Chicago is an excellent city if you want to experience the great nightlife, the fantastic dining scene, or explore a city with a lot to offer, whether 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 ten favorite AirBnBs and vacation rentals 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 miles 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 city’s 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 – the Museum of Contemporary Art, the 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
Chicago Brick Home
Located within the neighborhood of West Town, close to downtown Chicago, just two miles from Chicago Avenue, and close to bars, restaurants, and nightlife options.
This high-end home has everything you need for a bachelorette party, girl’s getaway, or family gathering.
Within this 4,500 square foot home, you will find wooden floors, five bedrooms, and four levels of living space.
There is space for 14 people at the dining table, a fully equipped kitchen with a breakfast bar, and outdoor porch areas with great views.
- Location: Noble Square
- Sleeps: 12 guests
- Size: 5 bedrooms / 10 beds / 5 baths
- Price: Check Latest Prices
Featured Guest Review: “This was the perfect spot for a post holiday family gathering. Great house in a good location. Host Erik was very attentive to our needs. I would highly recommend this place to stay in Chicago. Really special.” – Kathleen
One-of-a-Kind Four Bedroom Home
This home offers peace and tranquillity within the city but while still being 11 minutes from downtown and within walking distance of the United Center.
With a large open-plan living, dining, and kitchen area decorated with stylish and bright decor, this home is a great place to stay for a weekend or weeklong bachelorette party or family getaway.
It is filled with bright greens, blues, reds, and oranges.
Sleeping up to 12 people, in four bedrooms which are a mixture between king and queen beds.
The home also has a pull-down projector perfect for movie nights, a large kitchen with a breakfast bar, exposed brickwork features, and an outdoor terrace area with comfortable seating.
- Location: Cook County
- Sleeps: 12 guests
- Size: 4 bedrooms / 4 beds / 3 baths
- Price: Check Latest Prices
Historic Luxury Townhouse
Ideal for a bachelorette party or a girls’ trip, this townhouse sleeps up to 10 guests in four bedrooms.
One bedroom has a king bed, and one has a bunk bed, the third and fourth bedrooms both have queen beds.
Whether you are looking for somewhere to watch movies, have a few drinks before hitting the town, or cook great meals, this home is perfect for every occasion.
With modern features and furniture, a large open and bright living area, a fully equipped kitchen, a dining room, and four bathrooms.
Located within the Gold Coast of Chicago, this house is close to all the local amenities, trendy restaurants, shops, bars, and the Gold Coast Beach.
- Location: Gold Coast of Chicago
- Sleeps: 10 guests
- Size: 4 bedrooms / 5 beds / 4 baths
- Price: Check Latest Prices
Featured Guest Review: “This is a stunning home in the most ideal location. We were second time renters and feel so lucky to have had the opportunity to enjoy this VRBO. We will book again Thank you so much!” – Patti
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 enormous 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 large 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 it is fit for eight 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 city’s 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
This apartment is 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 great 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 standard 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.
This house is located within Wicker Park, 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 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, 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
Best AirBnBs for Small Groups and Families
Swing Swing
One of the apartment’s best features is the floor-to-ceiling windows offering incredible views from the open plan living and dining area as well as in the bedrooms.
There are three bedrooms, one with a king bed, one with a queen bed, and the third has two single beds. There is also a sofa bed in the living room area.
This apartment has a fully equipped kitchen that leads on from the living room area and a balcony.
It is located within Chicago’s South Loop, well known for being a music hub, with live music venues, bars, and various drinking options.
- Location: Chicago’s South Loop
- Sleeps: 6 guests
- Size: 3 bedrooms / 4 beds / 2 baths
- Price: Check Latest Prices
Windy City 3 Bedroom Apartment
Perfect for a family trip, small girl’s trip, or a couples trip, this three-bedroom flat sleeps up to six guests.
The three bedrooms all have queen beds, and there is one sofa bed.
This apartment has a fully equipped kitchen with a stylish black and grey design. The living room features bright greens, browns, and grays, with artwork on walls and windows letting in lots of natural light.
There is a dining room with a table and space for six guests, and there is also a desk area for working in one of the bedrooms.
Located within the West Ridge neighborhood, this area is close to all the city’s top attractions and dining options.
- Location: West Ridge
- Sleeps: 6 guests
- Size: 3 bedrooms / 3 beds / 2 baths
- Price: Check Latest Prices
Streeterville Two-bedroom Apartment
Perfect for a couples getaway, small family trip, or small girls trip, this apartment has plenty of space for four guests.
