The 12 Best Airbnbs In Chicago, Illinois

July 5, 2020
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If you’re looking for the best Airbnbs in Chicago, you’ve come to the right place. We combed through thousands of Airbnb listings in Chicago and the surrounding area to find the homes with the best amenities and the most positive reviews at the lowest prices.

#1 River North’s Rock N Roll Apartment

6 Guests | 2 Bedrooms | 2 Bathrooms

Book Now: $450 per night,

Enjoy this unique space that will make you feel like you’re a rock star! This beautiful apartment with two bedrooms is able to accommodate up to six guests, ideal for large groups of friends or families looking for a place to enjoy their stay in Chicago.

Here’s the description from Airbnb:

“Decorated with rock n’ roll memorabilia and located above a trendy restaurant, this cozy apartment also features high ceilings and a carved canopy bed. Minutes to Mag Mile and the Loop! Free parking available when requested at booking.”


Self check-in | Free parking on premises | Full kitchen | Washer | Dryer | Dishwasher | Room-darkening shades | Pets allowed | Suitable for events | Heating | Air conditioning | Pack ’n Play/travel crib

Guest Reviews

“Very nice place, exactly like on the photos. There is an excellent pub/tap house in the same building and location is just perfect. Everything that you may need for a nice trip in Chicago is there!” – Antoine
“Great location. The space is very nicely decorated and spacious. There is a bar/restaurant downstairs and they play loud music until 2am which can be easily heard. If that is not an issue then it’s a great place to say.” – Sina
“Perfect location. Just out of the traffic area. Easy access to major routes as well as public transport. Very clean. Responsive host. Comfortable and stylish!” – Andriy
“It was an amazing stay. We held a team retreat here and the living room space was perfect for 6-8 ppl to collaborate and brainstorm. Two of us stayed overnight and the decor and bedrooms were unique and impressive. We will definitely book this again!” – Meredith
“What can I say, this is now my go-to location in Chicago. It is located perfectly within walking distance of everything you need or want. The guitars and art make you feel like you are a rockstar.” – Preston

#2 Stunning Old Town Penthouse with Private Rooftop

16 Guests | 5 Bedrooms | 4 Bathrooms

Book Now: $1,310 per night,

This stunning and vintage penthouse combines the classic and the modern in one lovely space. Able to accommodate up to 16 guests in its 5 bedrooms, this is an ideal place for large family gatherings or even work-related trips with bigger teams.

Here’s the description from Airbnb:

“This is a beautiful 4000 sq ft penthouse loft combined in the heart of downtown. This building is truly one of a kind, built-in 1897, completely renovated in 2017, it has exposed brick, 20 ft ceilings and 120-year-old barn wood floors w/ roof deck overlooking downtown5 bedrooms: 4 w/ king beds & 1 w/ 3 twins. 4 full baths.


Self check-in | Paid parking off premises | Full kitchen | Washer | Dryer | Pets allowed | Suitable for events | Heating | Air conditioning | Garden or backyard | Wifi | TV

Guest Reviews

“Our second time in this amazing penthouse. Casey is a great host and a great communicator. He has been very helpful throughout our stay. One of the most intuitive and relaxed I’ve stayed. Wonderful experience.” – Mehmet
“We had an amazing time at this beautiful penthouse! The space is absolutely beautiful and in a great part of town. We had a big group and there was definitely enough room for everyone. The apt is super well laid out and Casey was really helpful in answering any questions we had.” – Sean
“We came to Chicago for a bachelor party and trying to find a place for 15 people was non-trivial. But once we saw the listing for Casey’s place we knew we found the perfect spot. The location was great with lots of bars, restaurants and a grocery/liquor store nearby.” – Damien
“As good (or even better) than what you see on the pictures. So nice, so clean, very stylish. This place feels like you’re staying at a friend’s house. Well located. And if you are a big group it’s not that expensive. Host answered questions rapidly.”- J.T.
“Loved the place, amazing penthouse suite and a great location. Very cool spot, very clean and had all the amenities we needed! Awesome for a big group.” – Shawn

#3 Radiant Home with a Spacious Rooftop Patio

5 Guests | 2 Bedrooms | 1 Bathrooms

Book Now: $440 per night,

This refined space is ideal for those looking for a more elegant option for their stay. This is a home that you cannot miss! It is able to accommodate 5 guests, perfect for small families and groups of friends.

