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House holiday rentals in Downtown Chicago

Find and book unique houses on Airbnb

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Popular amenities for house rentals in Downtown Chicago

House rentals with a pool

Home in Glen Ellyn
4.8 out of 5 average rating, 10 reviews

Pardizes Suites

LeslieRating, 5 stars2 weeks ago
It was a gorgeous home, she knew we were coming for my husbands bday and she got us a bottle of wine and balloons. She was very helpful and responsive if we needed anything. Great place to stay!
Guest favourite
Home in Glen Ellyn
4.95 out of 5 average rating, 20 reviews

Glen Ellyn Home

TimothyRating, 5 stars6 months ago
The property was very nice. It was well maintained and our family with our grandson were very comfortable. If we were to have a negative comment is that the heat distribution was not even throughout the home. The upstairs where the three bedrooms were located was very warm and the kitchen, living room and family were quite chilly. However, this did not impede us having a comfortable stay.
Home in Schaumburg
4.75 out of 5 average rating, 12 reviews

Spacious 3 Floor Townhome

Jocelyn DianeRating, 5 stars1 month ago
Super cool host, very flexible and kind. When I come back im definitely going thru him again!
Superhost
Home in Des Plaines
5 out of 5 average rating, 4 reviews

Rosemont 4BD2BA house with Pool

HannahRating, 5 stars3 weeks ago
Mike was very responsive leading up to our stay and very helpful whenever I had any questions about the property. The home was very clean and well maintained. Would recommend!
Guest favourite
Home in Bloomingdale
4.92 out of 5 average rating, 51 reviews

Now Open: Heated Pool with Entire House

TaraRating, 5 stars1 month ago
Moizs was an amazing host. Very accommodating, quick response, had some great recommendations for local restaurants, shopping, etc. Bloomingdale is a cute and nice suburb of Chicago. We had a great trip and we will definitely be back.
Guest favourite
Home in Schaumburg
4.92 out of 5 average rating, 26 reviews

Schaumburg Oasis:Private Pool & Enchanted Garden

SarahRating, 5 stars6 days ago
We stayed here while our floors were being refinished and Marzena’s Oasis did not disappoint! You can tell she takes great pride in her listing; everything was as described and more. The home was very clean with plenty of linens, dishes, and kitchen/pantry supplies. My kids left more crumbs on the floor than usual during breakfast one day…I could not find a broom so I messaged Marzena. She dropped off a stick vacuum AND some delicious treats. Above and beyond to make us feel welcome and comfortable. Thank you for a home away from home!
Home in Chicago
4.63 out of 5 average rating, 8 reviews

Stunning Home in Prime Chicago with Private Pool

LeandroRating, 5 stars3 weeks ago
Es una gran opción alternativa para vivir Chicago desde adentro. En una casa grande y cómoda, ideal para familias y para equipos de trabajos de paso por la ciudad. Gracias, volveremos.
Guest favourite
Home in Carol Stream
4.86 out of 5 average rating, 7 reviews

Spacious 4 Bed/3.5 Bath Sleeps 8+

CarmenRating, 5 stars8 months ago
Beautiful house very clean and comfortable. We'll be back very soon

Weekly house rentals

Guest favourite
Home in Chicago
4.96 out of 5 average rating, 91 reviews

City Cottage in Logan Square-Avondale

AshleyRating, 5 stars1 month ago
We loved this cute little house! Super walkable and close to lots of stuff in Logan Square; although we thoroughly enjoyed the peacefulness of hanging out in the private backyard. Would definitely stay again!
Superhost
Home in Oak Park
4.78 out of 5 average rating, 87 reviews

Rooftop Access with Views and Gym - LCP Collection

CynthiaRating, 5 stars1 week ago
Great place in a great location. Would definitely book again!
Guest favourite
Home in Chicago
4.96 out of 5 average rating, 74 reviews

NEW! 3BR/2.5B Duplex in Noble Sq

AdamRating, 5 stars1 month ago
Host is very accommodating and responsive. The place is nice and was in a great location. Only a short 10 minute drive that was a straight shot to Michigan Ave. The only thing we felt was slightly misleading was that we were under the impression that the 3rd bedroom with a couch was able to pull out and convert into a bed. Unfortunately, that wasn’t the case, so we ended up leveraging an air mattress we had packed as a contingency. Overall, we had an enjoyable stay and would recommend.
Superhost
Home in Chicago
4.9 out of 5 average rating, 72 reviews

Experience Chicago from Our 3-Story Retreat

SylviaRating, 5 stars1 day ago
The home is lovely we are seniors so the steps were a little bit tricky for us. I thought it was a bit closer to town but that was my mistake but the home is very relaxing and perfect for a large group or family I would highly recommend this home and our host was exceptional
Guest favourite
Home in Chicago
4.95 out of 5 average rating, 19 reviews

Big house in the BEST Location!

