Vacation rentals in Wicker Park, Chicago

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Top-rated vacation rentals in Wicker Park, Chicago

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

Guest favorite

Apartment in Wicker Park

4.97 out of 5 average rating, 235 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

Mar 21 – 28

R3,109 ZAR per night
Guest favorite

Apartment in Wicker Park

4.97 out of 5 average rating, 242 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.

Aug 31 – Sep 7

R3,918 ZAR per night
Superhost

Condo in West Town

4.87 out of 5 average rating, 433 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!

Apr 5 – 12

R1,729 ZAR per night

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Other great vacation rentals in Wicker Park, Chicago

Guest favorite

Apartment in West Town

4.96 out of 5 average rating, 117 reviews

Cozy Urban Getaway East Village Apartment

Oct 25 – Nov 1

R3,276 ZAR per night
Guest favorite

Guest suite in Logan Square

4.92 out of 5 average rating, 307 reviews

Luxe, Private Suite w/Own Entrance-2023 Renovated

Dec 1 – 8

R3,482 ZAR per night
Superhost

Apartment in Irving Park

4.92 out of 5 average rating, 584 reviews

Explore Chicago from an Urban Sanctuary with Free Parking

Apr 17 – 24

R2,488 ZAR per night
Guest favorite

Apartment in West Town

4.88 out of 5 average rating, 386 reviews

Checkerboard Studio with Private Outdoor Hot Tub and Yard

Sep 16 – 23

R3,464 ZAR per night
Guest favorite

Guest suite in Lincoln Square

4.91 out of 5 average rating, 416 reviews

Cozy, Quiet, Garden Getaway!

Jan 7 – 14

R1,945 ZAR per night
Guest favorite

Apartment in Logan Square

4.87 out of 5 average rating, 481 reviews

Logan Square Studio

Feb 24 – Mar 3

R1,940 ZAR per night
Guest favorite

Apartment in Wicker Park

4.95 out of 5 average rating, 88 reviews

Spacious Studio w/Balcony in Bucktown/Wicker Park

Mar 2 – 9

R2,465 ZAR per night
Guest favorite

Apartment in Logan Square

5.0 out of 5 average rating, 20 reviews

The Heart of Bucktown

Aug 23 – 30

R2,293 ZAR per night
Guest favorite

Home in Wicker Park

4.95 out of 5 average rating, 44 reviews

Cozy space in Wicker Park

Apr 15 – 22

R2,582 ZAR per night
Guest favorite

Apartment in Wicker Park

5.0 out of 5 average rating, 30 reviews

Apt in Vibrant Wicker Park, by Blue Line.

Jun 17 – 22

R3,115 ZAR per night
Guest favorite

Apartment in Logan Square

4.88 out of 5 average rating, 58 reviews

Lovely Studio, 3min walk to train for Downtown/ORD

Dec 17 – 24

R1,706 ZAR per night
Superhost

Apartment in Wicker Park

4.81 out of 5 average rating, 78 reviews

Delightful Wicker Park 1 BR with free parking spot

Feb 7 – 14

R3,262 ZAR per night

Quick stats about vacation 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

R379 ZAR before taxes and fees

Destinations to explore

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