Holiday Homes in West Side

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Check prices for these dates

In two weeks
12 Sept - 14 Sept
In two months
24 Oct - 26 Oct
In three months
21 Nov - 23 Nov
In four months
19 Dec - 21 Dec

Featured Holiday Homes in West Side

Our top choices for West Side holiday homes

Stylish 1BR in West Loop
Fridge, microwave, oven, stovetop

Stylish 1BR in West Loop

10.0 out of 10, Exceptional, (5)
The price is AU$369
includes taxes & fees
1 Sept - 2 Sept
Stylish 1BR in West Loop
Sun-Drenched 1BR Apartment
Fridge, microwave, oven, stovetop

Sun-Drenched 1BR Apartment

The price is AU$338
includes taxes & fees
3 Sept - 4 Sept
Sun-Drenched 1BR Apartment
NEW Private West Loop 1br with Backyard near Green Line and CTA
Fridge, microwave, oven, stovetop

NEW Private West Loop 1br with Backyard near Green Line and CTA

9.0 out of 10, Wonderful, (2)
"The apartment was clean and the host was very responsive and helpful. "
The price is AU$320
includes taxes & fees
9 Sept - 10 Sept
NEW Private West Loop 1br with Backyard near Green Line and CTA
3BR Complete and Spacious Apt
TV

3BR Complete and Spacious Apt

9.6 out of 10, Exceptional, (4)
"Spacious and well appointed. Great location with plenty of eating/drinking options within walking distance. "
The price is AU$372
includes taxes & fees
2 Sept - 3 Sept
3BR Complete and Spacious Apt
Urban Comfort • 2BR in West Town
2 bedrooms, iron/ironing board, travel cot, WiFi

Urban Comfort • 2BR in West Town

10.0 out of 10, Exceptional, (2)
"Very clean. Host was exceptionally communicative. Would stay again!"
The price is AU$370
includes taxes & fees
1 Sept - 2 Sept
Urban Comfort • 2BR in West Town
Modern 3 BR Apt - 5 Mins to Downtown Sleeps 10
Exterior

Modern 3 BR Apt - 5 Mins to Downtown Sleeps 10

The price is AU$475
includes taxes & fees
2 Sept - 3 Sept
Modern 3 BR Apt - 5 Mins to Downtown Sleeps 10
HUGE! 3BR Private Home+Garage+360° Roof Deck+Hot Tub+EV+Sleeps 12
Outdoor dining

HUGE! 3BR Private Home+Garage+360° Roof Deck+Hot Tub+EV+Sleeps 12

10.0 out of 10, Exceptional, (9)
"Great property and very kind and responsive hosts. I would be happy to stay here again. "
The price is AU$1,840
includes taxes & fees
17 Sept - 18 Sept
HUGE! 3BR Private Home+Garage+360° Roof Deck+Hot Tub+EV+Sleeps 12
The One: A 1BR Stay That Feels Like Home
Fridge, microwave, oven, stovetop

The One: A 1BR Stay That Feels Like Home

8.0 out of 10, Very good, (1)
"The apartment looked exactly like the pictures and was very well kept. Everything was clean and functional and we didn’t have any issues. The neighborhood is very quiet and safe and also has a target nearby for quick grocery trips. Connectivity wise, there’s a busy stop within walking distance but no train stations.The host was also very responsive and helpful. We didn’t have any trouble checking in or checking out.Overall a great experience and comfortable stay."
The price is AU$335
includes taxes & fees
2 Sept - 3 Sept
The One: A 1BR Stay That Feels Like Home
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
Exterior detail

Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.

2.0 star property
10.0 out of 10, Exceptional, (9)
"Very clean in a safe neighborhood. I would stay here again"
The price is AU$310
includes taxes & fees
2 Sept - 3 Sept
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
Cozy house in the city
Outdoor dining

Cozy house in the city

2.0 star property
8.8 out of 10, Excellent, (3)
"it was nice"
The price is AU$617
includes taxes & fees
4 Sept - 5 Sept
Cozy house in the city
4BR Retreat w/ Theater, Game Room & Backyard
Dining

4BR Retreat w/ Theater, Game Room & Backyard

8.0 out of 10, Very good, (8)
The price is AU$777
includes taxes & fees
23 Sept - 24 Sept
4BR Retreat w/ Theater, Game Room & Backyard
Great Layout – Spacious 2BR Apt
Fridge, microwave, oven, stovetop

Great Layout – Spacious 2BR Apt

10.0 out of 10, Exceptional, (3)
"Clean, comfortable, and would definitely stay again!"
The price is AU$404
includes taxes & fees
21 Sept - 22 Sept
Great Layout – Spacious 2BR Apt
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Dining

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

9.6 out of 10, Exceptional, (49)
"We had a short stay in this property and we wished it could have been longer. The house was very nice, clean and the communication was great!! It is a short drive to the airport and to downtown. We would definitely stay here again"
The price is AU$493
includes taxes & fees
21 Sept - 22 Sept
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
2BR, Sleeps7 • Coffee Station, Backyard w/ Grill
Travel cot, free WiFi, bed sheets

2BR, Sleeps7 • Coffee Station, Backyard w/ Grill

The price is AU$592
includes taxes & fees
2 Sept - 3 Sept
2BR, Sleeps7 • Coffee Station, Backyard w/ Grill
Charming 2-bedroom house with WiFi in peaceful Hazel Crest
Fridge, microwave, oven, stovetop

Charming 2-bedroom house with WiFi in peaceful Hazel Crest

7.4 out of 10, Good, (8)
"The property was very spacious and clean and customer service is very responsive and quick. "
The price is AU$465
includes taxes & fees
2 Sept - 3 Sept
Charming 2-bedroom house with WiFi in peaceful Hazel Crest
Master qtr close to nature & easy urban facilities
Exterior detail

Master qtr close to nature & easy urban facilities

9.8 out of 10, Exceptional, (61)
"Great spot."
The price is AU$315
includes taxes & fees
3 Sept - 4 Sept
Master qtr close to nature & easy urban facilities
Cozy Studio in Portage Park
Iron/ironing board, travel cot, WiFi, bed sheets

Cozy Studio in Portage Park

The price is AU$291
includes taxes & fees
1 Sept - 2 Sept
Cozy Studio in Portage Park
Enamored in Elmhurst
Smart TV

Enamored in Elmhurst

2.0 star property
10.0 out of 10, Exceptional, (12)
"Great stay"
The price is AU$764
includes taxes & fees
2 Sept - 3 Sept
Enamored in Elmhurst
Relaxing Chicago Studio
Desk, iron/ironing board, WiFi, bed sheets

Relaxing Chicago Studio

10.0 out of 10, Exceptional, (8)
"Had a great stay. Great location. "
The price is AU$296
includes taxes & fees
29 Sept - 30 Sept
Relaxing Chicago Studio
Comfortable 2BR Chicago Apt
2 bedrooms, iron/ironing board, WiFi, bed sheets

Comfortable 2BR Chicago Apt

9.6 out of 10, Exceptional, (4)
"Perfect location for our trip. Very functional and comfortable. "
The price is AU$363
includes taxes & fees
10 Sept - 11 Sept
Comfortable 2BR Chicago Apt
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

Find out more about West Side

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West Side Holiday Homes information

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