Condo vacation 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.

%{current} / %{total}1 / 1
Top guest favorite
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, 128 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.

Top guest favorite
A spacious rooftop deck features comfortable wooden seating arranged around a circular table. The area is adorned with vibrant flowers and a decorative rug, all set against a sweeping view of the Chicago skyline under a soft blue sky.
Condo in Wicker Park
4.94 out of 5 average rating, 171 reviews

CHIC DOWNTOWN PENTHOUSE w/ private roof +parking

Escape into this spacious, Chicago Penthouse! Guests love this home because: - Surrounded by top-notch restaurants/retail - Close to all popular attractions that make Chicago so great - Luxurious, newly-renovated interior filled with natural light - Open-floor plan for entertaining! - Private, spacious roof deck viewing the entire Chicago skyline! - Fast WiFi (600 mbps) - Master en-suite w/ separate walk-out - Designated parking spot! - Steps away from blue line Damen station (800 feet)

Guest favorite
A spacious studio is showcased with a king-size bed positioned against a contrasting dark wall. Natural light filters through large windows, highlighting the exposed brick and the vintage stone fireplace. A mirrored wall accents the room, while a desk complements the seating area.
Condo in Little Italy
4.94 out of 5 average rating, 232 reviews

Private hot tub - King bed suite - Free parking

Welcome to this urban retreat in the heart of Chicago's Little Italy neighborhood. Conveniently located adjacent to Chicago's downtown Loop and West Loop neighborhoods, you will find endless opportunities to experience the best of Chicago. At the end of your day, enjoy a relaxing soak in your private outdoor hot tub (open year-round) before sinking in to your Tempur-Pedic king bed for a restful night's sleep. Complimentary off-street parking provides rare convenience near the city center.

Guest favorite
An outdoor patio is showcased, featuring a rectangular fire table surrounded by four cushioned chairs. The wooden decking contrasts with the subdued colors of the furniture. A partial cover is draped over one corner, providing shade from the sun.
Condo in West Town
4.96 out of 5 average rating, 162 reviews

Downtown Chicago - Spa Bath, Patio, 3 blocks to L

Explore Chicago's charm just moments from downtown! This Airbnb boasts a spa bath with a luxurious rain shower and jetted tub, a fully equipped kitchen for culinary adventures, comfortable reclining sofas for relaxation, and ample space to unwind. Sleep like royalty in the master bedroom's king bed, and a queen murphy bed in the living area ensures a comfortable stay for up to four guests. Step outside to the patio with a fire pit for cozy evenings. Your Windy City getaway begins here!

Guest favorite
The living area features a modern sofa adorned with decorative cushions, a round coffee table, and a stylish media console. Large windows allow light to fill the space, with sheer curtains adding softness. A light-colored area rug complements the room's neutral palette.
Condo in Wicker Park
4.92 out of 5 average rating, 115 reviews

Elegant Wicker: Wolcott & Milwaukee Ave

Our 2 bedroom, 2 bath condo is Perfect for large families, event goers, and business travelers needing a place to rest. Lovely, mature, elegant & modern space! 5min walk to the Blue line Damen stop! The private condo is recently renovated and has all new upgraded appliances, gas wolf range, subzero double fridge and all the essentials! It is on Wolcott Ave exactly between Milwaukee & Division. Yes we are licensed and have a registration # with the city of Chicago # R20000058371.

Guest favorite
A bright living area is illustrated with large windows allowing natural light to fill the space. A comfortable beige sectional sofa provides seating, while a wooden coffee table sits on an area rug. A desk with modern design and a chair are present, enhancing the workspace.
Condo in Humboldt Park
4.93 out of 5 average rating, 141 reviews

Luxuriously bright 3-bedroom condo: The Treehouse

Experience a calm and soothing stay in a space bathed with light and nestled amongst the trees. This top floor unit in a 3-flat condominium building offers you the serenity of a neighborhood with tree lined streets, and the convenience of being 3 miles from the heart of downtown Chicago. As a bonus, you're a 2min walk from public transportation. For something closer to home, Wicker Park and Humboldt Park offer great dining and culture steps away. We look forward to hosting you!

Top guest favorite
A comfortable living area features a dark sofa with colorful accent pillows and a glass coffee table. Natural light streams through large windows, which are dressed with sheer white curtains. A modern floor lamp and a single chair add functional seating options.
Condo in Humboldt Park
4.93 out of 5 average rating, 279 reviews

Modern/Spacious 2BR/2BA West Town

Light, airy and luxurious, our duplex has a self-contained, 1400 sq. ft. 2nd floor with a private street entrance. There are two bedrooms and two baths. The master bedroom has a fireplace, a private balcony and a huge bathroom ensuite. In addition there is a dining room and living room. Minimal kitchen facilities include small fridge and micro. Easy commute downtown- 20 by car, 25 by bike and 30-40 minutes via public transportation. Close to hwy and public trans.

Top guest favorite
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
4.84 out of 5 average rating, 364 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 favorite
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, 125 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 favorite
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, 136 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 favorite
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, 145 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 favorite
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, 844 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.

Popular amenities for Wicker Park condo rentals

When is the best time to visit Wicker Park?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price€ 140€ 142€ 191€ 186€ 224€ 264€ 246€ 263€ 226€ 179€ 168€ 144
Avg. temp-3°C-1°C4°C10°C16°C22°C25°C24°C20°C13°C6°C0°C

Quick stats about condo rentals in Wicker Park

  • Total vacation rentals

    Explore 20 vacation rentals in Wicker Park

  • Nightly prices starting at

    Wicker Park vacation rentals start at € 43 per night before taxes and fees

  • Verified guest reviews

    Over 2,490 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Wicker Park vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Wicker Park rentals

  • 4.9 Average rating

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

  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Chicago
  6. Wicker Park
  7. Condo rentals