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Check prices for these dates

In two weeks
May 29 - May 31
In two months
Jul 10 - Jul 12
In three months
Aug 7 - Aug 9
In four months
Sep 4 - Sep 6

Our top choices for West Side vacation homes

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

Aloha 2.0 Tropical Oasis in the heart of Wicker Park that sleeps 23 + backyard patio

Aloha 2.0 Tropical Oasis in the heart of Wicker Park that sleeps 23 + backyard patio
West Town
10.0 out of 10, Exceptional, (12 reviews)
"We booked this apartment and their other one for a bachelorette. It was such an amazing time and everything Was so thoughtful . Perfect location too!"
United States
Lita T.
Aloha 2.0 Tropical Oasis in the heart of Wicker Park that sleeps 23 + backyard patio
Property grounds

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

Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
Robertsdale
9.6 out of 10, Exceptional, (25 reviews)
"I had a fun stay "
United States
Jusu K.
The price is ￥22,421
￥31,255 total
includes taxes & fees
May 13 - May 14
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
Interior

Near Lake and Museum • Modern • Game Area

Near Lake and Museum • Modern • Game Area
South Shore
The price is ￥18,802
￥91,495 total
includes taxes & fees
May 12 - May 13
Near Lake and Museum • Modern • Game Area
Exterior detail

Master qtr close to nature & easy urban facilities

Master qtr close to nature & easy urban facilities
Riverwoods
9.8 out of 10, Exceptional, (80 reviews)
"Had a lovely stay in a beautiful home! The setting is very secluded and quiet."
United States
Kyle M.
The price is ￥15,370
￥30,403 total
includes taxes & fees
May 14 - May 15
Master qtr close to nature & easy urban facilities
Smart TV

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Maywood
8.0 out of 10, Very Good, (24 reviews)
"Easy to access, big place, great for a group that needs to have several rooms and beds. Would definitely stay again"
United States
JOSE S.
The price is ￥23,267
￥47,017 total
includes taxes & fees
May 12 - May 13
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Outdoor dining

✽ Charming Cottage ✽ close to College/Town/Station

✽ Charming Cottage ✽ close to College/Town/Station
Wheaton
10.0 out of 10, Exceptional, (65 reviews)
"This is a cozy little home close to all the things we love about visiting Wheaton. "
United States
Nancy F.
The price is ￥26,636
￥48,321 total
includes taxes & fees
May 12 - May 13
✽ Charming Cottage ✽ close to College/Town/Station
Fridge, microwave, oven, stovetop

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
Westchester
9.8 out of 10, Exceptional, (20 reviews)
"Great location and the place was immaculate. Host was very nice."
United States
Carl M.
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
Fridge, microwave, oven, stovetop

Spacious 5-bedroom bungalow in welcoming Berwyn

Spacious 5-bedroom bungalow in welcoming Berwyn
Berwyn
10.0 out of 10, Exceptional, (3 reviews)
"We had an excellent stay. Our host was responsive & accommodated an extremely early check-in request for us. This helped tremendously. Instructions were clear to get in & the home was spacious & clean. The location was great & easily accessible to restaurants. We would stay here again. "
United States
Sarah H.
The price is ￥34,297
￥56,972 total
includes taxes & fees
May 19 - May 20
Spacious 5-bedroom bungalow in welcoming Berwyn
Fridge, microwave, oven, stovetop

Modern Stylish Comfort Near Casino and Hwy

Modern Stylish Comfort Near Casino and Hwy
Homewood
The price is ￥27,262
￥70,075 total
includes taxes & fees
May 12 - May 13
Modern Stylish Comfort Near Casino and Hwy
Dining

Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard

Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
Oak Park
10.0 out of 10, Exceptional, (2 reviews)
"Sweet hosts, beautiful place, and awesome movie/game room. Definitely would stay again."
United States
Willow M.
The price is ￥43,291
￥71,443 total
includes taxes & fees
May 28 - May 29
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
Fridge, microwave, oven, stovetop

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

The Comfy King Ranch/King Bed Suite/Fast Wi-Fi
Worth
9.4 out of 10, Exceptional, (60 reviews)
"Home was exactly what we were needing fir our stay. Host was responsive and timely. "
United States
Stephanie H.
The price is ￥29,613
￥59,337 total
includes taxes & fees
May 13 - May 14
The Comfy King Ranch/King Bed Suite/Fast Wi-Fi
Smart TV, fireplace, offices

