Wicker Park holiday rentals

We found 1,215 holiday rentals — enter your dates for availability
Discover a selection of 20 homes, 22 apartments and other holiday rentals in Wicker Park that are perfect for your trip. Whether you're travelling with your children and pets, with friends or just your children, holiday homes have the amenities that you expect for your stay, which might include Wi-Fi and a washer and dryer. No matter what you're looking for, you'll find a property to rent to meet everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Wicker Park

Showing deals for:15 Jan - 22 Jan

Dining
Our downtown Townhouse is in an amazing location
Interior
It is huge! With lots of areas for relaxing and entertaining
Exceptional
(92 reviews)

Historic luxury townhouse on Chicago's Gold Coast

Chicago

5% off
S$6,473
for 7 nights, 1 home
S$925 per night
includes taxes & fees
Historic luxury townhouse on Chicago's Gold Coast
The building
River North Luxury Living
French Bistro and Wine Bar - right downstairs
Interior
Exceptional
(107 reviews)

River North's Rock N' Roll - In The Heart of the City

Chicago

7% off
S$4,258
for 7 nights, 1 apartment
S$608 per night
includes taxes & fees
River North's Rock N' Roll - In The Heart of the City
Fun Mirror Wall Upstairs
Downstairs living area
Downstairs living room
Upstairs queen bedroom 2
Exceptional
(101 reviews)

Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!

Chicago

7% off
S$13,114
for 7 nights, 1 apartment
S$1,873 per night
includes taxes & fees
Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
Private kitchen
Interior
Interior
Living area
Exceptional
(54 reviews)

Modern Logan Square Luxury: 5 bedroom - sleeps 16!

Chicago

7% off
S$6,074
for 7 nights, 1 home
S$868 per night
includes taxes & fees
Modern Logan Square Luxury: 5 bedroom - sleeps 16!
Living Room with 60 in Smart TV
Chef kitchen with Sub-Zero refrigerator, Wolf stove, Bosch dishwasher.
Living Room with 60 in Smart TV
Living Room with 60 in Smart TV
Exceptional
(93 reviews)

Stunning Lincoln Park Single-Family House with Fantastic Game Room

Chicago

10% off
S$7,173
for 7 nights, 1 home
S$1,025 per night
includes taxes & fees
Stunning Lincoln Park Single-Family House with Fantastic Game Room
Interior
Private kitchen
Dining
Interior
Wonderful
(50 reviews)

Gorgeous 5 BDR/ 4BA in Logan Square w/Parking!

Chicago

7% off
S$4,516
for 7 nights, 1 home
S$645 per night
includes taxes & fees
Gorgeous 5 BDR/ 4BA in Logan Square w/Parking!
Interior
Living area
Dining
Living area
Exceptional
(14 reviews)

Wicker Park: Cozy Fireplace, Grand Piano

Chicago

24% off
S$3,916
for 7 nights, 1 apartment
S$559 per night
includes taxes & fees
Wicker Park: Cozy Fireplace, Grand Piano
Exterior
Living area
Private kitchen
Living area
Excellent
(11 reviews)

Spacious / New - 8BD/4BTH - Sleeps 16 + Garage!

Chicago

7% off
S$6,301
for 7 nights, 1 home
S$900 per night
includes taxes & fees
Spacious / New - 8BD/4BTH - Sleeps 16 + Garage!
Kitchen on Top Floor
Top floor kitchen and dining area
Bedroom 3 w/ Queen Bed
2 spots come with the unit- occupied by the van and SUV in this photo.
Exceptional
(35 reviews)

The Exclusive- 7 Bed, 6 Bath Retreat

Chicago

5% off
S$6,357
for 7 nights, 1 apartment
S$908 per night
includes taxes & fees
The Exclusive- 7 Bed, 6 Bath Retreat
Terrace/patio
Room
Interior
Interior
Exceptional
(76 reviews)

Private Historic Coach House Wicker Park

Chicago

6% off
S$3,168
for 7 nights, 1 home
S$453 per night
includes taxes & fees
Private Historic Coach House Wicker Park
Living room area
3 bedroom unit is top floor of historic greystone
Living room area opens into dining room & kitchen
Dining room area
Exceptional
(101 reviews)

Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.

Chicago

7% off
S$7,559
for 7 nights, 1 home
S$1,080 per night
includes taxes & fees
Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.
Living area
Belmont Harbor
Exterior
Private kitchen
Exceptional
(193 reviews)

Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24

Chicago

8% off
S$4,668
for 7 nights, 1 home
S$667 per night
includes taxes & fees
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Kitchen
Living area
Dining
Room
Exceptional
(32 reviews)

Sunny 2-Bedroom Logan Square Apartment – Your Perfect Chicago Base

Chicago

6% off
S$2,090
for 7 nights, 1 apartment
S$299 per night
includes taxes & fees
Sunny 2-Bedroom Logan Square Apartment – Your Perfect Chicago Base
Private kitchen
Interior
Interior
Room
Exceptional
(12 reviews)

Peaceful Living-2Bdrm/2Bath w/Private Parking, WiFi-Work Station-Wicker Park!

