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Condo holiday rentals in Wicker Park

Find and book unique condos on Airbnb

Top-rated condo rentals in Wicker Park

Guests agree: These condos are highly rated for location, cleanliness and more.

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Superhost
A modern living area features a dark sofa facing a wall-mounted flat-screen TV. A wooden shelf with decorative items and a lamp is positioned beside a designated work space with a chair. Exposed brick walls complement the sleek kitchen area visible in the background.
Condo in Bucktown
4.78 out of 5 average rating, 139 reviews

Sunny Getaway Steps from Bucktown + Wicker Park

Enjoy a relaxing and chic experience steps aways from the lively, sought-after Wicker Park and Bucktown! Our home is on a quiet, tree-lined street with its own private walk-up entrance and FREE parking space. Public transportation is also very accessible. There are endless options of restaurants, bars, and shopping. The 606 trail is also steps away! We are centrally located which makes it easy and convenient to explore Chicago! Come make some memories for the weekend or as long as you'd like!

Top Guest favourite
A cozy seating area features a green sectional sofa adorned with decorative pillows in various patterns. A small wooden coffee table sits at the center, topped with a book and a small plant. Exposed brick walls complement large windows dressed with dark curtains.
Condo in Wicker Park
4.97 out of 5 average rating, 136 reviews

3-bedroom exposed brick in Chicago's Wicker Park

Welcome to Wicker Park - one of Chicago's coolest walkable neighborhoods with endless restaurants, bars & shops. 2 blocks from the famous "L" train with access to the city & O'Hare airport. This 1893 vintage apartment has been freshly renovated and professionally designed blending historic details with a clean and modern aesthetic. The instagrammable one of a kind space has beautiful hardwood floors, soaring 10ft ceilings, exposed brick in all rooms, curated decor and a cozy private deck.

Guest favourite
A cozy living area features exposed brick walls, a rustic wooden coffee table, and a large leather sofa. A flat-screen television is positioned in front of the seating, while natural light enters through the windows. A vintage fan rests nearby, and additional storage is provided by a bookshelf.
Condo in Humboldt Park
4.86 out of 5 average rating, 492 reviews

Humboldt Park Traveler's Lodge

Come stay at my gorgeous condo! Featuring exposed brick, a private entrance, stainless steel appliances, and a queen bed -> all on a quiet tree lined street! It's a perfect place to re-energize between big city adventures. Free street parking, and a 5 min walk to some of the best independently owned shops, restaurants, and bars in the city. Also, the massive and incredible Humboldt Park is also just a 5 min walk away! Please reach out for recommendations - I love giving them to people!

Top Guest favourite
The living area features a spacious couch accompanied by two armchairs, all positioned around a circular dining table. A large window allows natural light to illuminate the space, adorned with potted plants and modern artwork that adds a touch of style.
Condo in Ukrainian Village
4.98 out of 5 average rating, 106 reviews

Spacious 3BR/3BA Condo in Trendy Ukrainian Village

Welcome to our Cozy and luxurious three-bedroom, three-bath property in Ukrainian Village, Chicago. With a modern design, natural light, and a private patio, our home offers a comfortable and stylish stay. Enjoy a fully equipped kitchen, cozy living area, high-speed Wi-Fi, and laundry facilities. Explore the vibrant neighborhood with its unique shops and restaurants, visit nearby Smith Park or venture to the trendy Wicker Park area. Downtown Chicago's attraction are also easily accessible.

Guest favourite
A modern living area showcases a coffered ceiling and stylish furnishings. Plush sofas and accent chairs are arranged around a coffee table, with a large wall-mounted television and a decorative painting enhancing the aesthetic. Natural light enters through multiple windows, illuminating the space.
Condo in West Town
4.98 out of 5 average rating, 191 reviews

Spacious 4 Bedroom Condo

Located in West Town in the heart of Noble Square, just north of West Loop with access to all the best restaurants and only minutes away from River North and Old town, enjoy this 4 bedroom, 3.5 bath condo with private parking, 2 living spaces, heated floors throughout the entire lower level and steam showers. A gourmet kitchen stocked with everything you will need including an espresso maker. This home is perfect for families, couples, friends or traveling for business.

Superhost
A spacious living area features a large flat-screen television and a circular glass coffee table, surrounded by comfortably upholstered seating. Natural light floods in through glass block windows, highlighting the open design that connects to a fully-equipped kitchen in the background.
Condo in Wicker Park
4.86 out of 5 average rating, 289 reviews

Spacious & Stylish Home at the ♥ of Wicker Park

Unwind at the spacious & modern apt in the very heart of Wicker Park. Explore the local area packed with restaurants, bars, shops & public transport options. The 2-story home, ideal for large groups, is equipped with everything you might need for a perfect Chicago visit: • Comfy Beds • Fully-Equipped Open Design Kitchen + Living Room • Steam Shower • Private Backyard • High-Speed Wi-Fi • Extremely safe neighborhood Learn more below!

