
House holiday rentals in Chicago
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Top-rated house rentals in Chicago
Guests agree: These houses are highly rated for location, cleanliness and more.
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Popular amenities for Chicago house rentals
House rentals with a pool

Pardizes Suites
I was speechless when I walked in her house it was beyond beautiful nothing was out of place at all when I say she had everything you can think of to accommodate us all she had all the toiletries you could think of the kitchen was stocked with all kind of seasonings dishes she even stocked breakfast sausages she put balloons out she really out done herself she went above and beyond it was plenty of games there the rooms were beautiful the beds were so comfortable I didn’t want to get up it was the best airbnb I ever stayed in we were all blown away by how beautiful and clean and neat it was Lisa is a very great hostess you all make sure to book with her she is great

Munster hide away
Nice house with updates. We used all four bedrooms, so everyone had their own space. Kitchen and living room looked nice, but a bit cozy if everyone was in the space at the same time. There was a large breakfast nook/counter in the kitchen instead of a table. More dishes, mugs, etc. in the kitchen would have been nice. The coffee maker and provided K-cups were great! Would definitely stay again if it's available when we are in the area 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
Really great place to stay, super responsive host! The pool was pretty great and so was the hot tub! Great location too, lots of stores, restaurants around, and parks like the Busse Woods (it’s huge and lots of walking paths)!

Schaumburg Oasis:Private Pool & Enchanted Garden
Beautiful Airbnb. Had everything we needed and more. Appreciated the special touches. Host tried to think of everything a guest might need. The beds were VERY comfortable, all of them. The place was clean and the backyard is amazing. We had a great time with family and spent a lot of time in the backyard. Would stay again.

Luxury Loft with Private Pool and Movie Theater
Damani was a great host, really responsive and easy to communicate with! The house was exactly as advertised and really nice! The pool was great!

Luxury fenced in modern ranch
It was a chaotic start to our vacation stemming off my daughter's graduation from Northwestern; however, Jennifer immediately took the stress off my shoulders and welcomed our family to a fabulous stay at her home. Words cannot express how grateful my family is and without Jennifer's help it would not have been as successfull. I highly recommend staying at any of her properties. She will go above and beyond to make sure you're stay is wonderful!

LUXURY - Movie Theater + Spa House
Nicholas was great house was really nice will definitely be back
Weekly house rentals

Gold Coast Home|Rooftop |PoolTable |Parking |Beach
Rasheed was very attentive. His home is in an excellent location, walking distance to resturants and shopping. The rooftop provided a spectular view of the city. I would definitely recommend Rasheed's home on a trip to Chicago!

The Modern Muse of Chicago! Close to everything!
Jasna was an amazing host! The house was absolutely spectacular—truly even better than the photos. Every room felt thoughtfully designed and full of warmth, making it feel just like home. We had all the amenities we needed, which made our stay super comfortable and stress-free. It was the perfect setting for a special girls’ trip with my mom and sister. The neighborhood was peaceful and beautiful, adding to the relaxing vibe. We’ll definitely be back! Thank you again for everything, Jasna!

Cheerful two bedroom home with patio/deck
Beautiful home in a quiet neighborhood with responsive and helpful hosts.

Garden/unit/1+1/cosy
Wonderful home close to train station. Very convenient and cozy. Would recommend!

Modern & Private Basement Retreat with Kitchenette
Great stay at Crystal's place! She was very responsive and helpful for check in. Even though this was in her home, it felt very private. It is immaculately kept and was comfortable with great amenities.

Sunny Historic Cottage on the Park
We loved Megan’s place! It’s adorably decorated and very cozy. We felt at home during our stay. The beds were comfortable and the kitchen was great for cooking dinner one night. Checking in and out was really simple. You’re not immediately by the train, but it’s a quiet safe neighborhood and there’s a little park across the street and a cute coffee shop a short walk from the house. As was clearly indicated by the hosts, it’s notably warmer upstairs than it is downstairs (we stayed in November) but it wasn’t a real issue. Would happily stay here again.

Big house in the BEST Location!
The house is lovely! Better than the pictures, just as all of the reviews say. The showers are incredible. The master bathroom is a dream. We had everything we needed & more. We don’t have a single complaint. We definitely plan on booking here again.

Spacious whole apt near shopping and city
Host was very nice and helpful with our questions, nice neighborhood some noise but nothing too extreme & house was clean.
Private house rentals

Family Friendly Duplex/9 min from MDW/Free Parking
Very nice space to bring friends over

CasaNova Modern City Living
Beautiful home layout and very spacious! Location was a quick drive to the city, which was convenient. Host was also very kind and attentive. Thank you Ms. Lilly for our stay!

Cozy Home in Brookfield
Juliana was a great host and we felt right at home. She was very friendly and helpful. The place was outstanding and the fenced in huge backyard was awesome. Our dogs loved it. I would highly recommend this place to anyone visiting the area.

Casa 22 | Luxury Modern House for 6 | 3 Bed,2 Bath
We had a truly wonderful stay at Casa22. The home is beautiful, luxurious, and impeccably maintained — everything was clean, spotless and thoughtfully arranged. It had all the essentials we needed for a comfortable extended stay with our family, including a well-equipped kitchen, and spacious layout. The hosts, Narcis and Gabriel, were fantastic — extremely responsive, clear in their communication. They provided detailed instructions that made check-in, check-out, and everything in between seamless. The neighborhood is quiet, safe, and very family-friendly, with easy access to main roads — a great location if you're planning to explore Chicago without the stress of city parking. Having a car made it easy to get around, and the area itself felt peaceful and well-kept. If you're visiting the Chicago area and looking for a clean, elegant, and well-managed place to stay, I highly recommend Casa22. We would absolutely love to return!

"Big" Tiny House yard 20 minutes from Chicago
Nam is a responsive and proactive host. While the house is advertised as tiny, it's not as small as I was expecting. It is basically the size of a one-bedroom apartment, and the bathroom is huge. Everything was new and clean. Metra is very close, the village is walkable, and you're just a few minutes by car from almost any type of restaurant or store you'd want. I would gladly stay again.

Culinary DREAM - Pizza Oven/BBQ/Smoker
Great house. Very clean and spacious.

Cozy getaway in the city.
“This place was an absolute gem! The house was spotless, stylish, and exactly as described. The location was perfect—close to everything but still peaceful at night. I’d definitely stay here again and highly recommend it to anyone visiting the area!”

Windy City White House (3br/2ba) *New Listing*
Our family of six enjoyed this pleasant apartment in a great Chicago location. Close to Ukrainian Village with lots of great eating options! Comfortable beds, very clean, Jamisyn provided water and snacks which was appreciated! Very easy access to 2nd floor unit. Some traffic noise in front bedroom but earplugs thoughtfully offered at the bedside! This was a great stay and we'll be back!
Quick stats about house rentals in Chicago
Total rentals
2K properties
Total number of reviews
84K reviews
Family-friendly rentals
1.1K properties are a good fit for families
Pet-friendly rentals
520 properties allow pets
Rentals with a pool
20 properties have a pool
Rentals with dedicated workspaces
1.3K properties have a dedicated workspace
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- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Oak Street Beach
- Shedd Aquarium
- Humboldt Park
- Six Flags Great America
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park
- Frank Lloyd Wright Home and Studio
- Garfield Park Conservatory
- Museum of Science and Industry
- Lincoln Park Zoo
- Willis Tower
- Brookfield Zoo
- Illinois Beach State Park
- Wicker Park
- Washington Park Zoo
- The 606
- Raging Waves Waterpark
- Moraine Hills State Park
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