The 15 Best Airbnbs in Chicago in 2023

Are you planning a trip to the windy city? If so, it is a good idea to search for Airbnbs to stay in during your vacation. Below are 15 of the best Airbnbs in the Chicago area to provide extra space and comfort.

Why Stay at a Chicago Airbnb?

There are many appealing attractions in the city of Chicago. Going there for a family vacation or even just a weekend getaway will allow you to see a fantastic culture and take in incredible restaurants and entertainment options. 

When staying in Chicago, you will see that hotels rooms can be limited in space. Due to the city’s size, the square footage of available properties is limited. Therefore, you will find that rooms are smaller to accommodate more rooms and visitors.

One way to work around this is to stay at an Airbnb instead of a hotel. With more space, furnished bedrooms, and kitchen access, you will often find more space for the price when going the route of an Airbnb. 

With the vast amount of Airbnb’s available today, it can be hard to narrow down your search to find the best ones. To help you plan, we have rounded up a list of the 15 best Airbnbs in Chicago.

Read Next: Where to Stay in Chicago

15 Best Airbnbs in Chicago

While there are hundreds of vacation homes to pick from in Chicago, we have found the top choices for your upcoming vacation or getaway.

1. Classic Greystone

• Location: Uptown, Chicago
• Average Cost Per Night: $65

Located close to Montrose Beach, this neoclassical beauty is available for your upcoming adventure. As an award winner for one of ten unbelievable Airbnbs in the city, this establishment has many benefits and offers a delightful stay.

Not only is this residence an award winner, but it also allows you to support a good cause in the area. As you will see when stepping into the apartment, there are many beautiful and intricate art pieces throughout your private room.

While you can take them in during your stay, you can also purchase them. The proceeds go to support local charities that aid homeless youths.

Other perks to staying at the Classic Greystone include:

• Local Coffee
• International Teas
• Library and Books For Reading
• Piano
• Stocked Kitchen
• Eating Area
• Self Check-In
• Private Room

Besides the nearby beach, there are many different restaurants in the neighborhood and ample street parking.

2. Former Factory Modern Loft Duplex

• Location: River West, Chicago
• Average Cost Per Night: $385

This beautiful loft has been restored from its previous life as a factory. With three bedrooms, a full kitchen, beautiful brick walls, and a pool table, you will have plenty of space for your entire family to stretch out and enjoy your time.

The beautiful and modern elements throughout the loft add a unique touch to the décor. Each bedroom includes a television, which allows you to relax and unwind at the end of the day. With plenty of natural sunlight, you will enjoy your time at the loft to the fullest.

In addition to the above, the loft offers:

• Self Check-In
• Free Parking
• Washer and Dryer
• Fireplace
• Pack and Play
• Child Safety Gates

When staying at this former factory modern loft duplex, you will have easy access to entertainment options, shopping, and parks.

3. Luxurious Top Floor Apartment

• Location: North Park, Chicago
• Average Cost Per Night: $73

This incredible two-bedroom Airbnb has ten-foot high ceilings and a private entrance. The interior design is done in neutral shades that give the entire space a relaxed and elegant look. In the bathroom are top-of-the-line fixtures and a jacuzzi tub for relaxing after a day of sightseeing.

The kitchen offers the basics for standard meal prep, and all the linens you’ll need during your stay are included. For those with young children, outlet covers are installed to keep little hands safe.

Other perks to this luxurious top floor apartment Airbnb include:

• Smart Locks
• Luggage Dropoff
• Outdoor Dining Area
• First Aid Kit
• Window Guards
• Cable TV
• Washer and Dryer

With proximity to many restaurants and grocery stores, you will be able to get everything you need with minimal effort.

4. Three Level Skyline View Penthouse

• Location: Noble Square, Chicago
• Average Cost Per Night: $430

One look into this gorgeous 2,800 square foot penthouse will have your jaw on the floor. Step out onto the balcony for a breathtaking skyline view. Back in the house, you will have three levels of bedrooms and common spaces for up to 14 guests.