Here’s the description from Airbnb:

“Sit down to a meal with friends within the sophisticated air of this refined home featuring enduring wood plank floors, vivid art, and an eclectic fusion of modern and old-world furnishings. At sunset, gather for drinks on the spacious roof patio. Over 10 guests becomes an event. That is priced at $250 per hour. There will be someone here to assist you. The first floor is a separate event space. Perfect for a gathering. Then come upstairs and relax and spend the night!”


Free parking on premises | Free street parking | Paid parking off premises | Full kitchen | Washer | Dryer | Indoor fireplace | Elevator | Pets allowed | Suitable for events | Heating | Air conditioning

Guest Reviews

“Linda was a great host with excellent communication. The stay went smoothly and the rental was even more luxurious than the pictures can illustrate. Thank you for hosting us!” – Daniel
“Linda is an amazing host. She went over and beyond for my stay. Words can’t express how grateful I am to have booked with Linda. She helped me with my husband’s surprise birthday party. The condo and rooftop are clean, spacious and absolutely beautiful.” – Ipek
“First of all Linda needs to be commended for her flexibility. Linda was extraordinarily kind and patient with us as things kept shifting.” – Sophia
“First time staying at an AirBnb and Linda was amazing throughout the entire process! Would definitely recommend her place! Very clean and everything we expected.” – Anas
“The pictures of Linda’s home just don’t do it justice! Amazing space!” – Maureen
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#4 Three Level Skyline View Chicago Penthouse

14 Guests | 3 Bedrooms | 2 Bathrooms

Book Now: $535 per night,

This luxurious penthouse is the place to stay for those who enjoy the fancy things in life. With a beautiful view of the city and three bedrooms, this space is able to accommodate up to 14 guests for reunions, ideal for work get-togethers in the city.

Here’s the description from Airbnb:

“This One-of-a-kind Luxury West Town Penthouse is stunning and spans 3 levels! At 2800ft² it boasts amazing unobstructed Chicago city skyline views and has its own private rooftop deck with panoramic city skyline views. Features include breathtaking 25′ tall ceilings, mahogany hardwood floors, huge tub, luxury walk-in showers, and marble bathrooms.”


Wifi | Cable TV | Laptop-friendly workspace | Dryer | TV | Iron | Washer | Heating | Essentials | Air conditioning | Ethernet connection | Hot water

Guest Reviews

“One of the coolest airbnb’s I have stayed in. Pics don’t do it justice. Definitely recommend and Candace was a fantastic host!” – Mike
“Nice location, ideal for those who like to walk. Close to the downtown areas by” – Manfred
“Great place to stay for larger groups. Lots of space, clean with great rooftop patio.” – Clayton
“I can not believe how amazing this experience was for us, it really was wonderful and Candace was the kindest host ever. I come from a very harsh background, and this was my first vacation in my life.” – Manda
“Candace was great!! She was very flexible for us when we ended up arriving late, which was much appreciated, and she took care of anything we needed.” – Jenna

#5 Classy South Loop Apartment

6 Guests | 2 Bedrooms | 2 Bathrooms

Book Now: $400 per night,

Sleek, modern and elegant are just some of the qualities of the beautiful and professionally decorated apartment. You can enjoy this gorgeous space in the midst of the bustling Chicago scene with your family or a group of friends.

Here’s the description from Airbnb:

“Come relax in this luxury apartment professionally managed by Kasa. This apartment is well-connected to the Chicago scene you’re seeking. Close to large companies and a short distance from Grant Park, a number of fantastic local restaurants, bars, and shopping options can also be found nearby. The property is fewer than two miles from McCormick Place and the Museum Campus. “


Wifi | Laptop-friendly workspace | Dryer | TV | Iron | Washer | Heating | Essentials | Air conditioning | Hot water | Room-darkening shades | Bathtub

