Some info has been automatically translated. Show original language

House holiday rentals in Chicago

Find and book unique houses on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Chicago house rentals

House rentals with a pool

Home in Glen Ellyn
4.83 out of 5 average rating, 12 reviews

Pardizes Suites

CrystalRating, 5 stars2 weeks ago
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
Guest favourite
Home in Munster
5 out of 5 average rating, 11 reviews

Munster hide away

ChristopherRating, 5 stars6 months ago
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.
Superhost
Home in Des Plaines
5 out of 5 average rating, 4 reviews

Rosemont 4BD2BA house with Pool

HannahRating, 5 stars1 month 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, 52 reviews

Now Open: Heated Pool with Entire House

AmyRating, 5 stars3 days ago
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)!
Guest favourite
Home in Schaumburg
4.93 out of 5 average rating, 28 reviews

Schaumburg Oasis:Private Pool & Enchanted Garden

AshleaRating, 5 stars1 day ago
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.
Superhost
Home in Lincoln Park
4.88 out of 5 average rating, 56 reviews

Luxury Loft with Private Pool and Movie Theater

RyanRating, 5 stars1 week ago
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!
Superhost
Home in Skokie
New place to stay

Luxury fenced in modern ranch

PatriciaRating, 5 stars1 week ago
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!
Home in Logan Square
New place to stay

LUXURY - Movie Theater + Spa House

CarlosRating, 5 stars2 weeks ago
Nicholas was great house was really nice will definitely be back

Weekly house rentals

Top Guest favourite
Home in Gold Coast
5 out of 5 average rating, 29 reviews

Gold Coast Home|Rooftop |PoolTable |Parking |Beach

MelissaRating, 5 stars2 weeks ago
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!
Guest favourite
Home in Chicago
5 out of 5 average rating, 10 reviews

The Modern Muse of Chicago! Close to everything!

VictoriaRating, 5 stars1 week ago
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!
Top Guest favourite
Home in Norwood Park
4.97 out of 5 average rating, 32 reviews

Cheerful two bedroom home with patio/deck

EricRating, 5 stars3 months ago
Beautiful home in a quiet neighborhood with responsive and helpful hosts.
Superhost
Home in Avondale
4.75 out of 5 average rating, 24 reviews

Garden/unit/1+1/cosy

RobertRating, 5 stars6 days ago
Wonderful home close to train station. Very convenient and cozy. Would recommend!
Top Guest favourite
Home in Highland Park
5 out of 5 average rating, 64 reviews

Modern & Private Basement Retreat with Kitchenette

MaryRating, 5 stars2 weeks ago
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.
Top Guest favourite
Home in Logan Square
5 out of 5 average rating, 26 reviews

Sunny Historic Cottage on the Park

MichelleRating, 5 stars7 months ago
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.
Guest favourite
Home in Chicago
4.96 out of 5 average rating, 23 reviews

Big house in the BEST Location!

JodiRating, 5 stars5 days ago
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.
Superhost
Home in Cicero
4.79 out of 5 average rating, 193 reviews

Spacious whole apt near shopping and city

CassieRating, 5 stars2 weeks ago
Host was very nice and helpful with our questions, nice neighborhood some noise but nothing too extreme & house was clean.

Private house rentals

Superhost
Home in West Lawn
4.92 out of 5 average rating, 48 reviews

Family Friendly Duplex/9 min from MDW/Free Parking

EhjayRating, 5 stars3 weeks ago
Very nice space to bring friends over
Guest favourite
Home in Chicago
4.88 out of 5 average rating, 51 reviews

CasaNova Modern City Living

HelenRating, 5 stars1 month ago
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!
Top Guest favourite
Home in Brookfield
4.97 out of 5 average rating, 29 reviews

Cozy Home in Brookfield

TomRating, 5 stars2 weeks ago
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.
Top Guest favourite
Home in Skokie
5 out of 5 average rating, 23 reviews

Casa 22 | Luxury Modern House for 6 | 3 Bed,2 Bath

SasmitRating, 5 stars3 weeks ago
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!
Superhost
Home in Westmont
4.69 out of 5 average rating, 13 reviews

"Big" Tiny House yard 20 minutes from Chicago

RyanRating, 5 stars1 week ago
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.
Guest favourite
Home in Skokie
4.95 out of 5 average rating, 57 reviews

Culinary DREAM - Pizza Oven/BBQ/Smoker

PritpalRating, 5 stars3 weeks ago
Great house. Very clean and spacious.
Guest favourite
Home in Burbank
4.83 out of 5 average rating, 24 reviews

Cozy getaway in the city.

KristiRating, 5 stars3 days ago
“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!”
Top Guest favourite
Home in Near West Side
5 out of 5 average rating, 77 reviews

Windy City White House (3br/2ba) *New Listing*

SophieRating, 5 stars3 days ago
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

Destinations to explore

  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Chicago
  6. House rentals