House vacation rentals in Wicker Park, Chicago

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Popular amenities for Wicker Park, Chicago house rentals

House rentals with a pool

Guest favorite
An outdoor deck features a modest above-ground pool surrounded by wooden fencing. Two lounge chairs are placed on a textured rug, providing a relaxing seating area. Lush greenery is visible in the background, under a clear blue sky.
Home in Schererville
4.94 out of 5 average rating, 51 reviews

Cozy house in Schererville

CarlosRating, 5 stars4 days ago
Kate’s place was exactly what I expected. Pristine condition and spotless. Kate accommodated my early arrival which was greatly appreciated. I would 100% book this place again. Highly recommend her place to anyone in the area for a weekend or just to get away from the city. Thank you again for your attention on such a short notice on my booking.
Guest favorite
A spacious living room is featured with a cream-colored sectional couch facing a mounted flat-screen TV. Natural light pours in through large windows adorned with blinds. A stone accent wall adds texture, complemented by two decorative pieces and a ceiling fan.
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.
Top guest favorite
A clear swimming pool is surrounded by lush greenery and a wooden deck. Lounge chairs are placed nearby, and a colorful inflatable pool float rests on the water's surface. Sunlight reflects off the pool, enhancing its inviting blue color.
Home in Bloomingdale
4.94 out of 5 average rating, 47 reviews

Whole House With Hot Tub And Spacious Bedrooms

KarinaRating, 5 stars1 week 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
Superhost
An above-ground pool is visible in the backyard, surrounded by greenery. Colorful floating loungers are placed in the water. A spacious deck with seating overlooks the pool area, while a grassy lawn provides additional space for outdoor activities.
Home in Miller
4.83 out of 5 average rating, 35 reviews

Entire House With Pool - Backyard Beach Getaway

CrystalRating, 5 stars4 months ago
This home was super cozy for my big family. Everything was clean, comfortable, and the way it is set up makes you feel right at home. This home had everything we needed. TV’s, kitchen items, recommendations, and even fun family games and activities to do. Every time I visit the area I’ll be checking to see if it’s available. 10/10
Guest favorite
A modern living room features a large blue sectional sofa accompanied by two plush chairs in a complementary shade. A decorative fireplace serves as a focal point, with a flat-screen television mounted above. Soft lighting is provided by recessed lights, enhancing the cozy atmosphere.
Home in Plainfield
4.93 out of 5 average rating, 75 reviews

Relaxing Spanish style Home (w/inground pool)

DevonRating, 5 stars7 months ago
House was lovely. I enjoyed the homes decor. Every day I woke up with something else I loved. The house had everything we needed. Only thing I wished the pool heater was working and the pillows were flat. I would definitely stay here again.
Superhost
A charming two-story farmhouse is surrounded by lush greenery and a manicured lawn. Vibrant pink flowering trees add color to the exterior, which features white siding and multiple windows. A stone pathway leads to the entrance, inviting guests to explore the property.
Home in Lake Forest
4.9 out of 5 average rating, 63 reviews

Beautiful 137 Year Old Farm Home (3night min)

MaribethRating, 5 stars8 months ago
Beautiful and eclectic home. It was perfect for our group of girls visiting from all over the U.S to attend our HS Reunion. Plenty of lovely spaces to gather or a private, quiet nook to read or rest. The pool was wonderful. Beds were super comfortable. Kitchen was large enough and well stocked to prepare meals. Andy was very responsive with any issues or questions. Highly recommend!
Superhost
Home in Miller
4.93 out of 5 average rating, 137 reviews

Bayless Dune Lodge at West Beach - Indiana Dunes!

KevinRating, 5 stars5 days ago
We had a great weekend getaway from Chicago and it was less than an hour (without traffic) away! Peaceful, quiet, near the beach. Cullen was an awesome host!
Guest favorite
An inviting above-ground pool is surrounded by a wooden deck, featuring a secure entry gate. The pool is set in a spacious backyard, with green grass and trees providing a natural backdrop. The clear blue water glistens under the daylight.
Home in Schaumburg
4.95 out of 5 average rating, 20 reviews

Paradise 4BR w/ Pool & Games

JasonRating, 5 stars7 months ago
We really enjoyed our stay at this beautiful home. It is close to everything. The place is clean and very organized. Lily and Nathan has been wonderful and very responsive and communicated well with us. I definitely recommend this place when you visit Schaumburg. Thank you guys for everything.

