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
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for West Side vacation rentals

1 bedroom, iron/ironing board, travel crib, WiFi

LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
8.8 out of 10, Excellent, (10 reviews)
"The service was top notch at this property. The hosts were super responsive and professional. The location was incredible. Loved being able to cook in the apartment. The apartment was newly renovated and very urban chic. "
United States
Michelle R.
$217 nightly
The price is $256
Jul 9 - Jul 10
Total with taxes and fees
LIVN West Loop Chicago Queen Superior Studio
TV, offices

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, (24 reviews)
"Great location. "
United States
Tom S.
$825 nightly
The price is $948
Aug 2 - Aug 3
Total with taxes and fees
Modern West Loop Gem-City Views & Prime Location 6
TV, offices

LIVN West Loop Chicago 2 BR City View

LIVN West Loop Chicago 2 BR City View
Downtown Chicago
9.2 out of 10, Wonderful, (9 reviews)
"Everything went well"
United States
Ryan W.
$322 nightly
The price is $380
Jul 9 - Jul 10
Total with taxes and fees
LIVN West Loop Chicago 2 BR City View
1 bedroom, iron/ironing board, travel crib, WiFi

LIVN West Loop Chicago Classic Queen Studio

LIVN West Loop Chicago Classic Queen Studio
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
$226 nightly
The price is $267
Jul 12 - Jul 13
Total with taxes and fees
LIVN West Loop Chicago Classic Queen Studio
1 bedroom, iron/ironing board, travel crib, WiFi

LIVN West Loop Chicago King Studio

LIVN West Loop Chicago King Studio
Downtown Chicago
10.0 out of 10, Exceptional, (4 reviews)
"Amazing studio apartment style room, super clean, very helpful staff, and great location."
United States
William
$201 nightly
The price is $237
Jul 8 - Jul 9
Total with taxes and fees
LIVN West Loop Chicago King Studio
1 bedroom, iron/ironing board, travel crib, WiFi

LIVN West Loop Chicago 1 BR

LIVN West Loop Chicago 1 BR
Downtown Chicago
2.0 out of 10, (1 review)
"Unfortunately, this property was in disrepair and the surroundings were so loud that it was impossible to sleep."
United States
Brittany C.
$305 nightly
The price is $360
Jul 10 - Jul 11
Total with taxes and fees
LIVN West Loop Chicago 1 BR
Interior

Modern West Loop Gem-City Views & Prime Location 3

Modern West Loop Gem-City Views & Prime Location 3
Downtown Chicago
10.0 out of 10, Exceptional, (7 reviews)
"Loved the place 4 bedroom & 4 bathrooms was ideal for our stayGreat locationLoved the well stocked convenience store a block away "
United States
Tina Y.
$797 nightly
The price is $913
Jul 23 - Jul 24
Total with taxes and fees
Modern West Loop Gem-City Views & Prime Location 3
Interior

10 Minutes to Downtown Chicago - Sleeps 12 - King Beds - Games and Arcades

10 Minutes to Downtown Chicago - Sleeps 12 - King Beds - Games and Arcades
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
$292 nightly
The price is $328
Jul 27 - Jul 28
Total with taxes and fees
10 Minutes to Downtown Chicago - Sleeps 12 - King Beds - Games and Arcades
Fridge, microwave, oven, stovetop

Luxurious, Cozy Beauty 10 min from Downtown Chicago

Luxurious, Cozy Beauty 10 min from Downtown Chicago
Lawndale
8.6 out of 10, Excellent, (9 reviews)
"Close to public transport, clean, helpful host"
United States
Aaron W.
$197 nightly
The price is $234
Aug 4 - Aug 5
Total with taxes and fees
Luxurious, Cozy Beauty 10 min from Downtown Chicago
Interior

Sleeps 12 - Games - 10 Min to Downtown - Arcades - Walking Distance to Train

Sleeps 12 - Games - 10 Min to Downtown - Arcades - Walking Distance to Train
Lawndale
$306 nightly
The price is $343
Jul 15 - Jul 16
Total with taxes and fees
Sleeps 12 - Games - 10 Min to Downtown - Arcades - Walking Distance to Train
Smart TV, books

