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
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for West Side holiday rentals

1 bedroom, iron/ironing board, travel cot, WiFi

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 HK$2,110
HK$2,835 total
includes taxes & fees
9 Aug - 10 Aug
LIVN West Loop Chicago King Studio
TV, offices

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
1 bedroom, iron/ironing board, travel cot, WiFi

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 HK$1,568
HK$2,083 total
includes taxes & fees
9 Aug - 10 Aug
LIVN West Loop Chicago Queen Superior Studio
1 bedroom, iron/ironing board, travel cot, WiFi

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)
"check-in was a mess , everything else was fabulous"
United States
HollyAnn N.
The price is HK$1,812
HK$2,407 total
includes taxes & fees
9 Aug - 10 Aug
LIVN West Loop Chicago Classic Queen Studio
TV, offices

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 HK$2,282
HK$3,066 total
includes taxes & fees
9 Aug - 10 Aug
LIVN West Loop Chicago 2 BR City View
Coffee/tea maker, fridge, microwave, oven

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
Coffee/tea maker, fridge, microwave, oven

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 HK$565
HK$1,649 total
includes taxes & fees
11 Aug - 12 Aug
Luxurious, Cozy Beauty 10 min from Downtown Chicago
Exterior

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
TV

9. Bright & Spacious Boho Oasis: A Warm Retreat

Bright & Spacious Boho Oasis: A Warm Retreat
West Town
The price is HK$949
HK$3,057 total
includes taxes & fees
1 Sept - 2 Sept
Bright & Spacious Boho Oasis: A Warm Retreat
Interior

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 HK$819
HK$2,378 total
includes taxes & fees
18 Aug - 19 Aug
Sleeps 12 - Games - 10 Min to Downtown - Arcades - Walking Distance to Train
Smart TV, books

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 HK$1,502
HK$2,657 total
includes taxes & fees
20 Aug - 21 Aug
Flexhome Ukrainian Village • 2BR • Convenient Walkability · Sleeps 6
2 bedrooms, desk, iron/ironing board, free WiFi

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 HK$949
HK$1,848 total
includes taxes & fees
9 Aug - 10 Aug
Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6
TV, books

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 HK$1,423
HK$2,530 total
includes taxes & fees
13 Aug - 14 Aug
Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony
1 bedroom, iron/ironing board, travel cot, WiFi

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 HK$1,804
HK$2,427 total
includes taxes & fees
9 Aug - 10 Aug
LIVN West Loop Chicago 1 BR
TV

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 HK$1,406
HK$3,658 total
includes taxes & fees
31 Aug - 1 Sept
Zen City Escape | Patio + Free Parking
2 bedrooms, desk, iron/ironing board, WiFi

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.
Flexhome Wicker Park • Stylish 2BR • Sleeps 6
Coffee/tea maker, fridge, microwave, oven

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 HK$1,379
HK$2,519 total
includes taxes & fees
9 Aug - 10 Aug
Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6
Smart TV

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
Dining

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 HK$1,850
HK$3,833 total
includes taxes & fees
6 Aug - 7 Aug
5 Mins to Downtown CHI Sleeps 10 - Parking + Games
TV

20. Modern Zen Retreat mins from Downtown

Modern Zen Retreat mins from Downtown
West Town
The price is HK$1,770
HK$4,102 total
includes taxes & fees
16 Aug - 17 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

Hyatt Place Chicago/Wicker Park

Hyatt Place Chicago/Wicker Park

8/10 Good
"You really can't beat the view from the lounge/restaurant/bar area! Good location for Wicker Park and for seeing shows at The Salt Shed. Great places to eat nearby. Park is valet only, unfortunately, but that's Chicago in general (hotels-wise)."
Alison 2-night trip
Posted 4 hours ago
Hyatt Place Chicago/Wicker Park

Find out more about West Side

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