West Town holiday rentals

We found 1,367 holiday rentals — enter your dates for availability
Discover a selection of 57 homes, 208 apartments and other holiday rentals in West Town that are perfect for your trip. Whether you're staying in a holiday rental with your children or with friends, you'll find the amenities that you need and want, including air conditioning and Wi-Fi. You're sure to find a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – West Town

Showing deals for:13 Nov - 20 Nov

Living area
Terrace/patio
Living area
Private kitchen
Wonderful
(12 reviews)

6BD/5BTH + Roofdeck - Downtown Chicago!

Chicago

8% off
AU$11,915
for 7 nights, 1 apartment
AU$1,702 per night
includes taxes & fees
6BD/5BTH + Roofdeck - Downtown Chicago!
The building
River North Luxury Living
French Bistro and Wine Bar - right downstairs
Outdoors at night
Exceptional
(104 reviews)

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

Chicago

7% off
AU$4,588
for 7 nights, 1 apartment
AU$655 per night
includes taxes & fees
River North's Rock N' Roll - In The Heart of the City
Living area
Living area
Exterior
Interior
Excellent
(11 reviews)

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

Chicago

8% off
AU$8,872
for 7 nights, 1 home
AU$1,267 per night
includes taxes & fees
Spacious / New - 8BD/4BTH - Sleeps 16 + Garage!
Private kitchen
Dining
Interior
Interior
Exceptional
(5 reviews)

5BR/4BA Modern SFH Logan Square!

Chicago

7% off
AU$4,564
for 7 nights, 1 home
AU$652 per night
includes taxes & fees
5BR/4BA Modern SFH Logan Square!
Interior
Private kitchen
Room
Interior
Exceptional
(74 reviews)

Private Historic Coach House Wicker Park

Chicago

7% off
AU$3,376
for 7 nights, 1 home
AU$482 per night
includes taxes & fees
Private Historic Coach House Wicker Park
Private kitchen
Interior
Lobby
6 steps to enter the unit.
Exceptional
(19 reviews)

Lofty Garden Retreat Artist-Music Friendly 2BR in Humboldt Park

Chicago

7% off
AU$2,979
for 7 nights, 1 home
AU$426 per night
includes taxes & fees
Lofty Garden Retreat Artist-Music Friendly 2BR in Humboldt Park
Dining room area
3 bedroom unit is top floor of historic greystone
View of Robey Hotel from back deck
Living room area opens into dining room & kitchen
Exceptional
(95 reviews)

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

Chicago

7% off
AU$6,356
for 7 nights, 1 home
AU$908 per night
includes taxes & fees
Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.
Kitchen
Living Room
Bedroom 1 (King Size) + 55Inch TV
Patio Deck 2
Exceptional
(21 reviews)

Spacious 5 BR / King Size Beds + Private Parking!

Chicago

8% off
AU$6,096
for 7 nights, 1 home
AU$871 per night
includes taxes & fees
Spacious 5 BR / King Size Beds + Private Parking!
Interior
Interior
Room
Living area
Exceptional
(10 reviews)

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

Chicago

7% off
AU$2,991
for 7 nights, 1 apartment
AU$427 per night
includes taxes & fees
Peaceful Living-2Bdrm/2Bath w/Private Parking, WiFi-Work Station-Wicker Park!
Upstairs queen bedroom 2
Downstairs living area
Downstairs living room
Fun Mirror Wall Upstairs
Exceptional
(97 reviews)

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

Chicago

7% off
AU$12,388
for 7 nights, 1 apartment
AU$1,770 per night
includes taxes & fees
Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
Dining
Interior
Exterior
Living area
Exceptional
(13 reviews)

Spacious Duplex - 4BD/3BA - Sleeps 12!

