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

West Side Holiday Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for West Side holiday rentals

A modern living room with a flat-screen TV, a sofa, a coffee table, and a dining area with a bar stool.

1. 3BR Complete and Spacious Apartment in Ideal Spot

3BR Complete and Spacious Apartment in Ideal Spot
West Town
8.4 out of 10, Very good, (25 reviews)
"My wife and I stayed here when we came to town for a concert at the united center. We actually walked to the venue and it was about 45 mins, a lovely walk. It was a very convenient location, lovely apartment, and the host communicated very well. Check in and out was easy. Great neighborhood. Would definitely stay here again."
United States
Francis
The price is AU$297
includes taxes & fees
11 Nov - 12 Nov
3BR Complete and Spacious Apartment in Ideal Spot
A modern kitchen with a central island, stainless steel dishwasher, pendant lighting, and hardwood flooring.

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

Flexhome West Town · Spacious 2BR Duplex · Sleeps 8
West Town
10.0 out of 10, Exceptional, (3 reviews)
"Thank you. We had a wonderful stay."
United States
Janice G.
The price is AU$338
includes taxes & fees
1 Dec - 2 Dec
Flexhome West Town · Spacious 2BR Duplex · Sleeps 8
A modern kitchen with a large island, coffee maker, and a view of the city.

3. Skyline View Apt - 5 minutes to Downtown - Games + Arcades - Free Parking

Skyline View Apt - 5 minutes to Downtown - Games + Arcades - Free Parking
Lower West Side
8.8 out of 10, Excellent, (6 reviews)
"Incredible place. Awesome neighborhood. Easy access to the freeways. Great neighborhood with tons of great local dining."
United States
Chad
The price is AU$466
includes taxes & fees
30 Nov - 1 Dec
Skyline View Apt - 5 minutes to Downtown - Games + Arcades - Free Parking
Private kitchen

4. Convenient 2BR Apt w/ In-Unit Laundry

Convenient 2BR Apt w/ In-Unit Laundry
West Town
The price is AU$406
includes taxes & fees
19 Nov - 20 Nov
Convenient 2BR Apt w/ In-Unit Laundry
A dining area with a table set for two, a bottle of wine, and a candle. A cityscape view is visible through a window.

5. Pilsen Sweet Life Up High

Pilsen Sweet Life Up High
Lower West Side
The price is AU$333
includes taxes & fees
19 Nov - 20 Nov
Pilsen Sweet Life Up High
A living room with a flat-screen TV, a round wooden coffee table, a sofa, and a potted plant.

6. Comfy 2 Bedroom - Games - 1 Garage Spot - Sleeps 6

Comfy 2 Bedroom - Games - 1 Garage Spot - Sleeps 6
Lawndale
The price is AU$322
includes taxes & fees
11 Nov - 12 Nov
Comfy 2 Bedroom - Games - 1 Garage Spot - Sleeps 6
A modern kitchen with grey cabinetry, a central island, and a built-in dishwasher.

7. 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.
The price is AU$639
includes taxes & fees
16 Nov - 17 Nov
Bright & Spacious Boho Oasis: A Warm Retreat
A bedroom with a bed, a desk, a chair, a TV, and a window with blinds.

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$255
includes taxes & fees
24 Nov - 25 Nov
Flexhome Wicker Park • Stylish 2BR • Sleeps 6
A hallway with a wooden floor, a white rug, and framed artwork on the walls.

9. 4BR Flat By Douglass Park & Transit - Free parking

4BR Flat By Douglass Park & Transit - Free parking
Lawndale
The price is AU$472
includes taxes & fees
11 Nov - 12 Nov
4BR Flat By Douglass Park & Transit - Free parking
A modern kitchen with a central island, stainless steel appliances, and a brick backsplash.

10. Modern Zen Retreat mins from Downtown

Modern Zen Retreat mins from Downtown
West Town
10.0 out of 10, Exceptional, (3 reviews)
"Perfect place to stay! We would definitely come back when we're in Chicago again."
United States
Caley C.
The price is AU$654
includes taxes & fees
11 Nov - 12 Nov
Modern Zen Retreat mins from Downtown
A room with a checkered table, a potted plant, and a bunk bed in the background.

