooftop patio, with outdoor furniture, and green space.
Located within Wicker Park, this house is close to all the local amenities, trendy restaurants, shops, bars, and a beautiful park.
- Location: Wicker Park
- Sleeps: 15 guests
- Size: 5 bedrooms / 11 beds / 3.5 baths
- Price: Check Latest Prices
Featured Guest Review: “Casey’s home in Chicago was much bigger then we expected and beautiful inside! Casey was very responsive and helpful with whatever we needed. The home was a great place for our family to spend the holidays!” – Meghan
Luxury Chicago Single Family Home
If you are looking for the perfect bachelorette party location or girls’ getaway weekend, look no further!
This 1890s home is perfect for up to 12 guests, sleeping in five bedrooms.
Two bedrooms have king beds and en-suite bathrooms, two bedrooms have bunk beds, and the fifth bedroom has a queen bed.
The home is 4,500 square feet, over four levels.
Each space is filled with luxury, from the large living area with a fireplace, and a separate full kitchen with a breakfast table, and a balcony, which leads out into the deck area.
Filled with intricate details and pastel features, the home is cozy and welcoming.
There is also an additional family room with a kitchenette and the home has four and a half bathrooms.
Outside there is a balcony with outdoor furniture on the second floor, and the ground floor has more furniture and a BBQ grill area.
- Location: Noble Square
- Sleeps: 12 guests
- Size: 5 bedrooms / 10 beds / 4.5 baths
- Price: Check Latest Prices
Featured Guest Review: “Huge, lovely home in a great location. Lots of shops and restaurants within an easy walk and close to the train. Very easy in and out and Erik is quick to respond to questions. A great AirBnB!” – Ellen
Logan Square Penthouse
This Chicago Airbnb is located in Logan Square, a thriving neighborhood with bars, restaurants, boutique shops, and a park.
The area is also only 10 minutes from the city and 20 minutes from the airport.
The house has colorful rugs, ethnic cushions, and Native American Art throughout.
The living area is large and open with a kitchen area and dining area.
There are two bathrooms and four bedrooms, all of which have queen beds and memory foam mattresses.
This house is perfect for a bachelorette party, or for a girls getaway with a huge outdoor area complete with a tipi, BBQ grill, outdoor dining table, outdoor furniture, great for dining al fresco or having a cocktail in the evening!
- Location: Logan Square
- Sleeps: 12 guests
- Size: 4 bedrooms / 4 beds / 2 baths
- Price: Check Latest Prices
Featured Guest Review: “Really cool place in a lively area of the city. The place was spotless & had artsy, thoughtful decor. The beds & linens were super comfy.” – Rebecca
Wrigleyville Apartment
Located in North Center Chicago, this apartment is surrounded by great dining options and close to a subway with easy access to the city.
Ideal for a family trip, girls trip, or bachelorette weekend, this private apartment has everything you need and more.
With luxury for up to 8 guests, sleeping in three bedrooms, all of which have king beds.
The living room has an L-shaped sofa with a balcony and a kitchen area at one end, with a dining area.
The living, dining, and kitchen area is decorated in greys and neutral colors, with ample natural light.
The bedrooms are decorated with greys and pinks, and intricate details that make the apartment feel homely and cozy throughout.
- Location: North Center Chicago
- Sleeps: 8 guests
- Size: 3 bedrooms / 3 beds / 2 baths
- Price: Check Latest Prices
Featured Guest Review: “I’ve stayed here twice before and keep coming back because it’s always such a good experience. I love the place, the location and the people running it do a fantastic job.” – Nicole
Best AirBnBs for Small Groups and Families
Historic Greystone Flat
Perfect for a family trip, girls trip, or a small group trip, this three-bedroom flat sleeps up to 6 guests.
The three bedrooms are made up of two with queen beds and one with a sofa bed.
This house has a large kitchen with a stylish black design and a balcony. The bedrooms have unique artwork, bookcases, and unique features.
There is also a small dining table with four chairs and a desk area for working.
This historic Greystone house is located in the Wrigleyville/East Lakeview/Southport Corridor, with great restaurants, cafes, shops, and breweries close by.
- Location: Wrigleyville/East Lakeview/Southport Corridor
- Sleeps: 6 guests
- Size: 3 bedrooms / 3 beds / 1 baths
- Price: Check Latest Prices
Featured Guest Review: “This place was super cute! Had everything you would need and then some. We loved all the details and decor. The location is amazing, so many places within walking distance.” – Eve
Lincoln Park Vintage Condo
This well deisgned condo is located in Chicago’s historic Lincoln Park neighborhood, close to downtown and Wrigley Field.
Lincoln Park has a great historic area to discover, as well as restaurants, bars, shops, and other local attractions.
