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Vacation Homes in West Side

Stylish 1BR in West Loop

10.0 out of 10, Exceptional, (5)
The price is ¥16,604
¥33,908 total
includes taxes & fees
Sep 3 - Sep 4
Stylish 1BR in West Loop

Sun-Drenched 1BR Apartment

The price is ¥16,604
¥33,908 total
includes taxes & fees
Sep 3 - Sep 4
Sun-Drenched 1BR Apartment

Stylish Evanston Retreat Near NU & Lakefront

The price is ¥31,319
¥73,186 total
includes taxes & fees
Sep 1 - Sep 2
Stylish Evanston Retreat Near NU & Lakefront

2 Connecting Suites at a 4⭐️ Hotel

The price is ¥80,926
¥109,225 total
includes taxes & fees
Sep 1 - Sep 2
2 Connecting Suites at a 4⭐️ Hotel

2 Connecting Suites at a 5⭐️ Hotel

The price is ¥390,329
¥526,786 total
includes taxes & fees
Sep 1 - Sep 2
2 Connecting Suites at a 5⭐️ Hotel

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 ¥5,525
¥30,512 total
includes taxes & fees
Sep 9 - Sep 10
NEW Private West Loop 1br with Backyard near Green Line and CTA

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 ¥23,951
¥47,648 total
includes taxes & fees
Sep 22 - Sep 23
3BR Complete and Spacious Apt

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 ¥16,250
¥35,422 total
includes taxes & fees
Sep 1 - Sep 2
Urban Comfort • 2BR in West Town

Modern 3 BR Apt - 5 Mins to Downtown Sleeps 10

Modern 3 BR Apt - 5 Mins to Downtown Sleeps 10

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

10.0 out of 10, Exceptional, (8)
"Great property and very kind and responsive hosts. I would be happy to stay here again. "
The price is ¥57,172
¥126,874 total
includes taxes & fees
Aug 27 - Aug 28
HUGE! 3BR Private Home+Garage+360° Roof Deck+Hot Tub+EV+Sleeps 12

Charming 1BR Apt in Evanston

The price is ¥12,931
¥28,577 total
includes taxes & fees
Sep 2 - Sep 3
Charming 1BR Apt in Evanston

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 ¥15,282
¥32,177 total
includes taxes & fees
Sep 3 - Sep 4
The One: A 1BR Stay That Feels Like Home

Cozy Room with Rooftop Lounge & City Views in River North

10.0 out of 10, Exceptional, (1)
"The hotel was very nice and the location was excellent. Was able to walk to many locations. Noise wasn't bad for a city experience. Hotel restaurant was very good."
The price is ¥25,528
¥37,270 total
includes taxes & fees
Sep 1 - Sep 2
Cozy Room with Rooftop Lounge & City Views in River North

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

2.0 star property
10.0 out of 10, Exceptional, (7)
"Very clean in a safe neighborhood. I would stay here again"
The price is ¥21,027
¥29,311 total
includes taxes & fees
Aug 28 - Aug 29
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.

Oak Park IL · Charming Retro 2BR Cottage/Train/Laundry/FREE PKG

2.0 star property
9.6 out of 10, Exceptional, (9)
"Lovely little cottage in great location with excellent restaurants close by. Had everything we needed for our stay. Kitchen was perfectly equipped and having the washer dryer was such a bonus. The communication with the landlord was very good. Would absolutely stay here again. "
The price is ¥16,841
¥42,534 total
includes taxes & fees
Aug 27 - Aug 28
Oak Park IL · Charming Retro 2BR Cottage/Train/Laundry/FREE PKG

Getaway Near ORD With Great Local Amenities

8.8 out of 10, Excellent, (3)
"Very nice and clean place to stay at. Great communication from property manager. I would absolutely stay here again!"
Getaway Near ORD With Great Local Amenities

Cozy house in the city

2.0 star property
8.8 out of 10, Excellent, (3)
"it was nice"
The price is ¥26,052
¥58,523 total
includes taxes & fees
Sep 1 - Sep 2
Cozy house in the city

Chic Studio in Heart of Chicago

10.0 out of 10, Exceptional, (1)
The price is ¥13,078
¥29,231 total
includes taxes & fees
Aug 27 - Aug 28
Chic Studio in Heart of Chicago

Guesthouse Gem 2BR, Smart TVs, W/D, & Parking

10.0 out of 10, Exceptional, (1)
"Very quiet and private and cl9se to alot of things "
The price is ¥14,767
¥40,451 total
includes taxes & fees
Sep 1 - Sep 2
Guesthouse Gem 2BR, Smart TVs, W/D, & Parking

4BR Retreat w/ Theater, Game Room & Backyard

8.0 out of 10, Very Good, (8)
The price is ¥8,599
¥73,203 total
includes taxes & fees
Sep 23 - Sep 24
4BR Retreat w/ Theater, Game Room & Backyard
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

Find out more about West Side

West Side Vacation Homes information

Number of reviews
54
Accommodation
82 Vacation Homes
Lowest Price
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