Near West Side vacation rentals
We found 1,032 vacation rentals — enter your dates for availability
Select from 17 houses, 20 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.
Vacation rentals with weekly discounts - Near West Side
Showing deals for:Nov 14 - Nov 21
Image gallery for HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony
9.29.2 out of 10 rating
Wonderful
(50 reviews)
HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony
Chicago, IL
18% off
Price is CA $249
CA $249
CA $2,567 total
CA $2,567 total
includes taxes & fees
Image gallery for Unbeatable Top Floor: Views, Central, Modern
1010 out of 10 rating
Exceptional
(7 reviews)
Unbeatable Top Floor: Views, Central, Modern
Chicago, IL
10% off
Price is CA $492
CA $492
CA $4,981 total
CA $4,981 total
includes taxes & fees
Image gallery for Downtown Charm: 2BR, Comfort, Great Amenities
1010 out of 10 rating
Exceptional
(6 reviews)
Downtown Charm: 2BR, Comfort, Great Amenities
Chicago, IL
10% off
Price is CA $442
CA $442
CA $4,498 total
CA $4,498 total
includes taxes & fees
Image gallery for River North's Rock N' Roll - In The Heart of the City
9.69.6 out of 10 rating
Exceptional
(90 reviews)
River North's Rock N' Roll - In The Heart of the City
Chicago, IL
10% off
Price is CA $450
CA $450
CA $4,501 total
CA $4,501 total
includes taxes & fees
Image gallery for Luxury Loft Collection 703 - Terrace - River North
1010 out of 10 rating
Exceptional
(16 reviews)
Luxury Loft Collection 703 - Terrace - River North
Chicago, IL
10% off
Price is CA $719
CA $719
CA $7,103 total
CA $7,103 total
includes taxes & fees
Image gallery for Kasa | Family Friendly 3 BD + Fast Wifi | Chicago
9.89.8 out of 10 rating
Exceptional
(12 reviews)
Kasa | Family Friendly 3 BD + Fast Wifi | Chicago
Chicago, IL
10% off
Price is CA $434
CA $434
CA $4,118 total
CA $4,118 total
includes taxes & fees
Image gallery for Kasa | Modern 2 BD + Near Local Eateries | Chicago
9.89.8 out of 10 rating
Exceptional
(21 reviews)
Kasa | Modern 2 BD + Near Local Eateries | Chicago
Chicago, IL
10% off
Price is CA $333
CA $333
CA $3,175 total
CA $3,175 total
includes taxes & fees
Image gallery for 3BR Luxury Modern Apartment
9.29.2 out of 10 rating
Wonderful
(13 reviews)
3BR Luxury Modern Apartment
Chicago, IL
10% off
Price is CA $439
CA $439
CA $4,487 total
CA $4,487 total
includes taxes & fees
Image gallery for Chic Corner 2BR in the Loop | City & Lake Views
9.89.8 out of 10 rating
Exceptional
(52 reviews)
Chic Corner 2BR in the Loop | City & Lake Views
Chicago, IL
10% off
Price is CA $443
CA $443
CA $4,375 total
CA $4,375 total
includes taxes & fees
Image gallery for Chic Penthouse Corner 3BR Loft In Fulton Market | Featured In Architectural Dige
1010 out of 10 rating
Exceptional
(17 reviews)
Chic Penthouse Corner 3BR Loft In Fulton Market | Featured In Architectural Dige
Chicago, IL
10% off
Price is CA $687
CA $687
CA $6,803 total
CA $6,803 total
includes taxes & fees
Image gallery for Breathtaking CHI unit in River North - Penthouse A!
8.28.2 out of 10 rating
Very good
(10 reviews)
Breathtaking CHI unit in River North - Penthouse A!
