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Wicker Park holiday rentals
We found 1,278 holiday rentals — enter your dates for availability
Discover a selection of 16 homes, 31 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:19 Dec - 26 Dec
Image gallery for Luxury SOHO Styled Two-Level Townhouse - Old Town

10 out of 10, Exceptional, (16 reviews)
Exceptional
(16 reviews)
Luxury SOHO Styled Two-Level Townhouse - Old Town
Chicago, IL
7% off
Price is AU$10,689
for 7 nights, 1 home
AU$1,527 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Find the best place to stay - Wicker Park

Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.
Sleeps 6 · 3 bedrooms · 2 bathrooms
10 out of 10
exceptional
(80 reviews)
Top rated rentals - Wicker Park

Wonderful stay!
10 out of 10
exceptional
(54 reviews)
Super neat, clean, easy check in and out, wonderful hosts, amazing location! I would definitely recommend! Oh and the sauna is a fantastic plus! Thank you for having us!
Meenakshi C.
Stayed May 2025
- Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value