West Side Vacation Rentals

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Our top choices for West Side vacation rentals

Sunlit 1BR Apartment | Warm & Welcoming Space

Sunlit 1BR Apartment | Warm & Welcoming Space
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Host was very friendly and informative. Place was clean and close to lots of fun. Trains loud and busy but knew that going in. "
United States
Tyler B.
$232 nightly
The price is $262
May 26 - May 27
Total with taxes and fees
Sunlit 1BR Apartment | Warm & Welcoming Space

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
9.8 out of 10, Exceptional, (10 reviews)
"Great spot next to the green line train a few restaurants and a Starbucks right up the street I will book again for sure "
United States
2k G.
$232 nightly
The price is $262
May 26 - May 27
Total with taxes and fees
West Loop Living – Bright 1BR

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
$147 nightly
The price is $174
May 21 - May 22
Total with taxes and fees
LIVN West Loop Chicago King Studio

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, (22 reviews)
"Everything was walking distance and had everything needed for a comfortable stay "
United States
Daniel
$749 nightly
The price is $854
Jun 17 - Jun 18
Total with taxes and fees
Modern West Loop Gem-City Views & Prime Location 6

1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry
Downtown Chicago
8.8 out of 10, Excellent, (3 reviews)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
$238 nightly
The price is $269
May 26 - May 27
Total with taxes and fees
1BR Modern Luxe Apt with In-Unit Laundry

LIVN West Loop Chicago 2 BR City View

LIVN West Loop Chicago 2 BR City View
Downtown Chicago
9.4 out of 10, Exceptional, (3 reviews)
"Super clean, great communication! Thanks for a great stay."
United States
Tracey L.
$184 nightly
The price is $217
May 21 - May 22
Total with taxes and fees
LIVN West Loop Chicago 2 BR City View

LIVN West Loop Chicago Classic Queen Studio

LIVN West Loop Chicago Classic Queen Studio
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Excellent stay. Great area and very happy with everything"
United States
Abigail B.
$150 nightly
The price is $177
May 26 - May 27
Total with taxes and fees
LIVN West Loop Chicago Classic Queen Studio

LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
$157 nightly
The price is $186
May 25 - May 26
Total with taxes and fees
LIVN West Loop Chicago Queen Superior Studio

Cozy Boho Chicago - 10 Minutes to Downtown Chicago

Cozy Boho Chicago - 10 Minutes to Downtown Chicago
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.
$202 nightly
The price is $227
Jun 16 - Jun 17
Total with taxes and fees
Cozy Boho Chicago - 10 Minutes to Downtown Chicago

Modern West Loop Gem-City Views & Prime Location 5

Modern West Loop Gem-City Views & Prime Location 5
Downtown Chicago
9.4 out of 10, Exceptional, (3 reviews)
"Great location, plenty of space and clean home. "
United States
Brittany T.
$905 nightly
The price is $1,047
Jun 3 - Jun 4
Total with taxes and fees
Modern West Loop Gem-City Views & Prime Location 5

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
8.8 out of 10, Excellent, (3 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
$262 nightly
The price is $294
May 26 - May 27
Total with taxes and fees
10 Minutes to Downtown Chicago - Sleeps 12 - King Beds - Games and Arcades

Cabin 105 by 747 Lofts

Cabin 105 by 747 Lofts
2.0 star property
West Town
10.0 out of 10, Exceptional, (1 review)
$170 nightly
The price is $199
Jun 3 - Jun 4
Total with taxes and fees
Cabin 105 by 747 Lofts

LIVN West Loop Chicago 1 BR

LIVN West Loop Chicago 1 BR
Downtown Chicago
$194 nightly
The price is $229
May 25 - May 26
Total with taxes and fees
LIVN West Loop Chicago 1 BR

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.
$384 nightly
The price is $482
Jun 8 - Jun 9
Total with taxes and fees
Newly Remodeled Gem | Heart of Chicago

15 mins DT| HumboldtPark Gem | Sleeps 8 | FreePark

15 mins DT| HumboldtPark Gem | Sleeps 8 | FreePark
West Town
10.0 out of 10, Exceptional, (1 review)
$266 nightly
The price is $273
May 25 - May 26
Total with taxes and fees
15 mins DT| HumboldtPark Gem | Sleeps 8 | FreePark

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.
$179 nightly
The price is $213
May 27 - May 28
Total with taxes and fees
Luxurious, Cozy Beauty 10 min from Downtown Chicago

Urban Comfort • 2BR in West Town

Urban Comfort • 2BR in West Town
West Town
9.6 out of 10, Exceptional, (8 reviews)
"The place was very clean and accommodating."
United States
Mark E.
$247 nightly
The price is $277
May 25 - May 26
Total with taxes and fees
Urban Comfort • 2BR in West Town

Flexhome Wicker Park • Stylish 2BR • Sleeps 6

Flexhome Wicker Park • Stylish 2BR • Sleeps 6
West Town
9.8 out of 10, Exceptional, (6 reviews)
"Great location. The apartment has everything you will need. Had a great time . Thanks"
United States
Wayne M.
$250 nightly
The price is $309
Jun 1 - Jun 2
Total with taxes and fees
Flexhome Wicker Park • Stylish 2BR • Sleeps 6

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
$290 nightly
The price is $325
Jun 1 - Jun 2
Total with taxes and fees
Sleeps 12 - Games - 10 Min to Downtown - Arcades - Walking Distance to Train

Vintage Arcade Apt with Parking

Vintage Arcade Apt with Parking
Lawndale
6.0 out of 10, (6 reviews)
"Very clean and private"
United States
Anthony B.
$174 nightly
The price is $195
May 26 - May 27
Total with taxes and fees
Vintage Arcade Apt with Parking
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

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 $186 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.