A greenhouse with a glass ceiling, various cacti, and a wooden structure in the center.

Holiday Rentals in West Side

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Our top choices for West Side holiday rentals

1. 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 €315
includes taxes & fees
9 Aug - 10 Aug
LIVN West Loop Chicago King Studio

2. 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, (26 reviews)
"Great location. "
United States
Tom S.
Modern West Loop Gem-City Views & Prime Location 6

3. LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
9.4 out of 10, Exceptional, (16 reviews)
"Highly recommend! Will be staying here again."
United States
Sheila M.
The price is €220
includes taxes & fees
10 Aug - 11 Aug
LIVN West Loop Chicago Queen Superior Studio

4. LIVN West Loop Chicago Classic Queen Studio

LIVN West Loop Chicago Classic Queen Studio
Downtown Chicago
10.0 out of 10, Exceptional, (6 reviews)
"Excellent stay. Great area and very happy with everything"
United States
Abigail B.
The price is €254
includes taxes & fees
10 Aug - 11 Aug
LIVN West Loop Chicago Classic Queen Studio

5. 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)
"Super clean, great communication! Thanks for a great stay."
United States
Tracey L.
The price is €339
includes taxes & fees
9 Aug - 10 Aug
LIVN West Loop Chicago 2 BR City View

6. Flexhome East Village • Modern 2BR • Quiet Street

Flexhome East Village • Modern 2BR • Quiet Street
West Town
9.8 out of 10, Exceptional, (21 reviews)
"Great location! "
United States
Andrea B.
Flexhome East Village • Modern 2BR • Quiet Street

7. 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.
The price is €174
includes taxes & fees
11 Aug - 12 Aug
Luxurious, Cozy Beauty 10 min from Downtown Chicago

8. Cabin 208 by 747 Lofts

Cabin 208 by 747 Lofts
West Town
9.2 out of 10, Wonderful, (11 reviews)
"Such a cute tiny place! We were only in the room to sleep so the size didn't matter to us. We also loved that there was a stove and big fridge! Would definitely stay here again!"
United States
Shelbi
Cabin 208 by 747 Lofts

9. Bright & Spacious Boho Oasis: A Warm Retreat

Bright & Spacious Boho Oasis: A Warm Retreat
West Town
The price is €349
includes taxes & fees
1 Sept - 2 Sept
Bright & Spacious Boho Oasis: A Warm Retreat

10. 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 €254
includes taxes & fees
17 Aug - 18 Aug
Sleeps 12 - Games - 10 Min to Downtown - Arcades - Walking Distance to Train

11. 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.
The price is €293
includes taxes & fees
20 Aug - 21 Aug
Flexhome Ukrainian Village • 2BR • Convenient Walkability · Sleeps 6

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

Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6
West Town
8.8 out of 10, Excellent, (14 reviews)
"Great location! Comfortable and quiet. "
United States
Jonalyn B.
The price is €271
includes taxes & fees
13 Aug - 14 Aug
Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6

13. Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony

Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony
West Town
10.0 out of 10, Exceptional, (1 review)
"Once we were in the place it was wonderful, met all of our needs.The entrance to our unit was filthy and steps kind of dangerous for 5 year old with no railing"
United States
PAT C.
The price is €260
includes taxes & fees
13 Aug - 14 Aug
Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony

14. 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 €269
includes taxes & fees
9 Aug - 10 Aug
LIVN West Loop Chicago 1 BR

15. Zen City Escape | Patio + Free Parking

Zen City Escape | Patio + Free Parking
West Town
10.0 out of 10, Exceptional, (3 reviews)
"I had an amazing stay at Tracee's place. It was quiet, clean, plenty of parking and served all of my needs. Tracee was responsive and very accommodating of my stay."
United States
Denise R.
The price is €408
includes taxes & fees
1 Sept - 2 Sept
Zen City Escape | Patio + Free Parking

16. Flexhome Wicker Park • Stylish 2BR • Sleeps 6

Flexhome Wicker Park • Stylish 2BR • Sleeps 6
West Town
10.0 out of 10, Exceptional, (3 reviews)
"Wouldn’t change a thing. Great location to downtown and all the things that we wanted to do."
United States
beth m.
The price is €189
includes taxes & fees
10 Aug - 11 Aug
Flexhome Wicker Park • Stylish 2BR • Sleeps 6

17. Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6

Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6
West Town
10.0 out of 10, Exceptional, (3 reviews)
"Excellent - highly recommended."
United States
Jay J.
The price is €259
includes taxes & fees
9 Aug - 10 Aug
Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6

18. 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.
Newly Remodeled Gem | Heart of Chicago

19. 5 Mins to Downtown CHI Sleeps 10 - Parking + Games

5 Mins to Downtown CHI Sleeps 10 - Parking + Games
Lower West Side
10.0 out of 10, Exceptional, (3 reviews)
"We loved the location, the area is awesome! Great stay, highly recommend. "
United States
Db D.
The price is €366
includes taxes & fees
6 Aug - 7 Aug
5 Mins to Downtown CHI Sleeps 10 - Parking + Games

20. Modern Zen Retreat mins from Downtown

Modern Zen Retreat mins from Downtown
West Town
The price is €411
includes taxes & fees
17 Aug - 18 Aug
Modern Zen Retreat mins from Downtown
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 €174 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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