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

West Side Vacation Rentals

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for West Side vacation rentals

A modern kitchen with white cabinets, a central island with stools, a microwave, and a refrigerator.

1. 3BR Complete and Spacious Apartment in Ideal Spot

3BR Complete and Spacious Apartment in Ideal Spot
West Town
8.4 out of 10, Very good, (23 reviews)
"My wife and I stayed here when we came to town for a concert at the united center. We actually walked to the venue and it was about 45 mins, a lovely walk. It was a very convenient location, lovely apartment, and the host communicated very well. Check in and out was easy. Great neighborhood. Would definitely stay here again."
United States
Francis
$240 nightly
The price is $266
Oct 26 - Oct 27
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.

2. 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 16 - Nov 17
Total with taxes and fees
Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6
A hotel room with a bed, two bedside lamps, a wall-mounted artwork, and a small table with a lamp.

3. 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
$229 nightly
The price is $255
Nov 2 - Nov 3
Total with taxes and fees
2BR Apt with 2 Baths & Laundry
A modern kitchen with white cabinetry, stainless steel appliances, and a central island.

4. Cozy Luxury 1BR - 10 Min to Downtown Chicago

Cozy Luxury 1BR - 10 Min to Downtown Chicago
Lawndale
7.8 out of 10, Good, (12 reviews)
"Don't miss out on this spot!! It's truly a must & great location!!! I really enjoyed my time here for real"
United States
Alexis R.
$180 nightly
The price is $214
Oct 26 - Oct 27
Total with taxes and fees
Cozy Luxury 1BR - 10 Min to Downtown Chicago
A rooftop terrace with a fire pit, seating area, and a city skyline view.

5. 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
9.8 out of 10, Exceptional, (6 reviews)
"Very happy with our stay. Loved the rooftop views! The host was very friendly and welcoming."
United States
Jessica C.
$204 nightly
The price is $237
Nov 4 - Nov 5
Total with taxes and fees
Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6
A neatly made bed with white linens and a grey throw blanket, a bedside lamp, and a geometric wall design.

6. 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
Interior

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

Convenient 2BR Apt w/ In-Unit Laundry
West Town
$221 nightly
The price is $246
Nov 4 - Nov 5
Total with taxes and fees
Convenient 2BR Apt w/ In-Unit Laundry
A residential street with houses, parked cars, and a city skyline in the background.

8. Pilsen Sweet Life Up High

Pilsen Sweet Life Up High
Lower West Side
$223 nightly
The price is $274
Nov 1 - Nov 2
Total with taxes and fees
Pilsen Sweet Life Up High
A bedroom with a bed, a potted plant, a wall hanging, and a mirror.

9. Zen City Escape | Patio + Free Parking

Zen City Escape | Patio + Free Parking
West Town
10.0 out of 10, Exceptional, (4 reviews)
"I had an amazing stay at Tracee's place. It was quiet, clean, plenty of parking and served all of my needs. Tracee was responsive and very accommodating of my stay."
United States
Denise R.
$368 nightly
The price is $430
Nov 3 - Nov 4
Total with taxes and fees
Zen City Escape | Patio + Free Parking
A modern living room with a sofa, armchair, coffee table, and a TV mounted on a wooden wall.

10. Flexhome Ukrainian Village • 2BR • Convenient Walkability · Sleeps 6

Flexhome Ukrainian Village • 2BR • Convenient Walkability · Sleeps 6
West Town
8.2 out of 10, Very good, (11 reviews)
"Excellent place and location."
United States
Josh L.
$200 nightly
The price is $247
Oct 29 - Oct 30
Total with taxes and fees
Flexhome Ukrainian Village • 2BR • Convenient Walkability · Sleeps 6
A bedroom with a bed, a desk, a chair, a TV, and a window with blinds.

11. Flexhome Wicker Park • Stylish 2BR • Sleeps 6

Flexhome Wicker Park • Stylish 2BR • Sleeps 6
West Town
9.8 out of 10, Exceptional, (8 reviews)
"We liked the location near lots of nice restaurants and nightlife."
United States
Scott F.
$172 nightly
The price is $213
Oct 21 - Oct 22
Total with taxes and fees
Flexhome Wicker Park • Stylish 2BR • Sleeps 6
A bedroom with a bed, a window with blinds, a door, a bedside table, and a mirror.