With 25 foot ceilings, mahogany floors, original Chicago masonry, and more, you will be in awe of your surroundings. Located near downtown attractions and in proximity to public transportation, you will easily be able to reach all the destinations on your itinerary.

Other notable features that come with your reservation are:

• High-Quality and Fast WiFi
• Free Parking
• Complimentary Toiletries
• Record Player
• Books
• Fully Stocked Kitchen
• Outdoor Dining
• Free Breakfast

If you’re planning a getaway with your closest friends, this incredible penthouse will provide you with the perfect backdrop for all of the memories you make!

5. The Noble Farmhouse

• Location: Noble Square, Chicago
• Average Cost Per Night: $141

Located in Noble Square, this quaint city farmhouse gives you all the standard comforts of country life with a location that is just steps from all the city life.

Complete with a garden area that offers a sense of tranquility in an otherwise chaotic area, this Airbnb will be the perfect resting place for your visit to Chicago. Besides the beautifully decorated interior and exemplary garden area, the farmhouse has a clawfoot tub and a full kitchen.

Your stay comes with additional amenities as well, including:

• Free Parking
• Washer and Dryer
• Linens
• Blow Dryer
• Basic Toiletries

Taking your morning coffee out in the garden will be the perfect start to a day full of sightseeing and memory-making. This farmhouse will be a great addition to your time away.

6. Vibrant Restored Mansion Near Wrigley

• Location: Uptown, Chicago
• Average Cost Per Night: $937

While owning a mansion would come with continuous cleaning, staying in one is different. This gorgeous restored mansion near Wrigley Field allows you to spend time in a mansion without all the responsibility!

With nine bedrooms, three and a half baths, and ten beds, you can bring your entire extended family on an extended vacation to the windy city. The property includes a garden area in the back and a meticulously clean and decorated interior.

Other features include:

• Free Parking
• Self Check-In
• Baby Bed
• Infant Bather
• High Chair
• Basic Toiletries
• Linens

You will have everything you need for a stay at this incredible mansion in Wrigleyville!

7. Fulton Market Condo

• Location: Fulton Market, Chicago
• Average Cost Per Night: $1,100

This beautiful condo is an excellent choice for families with children. The open space and child-oriented amenities allow parents to relax during their vacation. The floor-to-ceiling windows give off copious sunlight, illuminating the entire area.

Located just two minutes from the downtown area, you have easy access to many local restaurants and coffee shops. Right outside your door is an array of shopping opportunities and entertainment options. 

Aside from those, there are other features provided for you during your stay, including:

• High Chair
• Pack and Play
• Basic Kitchen Items
• Artisan Coffee
• Free Parking
• Pet-Friendly

Your entire family will enjoy their stay at this centrally located condo, with enough space for everyone and everything!

8. Historical Apartment in Old Town

• Location: Old Town, Chicago
• Average Cost Per Night: $196

One of the biggest attractions that people flock to during their visits to Chicago is the Lincoln Park Zoo. This beautiful family-friendly apartment is just a short walk from the zoo and many other fun activities.

With your stay in this two-bedroom and two-bathroom Airbnb, you will access various amenities such as a fireplace and a fully-equipped kitchen. Additionally, you can rent similar units in the same building for a large group or family reunion.

Other features include:

• High Chair
• Pack and Play
• Luggage Dropoff
• Cable TV
• Self Check-In

Staying in this historic district is a quieter option for your visit to Chicago. While it is a bit removed from the downtown area, it’s still just a short drive or subway ride away.

9. Roscoe Village Apartment

• Location: Roscoe Village, Chicago
• Average Cost Per Night: $216

As another option that is a bit removed from downtown but still within a short distance, this three-bedroom and two-bathroom apartment have plenty of room for everyone in your group.

Additionally, the space offers the use of garden space with a grill for family cookouts during your stay. The city of Chicago offers many activities, and this apartment gives you easy access to things like Shedd’s Aquarium, Millennium Park, and Magnificent Mile.

With a family-friendly focus, this Airbnb comes stocked with items like a pack and play and a high chair to make your travel easier.

