West Town holiday homes
We found 1,440 holiday rentals — enter your dates for availability
Discover a selection of 66 homes, 155 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:18 Jul - 25 Jul
Image gallery for Chicago Gold Coast Luxury Home Best Location walking distance to anywhere!

1010 out of 10 rating
Exceptional
(20 reviews)
Chicago Gold Coast Luxury Home Best Location walking distance to anywhere!
Chicago, IL
8% off
Price is NZ$82,588
NZ$82,588
NZ$11,798 per night
includes taxes & fees
Image gallery for 3BR Luxury Modern Apartment

9.69.6 out of 10 rating
Exceptional
(7 reviews)
3BR Luxury Modern Apartment
Chicago, Illinois
7% off
Price is NZ$11,186
NZ$11,186
NZ$1,598 per night
includes taxes & fees
Image gallery for City Center, River North Condo HUGE 3BR, Patio, Parking(2x)

1010 out of 10 rating
Exceptional
(27 reviews)
City Center, River North Condo HUGE 3BR, Patio, Parking(2x)
Chicago, IL
12% off
Price is NZ$15,028
NZ$15,028
NZ$2,147 per night
includes taxes & fees
Image gallery for #1613 - Kasa Magnificent Mile Chicago

9.89.8 out of 10 rating
Exceptional
(16 reviews)
#1613 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$5,001
NZ$5,001
NZ$714 per night
includes taxes & fees
Image gallery for Spacious,Chic & Steps from MichiganAve|The Hermes

1010 out of 10 rating
Exceptional
(7 reviews)
Spacious,Chic & Steps from MichiganAve|The Hermes
Chicago, Illinois
7% off
Price is NZ$14,155
NZ$14,155
NZ$2,022 per night
includes taxes & fees
Image gallery for Stunning Corner 2BR in the Loop | City & Lake Views

9.89.8 out of 10 rating
Exceptional
(38 reviews)
Stunning Corner 2BR in the Loop | City & Lake Views
Chicago, Illinois
7% off
Price is NZ$7,603
NZ$7,603
NZ$1,086 per night
includes taxes & fees
Image gallery for Gorgeous 3BR River North Condo - Free Parking

1010 out of 10 rating
Exceptional
(12 reviews)
Gorgeous 3BR River North Condo - Free Parking
Chicago, IL
8% off
Price is NZ$16,193
NZ$16,193
NZ$2,313 per night
includes taxes & fees
Image gallery for Modern Corner 2BR in Streeterville | Roof Deck | Lake Views

9.89.8 out of 10 rating
Exceptional
(31 reviews)
Modern Corner 2BR in Streeterville | Roof Deck | Lake Views
Chicago, Illinois
7% off
Price is NZ$7,631
NZ$7,631
NZ$1,090 per night
includes taxes & fees
Image gallery for Splendid Corner 3BR in the Loop | City Views

9.29.2 out of 10 rating
Wonderful
(9 reviews)
Splendid Corner 3BR in the Loop | City Views
Chicago, Illinois
7% off
Price is NZ$9,635
NZ$9,635
NZ$1,376 per night
includes taxes & fees
Image gallery for #2012 - Kasa Magnificent Mile Chicago

9.49.4 out of 10 rating
Exceptional
(10 reviews)
#2012 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$4,557
NZ$4,557
NZ$651 per night
includes taxes & fees
Image gallery for #1511 - Kasa Magnificent Mile Chicago

9.69.6 out of 10 rating
Exceptional
(15 reviews)
#1511 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$4,144
NZ$4,144
NZ$592 per night
includes taxes & fees
Image gallery for Stunning Corner 2BR in Streeterville | Roof Deck | Lake Views

9.49.4 out of 10 rating
Exceptional
(39 reviews)
Stunning Corner 2BR in Streeterville | Roof Deck | Lake Views
Chicago, Illinois
7% off
Price is NZ$7,737
NZ$7,737
NZ$1,105 per night
includes taxes & fees
Image gallery for #2011 - Kasa Magnificent Mile Chicago

9.89.8 out of 10 rating
Exceptional
(8 reviews)
#2011 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$4,144
NZ$4,144
NZ$592 per night
includes taxes & fees
Image gallery for Spectacular Penthouse Corner 2BR in Streeterville | Roof Deck | Lake Views

9.49.4 out of 10 rating
Exceptional
(25 reviews)
Spectacular Penthouse Corner 2BR in Streeterville | Roof Deck | Lake Views
Chicago, Illinois
7% off
Price is NZ$8,318
NZ$8,318
NZ$1,188 per night
includes taxes & fees
Image gallery for Downtown Chicago Studio in Prime Location