Weekly house rentals

Superhost
A decorated corner of the stairway features a brown wood accent wall with a geometric pattern. Above, a window allows natural light to illuminate the area, complemented by pastel artwork on the walls. A stylish lamp stands next to the wall.
Home in West Lawn
4.92 out of 5 average rating, 39 reviews

Family Friendly Duplex/9 min from MDW/Free Parking

JoannaRating, 5 stars1 week ago
Came for c2e2 with my friends and it was perfect for all of us! Would recommend 💗💗
Guest favorite
A brightly colored bedroom showcases a spacious bed adorned with a vibrant duvet. Natural light filters through large windows, illuminating the minimalist decor featuring a ceiling fan and playful wall art.
Home in Wicker Park
4.9 out of 5 average rating, 200 reviews

Tropical Penthouse in Wicker Park w/Backyard Patio

JennaRating, 5 stars5 months ago
Great Airbnb for a bachelorette party! Tons of space, beds and a great location in Chicago even for a local group. The hosts were very easy to communicate with. I would recommend the space to anyone looking for an Airbnb for a large group!
Guest favorite
The exterior of a modern brick home is showcased, featuring large windows and a welcoming entrance. A patio area includes a table with six chairs and a gas grill, set against a backdrop of a well-maintained lawn.
Home in Bridgeport
4.96 out of 5 average rating, 118 reviews

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

AnneRating, 5 stars1 week ago
Matt was a wonderful host and very responsive. The house was exactly as described. It felt like a home away from home. Everything you need is provided for you. I was traveling with my teen sons and we enjoyed the hot tub each night and watched a movie while soaking and relaxing. The house is on the Southside of the city and which was a nice break from the buzz of downtown. The train is about a 20-25 minute walk and the White Sox stadium is right near there. I definitely recommend this place if you’re looking for a home in Chicago.
Guest favorite
A well-lit entryway showcases a wooden staircase with elegant railing leading to upper levels. The dark front door contrasts with the light walls, while a stylish cabinet and framed photos add character to the space, inviting guests into the home.
Home in Roscoe Village
4.92 out of 5 average rating, 280 reviews

Duplex Home RoscoeVillage/Wrigley Free St Parking

BrigidRating, 5 stars2 weeks ago
We enjoyed preparing pizzas from scratch in the perfectly sized kitchen with our adult kids who live in Chicago and their friends. There was plenty of space to sit around the spacious kitchen island and talk while cooking. The whole experience was made even better by using the Wolf stove top and Bosch wall-mount oven, which produced perfectly crisp crust and tasty toppings. The neighborhood felt safe and peaceful while providing everything we needed within walking distance. Parking was also easy. We had no trouble finding a space in front of the house all 4 days we were there. As a special bonus, a new chocolate cafe opened a few days ago (Hotel Chocolat Velvetiser Cafe) and is just a short walk away! We had a great time in this lovely home.
Guest favorite
Home in Wicker Park
4.98 out of 5 average rating, 152 reviews

Spacious Five Bedroom Home in Trendy Chicago Neighborhood

Kevin And CourtneyRating, 5 stars2 months ago
Great experience at Casey’s place. The home is as well stocked with kitchen essentials and extras as any place that we have ever stayed. There were toys for the kids and the design of the place was awesome. We had a great stay and would definitely come back.
Superhost
A spacious two-story building features a welcoming front porch with wooden steps. The exterior is composed of light-colored stone and showcases decorative architectural elements. A green lawn is visible, bordered by a black wrought-iron fence, with a clear blue sky above.
Home in Humboldt Park
4.88 out of 5 average rating, 8 reviews

Massive 8bd/3ba Building w/ Two Car Garage!

SonyaRating, 5 stars2 months ago
I loved this place. Perfectly accommodated 14 adults and 3 children. Only thing it could use was at least 2 extra blankets and a sheet pan for baking. Other then that, it was perfect! Walking distance to the bus stop to get to the train stain. Aldi (grocery store) 5 minutes away walking distance.
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 Wicker Park
4.97 out of 5 average rating, 33 reviews

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

LaureenRating, 5 stars1 month ago
The location alone makes this home worth booking. Add that there’s ample room for family/friends and it’s a gem in the middle of a great Chicago neighborhood. We were a group of six and loved every minute.
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 Avondale
4.86 out of 5 average rating, 221 reviews

The Avondale Guesthouse

ErickaRating, 5 stars6 months ago
We absolutely loved the place! Great location, price and space! Jed was so kind and responsive, and we absolutely loved the the outdoor space! We would definitely stay again!