Guest Reviews

“Beautiful location with a great view. The home was clean and stocked with all the basics. Short walk to the grocery store and one subway stop away from the Loop and downtown. Check-in instructions were clear and host communication was excellent. Beautiful location with a great view. ” – Caleb
“The stay here was amazing, great location, and great customer service through KASA. However, every front desk person I encountered was so rude and not helpful at all. Would definitely stay here again though.” – Jacklynn
“The views are great. Beds are comfortable and the apartment was clean. Had everything we needed. All instructions for checking in/out were carefully laid out. Restaurant’s within walking distance. It really was a great place.” – Gina
“Kasa’s place was definitely spectacular! My stay here was amazing and for it being my first time in Chicago, the views Kasa’s place had to order definitely topped it off. ” – Alaina
“Beautiful home and amazing views! Easy check-in. Very secure building. The home was so clean and pretty. One free parking spot provided which was really convenient! Close to everything. Really enjoyed my stay!” – Vanessa

#6 Studio with Private Outdoor Hot Tub and Yard

2 Guests | Bedrooms | 1 Bathrooms

Book Now: $210 per night,

Cozy space with lovely decor ideal for couples in their honeymoon. Enjoy this adorable studio as you lounge in the hot tub with your special someone. This is a property you cannot miss!

Here’s the description from Airbnb:

“Soak in the private outdoor hot tub in the leafy, fenced-in yard outside this spacious studio. The home boasts high ceilings with exposed silver ducting and eclectic decorations, including cow print furniture, and an intricately carved bathroom door. While the decor is eclectic, the king-size bed sets the standard for comfort. The Checkerboard Studio is perfect for a cozy getaway and offers intimacy, but with enough space to move.”


Self check-in | Free street parking | Private hot tub | Kitchen | Room-darkening shades | Pets allowed | Heating | Air conditioning | Pack ’n Play/travel crib | Garden or backyard | Wifi | TV

Guest Reviews

“Brad’s Place was great – good location and loved having the outside space. Brad was easy to get a hold and super accommodating. Would definitely recommend!” – Gemma
“Wonderful place to stay. Loves finding out it was right in the Puerto Rican neighborhood. Easy to grab great food!!” – Miguel
“An amazing location, loved the apartment, furniture and decor. Brad was incredibly accommodating and helpful. Thanks for a great trip!” – Jason
“Brad was extremely helpful and easy to communicate with. The hot tub was a great addition to our stay and that was the comfiest bed we’ve ever slept on! My boyfriend and I had a great time and would definitely stay here again in the future.” – Julia
“The stay was great! The hot tub and back patio with grill was excellent and made it really feel like we were on vacation. The bed was super comfortable, I loved the artful touches around the apartment, and the neighbourhood was really cute and quiet.” – Keyla
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#7 Bright, Modern Apartment in a Vintage Greystone

4 Guests | 1 Bedrooms | 1 Bathrooms

Book Now: $170 per night,

This tastefully decorated apartment is one that you won’t want to miss! Enjoy the Chicago scene and come back to this gorgeous space as you enjoy your stay with significant other or family. Create some wonderful memories here!

Here’s the description from Airbnb:

“Enjoy morning coffee by the sunny bay window in this vintage apartment with classic modern style. The apartment features vintage charm with modern amenities, queen memory foam bed in bedroom and queen sofa bed in the living room. Parking is available in the back lot for an additional $25 per night. For reservations over three weeks, we require cleaning every 2 weeks at a cost of $60 per cleaning.”


Self check-in | Full kitchen | Washer | Dryer | Dishwasher | Heating | Air conditioning | Bathtub | Garden or backyard | Outlet covers | Wifi | TV

Guest Reviews

“This was a definite 5-star rental and priced very well. Everything you would ever possibly need is in the kitchen and the very well decorated. The location is great near good restaurants, bars and coffee shops. ” – Jesse
“Rob is outstanding. he’s a great dude and very thoughtful and helpful! A+ stay!” – Keegan
“Rob was a perfect Host. Everything was better then expected. The place is exceptionally designs with everything you may need at your disposal. Looking forward to staying there again soon. ” – Yann
“Great space!! It was hot but we made it happen. Everything about this place was amazing! Would love to come back very soon. Please make sure you make a stop here!” – Darien
“Gorgeous apartment in a great location. The interior is updated and beautifully decorated, bed/couch are super comfortable, and the hosts were so kind and accomodating during our stay.” – Krysten

#8 Eclectic Artist-Designed Sanctuary In The Heart of Pilsen

4 Guests | 2 Bedrooms | 1 Bathrooms

Book Now: $230 per night,

Start your day in the amazing city of Chicago by enjoying the feel of cold floors on this eclectic and tastefully decorated apartment in the heart of Pilsen. This is a place you must check out! It is ideal to enjoy your stay with your partner or a small group of friends.