The two bedrooms are made up of one with a king bed and the other with a queen bed.
Located within Streeterville, this apartment offers excellent views of the city and is just a five-minute walk from the Loop and other Chicago attractions.
The apartment has floor-to-ceiling windows in the living area, a dining table, a desk for home working with a view, and a fully equipped kitchen with all modern amenities.
- Location: Streeterville
- Sleeps: 4 guests
- Size: 2 bedrooms / 2 beds / 2 baths
- Price: Check Latest Prices
800sqft Condo
This condo is an excellent base for exploring the city, located close to shops, restaurants, supermarkets, nightlife venues, and transportation.
With one bedroom with a king bed and a queen sofa bed in the living room area.
The condo has modern furnishings and is decorated in beiges and light blues, which perfectly compliment the wooden floors.
An open-plan living room area with a fully equipped kitchen and dining table with enough spaces for everyone to sit comfortably. There is also a full bathroom and a fireplace.
The apartment is filled with unique touches such as plants and artwork, with pastel orange and blue color decor and lots of natural light.
- Location: Old Town Triangle
- Sleeps: 4 guests
- Size: 1 bedroom / 1 beds / 1 baths
- Price: Check Latest Prices
Featured Guest Review: “We enjoyed dinner on the patio on a warm evening. The kitchen had all the dishes and supplies for coffee that we needed. Communication was great and we were able to find street parking in front of the property. We really enjoyed our stay!” – Alyssa
Historic Greystone Flat
Perfect for a family trip, girl’s 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 nearby.
- 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-designed 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 and 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 couple’s group.
The apartment combines elegance with luxury and a cozy white feel with views of the city’s skyline from the windows and balcony.
The living area has a fireplace, 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 an excellent 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
The Guild #4
Located in Streeterville, this vacation rental is close to the Magnificent Mile, gyms, shops, cafes, bars, and restaurants.
This apartment has beautiful artwork, a fireplace, a roomy living room, and large windows letting in lots of natural light.
There is a fully equipped kitchen with great appliances.
With a full bathroom, a desk area, and a bedroom with a king bed and a sofa bed in the living room.
This Airbnb is great for a couple’s getaway or a small friend group exploring the city.
- Location: Streeterville
- Sleeps: 4 guests
- Size: 1 bedroom / 1 beds / 1 baths
- Price: Starting at $180 per night
Featured Guest Review: “This place has 3 redeeming qualities: the best was comfortable, it’s location near the Magnificent Mile, and it sits atop a delicious Cuban cafe called Cafecito.” – Alysha
Former Spring Factory Loft
Perfect for a couple’s getaway, this studio loft has one bed located in the corner of the open-plan condo.
There is a metallic kitchen with silver and aluminum furnishings and natural architectural elements.
The loft is located within a 1900s warehouse that used to be a distillery and spring factory in a former life.
With Chinese, Japanese, and industrial elements, wood furnishings, and vintage features, this loft is unique.
The long loft is filled with artwork in the living room area next to the fully equipped kitchen and bedroom space.
- Location: East Village
- Sleeps: 2 guests
- Size: Condo / 1 bed / 2 baths
- Price: Starting at $230 per night
Featured Guest Review: “Brett’s place was very clean and just as lovely and comfortable as the pictures show. We loved how well equipped the kitchen was so we could easily cook during our stay, but the place also is in a great neighborhood with plenty of restaurants if you don’t want to cook.” – Kathryn
Lake View Apartment
Perfect for a couple’s getaway, this one-bedroom apartment has a king bed.
Located in a neighborhood called Rogers Park, the district has homes is situated on the waterfront and close to bars, restaurants, shops, and great attractions to discover.
The apartment has a small open plan living, dining, and kitchen area with a blue sofa and a small breakfast bar.
Outside, this apartment has a huge deck area with lake views and outdoor furniture, ideal for relaxing or enjoying a drink in the evening watching the sunset over the lake.
- Location: Rogers Park
- Sleeps: 2 guests
- Size: 1 bedroom / 1 beds / 1 baths
- Price: Check Latest Prices
Featured Guest Review: “Super clean, updated 1 bedroom apartment overlooking Lake Michigan with shared open deck. Close to Evanston, train station and 10 miles to downtown.” – Marilyn
Modern Chicago Loft
This studio apartment has exposed brickwork, beautiful artwork, and an open-plan living area.
The studio has a full kitchen with a breakfast bar and great 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 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: “Everything 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 there are greys and browns throughout the apartment.
The living room area has a fireplace, a sofa, and two chairs. Next to the living area is a dining table leading to 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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