Chicago, IL
5% off
Price is CA $481
CA $481
CA $4,926 total
CA $4,926 total
includes taxes & fees
Image gallery for River North 3BR/2BA: HUGE, Parking, Center Chicago
9.89.8 out of 10 rating
Exceptional
(15 reviews)
River North 3BR/2BA: HUGE, Parking, Center Chicago
Chicago, IL
10% off
Price is CA $927
CA $927
CA $9,129 total
CA $9,129 total
includes taxes & fees
Image gallery for City Center, River North Condo HUGE 3BR, Patio, Parking(2x)
1010 out of 10 rating
Exceptional
(28 reviews)
City Center, River North Condo HUGE 3BR, Patio, Parking(2x)
Chicago, IL
15% off
Price is CA $820
CA $820
CA $8,136 total
CA $8,136 total
includes taxes & fees
Image gallery for Luxury Loft Collection 03 - Terrace - River North
9.49.4 out of 10 rating
Exceptional
(8 reviews)
Luxury Loft Collection 03 - Terrace - River North
Chicago, IL
10% off
Price is CA $734
CA $734
CA $7,244 total
CA $7,244 total
includes taxes & fees
Image gallery for Gorgeous 3BR River North Condo - Free Parking
1010 out of 10 rating
Exceptional
(20 reviews)
Gorgeous 3BR River North Condo - Free Parking
Chicago, IL
10% off
Price is CA $625
CA $625
CA $5,968 total
CA $5,968 total
includes taxes & fees
Image gallery for Kasa | Family Friendly 3 BD + Pet Friendly | Chicago
9.49.4 out of 10 rating
Exceptional
(10 reviews)
Kasa | Family Friendly 3 BD + Pet Friendly | Chicago
Chicago, IL
10% off
Price is CA $434
CA $434
CA $4,118 total
CA $4,118 total
includes taxes & fees
Image gallery for Kasa | Family Friendly 3 BD + Game Room Access | Chicago
9.69.6 out of 10 rating
Exceptional
(14 reviews)
Kasa | Family Friendly 3 BD + Game Room Access | Chicago
Chicago, IL
10% off
Price is CA $434
CA $434
CA $4,118 total
CA $4,118 total
includes taxes & fees
Image gallery for The Loop 2BR: Historic, Modern Luxury, Amenities
1010 out of 10 rating
Exceptional
(5 reviews)
The Loop 2BR: Historic, Modern Luxury, Amenities
Chicago, IL
10% off
Price is CA $442
CA $442
CA $4,498 total
CA $4,498 total
includes taxes & fees
Image gallery for Kasa | Inviting 1 BD + Game Room Access | Chicago
9.89.8 out of 10 rating
Exceptional
(9 reviews)
Kasa | Inviting 1 BD + Game Room Access | Chicago
Chicago, IL
10% off
Price is CA $283
CA $283
CA $2,729 total
CA $2,729 total
includes taxes & fees
Image gallery for Kasa | Classic 1 BD + Gym Access | Chicago
9.29.2 out of 10 rating
Wonderful
(5 reviews)
Kasa | Classic 1 BD + Gym Access | Chicago
Chicago, IL
10% off
Price is CA $249
CA $249
CA $2,392 total
CA $2,392 total
includes taxes & fees
Image gallery for Kasa | Relaxing 2 BD + Steps to the South Loop | Chicago
9.69.6 out of 10 rating
Exceptional
(37 reviews)
Kasa | Relaxing 2 BD + Steps to the South Loop | Chicago
Chicago, IL
10% off
Price is CA $333
CA $333
CA $3,175 total
CA $3,175 total
includes taxes & fees
Image gallery for Splendid Corner 3BR in the Loop | City Views
9.49.4 out of 10 rating
Exceptional
(16 reviews)
Splendid Corner 3BR in the Loop | City Views
Chicago, IL
10% off
Price is CA $626
CA $626
CA $6,268 total
CA $6,268 total
includes taxes & fees
Image gallery for Kasa | Classic 2 BD + Near Grant Park | Chicago
1010 out of 10 rating
Exceptional
(6 reviews)
Kasa | Classic 2 BD + Near Grant Park | Chicago
Chicago, IL
10% off
Price is CA $333
CA $333
CA $3,175 total
CA $3,175 total
includes taxes & fees
Image gallery for Spectacular Corner 3BR in the Loop | City Views
9.09.0 out of 10 rating
Wonderful
(24 reviews)
Spectacular Corner 3BR in the Loop | City Views
Chicago, IL
10% off
Price is CA $643
CA $643
CA $6,424 total
CA $6,424 total
includes taxes & fees
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
The Neighborhood Hotel-Little Italy
Sleeps 4 · 1 bedroom
9.69.6 out of 10
Exceptionalexceptional
188 reviews(188 reviews)
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Sleeps 4 · 1 bedroom
8.28.2 out of 10
Very goodvery good
340 reviews(340 reviews)
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Sleeps 2 · 1 bedroom
9.09.0 out of 10
Wonderfulwonderful
203 reviews(203 reviews)
Sonder by Marriott Bonvoy Greektown Apartments
Sleeps 4 · 1 bedroom
8.68.6 out of 10
Excellentexcellent
59 reviews(59 reviews)
Spacious 3-bedroom apartment near downtown, FREE PARKING
Sleeps 8 · 3 bedrooms · 2 bathrooms
8.68.6 out of 10
Excellentexcellent
4 reviews(4 reviews)
South Loop 2 Bedroom Apt
Sleeps 13 · 2 bedrooms · 2 bathrooms
7.67.6 out of 10
Goodgood
4 reviews(4 reviews)
Top rated rentals - Near West Side
Family trip to ball games
1010 out of 10
Exceptionalexceptional
248 reviews(248 reviews)
Great spot! Plenty of room for 8 adults! Comfy beds, great showers, all the amenities of home, easy checkin and checkout process, John was close by and responded quickly, close proximity to pink line train and many small extras to make the stay special! Highly recommend!
