House vacation rentals in Chicago

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Popular amenities for Chicago house rentals

House rentals with free parking

Superhost
Home in West Lawn
4.92 out of 5 average rating, 39 reviews

Family Friendly Duplex/9 min from MDW/Free Parking

JoannaRating, 5 stars2 weeks ago
Came for c2e2 with my friends and it was perfect for all of us! Would recommend 💗💗
Guest favorite
Home in Hazel Crest
4.86 out of 5 average rating, 22 reviews

Your Peaceful,Joyful,Cozy, Relaxing, Experience

DouglasRating, 5 stars5 months ago
This is definitely a gem in the middle of the South Suburbs. The place was really decorated nice, made us feel comfortable and right at home. Erica is a really great host and she is very attentive to any concerns we may have had during our stay. The neighborhood was really quiet and there was a park right on the corner for me to walk my puppy every morning. You will be pleased with this one. I recommend this place to anyone that wants to get away from the hustle and bustle of the big city and wants to enjoy quiet Suburban surroundings. I would definitely stay again, in fact I plan to.
Superhost
Home in Austin
4.86 out of 5 average rating, 124 reviews

Urban Chic 3beds w/2bath + free parking & W/D

LynneRating, 5 stars2 weeks ago
Tiffany's place in Oak Park is a fantastic place for a family stay! Super cute with room to spread out, a lovely neighborhood that is close to the essentials (like grocery stores) and only 20 minutes outside of downtown Chicago. Tiffany was very kind, helpful and quick to respond to questions that we had. We would love to visit again and will recommend our friends stay here as well!
Superhost
Home in Illinois Medical District
4.86 out of 5 average rating, 101 reviews

Casa PLZN Location | Entire Home | Garage Parking

RicardoRating, 5 stars2 weeks ago
Great place! I’ll definitely be coming back! The beds are amazing!
Superhost
Home in Blue Island
4.82 out of 5 average rating, 195 reviews

Warm and comfortable inviting Suburban home !

CasieRating, 5 stars4 days ago
Nice spot - place was very clean, comfy beds, lots of seating areas that were also comfy. We got used the the sounds of the trains after the first night. Bumped into Rich one day while he was mowing the grass; he was very kind. The place is a little older, but that’s in the description. We couldn’t figure out how to get the stove to turn on so we heated food in the microwave and on the gas grill outside. Neighborhood was very quiet and peaceful, and we liked having the fenced yard for our dog.
Superhost
Home in Matteson
4.87 out of 5 average rating, 71 reviews

Tranquil 2 bedroom ranch home

CRating, 5 stars1 month ago
It had everything we needed for our stay. The owner answered our call when we needed help working the oven. Nice, clean house! Thank you!!
Top guest favorite
Home in Oak Park
4.97 out of 5 average rating, 151 reviews

Clean, Cozy 1st Floor Flat, Kitchen, Parking

MatthewRating, 5 stars3 weeks ago
Lisa's place was perfect for our family of three both for accessing the city as well as enjoying the suburbs. The space itself served our needs well with enough room to spread out as well as the kitchen amenities to enjoy serving ourselves when desired. Lisa was very responsive to questions and was very, very clear in her instructions. A helpful welcome packet was in the living room which was chock full of information including recommendations on local sites. All in all, such a great place to stay for our trip.
Top guest favorite
Home in Bridgeport
4.96 out of 5 average rating, 111 reviews

Cozy, Quiet, Riverwalk Sanctuary

EmmaRating, 5 stars3 days ago
Great home for a short trip to the city with a smaller group. Space is utilized nicely. Easy drive to main attractions and busy areas. The hosts were very attentive and responsive, would recommend their listings to others!

House rentals with a hot tub

Superhost
Home in Maywood
4.75 out of 5 average rating, 53 reviews

1610 Entire home for your visiting Chicago IL

EneidaRating, 5 stars5 months ago
House was easy to find. It was very nice and clean. About 15 minutes to downtown. Will highly recommend. I will definitely be staying again.
Guest favorite
Home in Skokie
4.93 out of 5 average rating, 81 reviews

Quiet and welcoming house.

JustinRating, 5 stars6 days ago
Tsegie was gracious, responsive, and helpful. The home had every amenity listed, and the neighborhood was quiet with plentiful street parking. A few areas needed cleaning, but Tsegie had the housekeeper over within an hour to address. There were plenty of towels and linens, and my two kids (5 and 2.5) loved the backyard, which is spacious and fully fenced. Checking in and out was a breeze, and there was a fantastic new TV (75 inch?) with a soundbar for a cozy and entertaining living room. The basement is huge with an open floor for more kid-friendly play space, and a jacuzzi tub in the bathroom that was also a hit with the kids. A few items could use attention, like a few out light bulbs, a tub that needs paint, and a broken drawer. But overall, the place was in good shape. There were holiday decorations out, but other than that, the pictures were accurate. Very well regulated thermostat had the temp perfect throughout. I recommend this rental for families or those needing extra space.
Guest favorite
Home in West Town
4.85 out of 5 average rating, 314 reviews

Lux Urban 3BR/3BA Duplex + Parking!