Chicago

7% off
S$2,669
for 7 nights, 1 apartment
S$381 per night
includes taxes & fees
Peaceful Living-2Bdrm/2Bath w/Private Parking, WiFi-Work Station-Wicker Park!
Living area
Living area
Terrace/patio
Dining
Exceptional
(12 reviews)

Your Logan Square Oasis with Lush Outdoor Haven!

Chicago

7% off
S$2,425
for 7 nights, 1 apartment
S$346 per night
includes taxes & fees
Your Logan Square Oasis with Lush Outdoor Haven!
Private kitchen
Living area
Exterior
Room
Exceptional
(14 reviews)

Cozy apartment near zoo, DePaul, Oz Park and much more!

Chicago

7% off
S$4,107
for 7 nights, 1 apartment
S$587 per night
includes taxes & fees
Cozy apartment near zoo, DePaul, Oz Park and much more!

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

What is the most popular type of holiday rental accommodation in Wicker Park?
Apartments are the most popular kind of holiday rental in Wicker Park, according to our data. Even if you have something bigger or smaller in mind, Vrbo has properties in a variety of shapes and sizes. Compare our options to find your ideal fit.
How much does it cost to rent a holiday rental in Wicker Park?
Season, length of stay and property type are among the factors that can influence the price of a holiday home. Simply add your travel dates to find your perfect match. From cosy country cottages to expansive villas, all Vrbo holiday rentals offer unbeatable value.
How much does it cost to rent a beach house in Wicker Park?
The average price for a holiday home by the beach in Wicker Park depends on when you're travelling and the size and style of property you're searching for. You can easily and quickly find prices on Vrbo by entering your dates of travel. Then make use of the filter tool to choose the number of bedrooms and amenities that you prefer, such as WiFi, air conditioning and a hot tub.
Are there pet-friendly holiday rentals in Wicker Park?
You're in luck. There are. You'll have your pick of 28 stays that allow pets in Wicker Park on Vrbo. Our furry companions also deserve a little time out, so simply use our search function for pet-friendly holiday rentals to find a perfect pad where your doggie can be near his favourite humans.
What are popular rental amenities in Wicker Park?
Nearby museums, a barbecue grill and a firepit rank as the most popular rental amenities in Wicker Park. Whether you're travelling as a party of one, with your significant other or a bunch of friends, Vrbo can help you find a holiday home that matches your style with all the extras you're looking for.
Are there large group holiday rentals in Wicker Park?
Pick from three properties in Wicker Park that can accommodate 10 or more people. Whether you're organising time away with the family or a special event like a birthday party, there's plenty of space to get your group together under one roof.
Are there holiday rentals in Wicker Park that welcome kids?
With 27 family-friendly holiday properties to choose from in Wicker Park, now is a fantastic time to introduce the kiddos to the magic of travel. Click on our "Properties good for families" filter to browse stays that feature conveniences perfect for holidaying families, such as extra bedrooms, pools, entertainment units and bunk beds.
What are the top attractions for families in Wicker Park?
There are plenty of fabulous things to do and see with the family in Wicker Park, including:
  • Navy Pier
  • Chicago Riverwalk
  • Shedd Aquarium
Are there one-bedroom holiday rentals in Wicker Park?
Yes, Wicker Park has eight one-bedroom rentals on offer. Often positioned in prime areas thanks to their smaller size, a one-bedroom rental is great if you're getting away with your partner or a pal. And with comforts such as laundry facilities and more privacy than a standard hotel, you'll be able to kick back while enjoying this top destination.
Can I find two-bedroom holiday rentals in Wicker Park?
Wicker Park has five two-bedroom holiday properties for you to pick from. Enjoy a holiday home with all the comfort and privacy you want at a fantastic price on Vrbo.
Are there holiday rentals with WiFi in Wicker Park?
Wicker Park has 12 holiday rentals with WiFi, so you can stay connected while travelling. Simply check the "WiFi" box in our handy search filter for a list of properties with this feature. From streaming movies with your family to writing and sending emails, these Vrbo homes make it a cinch to get online.
How can I find holiday rentals with air conditioning in Wicker Park?
Select your travel dates and then use the filters to locate holiday rentals with ac in Wicker Park on Vrbo. With 24 air-conditioned properties to choose from here, you can look forward to a cool and comfortable stay.
How old do you have to be to rent a holiday rental in Wicker Park?
You'll need to check with the Wicker Park holiday property you want on Vrbo as the minimum age differs. However, normally it's 16, 18 or 21.
How long can I rent a holiday rental in Wicker Park for?
The length of time you can rent a holiday rental in Wicker Park varies according to the property. Just enter your chosen dates to display a list of options offering extended stays. With loads of creature comforts like washing machines and air conditioning, as well as some offering weekly or monthly discounted prices, you're sure to get someplace just right to call your home away from home in Wicker Park.

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