West Side Holiday Rentals

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Check prices for these dates

In two weeks
8 May - 10 May
In two months
19 Jun - 21 Jun
In three months
17 Jul - 19 Jul
In four months
14 Aug - 16 Aug

Our top choices for West Side holiday rentals

TV, offices

Sunlit 1BR Apartment | Warm & Welcoming Space

Sunlit 1BR Apartment | Warm & Welcoming Space
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Host was very friendly and informative. Place was clean and close to lots of fun. Trains loud and busy but knew that going in. "
United States
Tyler B.
The price is HK$1,034
HK$2,030 total
includes taxes & fees
4 May - 5 May
Sunlit 1BR Apartment | Warm & Welcoming Space
TV, offices

Modern Comfort: 1BR Unit w/ Laundry

Modern Comfort: 1BR Unit w/ Laundry
Downtown Chicago
8.8 out of 10, Excellent, (18 reviews)
"Great location, apt well equipped and host very responsive. Wonderful stay. "
United States
Gina G.
The price is HK$885
HK$1,788 total
includes taxes & fees
30 Apr - 1 May
Modern Comfort: 1BR Unit w/ Laundry
1 bedroom, iron/ironing board, travel cot, WiFi

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
9.8 out of 10, Exceptional, (10 reviews)
"Great spot next to the green line train a few restaurants and a Starbucks right up the street I will book again for sure "
United States
2k G.
The price is HK$1,246
HK$2,298 total
includes taxes & fees
27 Apr - 28 Apr
West Loop Living – Bright 1BR
Interior

Modern West Loop Gem-City Views & Prime Location 3

Modern West Loop Gem-City Views & Prime Location 3
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
"Loved the place 4 bedroom & 4 bathrooms was ideal for our stayGreat locationLoved the well stocked convenience store a block away "
United States
Tina Y.
Modern West Loop Gem-City Views & Prime Location 3
1 bedroom, WiFi, bed sheets

1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry
Downtown Chicago
8.0 out of 10, Very good, (2 reviews)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
The price is HK$1,199
HK$2,233 total
includes taxes & fees
26 May - 27 May
1BR Modern Luxe Apt with In-Unit Laundry
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
8.8 out of 10, Excellent, (3 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$917
HK$2,471 total
includes taxes & fees
4 May - 5 May
10 Minutes to Downtown Chicago - Sleeps 12 - King Beds - Games and Arcades
Interior

Your Perfect 2BR Home

Your Perfect 2BR Home
Near West Side
8.4 out of 10, Very good, (15 reviews)
"Great location! "
United States
Kourtney K.
The price is HK$768
HK$1,808 total
includes taxes & fees
27 Apr - 28 Apr
Your Perfect 2BR Home
2 bedrooms, desk, iron/ironing board, free WiFi

Flexhome Wicker Park • Stylish 2BR • Sleeps 6

Flexhome Wicker Park • Stylish 2BR • Sleeps 6
West Town
9.8 out of 10, Exceptional, (6 reviews)
"Great location. The apartment has everything you will need. Had a great time . Thanks"
United States
Wayne M.
The price is HK$509
HK$1,305 total
includes taxes & fees
26 Apr - 27 Apr
Flexhome Wicker Park • Stylish 2BR • Sleeps 6
TV, offices

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, (19 reviews)
"Everything was walking distance and had everything needed for a comfortable stay "
United States
Daniel
The price is HK$2,601
HK$6,354 total
includes taxes & fees
13 May - 14 May
Modern West Loop Gem-City Views & Prime Location 6
Interior

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$552
HK$2,042 total
includes taxes & fees
27 Apr - 28 Apr
Sleeps 12 - Games - 10 Min to Downtown - Arcades - Walking Distance to Train
Interior

Game Theme Apt + Free Parking

Game Theme Apt + Free Parking
Lawndale
The price is HK$426
HK$1,544 total
includes taxes & fees
5 May - 6 May
Game Theme Apt + Free Parking
Dining

Urban Comfort • 2BR in West Town

Urban Comfort • 2BR in West Town
West Town
9.6 out of 10, Exceptional, (8 reviews)
"The place was very clean and accommodating."
United States
Mark E.
The price is HK$768
HK$1,778 total
includes taxes & fees
26 Apr - 27 Apr
Urban Comfort • 2BR in West Town
2 bedrooms, desk, iron/ironing board, free WiFi

Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony

Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony
West Town
9.6 out of 10, Exceptional, (11 reviews)
"Great size space and very comfortable!"
United States
Jennifer H.
The price is HK$1,254
HK$2,292 total
includes taxes & fees
14 May - 15 May
Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony
TV, offices

Upscale 4BR Retreat: Wicker Park

Upscale 4BR Retreat: Wicker Park
West Town
8.6 out of 10, Excellent, (9 reviews)
"Great place in a great area. Would definitely stay here again!"
United States
John R.
The price is HK$1,473
HK$3,776 total
includes taxes & fees
26 Apr - 27 Apr
Upscale 4BR Retreat: Wicker Park
Interior

3BR Complete and Spacious Apt

3BR Complete and Spacious Apt
West Town
8.0 out of 10, Very good, (15 reviews)
"Great location and a nice property! Quiet, clean and a very reasonable rate. 👍"
United States
Christopher
The price is HK$1,403
HK$2,775 total
includes taxes & fees
11 May - 12 May
3BR Complete and Spacious Apt
Iron/ironing board, WiFi, bed sheets

Cabin 104 by 747 Lofts

Cabin 104 by 747 Lofts
West Town
10.0 out of 10, Exceptional, (9 reviews)
"The place was great"
United States
bonnie c.
The price is HK$1,052
HK$2,412 total
includes taxes & fees
4 May - 5 May
Cabin 104 by 747 Lofts
Interior

Chicago Third Floor Studio by 747 Lofts

Chicago Third Floor Studio by 747 Lofts
2.0 star property
West Town
9.8 out of 10, Exceptional, (7 reviews)
"Clean, easy to check in, all the household items you’d expect"
United States
Jason
The price is HK$1,713
HK$4,873 total
includes taxes & fees
9 May - 10 May
Chicago Third Floor Studio by 747 Lofts
Microwave, oven, stovetop, dishwasher

Modern Pilsen Apt 3 Bedrooms

Modern Pilsen Apt 3 Bedrooms
Lower West Side
8.0 out of 10, Very good, (1 review)
"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.
The price is HK$987
HK$2,741 total
includes taxes & fees
30 Apr - 1 May
Modern Pilsen Apt 3 Bedrooms
Exterior

New Rehab, FREE street parking, LAUNDRY, Mins to Downtown

New Rehab, FREE street parking, LAUNDRY, Mins to Downtown
West Town
10.0 out of 10, Exceptional, (1 review)
"We loved this spot! The home was clean, and the beds were comfortable. The kitchen was well stocked. The neighborhood is wonderful. Highly recommend."
United States
LeighAnn G.
The price is HK$1,234
HK$2,838 total
includes taxes & fees
10 May - 11 May
New Rehab, FREE street parking, LAUNDRY, Mins to 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

LIVN - West Loop Chicago

LIVN - West Loop Chicago

10/10 Excellent
"The room was spacious and clean. I was comfortable and felt safe. The availability of lockers to store my luggage was beneficial. The location near the train station and places to eat was great. I would stay again."
Bryon 1-night trip
Posted 13 hours ago
LIVN - West Loop Chicago

Find out more about West Side

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