AbhishekRating, 5 stars1 week ago
It was as pictured and suited our needs. Clean and well organized. When we reached out we were responded to promptly and thoroughly. The location is good and walkable. If planning to go to Navy Pier or the Miracle Mile to go shopping (or something in that general area of Chicago), expect about a 40 - 60 min drive.
Superhost
Home in Chicago
4.83 out of 5 average rating, 70 reviews

Brand New Spacious Duplex

LillianRating, 5 stars3 days ago
I just wanna say thank to each other to host. It was nice and big. The bed downstairs was a little hard. The water stain around the basement floor area and it did smell like mold. Other than that. It was good value for your money. Parking was a challenge for us, but we figured it out. Have a great day if you stay.
Superhost
Home in Chicago
4.89 out of 5 average rating, 28 reviews

Executive Contemporary Duplex

WaljimaRating, 5 stars1 week ago
My family and I enjoyed staying here. I was born and raised in Chicago just 4 blocks from this Airbnb! It was such a great experience to be back in my old neighborhood. Olusesan is a phenomenal host! I highly recommend this place.
Guest favourite
Home in Chicago
4.95 out of 5 average rating, 21 reviews

Smart Home King Bed Private Yard

DavidRating, 5 stars3 weeks ago
KB was a great host! Came for the Beyonce concert and this place had more than enough space for our group. The location was no more than a 15 min drive to soldier field and great food in the area!

Private house rentals

Guest favourite
Home in Chicago
4.95 out of 5 average rating, 40 reviews

Floresitas Oasis, your home in Chicago

KelvinRating, 5 stars4 days ago
Lizbeth’s place was a great stay! It was cozy, clean, and had more than enough space for me and my three friends. While it was a little farther from the city center than I initially expected, the neighborhood made up for it with tons of great restaurants nearby—there was always something good to eat just around the corner. Lizbeth was also a fantastic host—very friendly and super responsive whenever we had questions. Would definitely recommend her place to anyone visiting the area!
Guest favourite
Home in Chicago
4.98 out of 5 average rating, 97 reviews

Victorian House in Heart of Rogers Park

KrystleRating, 5 stars6 days ago
This was my second stay at this location, and our family had the BEST time! We stayed for five days. The house is very immaculate; not a trace of dirt or dust anywhere. Like last time, we were left with some yummy snacks and treats upon arrival. Kris & Daniel also went above and beyond when we wanted to go to the beach - they personally came right over and got some beach chairs, towels, and an umbrella from the basement for us. The house is very comfortable with high-tech smart devices and we were nice and cool despite the heat (and nice and warm when it got chilly later in our visit). Our last day, I accidentally pulled down a curtain rod when opening the drapes, and Kris & Daniel could not have been more gracious about it. Great house and great hosts! Thank you!
Superhost
Home in Cicero
4.79 out of 5 average rating, 190 reviews

Spacious whole apt near shopping and city

BrandiRating, 5 stars2 weeks ago
This was my first time using Airbnb and Daniel was so helpful through the entire process. Also the house was so clean and smelled so good! Pictures looked just like online. Parking was easy and didn’t have trouble or finding anything at all.
Top guest favourite
Home in Oak Park
4.98 out of 5 average rating, 96 reviews

Modern Victorian Charm | A+ Location in OP

SamRating, 5 stars3 days ago
Great place to stay while visiting family! Very kid friendly and baby items provided too! Loved this home away from home!
Top guest favourite
Home in Chicago
5 out of 5 average rating, 23 reviews

Villa Noir Chicago Victorian 7 min to downtown

EddieRating, 5 stars1 week ago
Great place. Great communication. Perfect for what we needed. Great house. Great neighborhood, right outside of downtown.
Top guest favourite
Home in Des Plaines
4.98 out of 5 average rating, 56 reviews

5 Star Luxury Stay Near Chicago O'hare Airport,

KenyaRating, 5 stars1 week ago
I just wanted to thank you for such a fantastic stay at your beautiful home. From start to finish, your communication was excellent — always clear, prompt, and helpful, which made everything so easy and enjoyable. The house itself was stunning, clean and incredibly comfortable. I especially loved all the techie touches — they added such a modern and thoughtful feel to the space. The peaceful and quiet neighborhood made it even better; it was the perfect place to relax and unwind. Thank you again for your hospitality. I would absolutely love to stay again in the future!
Guest favourite
Home in Chicago
4.91 out of 5 average rating, 77 reviews

Beverly House

StarrRating, 5 stars4 days ago
The home was cozy and super convenient for what we needed. The backyard was so nice to get some outside time with the kids and we walked to the park up the street a couple of times. The kitchen had everything we needed. Melissa was very helpful in sharing what to know before getting there and a printed manual of facts and tips about the home, the area and some games to play, too. We would book again!
Superhost
Home in Chicago
4.9 out of 5 average rating, 88 reviews

Modern SFH Near McCormick Place & Soldier Field

Sandra Rating, 5 stars1 month ago
Stayed with 4 adults and 5 kids. House was more than spacious and cozy. Furniture was nicely kempt. Beds were comfortable. Neighborhood was quiet. We rented a car and appreciated the garage to keep car in. We did have an issue with water temperature but was resolved quickly with host We loved the house!

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