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
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for West Side holiday rentals

A modern living room with a sectional sofa, a coffee table, and a dining area with chairs and a table.

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.
Modern West Loop Gem-City Views & Prime Location 2
A hotel room with a geometric-patterned wall, a bed with white bedding and a beige throw, two bedside lamps, and a window with blinds.

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 HK$4,858
HK$7,312 total
includes taxes & fees
9 Oct - 10 Oct
Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6
A modern kitchen with wooden cabinets, a stainless steel dishwasher, and a window with a view of a brick wall.

3. 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 HK$1,195
HK$3,348 total
includes taxes & fees
22 Sept - 23 Sept
Modern Zen Retreat mins from Downtown
A modern kitchen with white cabinets, a stainless steel refrigerator, a built-in oven, and a window above the sink.

4. 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
A modern bedroom with a brick wall, a large bed, a sofa, a nightstand, and a mirror.

5. 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 HK$2,055
HK$2,742 total
includes taxes & fees
27 Sept - 28 Sept
LIVN West Loop Chicago King Studio
A modern kitchen with a dishwasher, a sink, and a large island. There is a trash can and a dining area with a table and chairs.

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 HK$1,657
HK$2,571 total
includes taxes & fees
18 Oct - 19 Oct
Flexhome West Town · Spacious 2BR Duplex · Sleeps 8
A bedroom with a bed, a nightstand, a wall-mounted light fixture, and a framed picture.

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 HK$1,415
HK$3,620 total
includes taxes & fees
6 Oct - 7 Oct
Zen City Escape | Patio + Free Parking

8. Cozy Urban View Retreat Near Downtown - Sleeps 7

Cozy Urban View Retreat Near Downtown - Sleeps 7
Lawndale
The price is HK$552
HK$1,716 total
includes taxes & fees
30 Sept - 1 Oct
Cozy Urban View Retreat Near Downtown - Sleeps 7
A modern kitchen with stainless steel appliances, a dining area with a black table and red placemats, and a living area with a red sofa and black curtains.

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 HK$2,644
HK$4,191 total
includes taxes & fees
16 Oct - 17 Oct
Modern Pilsen 3BR - Near Downtown - Sleeps 10

10. The Boho House • Two Private Suites + Parking

The Boho House • Two Private Suites + Parking
West Town
The price is HK$1,916
HK$6,663 total
includes taxes & fees
29 Sept - 30 Sept
The Boho House • Two Private Suites + Parking
A compact kitchen with modern appliances, a dining table with chairs, and a living area with a sofa and a flat-screen TV.

11. 2BR Apt with 2 Baths & Laundry

2BR Apt with 2 Baths & Laundry
Near West Side
The price is HK$1,083
HK$2,294 total
includes taxes & fees
23 Sept - 24 Sept
2BR Apt with 2 Baths & Laundry
A modern living room with a grey sofa, a coffee table, a desk with a chair, a round mirror, and two framed leaf artworks on the wall.

12. Modern 1BR in Prime West Loop Location

Modern 1BR in Prime West Loop Location
Downtown Chicago
The price is HK$1,200
HK$2,725 total
includes taxes & fees
29 Sept - 30 Sept
Modern 1BR in Prime West Loop Location
A modern living room with a flat-screen TV, a wooden console, a round glass coffee table, and a beige sofa with blue cushions.

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 HK$926
HK$2,159 total
includes taxes & fees
28 Sept - 29 Sept
3BR Complete and Spacious Apartment in Ideal Spot
A living room with a sofa, coffee table, TV, and a ceiling fan.

14. 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 HK$5,254
HK$9,477 total
includes taxes & fees
11 Oct - 12 Oct
Newly Remodeled Gem | Heart of Chicago
A playground with a climbing structure and a fenced area, a parked car, and trees.

15. The Zen Duplex: Two Private Suites for Groups

The Zen Duplex: Two Private Suites for Groups
West Town
The price is HK$2,813
HK$6,886 total
includes taxes & fees
13 Oct - 14 Oct
The Zen Duplex: Two Private Suites for Groups
A modern kitchen with stainless steel appliances, including a refrigerator, oven, and microwave, and white cabinetry.

16. 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 HK$881
HK$2,967 total
includes taxes & fees
29 Sept - 30 Sept
Bright & Spacious Boho Oasis: A Warm Retreat
A modern kitchen with white cabinetry, stainless steel appliances, and a central island.

17. 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 HK$698
HK$1,938 total
includes taxes & fees
7 Oct - 8 Oct
Cozy Luxury 1BR - 10 Min to Downtown Chicago
A hotel room with a large bed, a window with a view of buildings, a nightstand with a lamp, and two framed pictures on the wall.

18. LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
9.6 out of 10, Exceptional, (23 reviews)
"Incredible location, very clean and easy! Would book again!"
United States
Andrea K.
The price is HK$1,443
HK$1,927 total
includes taxes & fees
27 Sept - 28 Sept
LIVN West Loop Chicago Queen Superior Studio
A modern room with a sofa, a dining table, and a window with a view of buildings.

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 HK$1,946
HK$2,594 total
includes taxes & fees
27 Sept - 28 Sept
LIVN West Loop Chicago 2 BR City View
A modern hotel room with a large bed, a small dining table, a bench, and a view of the city through a large window.

20. LIVN West Loop Chicago Classic Queen Studio

LIVN West Loop Chicago Classic Queen Studio
Downtown Chicago
10.0 out of 10, Exceptional, (8 reviews)
"Excellent stay. Great area and very happy with everything"
United States
Abigail B.
The price is HK$1,443
HK$1,927 total
includes taxes & fees
27 Sept - 28 Sept
LIVN West Loop Chicago Classic Queen 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

STAY

STAY

8/10 Good
"The advertisement for the room should not have included the couch as it was in a communal area. AC broke down halfway through our stay and if it wasn't for the cool weather, it would have been miserable. Amenities were replaced at least twice a day, and luckily one just happened to show up after a chair fell apart. It was adequate in all."
Chase 4-night trip
Posted less than an hour ago
STAY

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