9.69.6 out of 10 rating
Exceptional
(9 reviews)
Downtown Chicago Studio in Prime Location
Chicago, Illinois
5% off
Price is NZ$4,424
NZ$4,424
NZ$632 per night
includes taxes & fees
Image gallery for #1515 - Kasa Magnificent Mile Chicago

1010 out of 10 rating
Exceptional
(23 reviews)
#1515 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$5,001
NZ$5,001
NZ$714 per night
includes taxes & fees
Image gallery for Bee's Knees - Ritzy, 1924 Hollywoodesque Bungalow

1010 out of 10 rating
Exceptional
(8 reviews)
Bee's Knees - Ritzy, 1924 Hollywoodesque Bungalow
Chicago, IL
12% off
Price is NZ$7,420
NZ$7,420
NZ$1,060 per night
includes taxes & fees
Image gallery for Chic 4-Bedroom Haven: Designer's Dream Home

1010 out of 10 rating
Exceptional
(5 reviews)
Chic 4-Bedroom Haven: Designer's Dream Home
Chicago, Illinois
12% off
Price is NZ$11,502
NZ$11,502
NZ$1,643 per night
includes taxes & fees
Image gallery for Spectacular Corner 3BR in the Loop | City Views

8.88.8 out of 10 rating
Excellent
(20 reviews)
Spectacular Corner 3BR in the Loop | City Views
Chicago, Illinois
7% off
Price is NZ$9,718
NZ$9,718
NZ$1,388 per night
includes taxes & fees
Image gallery for Spacious 5 BR / King Size Beds + Private Parking!

9.69.6 out of 10 rating
Exceptional
(11 reviews)
Spacious 5 BR / King Size Beds + Private Parking!
Chicago, IL
8% off
Price is NZ$14,631
NZ$14,631
NZ$2,090 per night
includes taxes & fees
Image gallery for Luxe Single Family Home + Private Skyline Rooftop! Sleeps 10

9.69.6 out of 10 rating
Exceptional
(5 reviews)
Luxe Single Family Home + Private Skyline Rooftop! Sleeps 10
Chicago, IL
8% off
Price is NZ$23,059
NZ$23,059
NZ$3,294 per night
includes taxes & fees
Image gallery for Luxury 4-Bedroom Retreat in Chicago

9.89.8 out of 10 rating
Exceptional
(9 reviews)
Luxury 4-Bedroom Retreat in Chicago
Chicago, IL
32% off
Price is NZ$15,964
NZ$15,964
NZ$2,281 per night
includes taxes & fees
Image gallery for Cozy 1-bedroom house in charming Chicago with WiFi, AC, Washer/Dryer

9.69.6 out of 10 rating
Exceptional
(5 reviews)
Cozy 1-bedroom house in charming Chicago with WiFi, AC, Washer/Dryer
Chicago, IL
8% off
Price is NZ$4,152
NZ$4,152
NZ$593 per night
includes taxes & fees
Image gallery for Amazing 4BR/4BA Oasis w/ Rooftop & Stunning Design

8.08.0 out of 10 rating
Very good
(5 reviews)
Amazing 4BR/4BA Oasis w/ Rooftop & Stunning Design
Chicago, Illinois
8% off
Price is NZ$22,124
NZ$22,124
NZ$3,161 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find properties near top attractions in West Town
Map Attractions
Find the best place to stay - West Town
Sonder Market Hall
Sleeps 2 · 1 bedroom
8.68.6 out of 10
Excellentexcellent
271 reviews(271 reviews)
Charming 3-bedroom house in awesome Chicago with AC, WiFi
Sleeps 6 · 3 bedrooms · 2 bathrooms
Wicker Park 2-Bdrms 10 minutes to Downtown! Special 99.00 April 20-24
Sleeps 5 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
16 reviews(16 reviews)
Wicker Park 2Bdrm 10 minutes to Downtown! 199.00 April 25-27
Sleeps 4 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
22 reviews(22 reviews)
Centrally Located Condo with Parking and Deck!
Sleeps 12 · 4 bedrooms · 3 bathrooms
9.69.6 out of 10
Exceptionalexceptional
MODERN DOWNTOWN 5-LEVEL-HOME WITH ROOFTOP AND 360-DEGREES SKYLINE VIEWS
Sleeps 8 · 4 bedrooms · 3 bathrooms
8.08.0 out of 10
Very goodvery good
4 reviews(4 reviews)
- 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
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. Bookabach 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 Bookabach 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 Bookabach. 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 Bookabach, 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, Bookabach 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 Bookabach.
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 Bookabach homes will keep you online.
How can I find holiday homes with air conditioning in West Town?
You’ll find 129 Bookabach 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 Bookabach, 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 Bookabach 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.