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
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for West Side holiday rentals

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

LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
9.2 out of 10, Wonderful, (14 reviews)
"Highly recommend! Will be staying here again."
United States
Sheila M.
The price is HK$1,443
HK$1,897 total
includes taxes & fees
26 Jul - 27 Jul
LIVN West Loop Chicago Queen Superior Studio
TV, offices

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 HK$3,223
HK$7,238 total
includes taxes & fees
9 Aug - 10 Aug
Modern West Loop Gem-City Views & Prime Location 4
1 bedroom, iron/ironing board, travel cot, WiFi

LIVN West Loop Chicago Classic Queen Studio

LIVN West Loop Chicago Classic Queen Studio
Downtown Chicago
10.0 out of 10, Exceptional, (6 reviews)
The price is HK$1,262
HK$1,676 total
includes taxes & fees
26 Jul - 27 Jul
LIVN West Loop Chicago Classic Queen Studio
TV, offices

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 HK$1,521
HK$1,999 total
includes taxes & fees
26 Jul - 27 Jul
LIVN West Loop Chicago 2 BR City View
Coffee/tea maker, fridge, microwave, oven

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$612
HK$1,704 total
includes taxes & fees
11 Aug - 12 Aug
Luxurious, Cozy Beauty 10 min from Downtown Chicago
Interior

10 Minutes to Downtown Chicago - Sleeps 12 - King Beds - Games and Arcades

10 Minutes to Downtown Chicago - Sleeps 12 - King Beds - Games and Arcades
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 HK$1,178
HK$2,810 total
includes taxes & fees
27 Jul - 28 Jul
10 Minutes to Downtown Chicago - Sleeps 12 - King Beds - Games and Arcades
Interior

Cabin 105 by 747 Lofts

Cabin 105 by 747 Lofts
West Town
6.8 out of 10, (8 reviews)
"Such a great stay ! Bed was smaller than we thought ,but had a couch that turned into a pull out bed . Close to a lot of coffee shops ,food , a couple bars . The Blue line train was also near by an easy hop on to down town . Would recommend this stay."
United States
Guadalupe N.
The price is HK$730
HK$1,543 total
includes taxes & fees
28 Jul - 29 Jul
Cabin 105 by 747 Lofts
Coffee/tea maker, microwave, oven, stovetop

Modern 3 BR Apt - 5 Mins to Downtown Sleeps 10

Modern 3 BR Apt - 5 Mins to 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$1,390
HK$3,295 total
includes taxes & fees
28 Jul - 29 Jul
Modern 3 BR Apt - 5 Mins to Downtown Sleeps 10
Smart TV

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 HK$1,404
HK$4,034 total
includes taxes & fees
3 Aug - 4 Aug
Newly Remodeled Gem | Heart of Chicago
Smart TV, fireplace, video game console, books

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 HK$3,340
HK$7,418 total
includes taxes & fees
6 Aug - 7 Aug
Ukrainian Village 3BR/3BA • Private Patio, Parking
Exterior

Cabin 201 by 747 Lofts

Cabin 201 by 747 Lofts
West Town
8.4 out of 10, Very good, (5 reviews)
"Great spot. Pictures don’t do it justice. Close to cool neighbors as well. Definitely plan to stay again soon. "
United States
Patrick B.
Cabin 201 by 747 Lofts
Terrace/patio

Sleeps 18 • 7BR • Gym • Game Room • Theater

Sleeps 18 • 7BR • Gym • Game Room • Theater
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 HK$6,655
HK$14,939 total
includes taxes & fees
2 Aug - 3 Aug
Sleeps 18 • 7BR • Gym • Game Room • Theater
Coffee/tea maker, microwave, oven, stovetop

Modern Pilsen Apt 3 Bedrooms

Modern Pilsen Apt 3 Bedrooms
Lower West Side
5.0 out of 10, (2 reviews)
"Everything was wonderful except the bathroom. When we checked in there was quite a bit of hair on the floor of the bathroom and in the tub. Everything else was very clean. Beds comfortable. Water pressure good. Felt safe in the area. Hard to find a parking spot Friday night. The kids had fun with all the games. "
United States
Naomi D.
Modern Pilsen Apt 3 Bedrooms
Dining

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$1,959
HK$3,983 total
includes taxes & fees
6 Aug - 7 Aug
5 Mins to Downtown CHI Sleeps 10 - Parking + Games
Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,227 reviews)
"Great location. Great views of the lake. Great pool, lounge area. Great restaurants right next door."
United States
Patricia
The price is HK$1,249
HK$1,696 total
includes taxes & fees
23 Aug - 24 Aug
Sentral Michigan Avenue
Full-sized fridge, microwave, oven, stovetop

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (507 reviews)
"Perfect location"
United States
Diana
The price is HK$2,202
HK$2,779 total
includes taxes & fees
18 Aug - 19 Aug
Level Chicago – Old Town
Dining

LIVN Millennium Park Downtown Chicago Prem Studio

LIVN Millennium Park Downtown Chicago Prem Studio
Downtown Chicago
10.0 out of 10, Exceptional, (3 reviews)
"The check in and out process was very quick. Communication with the host was great. "
United States
Raquel W.
The price is HK$2,603
HK$3,521 total
includes taxes & fees
28 Jul - 29 Jul
LIVN Millennium Park Downtown Chicago Prem Studio
Fitness facility

South Loop Rooftop With In & Out Parking 1

South Loop Rooftop With In & Out Parking 1
Downtown Chicago
9.0 out of 10, Wonderful, (2 reviews)
"We loved the property! It was well kept, clean, with a seamless check in and check out process! I wish the parking garage would have been closer but otherwise everything was great! Shout out to the host for his promptness with all my questions! I would recommend this place if they are looking for a place to stay! "
United States
Bridney K.
The price is HK$2,094
HK$4,752 total
includes taxes & fees
29 Jul - 30 Jul
South Loop Rooftop With In & Out Parking 1
Interior

River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.8 out of 10, Exceptional, (7 reviews)
"Not a bad thing to say about this experience. Host was extremely responsive and helpful, looked exactly like the pictures, had everything we needed, location was perfect and the included parking was such a perk! Highly recommend staying here. I hope to be back! "
United States
Kara B.
The price is HK$2,078
HK$4,742 total
includes taxes & fees
19 Aug - 20 Aug
River North Rooftop With In and Out Parking 3
Interior

Premium Urban 4BR - Perfect Mix of Comfort & Location

Premium Urban 4BR - Perfect Mix of Comfort & Location
Near North Side
10.0 out of 10, Exceptional, (3 reviews)
"Nice place, clean property, great views "
United States
Zach L.
The price is HK$5,473
HK$9,598 total
includes taxes & fees
2 Aug - 3 Aug
Premium Urban 4BR - Perfect Mix of Comfort & Location
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

8/10 Good
"It’s a nice hotel in a good area. Nice rooftop too."
Raul 3-night trip
Posted less than an hour ago
Nobu Hotel Chicago

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