Other amenities available for use include:

• Washer and Dryer
• Fully Stocked Kitchen
• Free Parking
• Pet-Friendly
• Luggage Dropoff

With this Roscoe Village apartment Airbnb, you will see a unique side of Chicago while still experiencing all it offers.

10. West Loop Five Bedroom Home

• Location: West Loop, Chicago
• Average Cost Per Night: $718

West Loop is an up-and-coming area of Chicago with many attractions, restaurants, and shopping opportunities. One Airbnb available in this neighborhood is this five-bedroom home that sleeps ten.

The house is situated on three different levels and offers high-quality fixtures and furnishings. The greatest thing about this home is the amount of space available.

Additionally, having a deck and private backyard gives a sense of calmness after a day of exploring the city. With ultra-fast internet and a dedicated workspace, you can even stay long-term and work remotely.

Other top features include:

• Children’s Dinnerware
• Pack and Play
• High Chair
• Free Parking
• Long-Term Stays

Escaping the hustle and bustle can be a way to rejuvenate before another full day. This gorgeous Airbnb gives you that ability. 

11. Historic Church Home

• Location: Logan Square, Chicago
• Average Cost Per Night: $1,036

This highly unique Airbnb comes in the form of a church built in 1888. It has since been renovated but has many of the original features intact. With beautiful stained glass and gorgeous wooden ceilings, you are in an amazingly preserved piece of history for your stay in Chicago.

With the massive amount of history in this home, you will teeter between a vacation and an educational experience. Located in Logan Square, you have easy access to many restaurants, bars, coffee shops, and boutiques.

Additionally, you will have the following amenities in the house:

• Large Event Space
• Pet-Friendly
• Indoor Fireplace
• Free Breakfast
• Long-Term Stays

You will love exploring every inch of this great space and learning how it went from a local church to a highly recognized Airbnb.

12. Three Bedroom Luxury Penthouse

• Location: Streeterville, Chicago
• Average Cost Per Night: $226

There are many perks to staying at this gorgeous penthouse near Navy Pier. One of them is the bright colors, both from the large windows and the painted walls and accents. Another is the amenities within the building, such as the large gym and indoor pool.

For those with children, you will feel right at home. While they run around in all the extra space, you can take in the view from the large picture windows throughout the apartment. Additionally, the host provides items such as a pack and play and a high chair to make your stay more comfortable.

Other features include:

• Cable TV
• Extra Linens
• BBQ Grill
• Fully Equipped Kitchen
• Elevator

The area is perfect for families looking to experience all that Chicago offers. With a view of Navy Pier right outside your window, you can take it all in from the comfort of your Airbnb.

13. Stylish Chicago Apartment Near Wrigley

• Location: Lakeview, Chicago
• Average Cost Per Night: $118

Many people come into Chicago to catch a game at Wrigley Field. There are several Airbnbs to stay in while there. However, this one is at the top of the list for its beautiful decor and proximity to the field.

While there, you can take advantage of all that the three-bedroom apartment offers to guests. With exterior parking, clean interior design, and ample space, you’ll want to get season tickets just to stay at the Airbnb!

Other amenities include:

• Full Kitchen
• Pets Allowed
• Washer and Dryer
• Linens
• Basic Toiletries

This space sleeps up to five people, so if you decide to bring friends along to the game, there’s more than enough room for them to stay with you too!

14. Penthouse With Private Roof Top Terrace

• Location: Old Town, Chicago
• Average Cost Per Night: $243

While you may come to visit Chicago, you will absolutely fall in love with the rooftop terrace that this Airbnb offers. With unobstructed views of the skyline, you will spend hours up there just taking in all of the sights and sounds of the city.

Inside, you will have beautiful modern decor and a large, bright, and airy kitchen with all the necessary equipment. Located in Old Town, you have access to all of the top spots in Chicago and many restaurants and boutiques.

Other perks to this Airbnb include:

• All Toiletries
• Extra Linens
• Washer and Dryer
• Amazon Prime Video and Netflix
• Lockbox

You’ll feel safe and cozy in this beautifully maintained penthouse. With three bedrooms and two baths, you will have plenty of space for your whole family to enjoy their stay. 

