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

West Side Holiday Rentals

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Our top choices for West Side holiday rentals

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

Modern West Loop Gem-City Views & Prime Location 2
Downtown Chicago
9.6 out of 10, Exceptional, (11 reviews)
"Great location, lots of food options, park near by for children. Great communication with hosts."
United States
Jackie S.
The price is AU$984
includes taxes & fees
21 Oct - 22 Oct
Modern West Loop Gem-City Views & Prime Location 2

2. 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, (15 reviews)
"Great location! Comfortable and quiet. "
United States
Jonalyn B.
The price is AU$351
includes taxes & fees
1 Oct - 2 Oct
Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6

3. LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
9.6 out of 10, Exceptional, (25 reviews)
"Incredible location, very clean and easy! Would book again!"
United States
Andrea K.
The price is AU$354
includes taxes & fees
27 Sept - 28 Sept
LIVN West Loop Chicago Queen Superior Studio

4. Modern Zen Retreat mins from Downtown

Modern Zen Retreat mins from Downtown
West Town
10.0 out of 10, Exceptional, (2 reviews)
"Perfect place to stay! We would definitely come back when we're in Chicago again."
United States
Caley C.
The price is AU$839
includes taxes & fees
27 Sept - 28 Sept
Modern Zen Retreat mins from Downtown

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

Flexhome East Village • Modern 2BR • Quiet Street
West Town
9.6 out of 10, Exceptional, (23 reviews)
"Great location! "
United States
Andrea B.
Flexhome East Village • Modern 2BR • Quiet Street

6. Flexhome West Town · Spacious 2BR Duplex · Sleeps 8

Flexhome West Town · Spacious 2BR Duplex · Sleeps 8
West Town
10.0 out of 10, Exceptional, (1 review)
The price is AU$334
includes taxes & fees
26 Oct - 27 Oct
Flexhome West Town · Spacious 2BR Duplex · Sleeps 8

7. Zen City Escape | Patio + Free Parking

Zen City Escape | Patio + Free Parking
West Town
10.0 out of 10, Exceptional, (4 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 AU$595
includes taxes & fees
26 Oct - 27 Oct
Zen City Escape | Patio + Free Parking

8. 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 AU$552
includes taxes & fees
8 Oct - 9 Oct
Flexhome Wicker Park • Stylish 2BR • Sleeps 6

9. Modern Pilsen 3BR - Near Downtown - Sleeps 10

Modern Pilsen 3BR - Near 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.
The price is AU$773
includes taxes & fees
16 Oct - 17 Oct
Modern Pilsen 3BR - Near Downtown - Sleeps 10

10. Cozy Urban View Retreat Near Downtown - Sleeps 7

Cozy Urban View Retreat Near Downtown - Sleeps 7
Lawndale
The price is AU$340
includes taxes & fees
7 Oct - 8 Oct
Cozy Urban View Retreat Near Downtown - Sleeps 7

11. Newly Remodeled Gem | Heart of Chicago

Newly Remodeled Gem | Heart of Chicago
Humboldt Park
9.6 out of 10, Exceptional, (7 reviews)
"Super clean, comfortable beds, easy to access, easy checkout, and a very communicable host. Overall a great stay. "
United States
Kevin R.
The price is AU$1,692
includes taxes & fees
11 Oct - 12 Oct
Newly Remodeled Gem | Heart of Chicago

12. The Boho House • Two Private Suites + Parking

The Boho House • Two Private Suites + Parking
West Town
The price is AU$1,354
includes taxes & fees
28 Sept - 29 Sept
The Boho House • Two Private Suites + Parking

13. 3BR Complete and Spacious Apartment in Ideal Spot

3BR Complete and Spacious Apartment in Ideal Spot
West Town
8.2 out of 10, Very good, (22 reviews)
"absolutely would stay here again. Great property and great communcation"
United States
Daniel J.
The price is AU$386
includes taxes & fees
28 Sept - 29 Sept
3BR Complete and Spacious Apartment in Ideal Spot

14. 2BR Apt with 2 Baths & Laundry

2BR Apt with 2 Baths & Laundry
Near West Side
The price is AU$498
includes taxes & fees
27 Sept - 28 Sept
2BR Apt with 2 Baths & Laundry

15. The Zen Duplex: Two Private Suites for Groups

The Zen Duplex: Two Private Suites for Groups
West Town
The Zen Duplex: Two Private Suites for Groups

16. Modern 1BR in Prime West Loop Location

Modern 1BR in Prime West Loop Location
Downtown Chicago
The price is AU$511
includes taxes & fees
27 Sept - 28 Sept
Modern 1BR in Prime West Loop Location

17. Bright & Spacious Boho Oasis: A Warm Retreat

Bright & Spacious Boho Oasis: A Warm Retreat
West Town
10.0 out of 10, Exceptional, (1 review)
"We had the best stay! Saw a show at United Center and it was minutes away. Close enough for short drives to the major sights. Beautiful decor and an ultra comfortable bed were a huge bonus. Always found close street parking at the end of the day. We would definitely come back!"
United States
Natalie M.
Bright & Spacious Boho Oasis: A Warm Retreat

18. Cozy Luxury 1BR - 10 Min to Downtown Chicago

Cozy Luxury 1BR - 10 Min to Downtown Chicago
Lawndale
7.8 out of 10, Good, (12 reviews)
"Don't miss out on this spot!! It's truly a must & great location!!! I really enjoyed my time here for real"
United States
Alexis R.
The price is AU$361
includes taxes & fees
7 Oct - 8 Oct
Cozy Luxury 1BR - 10 Min to Downtown Chicago

19. LIVN West Loop Chicago 2 BR City View

LIVN West Loop Chicago 2 BR City View
Downtown Chicago
9.4 out of 10, Exceptional, (12 reviews)
"Great property"
United States
duane
The price is AU$460
includes taxes & fees
27 Sept - 28 Sept
LIVN West Loop Chicago 2 BR City View

20. LIVN West Loop Chicago King Studio

LIVN West Loop Chicago King Studio
Downtown Chicago
10.0 out of 10, Exceptional, (6 reviews)
"Amazing studio apartment style room, super clean, very helpful staff, and great location."
United States
William
The price is AU$374
includes taxes & fees
27 Sept - 28 Sept
LIVN West Loop Chicago King Studio
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, 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$354 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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