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House vacation rentals in Downtown Chicago

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Popular amenities for Downtown Chicago house rentals

House rentals with a pool

A spacious living area is characterized by a plush gray sofa and a round coffee table. Decorative wall elements and a vibrant red holiday tree enhance the modern decor. Soft lighting is provided by a statement chandelier hanging from the ceiling.
Home in Glen Ellyn
4.78 out of 5 average rating, 9 reviews

Pardizes Suites

AntoniaRating, 5 stars2 weeks ago
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!
Guest favorite
A swimming pool is seen surrounded by a white fence, with colorful pool floats inviting fun. Sunlight reflects off the clear blue water, and lush green trees provide a natural backdrop. A patterned mat lies at the edge, enhancing the relaxing atmosphere.
Home in Glen Ellyn
4.95 out of 5 average rating, 20 reviews

Glen Ellyn Home

TimothyRating, 5 stars6 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.
A single-story house is set against a backdrop of trees, featuring a stone facade and a sloped roof. A winding driveway leads to a two-car garage on the right. Lush green grass surrounds the home, contributing to a serene environment.
Home in Lockport
4.55 out of 5 average rating, 11 reviews

Hidden GEM OASIS in Chicagoland

BesjanaRating, 5 stars3 weeks ago
Everything was great! The place was just as imagined.
A living room is presented with light wooden flooring and a soothing grey wall. Two red sofas are arranged for seating, facing a wall-mounted television. Natural light filters through two textured window shades, and a lamp stands beside the furnishings, adding to the room's cozy layout.
Home in Schaumburg
4.75 out of 5 average rating, 12 reviews

Spacious 3 Floor Townhome

Jocelyn DianeRating, 5 stars3 weeks ago
Super cool host, very flexible and kind. When I come back im definitely going thru him again!
Superhost
A sunny backyard features a round in-ground pool surrounded by lush green grass and vibrant flower pots. The house showcases a two-story design with a balcony and large windows, providing views of the serene outdoor space and nearby landscaping.
Home in Des Plaines
5 out of 5 average rating, 4 reviews

Rosemont 4BD2BA house with Pool

HannahRating, 5 stars2 weeks 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!
Top guest favorite
A spacious basement game area features a classic pool table with a vibrant green felt surface, complemented by cues and an arranged set of colored balls. Nearby, a seating area with leather couches and an arcade machine is visible along the wooden-paneled wall.
Home in Bloomingdale
4.94 out of 5 average rating, 50 reviews

Now Open: Heated Pool with Entire House

TaraRating, 5 stars3 weeks ago
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.
Guest favorite
A vibrant backyard is depicted, featuring a lush green lawn with a variety of plants and flowers. A stone pathway leads towards a fire pit area surrounded by seating. Sunlight filters through trees, creating a warm and inviting atmosphere, complemented by colorful garden decor.
Home in Schaumburg
4.92 out of 5 average rating, 24 reviews

Schaumburg Oasis:Private Pool & Enchanted Garden

BrandonRating, 5 stars1 week ago
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.
Guest favorite
A bright living area features a light-colored sofa set and a wooden coffee table. A large television displays scenic nature visuals. Soft lighting accentuates neutral-toned walls, while a window with sheer curtains allows natural light to enter the space. Green plants add a touch of nature.
Home in Schaumburg
4.95 out of 5 average rating, 21 reviews

Paradise 4BR w/ Pool & Games

MariaRating, 5 stars1 month ago
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

Guest favorite
A spacious living area features a large sectional couch, adorned with decorative pillows. A sleek coffee table sits in front, and a framed cityscape photograph hangs on the wall. Natural light illuminates the space through three windows, enhancing the welcoming atmosphere.
Home in Chicago
4.92 out of 5 average rating, 288 reviews

Duplex Home RoscoeVillage/Wrigley Free St Parking

AlexanderRating, 5 stars1 week ago
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!
Guest favorite
Home in Chicago
4.93 out of 5 average rating, 154 reviews

Superhost Wrigley/Lakeview Duplex 3BR/2.5BA

JesseRating, 5 stars1 day ago
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.
Guest favorite
A cozy living room features a brick fireplace as a focal point, surrounded by comfortable leather seating arranged for relaxation. Light-colored curtains frame large windows, while a plush area rug adds warmth to the wooden floor. A wooden door and wall decor complement the inviting space.
Home in Glen Ellyn
4.91 out of 5 average rating, 152 reviews

Home in Glen Ellyn

JohnRating, 5 stars2 weeks ago
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!
Superhost
A modern kitchen is characterized by dark wood cabinetry and stainless steel appliances. A spacious dining table is surrounded by four chairs. Natural light enters through a door, which leads to the outside, creating a bright and functional cooking space.
Home in Maywood
4.76 out of 5 average rating, 123 reviews

Maywood Relaxation

MadiRating, 5 stars3 days ago
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.
Guest favorite
A stylish living room features a glass coffee table atop a textured rug, surrounded by two orange, velvet armchairs and a plush, patterned sofa. A decorative fireplace is framed by elegant vases, with a mirror reflecting natural light from the windows.
Home in Chicago
4.98 out of 5 average rating, 154 reviews