Here’s the description from Airbnb:

“Start the day with a soothing cup of tea or Nespresso on the front stoop in the morning sunshine. Gallery-like white hardwood floors combine with mismatched artwork, glossy houseplants, and a classic leather Chesterfield for restorative afternoon naps.”


Free parking on premises | Free street parking | Kitchen | Washer | Dryer | Dishwasher | Heating | Air conditioning | Pack ’n Play/travel crib | Garden or backyard | Wifi | TV

Guest Reviews

“The apartment is really beautiful and stylish as well as impeccably clean. The beds and pillows were extremely comfortable just like a hotel. We really enjoyed the neighbourhood.” – Cammi
“Daniel and Tess space exceeded our expectations. We enjoyed every aspect of it from location to decor to communicating with them. They made everything run so smoothly and the space they have created makes for such a fantastic vacation spot. ” – Britney
“Daniel was a very thoughtful host and checked in frequently to make sure I was enjoying my stay. Great communication and response quickly. The apartment is just like the photos and in a part of Chicago that is very walkable. Highly recommended!” – Steven
“We loved staying in this beautiful apartment with a lovely design. I loved all the art pieces and curated touches! The beds were comfortable and there were lots of pillows (different types so you could choose what you wanted which is always appreciated).” – Raina
“Daniel and Tes are great hosts! Their place and neighbourhood are fabulous and it was great to be able to explore such a great neighbourhood full of culture, very cool restaurants, coffee shops and great recommendations for a cozy spot to have a cocktail.” – Tamara

#9 Sleek Pad near Wrigleyville

8 Guests | 3 Bedrooms | 2 Bathrooms

Book Now: $360 per night,

This soothing and elegant place will definitely be most pleasing for those who enjoy the finer things in life. Sit down as you enjoy your evenings in this cozy space with your family or a large group of friends.

Here’s the description from Airbnb:

“Step into the chic, curved bathtub for a rejuvenating soak at this expansive escape featuring colour block walls in calming rose and cool graphite. Clean lines, upscale materials, and refined black-framed windows contrast with retro egg chairs.”


Self check-in | Free parking on premises | Free street parking | Kitchen | Washer | Dryer | Dishwasher | Elevator | Room-darkening shades | Pets allowed | Heating | Air conditioning

Guest Reviews

“Good place and quite big. Living room could use blinds if you plan on having someone sleep on the couch or the air mattress in that area. Overall good stay.” – Zack
“Beautiful place in a great location. Definitely would stay here again” – Peter
“The location was extremely convenient and every interior detail was beautiful and thoughtfully arranged. This location was the perfect space for a weekend staycation with my best friends! The host was extremely responsive and pleasant!” – Candis
“The condo was comfortable, clean, and had everything to make our stay comfortable. I could have stayed much longer. Tom responded very quickly when I had a question.” – Ramona
“I stayed here during a condo remodel and also had to work from here. this was a great space and location. there was a lot of food around and I enjoyed the neighbourhood and walking around. the bed and sheets were some of the comfiest I have ever slept on!” – Caitlin

#10 Cool and Modern Chicago Apartment near Transit

6 Guests | 3 Bedrooms | 1 Bathrooms

Book Now: $190 per night,

This cozy and stylish apartment is the place to stay for larger groups of friends looking for a place that will definitely look great in pictures! This apartment will have you not wanting to ever leave but even in case you do so, you’ll still be a short distance away from the bustling city and its bars and restaurants.

Here’s the description from Airbnb:

“Stretch out on a plush sectional sofa in the living room of this airy modern apartment. This apartment is decidedly cool, with chic and minimalist black-and-white decor, gleaming hardwood floors, and a full family-style kitchen.”