Guest favourite
The living area features a plush, gray sofa paired with a deep blue accent chair. A light-colored coffee table rests on a patterned rug, while warm lighting is provided by wall-mounted fixtures. A small bookshelf and decorative items add a personal touch to the space.
Condo in Wicker Park
4.83 out of 5 average rating, 378 reviews

Lively Wicker Park 2br, Steps to Damen Blue Line

Rehabbed 2BR 1BA garden unit in the very popular neighborhood of Wicker Park/Bucktown! 2 queen beds and full of amenities. Just a block from everything this neighborhood has to offer and 2 blocks from the 'L' to take you downtown or to O'hare Airport. Premium location to effortlessly walk from our quiet side street and be in the heart of all the entertainment! I provide all the essentials to make your stay easy and comfortable!

Top Guest favourite
An open kitchen and dining area features exposed wooden beams and stylish light fixtures. A modern dining table with black chairs provides seating, while a lounge chair is positioned nearby. Decorative plants and art add warmth to the contemporary space.
Condo in Wicker Park
4.95 out of 5 average rating, 134 reviews

Modern Izakaya Studio in Wicker Park

Stay in a sleek underground izakaya themed studio in one of Chicago's most desirable neighborhoods. Relax and enjoy the quiet zen decor. Find our hidden Japanese whisky room. Kick back in our pillowy loungers and dig into our ramen selection... The Izakaya Studio in the heart of Wicker Park is about giving you a uniquely luxurious guest experience from which to begin your adventures in Chicago.

Top Guest favourite
A spacious living area features a comfortable sectional sofa, a wooden dining table with matching chairs, and a cozy reading nook with an armchair. Large windows allow natural light to fill the room, which includes a decorative fireplace and tasteful artwork on the walls.
Condo in Wicker Park
5 out of 5 average rating, 149 reviews

Stunning Wicker-Park Flat with Parking!

Enjoy a stylish experience at this centrally-located gem. Beautifully renovated 3 bedroom, 2 bath full floor flat. While quietly situated on the 3rd floor, you can walk out your front steps to all that Wicker Park and Division street has to offer. Coffee shops, bars, unlimited restaurants, green space, farmers market, gyms, grocery stores, and so much more. Easy and nearby public transit.

Top Guest favourite
A bright living room features large windows that allow natural light to fill the space. Two red chairs are positioned for comfortable seating, complemented by a wooden frame and a patterned area rug. Plants are displayed by the window, adding a touch of greenery.
Condo in Wicker Park
4.94 out of 5 average rating, 147 reviews

Stylish & Spacious Wicker Park Airbnb!

This Airbnb is a 3-bedroom/1-bath home-away-from-home on the first floor of a historic 1890's Wicker Park landmark 3-flat on a quiet, tree-lined street. You're a few minutes' walk from the beating heart of the neighborhood, where you'll find some of Chicago's best restaurants, boutiques & art galleries. We welcome humans of all types and origins, and families with children.

Top Guest favourite
A spacious living room features three large windows allowing natural light to fill the space. Comfortable seating includes a leather couch and an armchair. A television is mounted on the wall, and a decorative area rug lies beneath a wooden table set for dining.
Condo in Noble Square
4.97 out of 5 average rating, 865 reviews

Great location. Free parking.

Great location in Chicago's Wicker Park/Bucktown community. Fully furnished living room, bedroom with queen bed and bathroom. Internet, central heating/ac, small refrigerator, microwave, cable TV, dvd/Blu-ray, coffee maker. Small safe. Private free parking. One block from blue line (Division). From O’Hare via train – 35 min. 10 min to the city via blue line.

Top Guest favourite
The bright living area features a blue sofa with decorative pillows, a wooden coffee table, and a desk chair facing a small workspace. Natural light enters through multiple windows, showcasing the hardwood flooring and modern decor elements, including a framed cityscape artwork.
Condo in Lake View
4.99 out of 5 average rating, 674 reviews

Urban Comfort in the Heart of Chicago

This is the PRIVATE first floor of our duplex condo, with your own entrance/exit, 75" flatscreen TV, central heat/air, and an en-suite bathroom. We are in the middle of Chicago's vibrant Northside while still having the benefit of coming home to a tree lined one lane residential street. Please contact us with any questions at all before you book your stay.

Popular amenities for Wicker Park condo rentals

When is the best time to visit Wicker Park?

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Avg. price$269 NZD$274 NZD$368 NZD$359 NZD$433 NZD$509 NZD$512 NZD$566 NZD$349 NZD$438 NZD$356 NZD$324 NZD
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Quick stats about condo rentals in Wicker Park

  • Total holiday rentals

    Explore 20 holiday rentals in Wicker Park

  • Nightly prices starting at

    Wicker Park holiday rentals start at $83 NZD per night before taxes and fees

  • Verified guest reviews

    Over 2,610 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Wicker Park holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Wicker Park rentals

  • 4.9 Average rating

    Wicker Park stays are highly rated by guests—averaging 4.9 out of 5!

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