Vacation rentals in Wicker Park

Find and book unique accommodations on Airbnb

Quick stats about vacation rentals in Wicker Park

  • Total vacation rentals

    Explore 170 vacation rentals in Wicker Park

  • Nightly prices starting at

    Wicker Park vacation rentals start at $28 CAD per night before taxes and fees

  • Verified guest reviews

    Over 13,100 verified reviews to help you choose

  • Family-friendly vacation rentals

    90 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 40 rentals that welcome pets

  • Rentals with dedicated workspaces

    120 properties have a dedicated workspace

  • Wifi availability

    170 of Wicker Park vacation rentals include wifi 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!

Top-rated vacation rentals in Wicker Park

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

1 of 1 pages1 / 1
Top guest favourite
Apartment in Wicker Park
4.97 out of 5 average rating, 309 reviews

Stylish First Flr. Studio. Best Location Division+Hermitage.

Clean! Private! Studio located in the popular Ukrainian Village. This quiet unit is located in a charming 19th century pink brick Victorian cottage. It is a great retreat from work or play when visiting Chicago. This welcoming space features modern amenities, stylish decor with unique artwork, tall ceilings and an inviting color palette. Hermitage House Studio a perfect home away from home with in unit laundry, cable with On Demand and green filled backyard patio perfect for sipping your morning coffee or tea. Need 2nd space same building? Check out airbnb.com/h/chicago-hermitage-loft2 This private –very hip studio apartment - completely renovated and newly decorated is set up like a posh hotel suite with all the amenities of home!! Used for guests only this cozy and modern first floor apartment is set in an 1892 vintage brick cottage with a beautiful outdoor rear patio on a quiet tree lined street! This richly colored designer decorated space with all original artwork has comfort in mind. It has plenty of seating including a comfortable leather sofa, a cool desk area and raised bar. Hardwood floors throughout living space, 9’ ceilings, washer/ dryer, central air and heating, hotel like bathroom with soaking tub and an in unit stacking washer/dryer. Modern white kitchen has granite countertops, quartz sink, gas stove-oven, dishwasher, garbage disposal , microwave. The kitchen has many fun gadgets like French press coffee maker, electric tea pot and more. Everything is available for you to use. The high counter with barstools separates the kitchen from the living/sleeping space. The relaxing bedroom area accommodates 2 with a queen pillow top Serta mattress, great lighting, beautiful Mediterranean blue curtains and storage end tables filled with additional blankets. A full aero bed can accommodate a third person if needed. There is a custom closet system with great storage for personals, shoes and folded clothing. Perfect for a couple or an Airbnb business user! Flat screen TV with cable and movie channels Fast Wi-Fi This unit is located in the quiet first floor rear of this building. The first floor rear patio is yours to enjoy! The upper level deck is private. This unit features a digital locks. You will be able to pick your own code before check-in. I am readily available but will respect your privacy unless you need me. I live in the building (Sometimes out of town) but always accessible by phone or internet if anything is needed but the place is yours to enjoy! Located just steps off bustling Division Street this neighborhood has it all without the fuss of downtown. Within walking distance there are restaurants with cuisines from around the world as well as comfort food. Nightlife options including live music and sports venues. There is boutique shopping, art galleries, a local gym and even a mini Target. This cozy Studio is quick walk from the Division St. Blue-Line train that will get you downtown or to O'hare Airport in minutes. Just two blocks to the Division Blue line running from O’Hare and downtown at the intersection of Division/Ashland/Milwaukee This is a great walking neighborhood but it is easily accessible to many buses, cabs, trains and even the new shared Divvy bike station just a block from the studio. If you choose to drive there is zoned parking permits available- 1 per day. I will happily provide directions to attractions, neighborhoods, great food, groceries, coffee and nightlife

Guest favourite
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, 315 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.