Chicago

7% off
AU$4,788
for 7 nights, 1 apartment
AU$684 per night
includes taxes & fees
Spacious Duplex - 4BD/3BA - Sleeps 12!
Private kitchen
Exterior detail
Dining
Room
Exceptional
(66 reviews)

Wicker Park by Downtown and the Salt Shed Last Minute Deal 115.00 August 11-14

Chicago

7% off
AU$2,171
for 7 nights, 1 apartment
AU$310 per night
includes taxes & fees
Wicker Park by Downtown and the Salt Shed Last Minute Deal 115.00 August 11-14

  • 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 home accommodation in West Town?
Based on our data, apartments are the most popular holiday home type in West Town. But as you know, everyone's idea of the perfect stay isn't going to be the same. Stayz has holiday homes of all sizes and shapes, and we'll help you locate the perfect fit for you.
How much does it cost to rent a holiday home in West Town?
The average price for a holiday home in West Town is based on a number of factors, such as length of stay, season and property type. Whether you'd like a sprawling villa with space for extended family or a cosy cabin just for the two of you, just add your travel dates to see stays with great value.
How much does it cost to rent a beach house in West Town?
The average price for a holiday home close to the beach in West Town depends on when you're going and the type and size of property you're searching for. Find prices easily on Stayz by entering your travel dates and destination. Then use our filters to pick the number of bedrooms and amenities important to you, like a pool, WiFi and air conditioning.
Are there pet-friendly holiday homes in West Town?
Good news. There are. You'll have your pick of 146 holiday homes that roll out the welcome mat in West Town on Stayz. Our furry companions deserve a break too, so simply use our search function for pet-friendly holiday homes to book a place where Rover can join the fun.
Can I rent a house with a pool in West Town?
Add a whole new level of fun to your adventure by booking your group into one of the five houses with a private pool in West Town. Use our search filter to find the kind of property you want on Stayz, and then spend your downtime playing and splashing in a swimming pool that's exclusively for you.
What are popular home amenities in West Town?
A nearby river, a nearby waterfront and a firepit rank as the most popular home amenities in West Town. Whether you're planning to travel by yourself, with your other half or a group of family members, Stayz will help you find a holiday home that suits your tastes with all the features you're looking for.
Are there large group holiday homes in West Town?
West Town has 15 holiday properties that can fit 10 or more guests. These stays come with the space and privacy you need to enjoy good times with loved ones.
Are there holiday homes in West Town that welcome kids?
With 139 family-friendly holiday properties to choose from in West Town, now is a fantastic time to introduce your little ones to the wonders of travel. Check our "Properties good for families" filter to look for stays packed with conveniences perfect for families on the move, like extra bedrooms, outdoor spaces, entertainment areas and bunk beds.
What are the top attractions for families in West Town?
There are plenty of amazing things to see and do with the family in West Town, including:
  • Navy Pier
  • Chicago Riverwalk
  • Shedd Aquarium
Are there one-bedroom holiday homes in West Town?
Yes, West Town has 30 one-bedroom homes on offer. Often positioned in sought-after areas because of their compact size, a one-bedroom holiday property is great if you're getting away with your partner or a friend. And with plenty of home comforts like laundry facilities and more privacy than a standard hotel, you'll be able to relax while enjoying this amazing destination.
Can I find two-bedroom holiday homes in West Town?
West Town has 38 two-bedroom holiday properties to choose from. Go for a holiday home with all the space and privacy you're looking for at a price you'll love on Stayz.
Are there holiday homes with WiFi in West Town?
West Town has 62 holiday homes with WiFi, so you'll be able to stay connected while you're away. Simply check the "WiFi" box in our handy search filter to find the perfect property. From streaming movie blockbusters to catching up on social media, these Stayz homes will keep you online.
How can I find holiday homes with air conditioning in West Town?
You'll find 129 Stayz holiday homes with air conditioning in West Town providing that cooling breeze and extra bit of comfort. Enter your preferred travel dates and then use our handy filters to locate properties with air conditioning.
How old do you have to be to rent a holiday home in West Town?
The minimum age is normally 16, 18 or 21. It can change from one property to another on Stayz, so check the rules of your chosen West Town holiday home before booking your stay.
How long can I rent a holiday home in West Town for?
It's up to the West Town property. To browse available options offering extended stays, just enter your travel dates and guest number into the Stayz search page. You can enjoy having the whole property to yourself, as well as amenities such as air conditioning, a fully-equipped kitchen and outdoor spaces where the kids can burn off energy. Keep your eyes peeled for any long-term stays that offer weekly or monthly discounts.

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