Apartment holiday rentals in Wicker Park

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Top-rated apartment rentals in Wicker Park

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Top guest favourite
Flat in Wicker Park
4.97 out of 5 average rating, 291 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 compact workspace is featured with a wooden desk and a comfortable chair in a blue-toned room. A decorative world map is mounted on the wall, and a small plant and lamp sit on the desk. Light enters through a glass-paneled door.
Flat in Wicker Park
4.95 out of 5 average rating, 110 reviews

CUTE, PRIVATE & QUITE STUDIO 1BD/1BA Wicker Park!!

Grateful location, Wicker Park has everything nearby based on walkability to explore! Many boutique shops, a number of coffee shops and locally own restaurants and bars. A 2 minute walk to CTA Blue Line subway excess to downtown Chicago, Lake, Museums or to O’Hare Airport and Midway Airport. SPACE: Entrance to building, very welcoming. Stairs and hall very clean, have laundry area coin washers and dryer (if needed). Studio very clean, professionally, to ensure the wellness to our guest's

Superhost
A spacious living room is feature a cozy sectional couch adorned with pillows and a soft throw. Two round coffee tables sit in front, complemented by an accent rug. Framed art prints of Chicago are displayed on the walls, enhancing the inviting atmosphere of the area.
Flat in Wicker Park
4.87 out of 5 average rating, 124 reviews

Explore Chicago from our Trendy Wicker Park Airbnb

Our stylish 2-bedroom Airbnb is the perfect choice for all types of travelers. Whether you're seeking a comfortable place to sleep, a productive environment to get work done, a convenient base to explore Chicago, enjoy a night out at the bars/nightlife , or a cozy space to spend quality time, we've got you covered. Tall ceilings make this Airbnb feel larger than life, a fully equipped kitchen is great for dinners at home, or visit the Michelin Star Awarded Kasama just 3 buildings away from here

Top guest favourite
An open-concept dining area is depicted, featuring a wooden table with multiple chairs. A vibrant table runner adds color. The kitchen is visible in the background, showcasing modern appliances. Ceiling fans enhance airflow while natural light enters through nearby windows, creating a bright atmosphere.
Flat in Wicker Park
4.95 out of 5 average rating, 236 reviews

Tastefully designed 1500 Sq of Homeyness!

Newly rehabbed, charming 2 bd duplex down apartment in Bucktown. + Tastefully FURNISHED with comforts of home + FULLY EQUIPPED KITCHEN with Calphalon cookware, bakeware and serveware. + COMPLETE TURNOVER with every booking. + 2 minutes to the train station to get to/from O'hare and downtown. + By the entrance to the 606. Walk to vibrant nightlife, restaurants and shopping. + Free street parking. Permit provided Please be aware that you may hear construction noises between the times 8am-8pm.

Top guest favourite
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.
Flat in Wicker Park
4.99 out of 5 average rating, 166 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 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.
Flat in Wicker Park
4.95 out of 5 average rating, 165 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.
Flat in Wicker Park
4.91 out of 5 average rating, 374 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.

Guest favourite
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.
Flat in Wicker Park
4.89 out of 5 average rating, 201 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 favourite
The kitchen features white cabinets with teal accents and a spacious layout. A wooden table is surrounded by four white chairs. Natural light enters through a window adorned with light curtains. Decorative plates and a mounted antler display add character to the wall.
Flat in Wicker Park
4.95 out of 5 average rating, 122 reviews

Ukrainian Village 3 Bedroom Apartment

Located on a quiet, tree-lined street in the heart of Ukrainian Village, our spacious 3-bedroom apartment sits on the 3rd floor of a classic Chicago building. 3 blocks away on Division St. you’ll find easy access to some of the city’s best restaurants, bars, and boutiques Public transportation is nearby—the #66 Chicago Ave. bus a 5-minute walk, the Blue Line train a 15-minute walk. You’re never far from downtown, ideally situated to explore Chicago’

Top guest favourite
The modern kitchen features navy blue cabinetry and a central island with seating for three. Stainless steel appliances include a refrigerator, stove, and dishwasher. Pendant lighting hangs above the island, and a window provides natural light, complementing decorative wall art.
Flat in Wicker Park
4.96 out of 5 average rating, 166 reviews

Stylish 2BR stunner w/ unbeatable location

Discover the perfect urban retreat in a newly renovated flat with all the modern amenities. Nestled at the border of Ukrainian Village and Wicker Park, this classic Chicago 2-flat offers modern amenities in a historic setting, tucked away in a peaceful corner just steps away from the vibrant city life of Division and Damen with its countless restaurants, watering holes, and one-of-a-kind shops.

Guest favourite
A cozy living area features a gray sofa positioned against a wood-paneled wall. Above the sofa, a large sign reading 'Beachwood' is displayed. A wooden coffee table with a small, rectangular box sits in front, and a round dining table is visible to the side.
Flat in Wicker Park
4.84 out of 5 average rating, 243 reviews

Ina's Beachwood Inn In the Heart of Wicker Park

Located on the second floor of Ina Mae Tavern & Packaged Goods, one of Chicago's best new restaurants, the Beachwood Inn has a private balcony overlooking the entire restaurant's bustling action so guests will never miss out on the happenings - from live music to brunch and dinner. The space is perfect for travelers who want to immerse themselves in a true local experience.

Top guest favourite
A cozy living space features wood flooring and tasteful decor. A brown sofa is paired with colorful pillows and a coffee table, while a cowhide rug adds texture. The open kitchen area is visible in the background, showcasing wooden cabinets and modern appliances.
Flat in Logan Square
4.88 out of 5 average rating, 321 reviews

Logan Square Modern Vintage Garden

This two-bedroom, cozy ground-level flat with a newly renovated bathroom is a great base from which to explore Logan Square's restaurants, coffee houses and farmers market. It's a perfect point of departure for Chicago's sites and attractions.

Popular amenities for Wicker Park apartment rentals

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Quick stats about flat rentals in Wicker Park

  • Total holiday rentals

    Explore 90 holiday rentals in Wicker Park

  • Nightly prices starting at

    Wicker Park holiday rentals start at £15 per night before taxes and fees

  • Verified guest reviews

    Over 6,180 verified reviews to help you choose

  • Family-friendly holiday rentals

    40 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

  • Wifi availability

    90 of Wicker Park holiday 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!

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