Spacious Five Bedroom Home in Trendy Chicago Neighborhood

ChristieRating, 5 stars2 weeks ago
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.
Top guest favorite
A bright dining area features a long wooden table surrounded by six blue chairs. A modern chandelier hangs above, illuminating the space. In the background, a staircase leads to the upper level, while a cozy living area is visible, providing an open and inviting layout.
Home in Chicago
4.97 out of 5 average rating, 36 reviews

Wicker Park 6bd/4ba, Steps from Cta, Parking Incl

JohnRating, 5 stars3 days ago
Great place and stay! Location is amazing!
Guest favorite
A comfortable living room is visible, featuring two sofa sets arranged around a coffee table on a soft area rug. A flat-screen TV is mounted on the wall, with a ceiling fan above providing a sense of airflow. Natural light streams through the windows, enhancing the welcoming atmosphere.
Home in Chicago
4.86 out of 5 average rating, 222 reviews

The Avondale Guesthouse

KelleyRating, 5 stars1 week ago
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.
Top guest favorite
The living room features a spacious sofa complemented by decorative pillows and a wooden coffee table. A reading lamp provides soft lighting. A wall art piece with a 'W' symbol and stars is displayed above the seating area. Natural light enters through the windows, framed by wooden trim.
Home in Chicago
4.95 out of 5 average rating, 189 reviews

Wrigleyville Greystone

Sneha PrabhakarRating, 5 stars1 week ago
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

Guest favorite
The exterior of a historic house features a two-story facade with a gabled roof and large windows on the first level. Lush greenery surrounds the property, creating a welcoming atmosphere and enhancing the home’s charm.
Home in Oak Park
5 out of 5 average rating, 5 reviews

Sleeps 12 Comfortably in 8 Bedrooms 3 Full Bath

VinceRating, 5 stars5 months ago
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.
Guest favorite
A modern kitchen features grey cabinetry and stainless steel appliances, including a microwave, oven, and refrigerator. A granite countertop provides ample space for food preparation. Soft lighting illuminates the area, enhancing functionality and comfort.
Home in Schaumburg
4.97 out of 5 average rating, 59 reviews

Paradise in Schaumburg Low Cleaning Fee, 3 BR, 4Bd

JanainaRating, 5 stars1 week ago
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.
Guest favorite
The kitchen features modern white cabinetry with sleek countertops and stainless steel appliances. A central island with a wooden top provides additional workspace. Two woven barstools are situated at the island, and natural light enters through the dual windows, illuminating the space.
Home in Naperville
4.87 out of 5 average rating, 131 reviews

Home away from home

MarenRating, 5 stars1 month ago
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.
Superhost
A cozy living area is displayed with a pair of beige sofas, accented by decorative pillows. Framed wall art complements the decor. A soft rug is positioned on the wooden floor, while a lampshade on a side table adds subtle illumination.
Home in Blue Island
4.81 out of 5 average rating, 198 reviews

Warm and comfortable inviting Suburban home !

DelaneyRating, 5 stars4 days ago
Beautiful area and home, wonderfully helpful and responsive host. Very grateful to have stayed here!
Superhost
A comfortably arranged living room features a gray sofa with multiple cushions and two teal accent chairs. Natural light enters through large windows dressed in light curtains, while a wooden floor adds warmth to the space. A flat-screen TV is mounted on the white wall.
Home in Markham
4.74 out of 5 average rating, 125 reviews

The Country Life! Entire House.

NikkiRating, 5 stars2 months ago
This house was so cozy my family and I will gladly come again for a stay
Superhost
The exterior of a two-story home is displayed, featuring a brick and siding facade. A driveway leads to a garage with a closed door. Lush landscaping includes various plants and flowers, while a tall fence provides privacy. The sky is partly cloudy.
Home in Homer Glen
5 out of 5 average rating, 3 reviews

4 bedroom home rental in quiet neighborhood

LoriRating, 5 stars72 months ago
Quiet neighborhood, spacious and comfortable home. The yard is inviting and a great entertaining space! Very kind hosts.
Superhost
A welcoming living room features a gray sofa opposite a wooden coffee table with a decorative bowl. Two armchairs sit beside a large window, providing natural light, while a television is positioned near a black fireplace. The warm-toned walls enhance the cozy atmosphere.
Home in Chicago
4.84 out of 5 average rating, 508 reviews

*ENTIRE CITY HOUSE/PARKING - 3 MIN WALK TO TRAIN

JessicaRating, 5 stars3 days ago
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.
Top guest favorite
A spacious ranch house is depicted, surrounded by matured trees and a well-maintained lawn. The facade features a combination of brick and siding, with a large garage and a welcoming front porch. Sunlight filters through the leaves, creating a serene atmosphere.
Home in Itasca
5 out of 5 average rating, 53 reviews

RANCH, House-tel: updated full kitchen, comfy beds

JanetRating, 5 stars1 month ago
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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