A greenhouse with a glass ceiling, various cacti, and a wooden structure in the center.

West Side Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for West Side vacation rentals

A hotel room with a bed, two bedside lamps, a wall-mounted artwork, and a small table with a lamp.

1. 2BR Apt with 2 Baths & Laundry

2BR Apt with 2 Baths & Laundry
Near West Side
10.0 out of 10, Exceptional, (1 review)
"The property was very clean and perfect for our overnight stay. Thank you"
United States
michele
$214 nightly
The price is $237
Nov 2 - Nov 3
Total with taxes and fees
2BR Apt with 2 Baths & Laundry
A modern living room with large windows, a flat-screen TV, a sofa, a coffee table, and a dining area with stools and a small table.

2. Modern West Loop Gem-City Views & Prime Location 6

Modern West Loop Gem-City Views & Prime Location 6
Downtown Chicago
10.0 out of 10, Exceptional, (28 reviews)
"Great location. "
United States
Tom S.
$819 nightly
The price is $940
Oct 28 - Oct 29
Total with taxes and fees
Modern West Loop Gem-City Views & Prime Location 6
A modern kitchen with white cabinets, a central island with stools, a microwave, and a refrigerator.

3. 3BR Complete and Spacious Apartment in Ideal Spot

3BR Complete and Spacious Apartment in Ideal Spot
West Town
8.2 out of 10, Very good, (22 reviews)
"absolutely would stay here again. Great property and great communcation"
United States
Daniel J.
$227 nightly
The price is $250
Oct 20 - Oct 21
Total with taxes and fees
3BR Complete and Spacious Apartment in Ideal Spot
A hotel room with a geometric-patterned wall, a bed with white bedding and a beige throw, two bedside lamps, and a window with blinds.

4. Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6

Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6
West Town
9.0 out of 10, Wonderful, (16 reviews)
"Great location! Comfortable and quiet. "
United States
Jonalyn B.
$134 nightly
The price is $165
Nov 2 - Nov 3
Total with taxes and fees
Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6
A neatly made bed with white linens and a grey throw blanket, a bedside lamp, and a geometric wall design.

5. Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony

Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony
West Town
10.0 out of 10, Exceptional, (1 review)
"Once we were in the place it was wonderful, met all of our needs.The entrance to our unit was filthy and steps kind of dangerous for 5 year old with no railing"
United States
PAT C.
$134 nightly
The price is $165
Nov 2 - Nov 3
Total with taxes and fees
Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony
Private kitchen

6. Cozy Boho - 10 Minutes to Downtown Chicago + Arcades

Cozy Boho - 10 Minutes to Downtown Chicago + Arcades
Lawndale
9.8 out of 10, Exceptional, (10 reviews)
"Wonderful space and convenient location. Really responsive host and super quiet neighborhood! "
United States
Jess S.
$199 nightly
The price is $223
Oct 20 - Oct 21
Total with taxes and fees
Cozy Boho - 10 Minutes to Downtown Chicago + Arcades
A modern kitchen with a large island, coffee maker, and a view of the city.

7. Skyline View Apt - 5 minutes to Downtown - Games + Arcades - Free Parking

Skyline View Apt - 5 minutes to Downtown - Games + Arcades - Free Parking
Lower West Side
9.0 out of 10, Wonderful, (4 reviews)
"We loved the location, the area is awesome! Great stay, highly recommend. "
United States
Db D.
$289 nightly
The price is $324
Oct 13 - Oct 14
Total with taxes and fees
Skyline View Apt - 5 minutes to Downtown - Games + Arcades - Free Parking
A hotel room with a large bed, a window with a view of buildings, a nightstand with a lamp, and two framed pictures on the wall.

8. LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
9.6 out of 10, Exceptional, (26 reviews)
"Incredible location, very clean and easy! Would book again!"
United States
Andrea K.
$416 nightly
The price is $491
Oct 15 - Oct 16
Total with taxes and fees
LIVN West Loop Chicago Queen Superior Studio
A rooftop terrace with a fire pit, seating area, and a city skyline view.

9. Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6

Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6
West Town
10.0 out of 10, Exceptional, (4 reviews)
"Excellent - highly recommended."
United States
Jay J.
$193 nightly
The price is $224
Nov 4 - Nov 5
Total with taxes and fees
Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6
A room with a checkered table, a potted plant, and a bunk bed in the background.

10. Spacious Group Stay - Sleeps 12 - 3 Kings + Arcades - 10 Min to Downtown

Spacious Group Stay - Sleeps 12 - 3 Kings + Arcades - 10 Min to Downtown
Lawndale
8.0 out of 10, Very good, (4 reviews)
"Great stay, perfect for our group of 6, everyone had there own room! Necessities right around the corner if needed Cermack rd a few feet away, gets you about everywhere! We wanted a real life Chicago experience, and it was great. Owner very responsive! Permit on street parking pretty accessible most times. Definitely will stay again!"
United States
Beth
$287 nightly
The price is $322
Oct 13 - Oct 14
Total with taxes and fees
Spacious Group Stay - Sleeps 12 - 3 Kings + Arcades - 10 Min to Downtown
A modern living room with a sectional sofa, a fireplace, and a dining area with a view through large windows.

11. Ukrainian Village 3BR/3BA • Private Patio, Parking

Ukrainian Village 3BR/3BA • Private Patio, Parking
West Town
10.0 out of 10, Exceptional, (41 reviews)
"Clean and convenient location for our stay. "
United States
Tony D.
$488 nightly
The price is $613
Nov 2 - Nov 3
Total with taxes and fees
Ukrainian Village 3BR/3BA • Private Patio, Parking
Interior

12. Convenient 2BR Apt w/ In-Unit Laundry

Convenient 2BR Apt w/ In-Unit Laundry
West Town
$255 nightly
The price is $286
Oct 26 - Oct 27
Total with taxes and fees
Convenient 2BR Apt w/ In-Unit Laundry
A living room with a sofa, coffee table, TV, and a ceiling fan.

13. Newly Remodeled Gem | Heart of Chicago

Newly Remodeled Gem | Heart of Chicago
Humboldt Park
9.6 out of 10, Exceptional, (7 reviews)
"Super clean, comfortable beds, easy to access, easy checkout, and a very communicable host. Overall a great stay. "
United States
Kevin R.
$964 nightly
The price is $1,209
Oct 11 - Oct 12
Total with taxes and fees
Newly Remodeled Gem | Heart of Chicago
A residential street with houses, parked cars, and a city skyline in the background.

14. Pilsen Sweet Life Up High

Pilsen Sweet Life Up High
Lower West Side
$267 nightly
The price is $328
Nov 1 - Nov 2
Total with taxes and fees
Pilsen Sweet Life Up High
A modern desk with a mirror, a lamp, and two potted plants.

15. West Town 2BR | Full Kitchen + In-Unit Laundry

West Town 2BR | Full Kitchen + In-Unit Laundry
West Town
$251 nightly
The price is $281
Oct 14 - Oct 15
Total with taxes and fees
West Town 2BR | Full Kitchen + In-Unit Laundry
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top West Side Hotel Reviews

Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

10/10 Excellent
"Headboard was damaged on bed"
David 1-night trip
Posted 1 hour ago
Crowne Plaza Chicago West Loop by IHG

Find out more about West Side

Everything you need to know about West Side vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the West Side vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect West Side vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

West Side vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in West Side. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit West Side in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $491 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on West Side rentals

At Expedia, we put the best West Side vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top West Side rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream West Side vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around West Side. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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