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

West Side Vacation Rentals

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Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for West Side vacation rentals

TV, offices

1. 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.
The price is ￥65,376
￥148,025 total
includes taxes & fees
Aug 2 - Aug 3
Modern West Loop Gem-City Views & Prime Location 6
TV, offices

2. 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)
"We spent most of this trip discussing our NEXT trip - this stay was one of the simplest, easiest, and most satisfying we've ever experienced with a short-term rental. Hands-down will stay again!Unit incredibly clean, close proximity to the areas we needed to be in, and the host was next-level communicative and kind! Thank you for making it so easy for us!"
United States
Stephanie G.
The price is ￥58,977
￥79,722 total
includes taxes & fees
Aug 5 - Aug 6
LIVN West Loop Chicago 2 BR City View
TV, offices

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

Modern West Loop Gem-City Views & Prime Location 4
Downtown Chicago
9.6 out of 10, Exceptional, (12 reviews)
"Amazing accommodation"
United States
Jiri N.
The price is ￥98,022
￥192,548 total
includes taxes & fees
Aug 13 - Aug 14
Modern West Loop Gem-City Views & Prime Location 4
1 bedroom, iron/ironing board, travel crib, WiFi

4. LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
9.2 out of 10, Wonderful, (15 reviews)
"Highly recommend! Will be staying here again."
United States
Sheila M.
The price is ￥38,229
￥51,736 total
includes taxes & fees
Aug 5 - Aug 6
LIVN West Loop Chicago Queen Superior Studio
TV, offices

5. Modern West Loop Gem-City Views & Prime Location 5

Modern West Loop Gem-City Views & Prime Location 5
Downtown Chicago
9.0 out of 10, Wonderful, (6 reviews)
"Great location, plenty of space and clean home. "
United States
Brittany T.
The price is ￥70,086
￥154,246 total
includes taxes & fees
Aug 10 - Aug 11
Modern West Loop Gem-City Views & Prime Location 5
1 bedroom, iron/ironing board, travel crib, WiFi

6. 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 ￥39,536
￥52,664 total
includes taxes & fees
Aug 6 - Aug 7
LIVN West Loop Chicago King Studio
1 bedroom, iron/ironing board, travel crib, WiFi

7. 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 ￥57,996
￥78,372 total
includes taxes & fees
Aug 5 - Aug 6
LIVN West Loop Chicago Classic Queen Studio
Coffee/tea maker, fridge, microwave, oven

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

Flexhome East Village • Modern 2BR • Quiet Street
West Town
9.8 out of 10, Exceptional, (21 reviews)
"Location was great for everything we were doing in Chicago. "
United States
Tom W.
Flexhome East Village • Modern 2BR • Quiet Street
Terrace/patio

9. 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
9.6 out of 10, Exceptional, (5 reviews)
"Comfortable apartment and the rooftop deck was a great bonus. Street parking was convenient. Would absolutely stay again. "
United States
Dennis R.
The price is ￥36,412
￥62,532 total
includes taxes & fees
Aug 9 - Aug 10
Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6
1 bedroom, iron/ironing board, travel crib, WiFi

10. 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.
LIVN West Loop Chicago 1 BR
Dining

11. 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 ￥38,205
￥79,392 total
includes taxes & fees
Aug 6 - Aug 7
5 Mins to Downtown CHI Sleeps 10 - Parking + Games
Smart TV, fireplace, video-game console, books

12. Ukrainian Village 3BR/3BA • Private Patio, Parking

Ukrainian Village 3BR/3BA • Private Patio, Parking
West Town
10.0 out of 10, Exceptional, (37 reviews)
"Wonderful place, great neighborhood, lots of space! "
United States
Caleb V.
The price is ￥45,550
￥120,883 total
includes taxes & fees
Aug 30 - Aug 31
Ukrainian Village 3BR/3BA • Private Patio, Parking
2 bedrooms, desk, iron/ironing board, WiFi (free)

13. 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 ￥25,067
￥46,253 total
includes taxes & fees
Aug 9 - Aug 10
Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6
Interior

14. Karlov Inn | Stylish Chicago 2BR Retreat

Karlov Inn | Stylish Chicago 2BR Retreat
Humboldt Park
9.0 out of 10, Wonderful, (16 reviews)
"Great place, clean and comfy. "
United States
Reann J.
The price is ￥47,189
￥105,474 total
includes taxes & fees
Aug 16 - Aug 17
Karlov Inn | Stylish Chicago 2BR Retreat
Exterior

15. 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
The price is ￥21,083
￥39,995 total
includes taxes & fees
Aug 5 - Aug 6
Cabin 208 by 747 Lofts
Smart TV

16. 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.
The price is ￥26,380
￥79,775 total
includes taxes & fees
Aug 3 - Aug 4
Newly Remodeled Gem | Heart of Chicago
2 bedrooms, desk, iron/ironing board, WiFi

17. 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 ￥25,067
￥46,253 total
includes taxes & fees
Aug 9 - Aug 10
Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony
2 bedrooms, desk, iron/ironing board, WiFi (free)

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

Flexhome Wicker Park • Stylish 2BR • Sleeps 6
West Town
9.8 out of 10, Exceptional, (8 reviews)
"Very cute spot in an amazing location!! The instructions were very clear, and getting in and out of the unit was simple and secure."
United States
Anonymous traveler
The price is ￥24,407
￥45,485 total
includes taxes & fees
Aug 10 - Aug 11
Flexhome Wicker Park • Stylish 2BR • Sleeps 6
Coffee/tea maker, fridge, microwave, oven

19. 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 ￥12,092
￥34,792 total
includes taxes & fees
Aug 4 - Aug 5
Luxurious, Cozy Beauty 10 min from Downtown Chicago
Coffee/tea maker, fridge, microwave, oven

20. 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)
"Great space, comfortable bed, and the private rooftop was a highlight. Appreciated the quick messaging responses."
United States
EricMolly W.
The price is ￥36,412
￥62,532 total
includes taxes & fees
Aug 9 - Aug 10
Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6
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

Nobu Hotel Chicago

Nobu Hotel Chicago

10/10 Excellent
"Great location, clean, stylish, large rooms. No spa, minimal lobby but excellent rooftop and restaurant of course."
Mitchell 3-night trip
Posted 11 hours ago
Nobu Hotel Chicago

Find out more about West Side

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