Self check-in | Free parking on premises | Free street parking | Kitchen | Washer | Dryer | Dishwasher | Room-darkening shades | Pets allowed | Heating | Air conditioning | Bathtub

Guest Reviews

“Ahsha was a wonderful host! She was quick to respond and her home is incredibly inviting and clean. The neighborhood is safe and provides easy access to the city with the nearby train and plenty of restaurants nearby! Great stay!” – Kira
“Beautiful apartment! Loved everything about it. Would recommend.” – Melanie
“This is my second stay in this lovely apartment and as before everything was perfect! Beautiful space, so comfortable and easy to get to! Everything was perfect for us! We will be back!” – Jenna
“Place was exactly as described! We really enjoyed our time there. The only thing was the rooms were a bit cold (we went in Feb.) with no vents in each room, we had to keep doors open to get heat from the living room.” – Pang
“Host and place were both great, would definitely stay here again!” – Nina

#11 Spacious Five Bedroom Home In Trendy Chicago Neighborhood

15 Guests | 5 Bedrooms | 3 Bathrooms

Book Now: $1,400 per night,

Trendy, stylish and wonderfully decorated are some adjectives to describe this beautiful home. This is the perfect stay for a family get-together. With 5 bedrooms and the space to accommodate up to 15 guests, this may be your next stay for Thanksgiving!

Here’s the description from Airbnb:

“Unwind on the private rooftop deck, soak in the luxurious jacuzzi tub or take a relaxing steam shower after you host a dinner party in your own spacious dining room. Then watch a movie in the entertainment center with popcorn machine and 75 inch TV.”


Self check-in | Free parking on premises | Kitchen | Washer | Dryer | Pets allowed | Heating | Air conditioning | Crib | Wifi | TV | Bathroom essentials

Guest Reviews

“The home was absolutely amazing and everything we needed for the weekend. Beautifully decorated, comfortable, and right near all the great places. Carey was attentive and accommodating and we would definitely stay here again.” – Markie
“Any family who doesn’t stay here is really missing out on a fantastic home! It’s beautifully decorated, has lots of space, and the bedding is so warm and cozy! While there were so many good things, my favourite feature is the heated floor in the master bedroom. ” – Leinani & Bob
“This the kind of home that makes you think the property value is 2x what book price actually is because it is styles so well. We were all quite comfortable, and really enjoyed the location/property/style.” – Andy
“We loved the Paulina house. Very nicely decorated and amenities were amazing. Love the location and entire setup! Would visit again for sure.” – Shay
“Had a group of nine people and we had a wonderful stay. Spacious, clean, stylish, and comfortable: this place has it all, including parking and a great location within walking distance to loads of great places!” – Nicolas

#12 Gorgeous House Steps from Evanston

5 Guests | 2 Bedrooms | 2 Bathrooms

Book Now: $90 per night,

This beautifully decorated house is a must you should definitely check out! With the space to accommodate up to 5 guests and lovely open spaces to relax throughout the day, this is the ideal stay for small families or little groups of friends.

Here’s the description from Airbnb:

“Pull up a leather stool at the breakfast bar for a morning coffee and browse through the guide book before heading out to explore. This open, city condo is dotted with leafy plants and unique, industrial-style metal finishing for a calm city vibe.

Use this space as a home base to discover Chicago, visit your family at college or snuggle up with a loved one for a quiet posh staycation. Use of the private carport and private entrance provides a stress-free stay.”


Self check-in | Free parking on premises | Free street parking | Kitchen | Dishwasher | Room-darkening shades | Heating | Air conditioning | Bathtub | Wifi | TV | Coffee maker

Guest Reviews

“D and B’s place was wonderful. Check-in was super easy and the apartment was so spacious, clean, as well as cozy. Definitely plan on staying there in the future.” – Telly
“D&B were great! My boyfriend and I were so impressed and felt very welcomed! This was our first time using Airbnb and it’s no question that we will be using it again in the future! ” – Jessica
“Nice place to stay. D and B are easy to reach through text. They are very helpful. The place is in a nice quiet area. Not a far drive from the lake. The place has character. The carport is a little small. Other than that we enjoyed our stay. Thanks D and B!” – Mwangelwa
“This place was absolutely gorgeous the hosts were very upfront on rules and extra notices about the place. They made it super easy to add a friend when she decided to come with us. I would 100% stay again!” – Bailey
“Beautiful, clean home in a convenient location. Check-in and check out was super easy and they were quick to respond and even let us check in a little early. Thoughtful touches throughout the place and a great list of recommendations on the fridge!” – Alita
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