11. Spacious Group Stay - Sleeps 12 - 3 Kings + Arcades - 10 Min to Downtown

Spacious Group Stay - Sleeps 12 - 3 Kings + Arcades - 10 Min to Downtown
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$461
includes taxes & fees
18 Nov - 19 Nov
Spacious Group Stay - Sleeps 12 - 3 Kings + Arcades - 10 Min to Downtown
A modern living room with a sofa, coffee table, and artwork on the walls.

12. Peaceful Zen Flat | 2BR Oasis with Free Parking

Peaceful Zen Flat | 2BR Oasis with Free Parking
West Town
10.0 out of 10, Exceptional, (8 reviews)
"The host was quick to respond, the place was nice and clean and there is a parking spot in the back"
United States
Gene H.
The price is AU$653
includes taxes & fees
7 Dec - 8 Dec
Peaceful Zen Flat | 2BR Oasis with Free Parking
A modern kitchen with white cabinetry, stainless steel appliances, and pendant lighting.

13. Peaceful Boho Retreat | Free Private Parking

Peaceful Boho Retreat | Free Private Parking
West Town
The price is AU$576
includes taxes & fees
16 Nov - 17 Nov
Peaceful Boho Retreat | Free Private Parking
A modern hotel room with a large bed, a small dining table, a bench, and a view of the city through a large window.

14. LIVN West Loop Chicago Classic Queen Studio

LIVN West Loop Chicago Classic Queen Studio
Downtown Chicago
9.8 out of 10, Exceptional, (9 reviews)
"Excellent stay. Great area and very happy with everything"
United States
Abigail B.
The price is AU$263
includes taxes & fees
11 Nov - 12 Nov
LIVN West Loop Chicago Classic Queen Studio
A neatly made bed with a headboard, two bedside tables with lamps, a wall-mounted artwork, and a patterned rug.

15. West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
The price is AU$348
includes taxes & fees
11 Nov - 12 Nov
West Loop Living – Bright 1BR
A modern kitchen with white cabinetry, stainless steel appliances, and pendant lighting.

16. Boho City Escape | Parking + Balcony

Boho City Escape | Parking + Balcony
West Town
The price is AU$695
includes taxes & fees
16 Nov - 17 Nov
Boho City Escape | Parking + Balcony
A modern living room with a sofa, coffee table, and a dining area with chairs and a table.

17. West Town 2BR | Full Kitchen + In-Unit Laundry

West Town 2BR | Full Kitchen + In-Unit Laundry
West Town
The price is AU$351
includes taxes & fees
16 Nov - 17 Nov
West Town 2BR | Full Kitchen + In-Unit Laundry
A modern living room with a sectional sofa, a dining table with chairs, and large windows offering city views.

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

Modern West Loop Gem-City Views & Prime Location 4
Downtown Chicago
9.4 out of 10, Exceptional, (15 reviews)
"Amazing accommodation"
United States
Jiri N.
The price is AU$972
includes taxes & fees
19 Nov - 20 Nov
Modern West Loop Gem-City Views & Prime Location 4
A cozy outdoor seating area with Adirondack chairs around a fire pit, string lights overhead, and a house in the background.

19. Firepit • Game Room • Theater • Gym • Sleeps 18

Firepit • Game Room • Theater • Gym • Sleeps 18
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$1,328
includes taxes & fees
11 Nov - 12 Nov
Firepit • Game Room • Theater • Gym • Sleeps 18
A modern kitchen with a central island, stainless steel dishwasher, pendant lighting, and hardwood flooring.

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

Flexhome West Town Spacious 2BR Duplex · Sleeps 8
West Town
8.0 out of 10, Very good, (1 review)
"We really liked staying at this property and would do so again in a heartbeat except for one major hesitation. The AC unit condensate pipe had come loose and was pouring water into the floorboard downstairs. Meaning most of our stay wound up with the basement being extremely humid and damp and generally not pleasant to be in. We notified the host promptly and it took 2 days for the landlord to have maintenance come out and address the issue once it was addressed. Everything was good from there...
United States
Lucas C.
The price is AU$327
includes taxes & fees
1 Dec - 2 Dec
Flexhome West Town Spacious 2BR Duplex · Sleeps 8
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

Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

10/10 Excellent
"Location was perfect for our stay. Easy in and out. Room was spacious and clean."
Janet 2-night trip
Posted 5 hours ago
Crowne Plaza Chicago West Loop by IHG

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$290 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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