PROMO 10% WEEKLY 15% MONTHLY DISCOUNT 2-Car Garage Cal King Bed Fenced Yard

PROMO 10% WEEKLY 15% MONTHLY DISCOUNT 2-Car Garage Cal King Bed Fenced Yard
Arlington Heights
9.0 out of 10, Wonderful, (6 reviews)
"Host was very responsive. Location was perfect for what we needed.Really liked having a garage for the car."
United States
Katie C.
The price is ￥25,829
￥66,184 total
includes taxes & fees
May 12 - May 13
PROMO 10% WEEKLY 15% MONTHLY DISCOUNT 2-Car Garage Cal King Bed Fenced Yard
Fridge, microwave, oven, stovetop

Luxury 4BR, 3BA, Game Rm Near O’Hare & Down Town Free Parking

Luxury 4BR, 3BA, Game Rm Near O’Hare & Down Town Free Parking
Bensenville
10.0 out of 10, Exceptional, (1 review)
"Easily the nicest place I have ever stayed at. Wonderful neighborhood, clean house, and great amenities. I’ll stay there again anyday. "
United States
Jacob F.
The price is ￥60,126
￥128,481 total
includes taxes & fees
May 17 - May 18
Luxury 4BR, 3BA, Game Rm Near O’Hare & Down Town Free Parking
Fridge, microwave, oven, stovetop

4BR Near Woodfield Mall & Metra | LCP Collection

4BR Near Woodfield Mall & Metra | LCP Collection
Schaumburg
8.4 out of 10, Very Good, (5 reviews)
"Home was perfect for us with two kids. Beds were comfortable and a nice quiet location."
United States
Randy G.
The price is ￥33,530
￥87,298 total
includes taxes & fees
May 12 - May 13
4BR Near Woodfield Mall & Metra | LCP Collection
Exterior detail

Oak Park Victorian by FLW Studio

Oak Park Victorian by FLW Studio
Oak Park
10.0 out of 10, Exceptional, (30 reviews)
"Wonderful place to gather for our annual corporate operations retreat. A great place to disconnect and focus. "
United States
Jennifer A.
The price is ￥26,792
￥79,101 total
includes taxes & fees
May 12 - May 13
Oak Park Victorian by FLW Studio
Private kitchen

Spacious Deck & Balcony, Game Area, Garage

Spacious Deck & Balcony, Game Area, Garage
Glen Ellyn
9.6 out of 10, Exceptional, (23 reviews)
"Great place to stay. "
United States
Jason T.
Spacious Deck & Balcony, Game Area, Garage
Dining

LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.8 out of 10, Excellent, (45 reviews)
"Nice overall"
United States
Hell
The price is ￥28,202
￥57,659 total
includes taxes & fees
May 13 - May 14
LUXE 3 BR, 2 BA + Hot Tub
Interior

PROMO 10% MONTHLY DISCOUNT! Comfy Home w Access to Major Roads/Hwys, Huge Yard

PROMO 10% MONTHLY DISCOUNT! Comfy Home w Access to Major Roads/Hwys, Huge Yard
Lombard
9.6 out of 10, Exceptional, (18 reviews)
"Location was easy to find and good as a base for day trips to Chicago. "
United States
Brian H.
The price is ￥17,109
￥43,372 total
includes taxes & fees
May 12 - May 13
PROMO 10% MONTHLY DISCOUNT! Comfy Home w Access to Major Roads/Hwys, Huge Yard
Interior

Great Value 3BR 2.5BA Game Rm Free Park, Safe Area

Great Value 3BR 2.5BA Game Rm Free Park, Safe Area
Carol Stream
9.6 out of 10, Exceptional, (5 reviews)
"The property was nice. Perfect for our guys trip. "
United States
Jay S.
Great Value 3BR 2.5BA Game Rm Free Park, Safe Area
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

Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

10/10 Excellent
"Clean hotel, no complaints at all!"
Kira 2-night trip
Posted 11 hours ago
Hampton Inn & Suites Chicago Medical District UIC

Find out more about West Side

West Side Vacation Homes information

Number of reviews
425
Accommodation
64 Vacation Homes
Lowest Price
￥30,403
Highest Price
￥128,481

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