Top guest favourite
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, 184 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 favourite
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
4.91 out of 5 average rating, 391 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 favourite
A vibrant living area features two orange armchairs positioned around a decorative wooden table. A floral wallpaper adorns the wall behind a wall-mounted television, while a rich area rug anchors the space. Natural light filters through sheer curtains, highlighting the room's colors.
Apartment in Wicker Park
4.97 out of 5 average rating, 184 reviews

COZY Bright*BOLD*FUN* Eclectic Wicker Park Home

Location! Location! Location! Prime Wicker Park Location on Milwaukee! This spacious, cool, vibrant, eclectic, fully equipped apartment is close to everything, making it easy to plan your visit. Bright top floor unit with a private patio to just chill and unwind or walk downstairs and your literally in the heart of Wicker Park. Super easy access to downtown nightlife/lake/museum all within 15 minutes and super easy commute to O'hare. CTA busses all around and a 2 minute walk to the Blue Line.

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
4.98 out of 5 average rating, 164 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 favourite
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
4.93 out of 5 average rating, 222 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 favourite
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
4.95 out of 5 average rating, 163 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.

Guest favourite
An industrial-style dining area features a wooden table surrounded by black chairs. Overhead, five pendant lights provide illumination against a textured exposed brick wall. A television is mounted nearby, and greenery is present in the space, adding a touch of nature.
Apartment in Wicker Park
4.91 out of 5 average rating, 184 reviews

Strictly Commercial Storefront: Humboldt, Bucktown

Enjoy a private entrance to your street-level storefront apartment at the intersection of Bucktown, Wicker Park, Humboldt Park and Logan Square neighborhoods. Easy access to transport. Rest in comfort and check out the 606 elevated trail, Humboldt Park, restaurants, shopping, and nightlife. Well-outfitted apartment features exposed brick, unique lighting, and lofted bedroom. Anthropologist? Watch the street scene through one way glass. You can see out, but your subjects can't see in.

Superhost
A serene bedroom features a spacious bed with crisp white linens and a light gray upholstered headboard. Natural light flows through large windows, illuminating the neutral walls and wood flooring. A small bedside table with a decorative lamp adds a touch of elegance to the space.
Apartment in Downtown Chicago
4.81 out of 5 average rating, 1,029 reviews

Kasa | Views from your Private Balcony | Chicago

When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chicago easy. Located just north of downtown Chicago, you'll be steps from Oak Street Beach, a short walk to Michigan Avenue and Millennium Park. With fantastic amenities, our apartments are ideal for extended stays or long vacations. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text or phone, and a Virtual Front Desk accessed via mobile device.

Top guest favourite
A spacious dining area is highlighted by a contemporary chandelier above a wooden table set for four. Transparent chairs provide a modern touch, complemented by decorative accents on the sideboard and the elegant wooden columns framing the open space, enhancing the flow between rooms.
Apartment in Wicker Park
5 out of 5 average rating, 108 reviews

The Bell House: Apartment #1

Charming 2BR Wicker Park apartment blends modern luxury with historical charm. Fully renovated; new appliances, private deck, full kitchen with cookware, & dedicated workspace. Steps from bars, restaurants, and Blue Line for city/airport access. Ideal for both leisure and business travelers seeking a comfortable, convenient Chicago stay. We offer a unique blend of comfort and location in a vibrant neighborhood. Perfect for exploring on foot, but ample street parking as well!

Top guest favourite
A landscaped garden patio is illuminated by soft lighting, highlighting a central tree and neatly arranged plants. An outdoor dining table with several chairs stands on stone paving, creating a welcoming space for relaxation. The brick facade of the coach house is visible in the background.
Guesthouse in Wicker Park
4.98 out of 5 average rating, 101 reviews

Coach House with Garage Parking & EV Charging

Immerse in solar-powered serenity amidst the bustling restaurant, shopping and nightlife scene of the Wicker Park neighborhood of Chicago. Large, loft-like and super sunny one bedroom includes full kitchen with new appliances, landscaped garden patio, and EV charging in an enclosed and attached garage space. All powered by a full array of high-efficiency rooftop solar panels. Five minute walk to the Damen Blue Line and the 606 Elevated Trail for cyclists and runners.

Popular amenities for Wicker Park vacation rentals