Holiday rentals in Wicker Park, Chicago

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Top-rated holiday rentals in Wicker Park, Chicago

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

Guest favourite
Flat in Wicker Park
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
11–18 Dec
$189 SGD per night
4.97 out of 5 average rating, 235 reviews
Guest favourite
Flat in West Town
Bright, Modern Apartment in a Vintage Greystone
Enjoy morning coffee by the sunny bay window in this vintage apartment with classic modern style. The apartment features vintage charm with modern amenities, queen memory foam bed in bedroom and queen sofa bed in living room. Parking is available in the back lot for an additional $25 per night. For reservations over three weeks, we require a cleaning every 2 weeks at a cost of $60 per cleaning. Apartment is located on the 3rd floor of a three story building and you will need to climb stairs. This is a large 1100 square foot fully renovated 1 bedroom apartment on the third floor of a beautiful vintage Chicago Grey Stone. Located directly on Chicago Ave. The space was thoughtfully designed by the design firm of Inside Home with the modern traveler in mind. The furnishings are a mix of vintage and new pieces specially curated for the space. The bedroom features a queen memory foam mattress as well as a 42" TV. The kitchen is equipped with cutlery, cooking utensils, coffee maker, espresso machine, pots & pans, baking sheets. Walking Rating of 96! You will have access to the full 1100 square foot apartment as well as a parking spot if needed located directly out back for an additional $20 per night, please notify us at the time of booking if you will require parking and we will add this fee to your reservation. There is also a washer and dryer in the basement if need (please request access) We will be on site at the furniture store located on the ground floor of the building should you need anything during your stay. Ukrainian Village is a historic community known for the contemporary restaurants, bars, and shops along bustling Chicago and Division Streets, but explore the neighborhood further to discover homes and businesses as old as the city itself. You are steps away from the 66 bus, which will take you directly to Navy Pier, rent a bike and explore the city or catch a cab right out side the front door or jump on the blue line "EL" train. This apartment has a walk rating of 96, bike rating of 90 and a transit rating of 72! This apartment is located on the third floor of a three story walk up. There is a additional queen bed in the sofa of the main room and all the additional bed linens are located in the bedroom night stand and closet.
18–25 Jan
$165 SGD per night
4.93 out of 5 average rating, 322 reviews
Guest favourite
Flat in Wicker Park
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.
26 Jul – 2 Aug
$242 SGD per night
4.97 out of 5 average rating, 240 reviews

Popular amenities for Wicker Park, Chicago holiday rentals

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Other great holiday rentals in Wicker Park, Chicago

Guest favourite
Flat in Wicker Park
Spacious Studio w/Balcony in Bucktown/Wicker Park
23–30 Nov
$150 SGD per night
4.95 out of 5 average rating, 88 reviews
Guest favourite
Apartment in Wicker Park
Private Urban Hideaway in the Heart of Wicker Park
7–14 Jul
$178 SGD per night
4.86 out of 5 average rating, 58 reviews
Guest favourite
Flat in Wicker Park
Apt in Vibrant Wicker Park, by Blue Line.
11–16 Jun
$200 SGD per night
5.0 out of 5 average rating, 29 reviews
Guest favourite
Flat in Logan Square
The Heart of Bucktown
9–16 Apr
$119 SGD per night
5.0 out of 5 average rating, 20 reviews
Superhost
Flat in Wicker Park
Strictly Commercial Storefront: Humboldt, Bucktown
11–18 Jul
$172 SGD per night
4.9 out of 5 average rating, 88 reviews
Superhost
Loft in Wicker Park
Entire Loft in Heart of Wicker Park with Parking
8–15 May
$292 SGD per night
4.86 out of 5 average rating, 92 reviews
Guest favourite
Flat in Wicker Park
Welcome to the Concrete Jungle! Roar! WicKer PaRK
16–23 May
$233 SGD per night
4.95 out of 5 average rating, 20 reviews
Guest favourite
Flat in Logan Square
Colorful Bucktown Apartment
1–8 Aug
$194 SGD per night
4.98 out of 5 average rating, 46 reviews
Guest favourite
Flat in Logan Square
Bucktown Brick Cottage Apartment
29 Nov – 6 Dec
$202 SGD per night
5.0 out of 5 average rating, 34 reviews
Guest favourite
Flat in Wicker Park
Beautiful, Clean 2BD/1BA/parking;Centrally located
3–10 Jun
$264 SGD per night
5.0 out of 5 average rating, 31 reviews
Guest favourite
Guest suite in Wicker Park
Exemplary Wicker Park Manor Two Bed Guest Suite
27 Mar – 3 Apr
$280 SGD per night
5.0 out of 5 average rating, 13 reviews
Guest favourite
Loft in Wicker Park
Loft8 - Vibey & Unique Design in Prime Location
17–24 Aug
$1,042 SGD per night
4.97 out of 5 average rating, 31 reviews

Quick stats about holiday rentals in Wicker Park, Chicago

Total rentals

180 properties

Rentals with dedicated workspaces

120 properties have a dedicated workspace

Pet-friendly rentals

40 properties allow pets

Family-friendly rentals

90 properties are a good fit for families

Total number of reviews

9.7K reviews

Nightly prices starting at

$27 SGD before taxes and fees

Destinations to explore

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