
House holiday rentals in Downtown Chicago
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Top-rated house rentals in Downtown Chicago
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Popular amenities for house rentals in Downtown Chicago
House rentals with a pool

Pardizes Suites
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!

Glen Ellyn Home
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.

Spacious 3 Floor Townhome
Super cool host, very flexible and kind. When I come back im definitely going thru him again!

Rosemont 4BD2BA house with Pool
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!

Now Open: Heated Pool with Entire House
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.

Schaumburg Oasis:Private Pool & Enchanted Garden
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!

Stunning Home in Prime Chicago with Private Pool
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.

Spacious 4 Bed/3.5 Bath Sleeps 8+
Beautiful house very clean and comfortable. We'll be back very soon
Weekly house rentals

City Cottage in Logan Square-Avondale
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!

Rooftop Access with Views and Gym - LCP Collection
Great place in a great location. Would definitely book again!

NEW! 3BR/2.5B Duplex in Noble Sq
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.

Experience Chicago from Our 3-Story Retreat
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

Big house in the BEST Location!
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.

Brand New Spacious Duplex
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.

Executive Contemporary Duplex
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.

Smart Home King Bed Private Yard
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

Floresitas Oasis, your home in Chicago
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!

Victorian House in Heart of Rogers Park
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!

Spacious whole apt near shopping and city
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.

Modern Victorian Charm | A+ Location in OP
Great place to stay while visiting family! Very kid friendly and baby items provided too! Loved this home away from home!

Villa Noir Chicago Victorian 7 min to downtown
Great place. Great communication. Perfect for what we needed. Great house. Great neighborhood, right outside of downtown.

5 Star Luxury Stay Near Chicago O'hare Airport,
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!

Beverly House
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!

Modern SFH Near McCormick Place & Soldier Field
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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- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Oak Street Beach
- Shedd Aquarium
- Six Flags Great America
- Humboldt Park
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Lincoln Park
- Lincoln Park Zoo
- Garfield Park Conservatory
- Illinois Beach State Park
- Willis Tower
- Wicker Park
- Washington Park Zoo
- Brookfield Zoo
- The 606
- Moraine Hills State Park
- Chicago Cultural Center
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