12. Private Apartment in Fulton Market

Private Apartment in Fulton Market
West Town
$172 nightly
The price is $197
Nov 2 - Nov 3
Total with taxes and fees
Private Apartment in Fulton Market
A modern kitchen with dark cabinetry, stainless steel appliances, and a white countertop.

13. 1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry
Downtown Chicago
$294 nightly
The price is $326
Oct 26 - Oct 27
Total with taxes and fees
1BR Modern Luxe Apt with In-Unit Laundry
A modern desk with a mirror, a lamp, and two potted plants.

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

West Town 2BR | Full Kitchen + In-Unit Laundry
West Town
$239 nightly
The price is $267
Oct 18 - Oct 19
Total with taxes and fees
West Town 2BR | Full Kitchen + In-Unit Laundry
A modern living room with a sectional sofa, a fireplace, and a dining area with a view through large windows.

15. 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.
$508 nightly
The price is $638
Nov 2 - Nov 3
Total with taxes and fees
Ukrainian Village 3BR/3BA • Private Patio, Parking
A modern living room with a sectional sofa, a coffee table, and a dining area with chairs and a table.

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

Modern West Loop Gem-City Views & Prime Location 2
Downtown Chicago
9.6 out of 10, Exceptional, (12 reviews)
"Great location, lots of food options, park near by for children. Great communication with hosts."
United States
Jackie S.
$593 nightly
The price is $662
Oct 21 - Oct 22
Total with taxes and fees
Modern West Loop Gem-City Views & Prime Location 2
A modern hotel room with a large bed, a small dining table, a bench, and a view of the city through a large window.

17. LIVN West Loop Chicago Classic Queen Studio

LIVN West Loop Chicago Classic Queen Studio
Downtown Chicago
10.0 out of 10, Exceptional, (8 reviews)
"Excellent stay. Great area and very happy with everything"
United States
Abigail B.
$362 nightly
The price is $428
Oct 23 - Oct 24
Total with taxes and fees
LIVN West Loop Chicago Classic Queen Studio
A circular fire pit with chairs around it, string lights overhead, and a house in the background.

18. Sleeps 18 • 7BR • Gym • Game Room • Theater

Sleeps 18 • 7BR • Gym • Game Room • Theater
Austin
6.0 out of 10, (1 review)
"Ok place to fit large families if no other option available. Not suitable for kids with allergies as there are some opportunities in the cleanness and maintenance of the property.The communication were ok for reserving but very limited during the stay.The floor os severely damaged as well."
United States
Adrian Cesar C.
$794 nightly
The price is $981
Oct 20 - Oct 21
Total with taxes and fees
Sleeps 18 • 7BR • Gym • Game Room • Theater
A modern kitchen with a dishwasher, a sink, and a large island. There is a trash can and a dining area with a table and chairs.

19. Flexhome West Town Spacious 2BR Duplex · Sleeps 8

Flexhome West Town Spacious 2BR Duplex · Sleeps 8
West Town
8.0 out of 10, Very good, (1 review)
"We really liked staying at this property and would do so again in a heartbeat except for one major hesitation. The AC unit condensate pipe had come loose and was pouring water into the floorboard downstairs. Meaning most of our stay wound up with the basement being extremely humid and damp and generally not pleasant to be in. We notified the host promptly and it took 2 days for the landlord to have maintenance come out and address the issue once it was addressed. Everything was good from there...
United States
Lucas C.
$153 nightly
The price is $177
Nov 17 - Nov 18
Total with taxes and fees
Flexhome West Town Spacious 2BR Duplex · Sleeps 8
A rooftop terrace with a fire pit, seating area, and a city skyline view.

20. 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.
$204 nightly
The price is $237
Nov 4 - Nov 5
Total with taxes and fees
Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top West Side Hotel Reviews

The Emily Hotel

The Emily Hotel

10/10 Excellent
"Clean room, great staff"
Megan 1-night trip
Posted 15 hours ago
The Emily Hotel

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 $338 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.

Explore a world of travel with Expedia