Vacation rentals in Wicker Park

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Top-rated vacation rentals in Wicker Park

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Top guest favorite
A spacious living area features a comfortable sofa adorned with orange and green cushions. A sleek black coffee table sits atop a striped rug. Floor-to-ceiling sheer curtains allow natural light to filter in, while an artwork hangs on a contrasting blue wall.
Home in Wicker Park
4.92 out of 5 average rating, 293 reviews

Cool Quiet Coach House, Private Access + Patio

Retreat to the brick patio of this lovingly renovated home after a long day traversing the neighborhood. The interior is an expression of creativity, greyscale walls, rustic accents, and a varied selection of art and wall hangings tie in the decor. Split Level Floor plan. 1st floor = Living, Eat in Kitchen, bedroom 1 and bathroom. 2nd Floor = 2nd bedroom , bath and an additional sleeping area and desk area. Also features a gorgeous shared yard. The entire coach house is yours!! The coach house is set back behind a 2 unit building and the yard is shared between both. We are available via text or airbnb messaging and try to respond quickly. Please reach out anytime if you need anything at all. Extra supplies, neighborhood recommendations or tips in the neighborhood. The home is located on the border of Wicker Park and Bucktown which is Chicago's original hub of cool. It is a vibrant enclave of culture and commerce, explore vintage finds, record stores, and plenty of indie shopping in this trendy part of town The 24 hour Blue Line EL train is just a 5 minute walk. Door to Door it's only 25 minutes to Millennium park. (5 min walk to the blue line, 10 min ride on the train, 10 minute walk to the Park). The neighborhood is pedestrian and bike friendly , the 606 trail is just a few blocks away also.

Guest favorite
The image displays an advertisement featuring the text 'Western Avenue Lofts + Studios' in bold letters. Below it, details regarding artist studios and loft availability are presented. An artistic design element, representative of the historical context, is visible in the background.
Apartment in Wicker Park
4.82 out of 5 average rating, 468 reviews

WESTERN AVE ARTISTS LOFTS- Park Free

FREE street PARKING. Walk to Wicker Park restaurants, bars & shopping. 10 MINUTE WALK to CTA Blue line TRAIN-Damen stop. Premium queen mattress ( small bedroom but a queen bed) & brand new sofa bed. Full kitchen & washer & dryer in apartment. Resident artists work on first floor of this historic former telephone repair and switching station. Very laid back vibe. EVERYONE is Welcome. All guests must be on the reservation for $total. Note $30 per night per guest charge AFTER 2 Guests ( 3&4)

Top guest favorite
A cozy living area features a light-colored sofa adorned with patterned cushions, set against a warm brick wall. Natural light floods through two windows, illuminating the plants and wooden coffee table. A television is positioned on a modern media console, enhancing the space's functionality.
Apartment in Wicker Park
4.99 out of 5 average rating, 152 reviews

Chic City Escape | 2BR Retreat w/ Parking.

PRIME LOCATION -heart of Wicker Park: Clean, modern, and eccentric condo with 11 ft ceiling, brick wall, and lots of natural light! Our home is in the heart of Wicker Park- one minute walk to the busy Milwaukee street bustling with restaurants, cafes, bars, shops, and theaters. The condo is a five minute walk away from the Damen Blue Line allowing easy access to the city and to O’Hare airport. We’re also a 12 minute drive to beautiful Lake Michigan. Early checkin/late checkouts upon availability

Top guest favorite
A spacious living area features large sliding glass doors that open to a balcony, allowing natural light to fill the room. Two dark blue bean bags and a glass coffee table are positioned in front of a white sofa, creating a relaxed seating arrangement.
Apartment in Wicker Park
4.95 out of 5 average rating, 159 reviews

Spacious Studio w/Balcony in Bucktown/Wicker Park

My place is in the heart of one of Chicago's Hottest and Hippest neighborhoods(Wicker Park/Bucktown) with everything you need or want within a short walk - Transportation(Blue Line Train) which is a direct shot to and from O'hare airport, Dining, Nightlife, High End boutique shopping. 15 minutes to the Magnificent Mile, Millennium Park, Wrigley Field. Perfect for couples, solo adventurers, and business travelers with Internet and Cable TV included. Sleeps 2 adults comfortably w/sleeper sofa.

Guest favorite
The living area features a sleek television mounted on the wall, complemented by a stylish wooden cabinet. A light-colored sofa is positioned in front of a rectangular coffee table, with a decorative bowl resting on it. The space is enhanced by natural light from the windows and greenery.
Apartment in Wicker Park
4.92 out of 5 average rating, 356 reviews

Newly remodeled 1BR! Only 5 MIN walk to BLUE LINE!

Located in the heart of Wicker Park, just a 5 min walk to the Damen blue line stop. This phenomenal location allows you to access EVERYTHING Chicago has to offer without having to rent a car. Experience the best of Chicago, all within a short walk from your stay. World class bars, restaurants, and shopping all within walking distance. Want to explore downtown or catch a Cubs game at Wrigley? Hop on the "L" train and use the CTA to go anywhere in the city. This cozy garden apartment has it all.