This apartment has three bedrooms, two have queen beds, and the third bedroom has a bunk bed, making the flat ideal for a family of 6, a group of friends, or a couples group.
With views of the city’s skyline from the windows and balcony, the apartment combines elegance with luxury and a white cozy feel.
The living area has a fireplace and two large sofas for relaxing, a full kitchen with a breakfast bar, and two bathrooms.
There is also a dining table with two chairs on the balcony.
- Location: Lincoln Park
- Sleeps: 6 guests
- Size: 3 bedrooms / 6 beds / 2 baths
- Price: Check Latest Prices
Featured Guest Review: “This is a beautiful condo in an excellent location. Beautiful neighborhood, close to the lake, many restaurants and easy transportation anywhere in the city. Colin is a kind and considerate host!” – Reni
Logan Square Modern Apartment
Located in Logan Square close to shops, restaurants, nightlife venues, and downtown, this house is a great base for exploring the city.
With three bedrooms, all with queen beds and plenty of space, this apartment is great for up to 6 guests.
The living area has a large L-shaped sofa and an additional sofa.
There is a fully equipped kitchen with a coffee machine and other appliances. There is also a full bathroom and a separate dining area.
The apartment is filled with unique touches such as plants and artwork, with pastel color decor and natural light.
- Location: Logan Square
- Sleeps: 6 guests
- Size: 3 bedroom / 3 beds / 1 baths
- Price: Starting from $117 per night
Featured Guest Review: “One of the best Airbnb’s I have ever stayed in! Beautiful, clean and had everything you could need. Such a comfortable bed and the neighbourhood is safe and quiet.” – Sarah
Best AirBnBs for Solo Travelers and Couples
Modern Chicago Loft
This studio apartment has exposed brickwork, beautiful artwork, and an open-plan living area.
There is a full kitchen in the studio with a breakfast bar and ample appliances.
With a full bathroom, a study, and a bedroom area with a queen bed with a memory foam mattress.
This Airbnb is great for a couple’s getaway exploring the city or just taking a romantic weekend away.
Outside there is a dining table and patio area ideal for relaxing, drinking your morning coffee, or sitting drinking your wine in the evenings.
Located in Avondale, this vacation rental is close to shops, cafes, bars, and restaurants, this studio is a great place to explore the city.
- Location: Avondale
- Sleeps: 2 guests
- Size: Studio / 1 beds / 1 baths
- Price: Starting at $100 per night
Featured Guest Review: “This flat is cozy and clean with easy connections for most areas of Chicago. In addition the parking was easily accessible and safe. We highly recommend this property to anyone visiting Chicago!” – Konstantinos
Cozy & Stylish Studio
Located close to South Old Irving and Kilbourn Park, in a historical neighborhood of the city, this comfortable Airbnb is near great restaurants, bars, and shops nearby.
This open plan studio is set out with the kitchen just as you walk in, and opens up into the dining area and bedroom area with a queen bed.
Outside there is a small deck area with a table and is a great place to relax.
The studio is decorated in whites, pastel, beige, and turquoise features.
- Location: South Old Irving And Kilbourn Parks
- Sleeps: 2 guests
- Size: Studio / 1 beds / 1 baths
- Price: Starting at $100 per night
Featured Guest Review: “Everthing was well presented in a clean orderly manner and we had no issues throughout our stay. The location is really nice with some local restaurants and bars and 15mins walk to train.” – Graeme
Vintage Greystone Apartment
Perfect for a couple’s getaway, this one-bedroom apartment has a queen bed and a sofa bed.
Decorated with vintage charm, modern amenities, and a classic style. The walls are mainly white but throughout the apartment, there are greys and browns featured.
The living room area has a fireplace, a sofa, and two chairs. Next to the living area is a dining table which leads into the fully equipped kitchen.
Located in a neighborhood called Ukrainian Village, the neighborhood has homes with unique architecture, bars, restaurants, shops, and great attractions to discover.
- Location: Ukrainian Village
- Sleeps: 4 guests
- Size: 1 bedroom / 2 beds / 1 baths
- Price: Starting at $115 per night
Featured Guest Review: “Stylish, well equipped apartment, in an up and coming part of town with easy access to everything. Rob was very friendly and helpful. We really enjoyed our stay.” – Janet
Ready To Book Your Stay?
Chicago is the perfect destination for a weekend getaway, family reunion, bachelorette party, or a girl’s getaway in both the winter and summer.
To plan the perfect trip to the Windy City, bookmark our Ultimate Chicago City Guide filled with everything you need to know!
Be sure to check our growing Airbnb Directory for all of our favorite places to stay.
Do you know of a unique AirBnB that belongs on our list? Let us know in the comments below!
Ready to go to Chicago? Read on for more inspiration
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