Holiday Rentals in West Side

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Our top choices for West Side holiday rentals

Sunlit 1BR Apartment | Warm & Welcoming Space

Sunlit 1BR Apartment | Warm & Welcoming Space
Downtown Chicago
8.0 out of 10, Very good, (3 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.
The price is €252
includes taxes & fees
21 Jun - 22 Jun
Sunlit 1BR Apartment | Warm & Welcoming Space

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
9.2 out of 10, Wonderful, (12 reviews)
"The host was great at communicating and the apartment was very clean! "
United States
Hannah C.
The price is €262
includes taxes & fees
30 Jun - 1 Jul
West Loop Living – Bright 1BR

LIVN West Loop Chicago Classic Queen Studio

LIVN West Loop Chicago Classic Queen Studio
Downtown Chicago
10.0 out of 10, Exceptional, (3 reviews)
The price is €185
includes taxes & fees
21 Jun - 22 Jun
LIVN West Loop Chicago Classic Queen Studio

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.
The price is €596
includes taxes & fees
21 Jun - 22 Jun
Modern West Loop Gem-City Views & Prime Location 3

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
The price is €262
includes taxes & fees
30 Jun - 1 Jul
1BR Modern Luxe Apt with In-Unit Laundry

LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
10.0 out of 10, Exceptional, (8 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 €217
includes taxes & fees
21 Jun - 22 Jun
LIVN West Loop Chicago Queen Superior Studio

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
The price is €267
includes taxes & fees
30 Jun - 1 Jul
10 Minutes to Downtown Chicago - Sleeps 12 - King Beds - Games and Arcades

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

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 €229
includes taxes & fees
25 Jun - 26 Jun
LIVN West Loop Chicago King Studio

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.
Modern West Loop Gem-City Views & Prime Location 4

Chicago Third Floor Studio by 747 Lofts

Chicago Third Floor Studio by 747 Lofts
2.0 star property
West Town
9.8 out of 10, Exceptional, (7 reviews)
"Clean, easy to check in, all the household items you’d expect"
United States
Jason
The price is €281
includes taxes & fees
22 Jun - 23 Jun
Chicago Third Floor Studio by 747 Lofts

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 €279
includes taxes & fees
6 Jul - 7 Jul
Sleeps 12 - Games - 10 Min to Downtown - Arcades - Walking Distance to Train

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 €394
includes taxes & fees
23 Jun - 24 Jun
Karlov Inn | Stylish Chicago 2BR Retreat

LIVN West Loop Chicago 2 BR City View

LIVN West Loop Chicago 2 BR City View
Downtown Chicago
9.2 out of 10, Wonderful, (7 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 €532
includes taxes & fees
24 Jun - 25 Jun
LIVN West Loop Chicago 2 BR City View

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

Cozy Chic Retreat Near Downtown - Sleeps 7 - Urban City View
Lawndale
The price is €267
includes taxes & fees
2 Jul - 3 Jul
Cozy Chic Retreat Near Downtown - Sleeps 7 - Urban City View

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.
The price is €204
includes taxes & fees
8 Jul - 9 Jul
Cabin 104 by 747 Lofts

Flexhome East Village • Modern 2BR • Quiet Street

Flexhome East Village • Modern 2BR • Quiet Street
West Town
9.8 out of 10, Exceptional, (17 reviews)
"Location was great for everything we were doing in Chicago. "
United States
Tom W.
The price is €212
includes taxes & fees
22 Jun - 23 Jun
Flexhome East Village • Modern 2BR • Quiet Street

Flexhome Wicker Park • Stylish 2BR • Sleeps 6

Flexhome Wicker Park • Stylish 2BR • Sleeps 6
West Town
The price is €254
includes taxes & fees
19 Jul - 20 Jul
Flexhome Wicker Park • Stylish 2BR • Sleeps 6

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.
The price is €282
includes taxes & fees
29 Jun - 30 Jun
Urban Comfort • 2BR in West Town

Modern 3 BR Apt - 5 Mins to Downtown Sleeps 10

Modern 3 BR Apt - 5 Mins to Downtown Sleeps 10
Lower West Side
The price is €396
includes taxes & fees
5 Jul - 6 Jul
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

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, apart-hotels, 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 favorite 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 depends 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 €181 per night. Entering your travel dates in the search wizard you might find 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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