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 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for West Side vacation rentals

Room

Charming 2-bedroom apartment with AC in fantastic Chicago

Charming 2-bedroom apartment with AC in fantastic Chicago
Downtown Chicago
$10,133 nightly
The price is $12,503
Jul 15 - Jul 16
Total with taxes and fees
Charming 2-bedroom apartment with AC in fantastic Chicago
TV, offices

Modern West Loop Gem-City Views & Prime Location 5

Modern West Loop Gem-City Views & Prime Location 5
Downtown Chicago
9.0 out of 10, Wonderful, (6 reviews)
"Great location, plenty of space and clean home. "
United States
Brittany T.
$698 nightly
The price is $791
Aug 10 - Aug 11
Total with taxes and fees
Modern West Loop Gem-City Views & Prime Location 5
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)
"Beautiful place exciting city everything was wonderful"
United States
Kyna C.
$208 nightly
The price is $246
Jul 19 - Jul 20
Total with taxes and fees
LIVN West Loop Chicago Queen Superior Studio
TV, offices

Modern West Loop Gem-City Views & Prime Location 4

Modern West Loop Gem-City Views & Prime Location 4
Downtown Chicago
9.6 out of 10, Exceptional, (10 reviews)
"Amazing accommodation"
United States
Jiri N.
$706 nightly
The price is $801
Aug 9 - Aug 10
Total with taxes and fees
Modern West Loop Gem-City Views & Prime Location 4
TV, offices

Modern West Loop Gem-City Views & Prime Location 1

Modern West Loop Gem-City Views & Prime Location 1
Downtown Chicago
9.4 out of 10, Exceptional, (3 reviews)
"Great location, HUGE space, and great service at a great rate!"
United States
Ernest C.
$758 nightly
The price is $865
Aug 9 - Aug 10
Total with taxes and fees
Modern West Loop Gem-City Views & Prime Location 1
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, (6 reviews)
$177 nightly
The price is $209
Jul 19 - Jul 20
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
$238 nightly
The price is $281
Jul 19 - Jul 20
Total with taxes and fees
LIVN West Loop Chicago King Studio
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.
$337 nightly
The price is $398
Jul 16 - Jul 17
Total with taxes and fees
LIVN West Loop Chicago 2 BR City View
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, (25 reviews)
"Great location. "
United States
Tom S.
$862 nightly
The price is $994
Aug 2 - Aug 3
Total with taxes and fees
Modern West Loop Gem-City Views & Prime Location 6
TV, offices

Modern West Loop Gem-City Views & Prime Location 2

Modern West Loop Gem-City Views & Prime Location 2
Downtown Chicago
9.4 out of 10, Exceptional, (9 reviews)
"Excellent location, very clean & comfortable. West Loop is an awesome area to stay in Chicago. Seamless check in process."
United States
Dean R.
$778 nightly
The price is $890
Jul 26 - Jul 27
Total with taxes and fees
Modern West Loop Gem-City Views & Prime Location 2
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.
$960 nightly
The price is $1,114
Jul 23 - Jul 24
Total with taxes and fees
Modern West Loop Gem-City Views & Prime Location 3
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.
LIVN West Loop Chicago 1 BR
Smart TV

Newly Remodeled Gem | Heart of Chicago

Newly Remodeled Gem | Heart of Chicago
Humboldt Park
9.4 out of 10, Exceptional, (6 reviews)
"Super clean, comfortable beds, easy to access, easy checkout, and a very communicable host. Overall a great stay. "
United States
Kevin R.
$419 nightly
The price is $526
Aug 3 - Aug 4
Total with taxes and fees
Newly Remodeled Gem | Heart of Chicago
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
$312 nightly
The price is $350
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.
$187 nightly
The price is $222
Aug 11 - Aug 12
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
$302 nightly
The price is $339
Jul 20 - Jul 21
Total with taxes and fees
Sleeps 12 - Games - 10 Min to Downtown - Arcades - Walking Distance to Train
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
$175 nightly
The price is $216
Jul 19 - Jul 20
Total with taxes and fees
Flexhome Wicker Park • Stylish 2BR • Sleeps 6
TV, books

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

Flexhome Ukrainian Village • 2BR • Convenient Walkability · Sleeps 6
West Town
8.0 out of 10, Very Good, (1 review)
"On busy street so was a little noisy."
United States
Diane M.
$182 nightly
The price is $224
Jul 19 - Jul 20
Total with taxes and fees
Flexhome Ukrainian Village • 2BR • Convenient Walkability · Sleeps 6
Exterior

Cabin 302 by 747 Lofts

Cabin 302 by 747 Lofts
West Town
10.0 out of 10, Exceptional, (6 reviews)
"Easy in and out and good price!"
United States
Curtis A.
$250 nightly
The price is $295
Jul 16 - Jul 17
Total with taxes and fees
Cabin 302 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.
$382 nightly
The price is $429
Jul 28 - Jul 29
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

Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

8/10 Good
"Pros - We had a suite with our adult daughter and there was plenty of room. The hotel wasn't fancy but was clean and staff was friendly. The area was very walkable. We parked right below our window and never moved our truck until checkout. There is a Whole Foods, Jewel, and Walgreens less than 1 mile easy walk and there are bikes and scooters to rent on the way too. Plenty of restaurants in that area too. Recommend Ahuevo in front of hotel for breakfast - amazing breakfast burritos and they even had a vegan option. Cons - Parking was $$$$ at $65/day. We used spot hero to find a lot right in front of the hotel for $55 total, pulled in, and saw multiple piles of broken windows. So we left, canceled the spot hero, and used the hotel parking. The hotel isn't in the middle of all the action, which means either a walk or a ride but we were OK with that."
Nicole 2-night trip
Posted 1 hour ago
Holiday Inn & Suites Chicago - Downtown 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 $246 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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