15. Hip and Modern Logan Square Apartment

• Location: Logan Square, Chicago
• Average Cost Per Night: $123

Staying in this great apartment in Logan Square will feel like you reserved a pricy hotel suite. With the special touches like complimentary snacks and bottled water and the rolled towels in the bathroom, you will feel like housekeeping came in and prepared the space just for you!

With a surplus of amenities, you will have the ultimate comfort during your stay. With a central location to all the hottest areas of Chicago, you’ll have the perfect place to come back to after a day of exploring.

Top features of this Airbnb include:

• Fireplace
• Pet-Friendly
• Basic Toiletries
• Linens
• Stocked Kitchen

This immaculate and well-designed home will give you a sense of relaxation as soon as you walk in the door, which you will appreciate during your stay in the busy city of Chicago!

Finding the Best Chicago Airbnb for You

After looking through the top Airbnb’s listed above, it’s best to review all the details and requirements when renting. Airbnb differs from standard hotels in several ways, which we outline below.

How to Check in

When you stay at a hotel or resort, you are given a room key. Typically this is in the form of a card that you swipe or tap. However, an Airbnb also operates as a home. You will sometimes be given a unique code for use during your stay.

This code will be randomly created and specific to you. Other times you will be provided with a set of keys to use during your time at the Airbnb. As time goes on, this option is becoming less common in favor of smart locks.

Regardless of which entrance option is presented to you, be mindful of your safety. If you stay in a busy area, be discreet with your security code. 

Additionally, be careful not to misplace your keys to your Airbnb. If you have lost them, you may not be able to enter your Airbnb for quite some time while a new set is provided. You will likely be subject to additional fees in this situation as well. 

Average Prices vs. Hotels

At times, especially in big cities like Chicago, the cost of a hotel can be quite high. Additionally, there is limited space in your hotel room or suite due to the large city population. Renting an Airbnb will not only afford you more space during your vacation, but it often comes at a reduced cost.

When entertaining the idea of a visit to a new city, be sure to explore the costs of both a hotel and Airbnb, as well as the amenities that come with each one. You will likely discover that each is vastly different and cater to different audiences. 

Advantage of Airbnb

While you won’t have access to perks such as daily housekeeping while staying at an Airbnb, you will have many amenities that you won’t find at a hotel. Some of these include:

• Multiple Rooms
• Fully Stocked Kitchen
• Private Entrances
• Designated Parking
• Pet-Friendly Accommodations
• Long-Term Stays
• Balconies or Decks
• Supplies for Children

While not all Airbnbs will offer the same set of amenities, you will find that many provide perks that will elevate your stay. Whether it’s a fully stocked kitchen or a BBQ grill, each feature adds to your visit positively.

Planning Your Visit to Chicago

Chicago is a cultural hub that offers many attractions and festivals throughout the year. If visiting for the first time, you will want to allow several days to fit in all of the top experiences. Some of the most popular include:

• Shedd’s Aquarium
• Legoland
• Museum of Science and Industry
• Field Museum
• Navy Pier
• The Art Institute of Chicago
• Millennium Park
• Grant Park
• Museum of Contemporary Art
• Lincoln Park Zoo
• Willis Tower
• Adler Planetarium
• Wrigley Field
• Chicago History Museum
• Chicago Riverwalk
• The Chicago Theatre

The great thing about visiting Chicago is that there is something for everyone. Whether you are traveling with young children or going to the city for a bachelorette party, there is something available that will entertain everyone in your group. 

Which Chicago Airbnb Is Best?

While we would love to point to just one option and declare it the best choice for your Chicago getaway, every visitor has their vision for the perfect accommodation. Therefore, there is no one size fits all selection that meets the needs and wants of everyone. 

The Airbnbs listed above have many positive reviews and offer high-quality amenities to their guests. When you’re planning your next visit to Chicago, be sure to reference this comprehensive list to find the best Airbnb for you and your group!