LauraRating, 5 stars2 weeks ago
Our host was extremely tentative and helpful. We really enjoyed our stay at the home. It was big enough to accommodate our family plus a few other visitors, plenty of beds, plenty of living space so people didn’t have to be on top of each other. Very close to downtown and the blue line which made going to the airport and downtown much more accessible. we didn’t even have to rent a car.
Guest favorite
Home in Bridgeport
4.96 out of 5 average rating, 119 reviews

Modern Lux Getaway w/ Hot Tub, Lrg Yard, Parking

ErikaRating, 5 stars1 week ago
Our time at Matthew’s place was phenomenal! Everything is as pictured, but the pictures doesn't do much just for how nice this house was. I'm an extreme clean freak when traveling, and usually bring my own cleaning products, but I had nothing to worry about here. If you're considering this home, DO IT!
Guest favorite
Home in Lake View
4.88 out of 5 average rating, 72 reviews

Entire house in Lakeview with yard and garage

AnnieRating, 5 stars1 week ago
The absolute best location for all that Chicago has to offer. With a family of 6 it’s rare to find a place where everyone can fit… even the dog:)
Guest favorite
Home in Whiting
4.84 out of 5 average rating, 153 reviews

The Spa of Downtown Whiting

YesyRating, 5 stars2 weeks ago
Thank you for allowing us to enjoy your home. It was a wonderful experience. It is incredible. The place is very cozy. You feel an atmosphere of relaxation and peace.
Superhost
Home in Homewood
5 out of 5 average rating, 6 reviews

Fore! Peace & Love @ Golf House

TamiekaRating, 5 stars4 months ago
Michael & KP’s place was amazing! Communication was excellent! My family and I absolutely loved our time here. The Christmas Tree and Decor were beautiful!! There was more than enough room for everyone to be comfortable. Michael & KP were amazing went above and beyond. Every room had a tv including the kitchen which was awesome. There was a nice selection of games in the game room for the family to enjoy. My family and I created beautiful memories here! Thank you guys for hosting us. Overall an A+ and we will be returning.
Top guest favorite
Home in Andersonville
4.97 out of 5 average rating, 60 reviews

Andersonville Home for Groups! Hot Tub Yard Garage

ThomasRating, 5 stars4 days ago
The listing was very spacious and easily allowed for our bigger group to spread out and enjoy amenities like the ping pong table, darts and the hot tub. The area is very convenient to walk to the store or restaurants. The hosts were very communicative before and during our stay. A great value and fun place to stay!

House rentals with a pool

Guest favorite
Home in Highland Park
4.92 out of 5 average rating, 142 reviews

2-Acre Highland Park Retreat with Heated Pool ~ 5*

JeffRating, 5 stars5 months ago
We were in town for Thanksgiving visiting family with our dogs for 4 nights. Communication with host was great. The house was very clean, well furnished (we cooked the Thanksgiving meal there), recently renovated kitchen (huge kitchen island) with high end appliances, and yes there are 6 bedrooms (some small but nice). Rooms are split between three floors so everyone had room/privacy. Backyard with pool was great, lots of space for dogs, everything is fenced in but the front which was not a problem as the house is on a dead-end street with very little traffic. This is definitely a superhost home, all your condiments, lots of nice touches and snacks/gifts. We will definitely stay there again on our next visit to family in Chicago. House is locate between 41 and 94 making travel around Chicago easy.
Home in Glen Ellyn
4.8 out of 5 average rating, 5 reviews

Pardizes Suites

FernandaRating, 5 stars1 week ago
Really nice and spacious place. Everything was clean and comfy.
Guest favorite
Home in Glen Ellyn
4.95 out of 5 average rating, 20 reviews

Glen Ellyn Home

TimothyRating, 5 stars5 months ago
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.
Guest favorite
Home in Munster
5 out of 5 average rating, 10 reviews

Munster hide away

ChristopherRating, 5 stars4 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.
Home in Schaumburg
4.78 out of 5 average rating, 9 reviews

Spacious 3 Floor Townhome

AndresRating, 5 stars4 days ago
My spouse and I couldn't of had a better weekend without Alex's listing! Everything was as Alex had described it in the post. It was close to restaurants, grocery stores and entertainment needs. Alex made it easy check in and check out. We would definitely recommend this place to any couple or small family.
Top guest favorite
Home in Bloomingdale
4.94 out of 5 average rating, 48 reviews

Whole House With Hot Tub And Spacious Bedrooms

KarinaRating, 5 stars2 weeks ago
Amazing stay! This place has everything you need for both short and long visits. The location is extremely safe and convenient with shops within walking distance. My family and I thoroughly enjoyed the entire property, especially the game room and TV room which were perfect for entertainment. Moiz, the host, was very kind and quick to respond to any needs we had. Thank you for everything! We would definitely stay here again
Guest favorite
Home in Schaumburg
4.91 out of 5 average rating, 22 reviews

Schaumburg Oasis with a Pool and Hidden Garden

GotimukulRating, 5 stars3 weeks ago
had such a wonderful stay! The place was exactly as described—clean, cozy, and beautifully maintained. The host was incredibly kind and responsive, making the whole experience smooth and stress-free. Would definitely stay here again and highly recommend it to anyone looking for a comfortable and welcoming place to stay!
Home in Glenwood
4.8 out of 5 average rating, 56 reviews

Spacious Family Glenwood Estates Home w/ Hot Tub!

Nicole And ArnoRating, 5 stars1 month ago
Loved this Airbnb! Didn’t want to leave.

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

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