
House vacation rentals in Downtown Chicago
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Top-rated house rentals in Downtown Chicago
Guests agree: these houses are highly rated for location, cleanliness, and more.
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Popular amenities for Downtown Chicago house rentals
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.

Hidden GEM OASIS in Chicagoland
Everything was great! The place was just as imagined.

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!

LUXURY - Movie Theater + Spa House
Great getaway place to stay at. Beautiful patio area as well!
Weekly house rentals

The Modern Muse of Chicago! Close to everything!
This Airbnb exceeded our expectations in every way! It was even better in person—much more spacious than we anticipated. The home was stocked with thoughtful amenities, especially in the kitchen, which made our stay incredibly convenient. The outdoor seating area was a great place to relax, and we loved the location. It truly felt like a home away from home, with everything we could possibly need already there. The host was also very attentive and accommodating, making the experience even better. We would definitely stay here 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.

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!

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.

5BR/4BA Home - Theatre, Hot Tub, Sauna, Rooftop!
Patty was a great host and the home was wonderful. Patty was very responsive, helpful, and attentive towards our questions. The home was very spacious, clean, in a nice area, with all the listed amenities that were so nice and fun to have. We had a great stay, and I highly recommend this place!

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.
Private house rentals

Family Friendly Duplex/9 min from MDW/Free Parking
Very comfortable place and nice and very responsive host! Definitely recommend this stay!

A home away from home.
Me my freinds and family enjoyed our stay. The host was very quick to respond to any concerns. The home was clean and spacious. The decor was nice to take pictures. I liked that it had a bathroom downstairs for easy assess. We will come back when we visit Chicago again. Thanks you guy you were awesome.

Victorian House in Heart of Rogers Park
The house is like a page out of an Interior Decorating magazine, an immersion experience. Like the house the grounds were equally beautiful. There was a lot of thought and love in remodeling this property. The hosts were communicative and gracious. It is located in a great neighborhood close to many dining options. I appreciated the modern touches and the cleanliness of the place. I would book this place again. Highly recommended.

Windy City White House (3br/2ba) *New Listing*
Beautiful place! Very clean! The host was very responsive. The kitchen was stocked with tea, coffee and extras. I love that they had a tea kettle. The rental had everything we needed, extra bedding and towels. We arrived to a basket of snacks and drinks 😊. Comfy beds and sofa in the sitting room. Lots of room for a family of 4. It is an upstairs unit so stairs to climb. Location was ok.

Executive Contemporary Duplex
Olusesan had a clean and peaceful space. I was only a couple of miles away from the concert venue to see Beyoncé. We had our own parking space and Hyde Park was such a cute little community. We did not want to leave! Thank you so much for your hospitality. May God bless you and all of your spaces. 🙏🏽🙏🏽

Beverly House
Melissa’s house is beautiful and in a quiet neighborhood. The beds were comfortable- one of us even slept on the couch and was comfortable. The kitchen was fully stocked with pans, etc. and we loved hanging out in the backyard. We appreciated the heads up about the air fresheners and flexibility to unplug them.

① Lux | Spa | Rooftop | Modern | 4 Mi to Downtown
Anita’s place was absolutely stunning and looked just like the photos. Extremely clean and very spacious. We hosted a 50th birthday brunch here and it was more than enough space and amenities to accommodate everyone. The rooftop was just amazing and a great addition to the place. Thank you Anita for letting us book your gorgeous home and we would love to book again and again! ⭐️⭐️⭐️⭐️⭐️

Sophisticated Twnhm in Prestigious S. Lincoln Park
We really enjoyed Kyriako’s space! My husband, two toddlers, and I spent the long weekend in Chicago. This space had everything we needed for a comfortable stay. The location was great and we had access to tons of activities for family fun. We would definitely recommend this space for a family trip to Chicago!
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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
- Lincoln Park
- Museum of Science and Industry
- Lincoln Park Zoo
- Garfield Park Conservatory
- Illinois Beach State Park
- Wicker Park
- Willis Tower
- Washington Park Zoo
- Brookfield Zoo
- The 606
- Moraine Hills State Park
- Chicago Cultural Center
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