
Near West Side vacation rentals
We found 959 vacation rentals — enter your dates for availability
Select from 18 houses, 22 condos, and other vacation rentals to find the perfect place for your stay in Near West Side. Vacation rentals provide the amenities you need and want for you and your friends, family, or even pets, including parking and a garden. You'll be sure to find a rental to meet everyone's needs, including places that are non-smoking or accessible.
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find properties near top attractions in Near West Side
Map Attractions

2
University of Illinois Chicago
Find the best place to stay - Near West Side
Sonder Market Hall
Sleeps 2 · 1 bedroom
8.68.6 out of 10
Excellentexcellent
277 reviews(277 reviews)
Sonder The Burnham Apartments
Sleeps 2 · 1 bedroom
9.09.0 out of 10
Wonderfulwonderful
163 reviews(163 reviews)
Sonder Greektown
Sleeps 8 · 3 bedrooms
9.09.0 out of 10
Wonderfulwonderful
47 reviews(47 reviews)
The Neighborhood Hotel-Little Italy
Sleeps 4 · 1 bedroom
9.89.8 out of 10
Exceptionalexceptional
154 reviews(154 reviews)
Sentral Michigan Avenue
Sleeps 4 · 2 bedrooms
9.29.2 out of 10
Wonderfulwonderful
737 reviews(737 reviews)
Kasa South Loop Chicago
Sleeps 2 · 1 bedroom
9.49.4 out of 10
Exceptionalexceptional
279 reviews(279 reviews)
Top rated rentals - Near West Side
Great Spot
1010 out of 10
Exceptionalexceptional
286 reviews(286 reviews)
Family trip to ball games
1010 out of 10
Exceptionalexceptional
232 reviews(232 reviews)
A Gem in Little Italy
1010 out of 10
Exceptionalexceptional
133 reviews(133 reviews)
Great Location, Stunning View
1010 out of 10
Exceptionalexceptional
107 reviews(107 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, yards and more
- More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
What is the most popular type of vacation rental accommodation in Near West Side?
Based on our data, apartments are considered the most popular type of vacation property in Near West Side. But naturally, everyone’s idea of an awesome stay isn’t going to be the same. Vrbo has vacation rentals of all shapes, sizes and budgets, so you’re sure to discover the perfect fit.
How much does it cost to rent a vacation rental in Near West Side?
Length of stay, property type and season are some factors that can affect the price of a vacation home. Simply add your dates of travel to find your ideal match. From cozy chalets to plush villas, all Vrbo vacation rentals offer amazing value.
How much does it cost to rent a beach house in Near West Side?
The average price for a vacation home near the beach in Near West Side will depend on when you’re going and the size and type of property you’re looking for. You can find prices quickly and easily on Vrbo by entering your dates of travel. Then use our handy filter tool to choose the number of bedrooms and amenities that you prefer, like air conditioning, WiFi and a hot tub.
Are there pet-friendly vacation rentals in Near West Side?
Yes, there are. You can choose from 159 vacation homes that allow pets in Near West Side on Vrbo. Our cuddly best friends also need a break, so simply use our search function for pet-friendly vacation rentals to find a property where your puppy dog can share in the good times.
Can I rent a house with a pool in Near West Side?
Dig out your swimsuit and inflatable flamingo, because there are 48 houses with a private pool in Near West Side. Stay at one of these popular vacation rentals and you’ll enjoy pool days every day. Simply enter your travel dates into Vrbo, then use the “pool” filter to find a place to make a splash!
What are popular rental amenities in Near West Side?
Some of the most popular rental amenities guests are looking for in Near West Side include a nearby river, a garden and a fireplace. Whether you’re going on vacation with pals, family or even pets, Vrbo vacation properties include the best amenities for starting a new adventure with the people that matter most.
Are there large group vacation rentals in Near West Side?
With 11 properties that can host 10 or more people in Near West Side, you won’t have to leave anyone off your guest list. From vacations with the extended family to events like birthday parties and weddings, Vrbo can help you find a large group rental that fits the occasion.
Are there vacation rentals in Near West Side that welcome kids?
Bring the whole group together for a memorable adventure in Near West Side at one of our 159 family-friendly vacation properties. Many of these stays provide amenities that are ideally suited to trips with children, including laundries, living rooms and swimming pools. Simply click on the “Properties good for families” filter and pick out your favorite.
What are the top attractions for families in Near West Side?
Keeping the kids occupied during your stay in Near West Side is simple with these cool family-friendly attractions:
- Navy Pier
- Chicago Riverwalk
- Shedd Aquarium
Are there one-bedroom vacation rentals in Near West Side?
Yes, you can take your pick from 72 one-bedroom rentals in Near West Side. Whether you’d prefer a cozy cottage or a condo, our one-bedroom rentals are ideal if you don’t require lots of room. One of the best things about having your own digs? You won’t need to share your adventure with strangers.
Can I find two-bedroom vacation rentals in Near West Side?
You can pick from 29 two-bedroom rentals in Near West Side. Settle the kids into the second room or maybe fill it with a couple of your nearest and dearest friends. There’s enough space for whoever’s fortunate enough to come along for the ride.
Are there vacation rentals with WiFi in Near West Side?
Choose from 19 vacation rentals with WiFi in Near West Side. If you’d like to disconnect from the world on your vacation, but still want to be connected to the web, these properties are just what you need. Narrow your search by applying the WiFi filter on Vrbo.
How can I find vacation rentals with air conditioning in Near West Side?
You’ll have a choice of 157 vacation homes with air conditioning in Near West Side offering that cool, cool breeze and extra bit of comfort. Simply enter your preferred travel dates and then use our handy filters to find stays with air conditioning.
How old do you have to be to rent a vacation rental in Near West Side?
The minimum age can differ across properties on Vrbo, so look at the rules of the vacation rental in Near West Side you’re interested in. But normally, it’s 16, 18 or 21.
How long can I rent a vacation rental in Near West Side for?
It’s up to the Near West Side property. To look at a list of options offering extended stays, just type your dates and guest number into Vrbo. Enjoy having the entire place to yourself, as well as amenities such as a fully-equipped kitchen, air conditioning and a backyard to play in. Be on the lookout for any long-term stays that offer discounted weekly or monthly prices.