West Town holiday rentals

We found 1,555 holiday rentals — enter your dates for availability

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September 2025

October 2025

Discover a selection of 62 homes, 166 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:28 Nov - 5 Dec

Exceptional

(16 reviews)

Luxury SOHO Styled Two-Level Townhouse - Old Town

Chicago, IL

7% off

S$872 per night

includes taxes & fees

Open living room and dining space with lake views and great light

Exceptional

(29 reviews)

Spectacular Penthouse Corner 2BR in Streeterville | Roof Deck | Lake Views

Chicago, IL

7% off

S$546 per night

includes taxes & fees

Exceptional

(7 reviews)

Modern Apartment with Private Rooftop Patio & Free Parking in Downtown Chicago

Chicago, IL

7% off

S$881 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find properties near top attractions in West Town

Humboldt Park

Find the best place to stay - West Town

Rooftop, West Loop Chicago

Sleeps 10 · 3 bedrooms · 2 bathrooms

Wicker Park 2Bdrm Near Downtown & Salt Shed Weekend Special 149.00 August 22-24

Sleeps 4 · 2 bedrooms · 1 bathroom

Top rated rentals - West Town

Premier Host

Great for bonding, cute neighbourhood

Came here for a weekend for a girls + partners trip and we immediately fell in love with the space. The rooftop was lovely to lounge and have food on; it had everything from cushions to blankets and a view of the Chicago skyline. We also made use of the sofa pull out bed to watch movies at night. Everyone complimented my choice of apartment! Communication from the host was excellent. The place was well stocked with cutleries and some coffee pods, and we walked to the nearest CVS to get toiletries. I was nervous the Vrbo was too far from downtown but the neighbourhood turned out to be great. It’s walking distance to coffee shops and the famous Kasama restaurant, and a 10 minute drive to avenues with restaurants, bars and other spots. It wasn’t hard to get to the city with an Uber and public transportation. Highly recommend to big groups who want to stay in a tranquil neighbourhood with a nice space for lounging! Note that 2 bedrooms to fit 7-9 people can be cramped, but it worked out for us.

Celeste C.

Stayed May 2024

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 West Town?

Based on our data, apartments are the most popular holiday rental type in West Town. But as you know, everyone's idea of the perfect stay isn't going to be the same. Vrbo has holiday rentals 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 rental in West Town?

The average price for a holiday rental 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 Vrbo 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 rentals 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 Vrbo. Our furry companions deserve a break too, so simply use our search function for pet-friendly holiday rentals 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 Vrbo, and then spend your downtime playing and splashing in a swimming pool that's exclusively for you.

What are popular rental amenities in West Town?

A nearby river, a nearby waterfront and a firepit rank as the most popular rental amenities in West Town. Whether you're planning to travel by yourself, with your other half or a group of family members, Vrbo will help you find a holiday rental that suits your tastes with all the features you're looking for.

Are there large group holiday rentals 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 rentals 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 rentals in West Town?

Yes, West Town has 30 one-bedroom rentals 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 rentals 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 Vrbo.

Are there holiday rentals with WiFi in West Town?

West Town has 62 holiday rentals 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 Vrbo homes will keep you online.

How can I find holiday rentals with air conditioning in West Town?

You'll find 129 Vrbo holiday rentals 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 rental in West Town?

The minimum age is normally 16, 18 or 21. It can change from one property to another on Vrbo, so check the rules of your chosen West Town holiday home before booking your stay.

How long can I rent a holiday rental 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 Vrbo 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.