Wicker Park holiday rentals

We found 1,213 holiday rentals — enter your dates for availability
Discover a selection of 20 homes, 25 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:18 Dec - 25 Dec

Exterior
Interior
Room
Living area
Exceptional
(39 reviews)

Private Historical Mansion,Luxury Home in Chicago’s Gold Coast, Event-Capable.

Chicago

8% off
S$32,643
for 7 nights, 1 home
S$4,663 per night
includes taxes & fees
Private Historical Mansion,Luxury Home in Chicago’s Gold Coast, Event-Capable.
Interior
Our downtown Townhouse is in an amazing location
Room
Dining
Exceptional
(91 reviews)

Historic luxury townhouse on Chicago's Gold Coast

Chicago

5% off
S$9,922
for 7 nights, 1 home
S$1,417 per night
includes taxes & fees
Historic luxury townhouse on Chicago's Gold Coast
Private kitchen
Dining
Interior
Interior
Exceptional
(8 reviews)

5BR/4BA Modern SFH Logan Square!

Chicago

8% off
S$4,613
for 7 nights, 1 home
S$659 per night
includes taxes & fees
5BR/4BA Modern SFH Logan Square!
Dining Area
Top floor kitchen and dining area
Kitchen on Top Floor
Bedroom 3 w/ Queen Bed
Exceptional
(34 reviews)

The Exclusive- 7 Bed, 6 Bath Retreat

Chicago

5% off
S$9,125
for 7 nights, 1 apartment
S$1,304 per night
includes taxes & fees
The Exclusive- 7 Bed, 6 Bath Retreat
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
(92 reviews)

Stunning Lincoln Park Single-Family House with Fantastic Game Room

Chicago

11% off
S$9,443
for 7 nights, 1 home
S$1,349 per night
includes taxes & fees
Stunning Lincoln Park Single-Family House with Fantastic Game Room
Dining room area
3 bedroom unit is top floor of historic greystone
Living room area opens into dining room & kitchen
View of Robey Hotel from back deck
Exceptional
(100 reviews)

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

Chicago

7% off
S$5,700
for 7 nights, 1 home
S$814 per night
includes taxes & fees
Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.
Upstairs queen bedroom 2
Downstairs living area
Kitchen (upstairs)
Downstairs living room
Exceptional
(99 reviews)

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

Chicago

8% off
S$10,985
for 7 nights, 1 apartment
S$1,569 per night
includes taxes & fees
Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
Room
Interior
Private kitchen
Interior
Exceptional
(12 reviews)

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

Chicago

7% off
S$2,676
for 7 nights, 1 apartment
S$382 per night
includes taxes & fees
Peaceful Living-2Bdrm/2Bath w/Private Parking, WiFi-Work Station-Wicker Park!
Dining
Interior
Interior
Private kitchen
Exceptional
(18 reviews)

Modern + Cozy Chicago stay w/garage parking & 20min to downtown

Chicago

7% off
S$2,276
for 7 nights, 1 apartment
S$325 per night
includes taxes & fees
Modern + Cozy Chicago stay w/garage parking & 20min to downtown
Private kitchen
Belmont Harbor
Living area
Exterior
Exceptional
(192 reviews)

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

Chicago

14% off
S$6,240
for 7 nights, 1 home
S$891 per night
includes taxes & fees
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Dining
Exterior detail
Room
Private kitchen
Exceptional
(71 reviews)

Wicker Park near Downtown and the Salt Shed Special 125.00 Sept 21-23

Chicago

7% off
S$2,291
for 7 nights, 1 apartment
S$327 per night
includes taxes & fees
Wicker Park near Downtown and the Salt Shed Special 125.00 Sept 21-23
Interior
Room
Exterior
Private kitchen
Exceptional
(6 reviews)

Peaceful Zen Flat | 2BR Oasis with Free Parking

Chicago

8% off
S$3,162
for 7 nights, 1 apartment
S$452 per night
includes taxes & fees
Peaceful Zen Flat | 2BR Oasis with Free Parking
Room
Living area
Living area
Private kitchen
Exceptional
(14 reviews)

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

Chicago

7% off
S$3,959
for 7 nights, 1 apartment
S$566 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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