Private house rentals

Guest favorite
Home in Lincoln Park
4.94 out of 5 average rating, 124 reviews

Spacious Full Home Near the Heart of Wrigleyville

JessicaRating, 5 stars1 month ago
We had an amazing stay at Dustin’s place! We had a group of 9 ladies who fit perfectly with plenty of cozy beds and linens. The location was very walkable and we felt safe. We walked over to Barcocina Lakeview on Friday, and then jumped on the train to River North on Saturday to celebrate St. Patrick’s Day. We had a couple of questions during our visit, and Dustin was speedy on the replies! Everyone in the group said the experience was 10 out of 10. We hope to visit again.
Top 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 stars4 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.
Superhost
A spacious living area is designed with high ceilings and natural light. Comfortable seating is provided by two leather sofas, while a wooden coffee table anchors the space. A large flat-screen TV is mounted on a dark accent wall, and subtle decor includes plants and wall art.
Home in Illinois Medical District
4.86 out of 5 average rating, 100 reviews

Casa PLZN Location | Entire Home | Garage Parking

CecilioRating, 5 stars3 weeks ago
Great place near restaurants and cafes. Garage access is a plus. Train noise is noticeable at first but you get used to it and it's only noise as the house doesn't rumble when the train passes.
Superhost
The exterior of the brick duplex is showcased, featuring a modern architectural design with large windows and a welcoming front entrance. The steps lead up to the dark front door, framed by a simple wrought iron railing and surrounded by a manicured yard.
Home in Chicago
4.82 out of 5 average rating, 38 reviews

Exec Lux home wth 3 Level,6 Bdrms/3bth & 2 Kitchen

ShareseRating, 5 stars2 months ago
This is a Beautiful Home, with a peaceful atmosphere. A Great place to walk into and relax after a long trip, and spacious enough for a small group to enjoy one another's company without feeling overcrowded. 2 Full Refrigerators and 2 Full size stoves makes this location a rare find.
Guest favorite
Home in Logan Square
4.95 out of 5 average rating, 38 reviews

Gorgeous and Luxurious 3 BR Home

SeanRating, 5 stars6 months ago
This is a great house to stay for a family or two couples. Out of several ABNBs, this one gets the award for most clean. There is a fairly new Italian restaurant, Il Girasole Trattoria, that is walk-able and delicious. You will not be disappointed with your stay.
Superhost
The exterior of a three-story house is showcased, featuring a beige siding facade and a welcoming entrance with a white door. A balcony with railings is visible on the upper level, surrounded by clear blue skies and complemented by a small staircase leading to the front yard.
Home in Austin
4.88 out of 5 average rating, 48 reviews

Grand Victorian Mansion in Austin Area

SaifRating, 5 stars6 months ago
The accommodation was spacious and very comfortable for our large group of 16. While the floors creak a bit, it wasn’t an issue. Samantha was always quick to address any questions and issues. The gated parking area provided ample space for our cars, which was a great convenience.
Guest favorite
A two-story home features a combination of brick and siding exteriors with a well-maintained lawn. Large windows with dark shutters are visible, allowing natural light to illuminate the interior. A walkway leads to the front entrance, bordered by neatly trimmed shrubs.
Home in Des Plaines
4.74 out of 5 average rating, 91 reviews

Home for rent to traveling family and work.

DavidRating, 5 stars3 months ago
Raul was very friendly and responsive and the listing was just as described. It was very nice to have such a close place to our relatives. The only minor downside is that the master bed mattress, while workable, is a bit lumpy and the headboard squeaks whenever you toss and turn. Everything else was great! Thanks for a great stay, Raul! We'll definitely be back! :)
Superhost
The exterior of the home is showcased, featuring a beige brick facade and a prominent white front door. A driveway leads to the attached garage, with trees and colorful shrubs visible in the surrounding landscape, indicating a well-maintained front yard.
Home in Glenview
5 out of 5 average rating, 19 reviews

Delightful Cozy Home

Jason LawrenceRating, 5 stars1 month ago
We love this home for our family get togethers! The home is always spotless and the living room is perfect for board games!

Quick stats about house rentals in Wicker Park, Chicago

  • Total rentals

    30 properties

  • Nightly prices starting at

    ﺩ.ﺇ73 before taxes and fees

  • Total number of reviews

    1.5K reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

Destinations to explore

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