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

Pardizes Suites
My family and I enjoyed our stay at this lovely home. We felt extremely welcomed, comfortable, had everything we could have thought of and more. We definitely had a wonderful experience from the time we checked in the home until we checked out. The host, Lisa, was responsive and accommodating. Any issue that occurred, which there really weren’t many, she took care of right away. We had an issue with the temperature in the house due to not knowing how to work the thermostat but other than that everything exceeded our expectations. This home and host deserves the 5 stars I provided all the way. I look forward to staying in the future. Thank you for having us!

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
Marzena was an awesome host, she responded super quickly and helped with anything we needed. the pictures do not do the backyard justice, it is so beautiful and fun. I will definitely stay again.

Paradise 4BR w/ Pool & Games
We recently moved backed to the Chicagoland area from Texas. We needed a place to stay while our Chicago home was being renovated. Lily’s place was perfect. It had everything we needed for the duration of our extended stay. It was well appointed. Exceptionally clean. It had all the amenities necessary for our family to live comfortably and it was close to grocery stores, shopping, restaurants, and downtown Chicago. Highly recommend.
Weekly house rentals

Duplex Home RoscoeVillage/Wrigley Free St Parking
What a lovely home! We and our two daughters had a great stay. The master bedroom is quite spacious, the beds are comfortable, there was ample closet space, and the kitchen is fantastic! The Roscoe Village neighborhood more generally is charming and walkable to any trips for essentials (multiple grocery stores and pharmacies within half a mile). While the Cubs were on the road during our trip, the house is an easy 20-minute walk to Wrigley Field. And Sharleen was always prompt and very helpful in answering the questions we had. We would happily return!

Superhost Wrigley/Lakeview Duplex 3BR/2.5BA
This house was just as described on the website. It was in a great location. The house is beautiful and clean. Walking distance to Wrigley, many restaurants and also the train. We really enjoyed our stay.

Home in Glen Ellyn
We really enjoyed the space and luxury of Mir’s home! The only thing was that there was not enough toilet paper during our visit. Other than that, we had a wonderful time and would absolutely recommend to anyone!

Maywood Relaxation
We came for The Weeknd concert in the city, so we got ready there, then spent the night and morning in the house. It was a beautiful house and felt super peaceful and safe! The beds were insanely comfy and we all slept so well! So much space! Everything was just so homey and comfortable.

Spacious Five Bedroom Home in Trendy Chicago Neighborhood
We (group of 10 women) stayed here for a weekend reunion. There were enough beds, including a few to double-up. We spent most of our time on the main floor hanging out in the front room and dining room areas. Kitchen has all the amenities (although we didn't cook much) - mostly used the fridge and coffee maker! Getting into the house was super easy for everyone since its a code access. The location is great for walking to shops and restaurants and a nearby L station.

Wicker Park 6bd/4ba, Steps from Cta, Parking Incl
Great place and stay! Location is amazing!

The Avondale Guesthouse
This was our second stay at Jed’s place. We enjoyed our visit to the area. The guesthouse was very clean and neat. Jed was very responsive, providing all of the information we needed for our stay.

Wrigleyville Greystone
Mark and his partner have clearly put their heart and soul into preparing this home for guests. Every detail has been thoughtfully considered, and any instructions you might need seem to appear just when you need them. The house itself is cozy, clean, and incredibly comfortable. To future guests, make sure to spend some time in the beautiful backyard. Whether you’re sipping a drink, reading a book, or simply having a chat, it’s a lovely, peaceful spot that adds something special to the stay.
Private house rentals

Sleeps 12 Comfortably in 8 Bedrooms 3 Full Bath
This is the 2nd time this year we rented from Michael. He continued to impress with the responsiveness. This time we filled the whole house, all bedrooms and both floors, 12 in total, mix of kids and adults. We decorated for Christmas, made it feel like we were home for the holidays. We walked all around the neighborhood, got coffee in the morning, fresh bread from a fabulous bakery in Downtown Oak Park and always felt safe and enjoyed the friendly neighborhood. The home and bedrooms were warm when you wanted them warm during the day and cool at night to sleep in. Kitchens were well equipped and all the appliances worked perfectly. The tankless water heater was a blessing when we were all trying to get out for a family event. At one point we realized that we were out of trash bags on Christmas morning. Michael had them there in less than 30 minutes. Over the top responsiveness. Being 10 minutes from the Eisenhower makes this convenient to either Downtown or Oak Brook.

Paradise in Schaumburg Low Cleaning Fee, 3 BR, 4Bd
O imóvel era exatamente como nas fotos, aconchegante, bem limpo, meu cachorro adorou a área atrás da casa para brincar. Vizinhança super tranquila, supermercados próximos, Syed respondia super rápido. Com certeza eu voltaria para me hospedar novamente.

Home away from home
Your place was perfect for my needs. It was larger than necessary for just myself but the location was perfect. My son attends BenU and I loved that I could meet up with him in minutes. Lisle and Naperville are great communities. The house was very well equipped and the yard was perfect. If you are going to have the full 6 people staying there is only one bathroom. Not a problem but if you come with a larger group I just wanted to note that as it is sometimes important. I highly recommend this place and I hope to use it again next year when my son graduates from BenU. Thanks for a great place and stay.

Warm and comfortable inviting Suburban home !
Beautiful area and home, wonderfully helpful and responsive host. Very grateful to have stayed here!

The Country Life! Entire House.
This house was so cozy my family and I will gladly come again for a stay

4 bedroom home rental in quiet neighborhood
Quiet neighborhood, spacious and comfortable home. The yard is inviting and a great entertaining space! Very kind hosts.

*ENTIRE CITY HOUSE/PARKING - 3 MIN WALK TO TRAIN
excellent central location for getting around Chicago. well taken care of home, and while the neighborhood is exactly what Joyce described, at first I felt worried, and then relieved as I walked from the train station to her home. everyone was so nice, and friendly. loved staying here.

RANCH, House-tel: updated full kitchen, comfy beds
This was our second time staying at Jehu's home in Itasca, IL. We have family and friends nearby so the location is perfect. The beds are comfortable, and the house is very clean. Having bottled water, coffee, a variety of beverages and snacks at our disposal was a plus. Jehu was very responsive to any questions we had. We would definitely book this property again for our next visit to the Chicagoland area.
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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
- Garfield Park Conservatory
- Lincoln Park
- Lincoln Park Zoo
- Willis Tower
- Illinois Beach State Park
- Wicker Park
- Washington Park Zoo
- Brookfield Zoo
- The 606
- Moraine Hills State Park
- Chicago Cultural Center
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