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Apartment holiday rentals in Wicker Park

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Top-rated apartment rentals in Wicker Park

Guests agree: these apartments are highly rated for location, cleanliness and more.

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Top guest favourite
The living area showcases a spacious layout, featuring a comfortable couch, a modern glass coffee table, and a stylish armchair. Natural light floods the room through large windows, accentuated by hardwood flooring and a decorative rug. A dining table for four is positioned nearby, along with a colorful wall art.
Apartment in Wicker Park
4.92 out of 5 average rating, 140 reviews

WONDERFUL WICKER PARK 2BD/2BA w/ patios +parking

Escape into this spacious condo in a bustling top-notch, Chicago neighborhood! 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! - 2 private walk-out patios! - Fast WiFi (600 mbps) - Master en-suite w/ separate walk-out patio - Designated parking spot! - Steps away from blue line Damen station (800 feet)

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.
Apartment in Bucktown
4.79 out of 5 average rating, 140 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.
Apartment in Wicker Park
4.97 out of 5 average rating, 137 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.
Apartment 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!

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.
Apartment 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.

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.
Apartment 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!

Superhost
A bright sleeping area features a spacious bed with a navy blue coverlet and a decorative pillow. A white towel is neatly placed at the foot of the bed. Natural light filters in through two windows, complemented by a modern floor lamp and a vintage airplane propeller accent above the bed.
Apartment in River West
4.75 out of 5 average rating, 170 reviews

Cabin 302 at 747 Lofts

This studio apartment is in the perfect location in Chicago for getting to Downtown via the Blue Line L or to the Hot West Loop and Randolph street restaurant row. Walk to bars, shops, restaurants, coffee liquor stores and transportation with ease! You will love our spa baths, in unit laundry and full modern kitchens to make it feel like a home away from home. One of the best pizza spots in Chicago is only steps away!

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.
Apartment in Wicker Park
4.95 out of 5 average rating, 135 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.
Apartment 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.
Apartment 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.
Apartment in Noble Square
4.97 out of 5 average rating, 869 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.

Guest favourite
A modern living room features a light-colored sectional sofa adorned with various cushions. A sleek black coffee table sits in front of it, and a mounted television occupies the wall above a low console. Soft lighting highlights the textured wall panels.
Apartment in Bucktown
4.95 out of 5 average rating, 104 reviews

Wicker Park/Bucktown condo with outdoor patio

This freshly remodeled condo decorated in the Japandi style is set in the trendy yet peaceful neighborhood of Bucktown - a perfect base for exploring Chicago. A short walking distance to 2 Blue line CTA stops (Western and Damen), it is surrounded by quaint neighborhood bars, restaurants, and coffee shops as well as grocery stores and trendy shopping.

Popular amenities for Wicker Park apartment rentals

When is the best time to visit Wicker Park?

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Avg. price€ 137€ 139€ 186€ 182€ 219€ 258€ 260€ 287€ 177€ 222€ 181€ 165
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Quick stats about apartment rentals in Wicker Park

  • Total holiday rentals

    Explore 20 holiday rentals in Wicker Park

  • Nightly prices starting at

    Wicker Park holiday rentals start at € 42 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 & child-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 of Wicker Park holiday rentals include wifi 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!

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