West Side Holiday Rentals

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Our top choices for West Side holiday rentals

LIVN West Loop Chicago 2 BR City View

LIVN West Loop Chicago 2 BR City View
Downtown Chicago
9.0 out of 10, Wonderful, (8 reviews)
"The parking situation is pretty rough. You have to park a half a mile away from the property. The room looks very luxurious in the pictures. However, once you get there, it does show some age and you can hear the other guest from above and below at all night not to mention that the city sounds are in full effect horns and traffic all night long and it’s difficult to get the room dark"
United States
Robert
The price is AU$372
includes taxes & fees
1 July - 2 July
LIVN West Loop Chicago 2 BR City View

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.
The price is AU$1,211
includes taxes & fees
28 June - 29 June
Modern West Loop Gem-City Views & Prime Location 2

LIVN West Loop Chicago Classic Queen Studio

LIVN West Loop Chicago Classic Queen Studio
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
The price is AU$304
includes taxes & fees
28 June - 29 June
LIVN West Loop Chicago Classic Queen Studio

LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
9.2 out of 10, Wonderful, (9 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.
The price is AU$357
includes taxes & fees
28 June - 29 June
LIVN West Loop Chicago Queen Superior Studio

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
The price is AU$379
includes taxes & fees
1 July - 2 July
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, (24 reviews)
"Great location. "
United States
Tom S.
The price is AU$1,668
includes taxes & fees
23 July - 24 July
Modern West Loop Gem-City Views & Prime Location 6

Modern West Loop Gem-City Views & Prime Location 4

Modern West Loop Gem-City Views & Prime Location 4
Downtown Chicago
10.0 out of 10, Exceptional, (9 reviews)
"Amazing accommodation"
United States
Jiri N.
The price is AU$1,576
includes taxes & fees
2 July - 3 July
Modern West Loop Gem-City Views & Prime Location 4

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.
The price is AU$389
includes taxes & fees
28 June - 29 June
LIVN West Loop Chicago 1 BR

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
The price is AU$412
includes taxes & fees
30 June - 1 July
10 Minutes to Downtown Chicago - Sleeps 12 - King Beds - Games and Arcades

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
The price is AU$443
includes taxes & fees
6 July - 7 July
Sleeps 12 - Games - 10 Min to Downtown - Arcades - Walking Distance to Train

Cabin 104 by 747 Lofts

Cabin 104 by 747 Lofts
West Town
10.0 out of 10, Exceptional, (9 reviews)
"The place was great"
United States
bonnie c.
Cabin 104 by 747 Lofts

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.
The price is AU$690
includes taxes & fees
28 June - 29 June
Karlov Inn | Stylish Chicago 2BR Retreat

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
The price is AU$267
includes taxes & fees
8 July - 9 July
Ground Floor Studios in Chicago by 747 Lofts

Flexhome Wicker Park • Stylish 2BR • Sleeps 6

Flexhome Wicker Park • Stylish 2BR • Sleeps 6
West Town
9.8 out of 10, Exceptional, (7 reviews)
"Great location. The apartment has everything you will need. Had a great time . Thanks"
United States
Wayne M.
The price is AU$414
includes taxes & fees
19 July - 20 July
Flexhome Wicker Park • Stylish 2BR • Sleeps 6

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.
The price is AU$1,417
includes taxes & fees
6 July - 7 July
Sleeps 18 • 7BR • Gym • Game Room • Theater

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,198 reviews)
"Great location"
United States
JAVIER
The price is AU$324
includes taxes & fees
1 July - 2 July
Sentral Michigan Avenue
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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Find out more about West Side

Everything you need to know about West Side holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the West Side holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

West Side holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A West Side holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of West Side holiday rentals we have selected for you start as low as AU$267 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on West Side rentals

At Expedia, we put the best West Side holiday 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 holiday.

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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