Shauna A.
Stayed Aug 2024
A Gem in Little Italy
1010 out of 10
Exceptionalexceptional
150 reviews(150 reviews)
Very good location. Clean and peaceful neighbourhood, Close to the Pink Line and so many amenities. The place was exceptionally clean and tidy, well supplied with linens and household products. The kitchen was well equipped you can cook your own meals. Perfect for families. Our host John was very kind and helpful, He promptly answered my messages . Because this is an apartment on the first floor, one can hear footsteps and objects being dragged across their floor from upstairs.. There were days I heard nothing depending on how kind and considerate the upstairs occupants are I would stay here again on my next Chicago trip.
Christina L.
Stayed Jul 2024
Great Location, Stunning View
1010 out of 10
Exceptionalexceptional
109 reviews(109 reviews)
One couldn't ask for a better location and the view is just out of this world. Lots of great restaurants literally just out the door. A short ride by transit or Uber downtown. The apartment is very well stocked and Michelle, our hostess, was very gracious. Definitely would stay again. The only quibble we had was there were no tea towels to dry dishes with.
Terence J.
Stayed May 2019
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 in Near West Side?
In Near West Side, apartments are the predominant type of vacation rental, with approximately 73 available in the area. These apartments are typically modern and well-equipped, featuring amenities such as fully furnished kitchens, spacious living areas, and convenient access to local attractions. Many also include laundry facilities and Wi-Fi, suiting both short and extended stays.
How much does it cost to rent a vacation home in Near West Side?
Prices for vacation rentals in Near West Side vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Near West Side to more spacious homes.
Are there any discounts for Near West Side vacation house rentals?
You can find great discounts on house rentals in Near West Side on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Are there any Near West Side vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Near West Side with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Can I find long-stay vacation rentals in Near West Side?
A long-stay vacation rental in Near West Side is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
When is the best time to visit Near West Side for a vacation rental?
January is the most popular time to visit the Near West Side, particularly for those looking to experience the vibrant culture and local attractions of Chicago during the winter months. While the peak tourist season typically spans from May to July, when outdoor events and festivals abound, January offers a unique charm with fewer crowds and a more intimate atmosphere.
During this winter month, temperatures can hover around freezing (0 degrees Celsius), making it a great time for indoor activities such as exploring the Art Institute of Chicago or enjoying the warm ambiance of local cafés. Additionally, visitors can take advantage of the city's renowned theatre scene, with many performances showcasing top talent in a more relaxed setting.
If you're seeking a more budget-friendly experience, consider planning your trip in October. This month boasts pleasant autumn weather, with temperatures averaging in the mid-teens Celsius, ideal for strolling through parks or enjoying seasonal events without the peak crowd.
Are there any remote work vacation rentals in Near West Side?
In the Near West Side of Illinois, there are numerous remote work-friendly vacation rentals available, with around 59 options to choose from. This vibrant area, characterised by its mix of historic architecture and modern developments, offers a variety of properties that cater well to those looking to work remotely. Many of these rentals come equipped with essential amenities such as high-speed Wi-Fi, dedicated desk spaces, and comfortable office chairs, ensuring a productive environment.
Travellers can expect to find spacious apartments or homes that often feature open-plan layouts, allowing for a good balance between work and leisure. Additionally, some properties may include access to communal amenities like fitness centres or rooftop terraces, providing a pleasant break from work hours. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Near West Side vacation rental?
Book your Near West Side vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.
*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Near West Side?
In the Near West Side of Chicago, visitors can explore an array of attractions that highlight the area's vibrant culture and history. The United Centre, home to the Chicago Bulls and Blackhawks, draws sports fans and hosts major concerts throughout the year. Just a short distance away, the Illinois Medical District offers unique architecture and is home to several museums, including the National Museum of Health and Medicine.
Can I change or cancel my Near West Side home rental booking on Vrbo?
To find Near West Side vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Near West Side vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.