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)
"Great location for whom we were visiting. Lots of street noise- city living!"
United States
aileen s.
$240 nightly
The price is $296
Jul 19 - Jul 20
Total with taxes and fees
Flexhome Ukrainian Village • 2BR • Convenient Walkability · Sleeps 6
Fridge, microwave, oven, stovetop

Flexhome East Village • Modern 2BR • Quiet Street

Flexhome East Village • Modern 2BR • Quiet Street
West Town
9.8 out of 10, Exceptional, (18 reviews)
"Location was great for everything we were doing in Chicago. "
United States
Tom W.
$189 nightly
The price is $233
Jul 9 - Jul 10
Total with taxes and fees
Flexhome East Village • Modern 2BR • Quiet Street
2 bedrooms, desk, iron/ironing board, free WiFi

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

Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6
West Town
9.2 out of 10, Wonderful, (13 reviews)
"Great location! Comfortable and quiet. "
United States
Jonalyn B.
$186 nightly
The price is $230
Jul 9 - Jul 10
Total with taxes and fees
Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6
Interior

Cozy Chic Retreat Near Downtown - Sleeps 7 - Urban City View

Cozy Chic Retreat Near Downtown - Sleeps 7 - Urban City View
Lawndale
Cozy Chic Retreat Near Downtown - Sleeps 7 - Urban City View
2 bedrooms, desk, iron/ironing board, WiFi

Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony

Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony
West Town
$186 nightly
The price is $230
Jul 9 - Jul 10
Total with taxes and fees
Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony
Interior

Karlov Inn | Stylish Chicago 2BR Retreat

Karlov Inn | Stylish Chicago 2BR Retreat
Humboldt Park
9.0 out of 10, Wonderful, (15 reviews)
"Great place, clean and comfy. "
United States
Reann J.
$362 nightly
The price is $454
Jul 9 - Jul 10
Total with taxes and fees
Karlov Inn | Stylish Chicago 2BR Retreat
Terrace/patio

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.
$826 nightly
The price is $1,022
Jul 14 - Jul 15
Total with taxes and fees
Sleeps 18 • 7BR • Gym • Game Room • Theater
2 bedrooms, desk, iron/ironing board, free WiFi

Flexhome Wicker Park • Stylish 2BR • Sleeps 6

Flexhome Wicker Park • Stylish 2BR • Sleeps 6
West Town
9.8 out of 10, Exceptional, (7 reviews)
"Very cute spot in an amazing location!! The instructions were very clear, and getting in and out of the unit was simple and secure."
United States
Anonymous traveler
$228 nightly
The price is $281
Jul 19 - Jul 20
Total with taxes and fees
Flexhome Wicker Park • Stylish 2BR • Sleeps 6
Exterior

Ground Floor Studios in Chicago by 747 Lofts

Ground Floor Studios in Chicago by 747 Lofts
2.0 star property
West Town
8.6 out of 10, Excellent, (23 reviews)
"Great area and surprisingly nice room!"
United States
Michael
$189 nightly
The price is $189
Aug 3 - Aug 4
Total with taxes and fees
Ground Floor Studios in Chicago by 747 Lofts
Microwave, oven, stovetop, dishwasher

Modern 3 BR Apt - 5 Mins to Downtown Sleeps 10

Modern 3 BR Apt - 5 Mins to Downtown Sleeps 10
Lower West Side
8.0 out of 10, Very Good, (1 review)
"It was decent for what we needed. Owner sends a lot of automated messages. Place was maintained, parking free, but is difficult to find."
United States
Marie Leola K.
$377 nightly
The price is $423
Jul 13 - Jul 14
Total with taxes and fees
Modern 3 BR Apt - 5 Mins to Downtown Sleeps 10
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

8/10 Good
"The room was clean and so was the balcony. All staff were wonderful and very professional. Parking was in a lot and in and out privileges were simple. The breakfast was better than expected and the restaurant was clean and the food was hot and filling. The only downside is that the bed wasn’t that comfortable to sleep through the night, but it was cozy. I would love to come back, if the bed situation was better. It was definitely a vibe in there when we walked in and we loved it."
Tralesser 1-night trip
Posted 4 hours 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 $189 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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