Top guest favorite
A cozy living room features a gray sectional sofa and a teal accent chair, complemented by patterned curtains. A TV is positioned on a low stand, with framed artwork on the walls. Natural light filters through multiple windows, enhancing the vibrant decor.
Apartment in Wicker Park
4.98 out of 5 average rating, 121 reviews

Colorful Bucktown Garden Apartment

Enjoy a stylish experience at this centrally-located apartment. Close to all of the neighborhood amenities including the 606 trail, shopping district, highly reviewed restaurants, blue line "el" train, neighborhood parks, and more. Walk to everything you need or jump on the blue line to get downtown quickly. Our colorful space is perfect for your city stay. Enjoy comfortable spaces including an oversized bedroom, cozy living room, fully appointed bathroom, dining area, and a kitchenette.

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, 176 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)

Top guest favorite
A dining area features a wooden table with seating for four, positioned against a textured brick wall. Two windows allow natural light to fill the space, with sheer curtains gently framing them. A vibrant green plant and neon 'CHICAGO' sign add character to the room.
Apartment in Wicker Park
4.94 out of 5 average rating, 127 reviews

【Central】- Eclectic Fun 1BR APT in Wicker Park

Located in the heart of Wicker Park! Just a 5-min walk from the CTA blue line Damen station. This bright second floor 1-bedroom, 1-bath apartment allows you to access EVERYTHING Chicago has to offer all within short walking distance, with great nightlife. Just walk downstairs, you will find trendy restaurants, cocktail bars, cozy coffee shops and a variety of shops in this popular neighborhood. Want to explore downtown? Uber/Lyft or Hop on the CTA "L" train to go anywhere in the city.

Top guest favorite
The living room is well-lit by sunlight streaming through three large windows, accentuating a comfortable brown sofa and a stylish armchair. A wooden coffee table and a small dining table with two chairs offer ample seating. Unique artwork and decorative items add character to the space.
Apartment in Noble Square
4.97 out of 5 average rating, 570 reviews

Fully Furnished Apartment Wicker Park Free Parking

Hello and welcome to all seeking a comfortable and convenient place to stay in Chicago! Please enjoy your time away from home in our fully furnished apartment located in the trendy neighborhood of Wicker Park! Please view the list below of all the wonderful amenities we offer to every guest staying out apartment. Again if you have any questions or comments please do not hesitate to ask. I look forward to seeing you and having your apartment ready soon! Thank you! One night available

Guest favorite
A spacious dining area features a large wooden table surrounded by two long benches. Artwork is displayed on the light gray walls, and natural light floods in from a large window. A small desk and chair are positioned in the corner, adding functionality to the space.
Apartment in Wicker Park
4.89 out of 5 average rating, 193 reviews

Charming Two Bedroom in Wicker Park

Our apartment is on a quiet street in a trendy neighborhood that always has something cool going on. Wicker Park is a hive of activity that draws shoppers hunting for unique finds, foodies looking for the trendiest eats, and bar hoppers searching for late-night buzz. Ideal for couples, solo travelers, business travelers, and small groups looking for a central, comfortable spot. COVID note: We are taking an extra effort to disinfect and sanitize all surfaces during each cleaning.

Top guest favorite
A comfortable living area is presented with a light gray sofa adorned with colorful throw pillows. A wooden coffee table sits in front, accompanied by coasters. The warm light from a nearby lamp complements the wooden window shutters and artworks on the wall.
Apartment in Wicker Park
4.92 out of 5 average rating, 426 reviews

CLEAN Cozy Vintage Chicago Apartment near Downtown

This is your launching pad to see the city! It is a vintage apartment with your own private entrance and space. It is within walking distance of a large selection of restaurants, bars and cafes. With a bicycle, cab, Uber/Lyft, bus or EL train you can be downtown in minutes. In close proximity to many of Chicago's great locations such as Wrigley Field, The United Center, White Sox Park, etc...Located in the Ukrainian Village a safe, welcoming neighborhood with plenty of history.

Guest favorite
A spacious living area features a stylish gray sofa and a large white coffee table at its center. Dark curtains frame the windows, allowing natural light to illuminate the space, which is adorned with arcade games and art on the walls.
Apartment in Wicker Park
4.88 out of 5 average rating, 336 reviews

Logan Square Video Game Loft

Treat yourself to a unique stay in this hip video game themed studio. Enjoy the comfort of this large, bright space—and the games and artwork on display—during your trip. Explore the happening neighborhood scene in the Logan/Bucktown/Wicker Park area via the 606 walking trail (right outside the door) or walk two blocks to the Blue Line el stop for easy access to downtown or the airport. *Please be sure to review the Other Things to Note section as well as our house rules.

Popular amenities for Wicker Park vacation rentals

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Quick stats about vacation rentals in Wicker Park

  • Total vacation rentals

    Explore 200 vacation rentals in Wicker Park

  • Nightly prices starting at

    Wicker Park vacation rentals start at € 17 per night before taxes and fees

  • Verified guest reviews

    Over 13,140 verified reviews to help you choose

  • Family-friendly vacation rentals

    100 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 50 rentals that welcome pets

  • Rentals with dedicated workspaces

    140 properties have a dedicated workspace

  • Wi-Fi availability

    200 of Wicker Park vacation rentals include wi-fi access

  • Popular amenities for guests

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

  • 4.8 Average rating

    Wicker Park stays are highly rated by guests—averaging 4.8 out of 5!

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