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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Southwest Side vacation homes

A hotel room with a large bed, dark curtains, a ceiling fan, and a bedside lamp.

1. Back Unit Patio, Balcony, Yard, Smart TVs, W/D

Back Unit Patio, Balcony, Yard, Smart TVs, W/D
Westmont
The price is ￥17,588
￥44,764 total
includes taxes & fees
Oct 19 - Oct 20
Back Unit Patio, Balcony, Yard, Smart TVs, W/D
A wooden deck with a railing, a staircase, and a window with a wreath.

2. 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
9.8 out of 10, Exceptional, (36 reviews)
"I had a fun stay "
United States
Jusu K.
The price is ￥22,613
￥32,938 total
includes taxes & fees
Oct 19 - Oct 20
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
A dining table with a bottle of wine, two glasses, a vase with white flowers, and a cheese board with fruits.

3. Sleeps 18 • 8BR • Game Room • Gym • Theater

Sleeps 18 • 8BR • Game Room • Gym • Theater
Portage Park
10.0 out of 10, Exceptional, (10 reviews)
"The house is beautiful with plenty of space, the park is right across the street, was able to host a birthday party with lots to keep the kids entertained and have space to eat and mingle, the rooms were comfortable and surprisingly large for how small the house looks from the outside. The host responded promptly and was accommodating. Would book and recommend to others!"
United States
Ashley Y.
The price is ￥29,082
￥154,700 total
includes taxes & fees
Oct 22 - Oct 23
Sleeps 18 • 8BR • Game Room • Gym • Theater
Room

4. Arcade • Theater • Gym • Office • Sleeps 15

Arcade • Theater • Gym • Office • Sleeps 15
Portage Park
9.0 out of 10, Wonderful, (4 reviews)
"Good place for a large group or family."
United States
Daniel J.
The price is ￥24,333
￥126,201 total
includes taxes & fees
Oct 21 - Oct 22
Arcade • Theater • Gym • Office • Sleeps 15
A modern living room with a grey sofa, a blue bench, and a white door leading to another room.

5. Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.

Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
Westmont
9.4 out of 10, Exceptional, (3 reviews)
"Very welcoming and smells good, cozy feeling to it and quiet neighborhood."
United States
Tomas R.
The price is ￥26,863
￥42,537 total
includes taxes & fees
Nov 9 - Nov 10
Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
A living room with a sectional sofa, a glass coffee table, a fireplace, and a flat-screen TV mounted on the wall.

6. 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
7.8 out of 10, Good, (34 reviews)
"Very nice home with basement bar. Host was very accommodating."
United States
Carl T.
The price is ￥23,466
￥47,757 total
includes taxes & fees
Oct 19 - Oct 20
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
A single-story house with a covered porch, a front door, and a small garden area.

7. 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, (4 reviews)
"Sweet hosts, beautiful place, and awesome movie/game room. Definitely would stay again."
United States
Willow M.
The price is ￥30,861
￥55,228 total
includes taxes & fees
Nov 16 - Nov 17
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
A kitchen with a built-in counter, pendant lights, and decorative wall art.

8. 4 BR • Theater Room • Gym • Walk to Lincoln Park!

4 BR • Theater Room • Gym • Walk to Lincoln Park!
Lincoln Park
The price is ￥26,595
￥115,345 total
includes taxes & fees
Oct 20 - Oct 21
4 BR • Theater Room • Gym • Walk to Lincoln Park!
A dining area with a glass-top table, beige upholstered chairs, a patterned rug, and a chandelier.

9. LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.6 out of 10, Excellent, (64 reviews)
"We had a wonderful stay"
United States
Anonymous traveler
The price is ￥28,444
￥58,830 total
includes taxes & fees
Oct 26 - Oct 27
LUXE 3 BR, 2 BA + Hot Tub
A bedroom with a stone wall, a TV mounted on it, a bed with a white comforter, and a view of the outdoors through a window.

10. Beautifully furnished one bedroom loft located in Chicago's South side suburb

Beautifully furnished one bedroom loft located in Chicago's South side suburb
Hazel Green
10.0 out of 10, Exceptional, (1 review)
"Super great location, we had a concert at Tinley Park, then explored Chicago with a river cruise and Second City Everything was perfect and so eat to just chill, come and go as we pleased In a nice neighborhood and interior was furnished beautifully. Definitely worth the price !!"
United States
Nick L.
The price is ￥38,715
￥54,771 total
includes taxes & fees
Oct 19 - Oct 20
Beautifully furnished one bedroom loft located in Chicago's South side suburb
A cozy living room with a neon sign, a fireplace, a television, and a guitar.

11. Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops

Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops
Lincoln Park
9.6 out of 10, Exceptional, (45 reviews)
"Location was great, beds were comfortable, overall the apartment was well appointed. Unfortunately there was a strong musty smell, mainly in the common areas. We opened the windows and tried running the AC, but couldn’t get rid of it. We did report it to our host, who was going to check it out following our departure."
United States
Alison G.
The price is ￥49,618
￥102,375 total
includes taxes & fees
Oct 29 - Oct 30
Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops
A modern kitchen with white cabinets, a central island, stainless steel appliances, and a ceiling fan.

12. Classic Forest Park Foursquare < 1 Mi to Blue Line

Classic Forest Park Foursquare < 1 Mi to Blue Line
Forest Park
10.0 out of 10, Exceptional, (2 reviews)
"Great location, great place to stay, host was friendly. Parking was great. Hoping to be able to stay again in the near future."
United States
LEM R.
The price is ￥30,340
￥76,242 total
includes taxes & fees
Oct 27 - Oct 28
Classic Forest Park Foursquare < 1 Mi to Blue Line
A modern kitchen with stainless steel appliances, wooden cabinets, and a tiled backsplash.

13. 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
9.6 out of 10, Exceptional, (24 reviews)
"Great place Great location "
United States
Josh W.
The price is ￥35,009
￥77,687 total
includes taxes & fees
Oct 20 - Oct 21
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
Thoughtful design touches — from soft textures to greenery and mirrored accents — make this space feel both serene and sophisticated.

14. Theater • Game Room • Gym • Firepit • 4BR Home

Theater • Game Room • Gym • Firepit • 4BR Home
Belmont Cragin
10.0 out of 10, Exceptional, (7 reviews)
"Great location, safe and quiet. Perfect for our family of 6!"
United States
Jason
The price is ￥30,985
￥113,348 total
includes taxes & fees
Oct 25 - Oct 26
Theater • Game Room • Gym • Firepit • 4BR Home
A backyard with a barbecue grill, a dining table with chairs, and a fire pit.

15. PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central

PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
Lisle
9.4 out of 10, Exceptional, (36 reviews)
"This property was perfect for our weekend stay in the Chicagoland area. It was conveniently located to activities, shops and restaurants. Vic is a wonderfully attentive host who responds quickly and is happy to answer any questions or concerns."
United States
Christine M.
The price is ￥18,583
￥45,819 total
includes taxes & fees
Oct 19 - Oct 20
PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
A modern kitchen with dark cabinets, stainless steel appliances, and a patterned tile backsplash.

16. 5-minute walk to the largest old school arcade in America! Family friendly.

5-minute walk to the largest old school arcade in America! Family friendly.
Brookfield
8.6 out of 10, Excellent, (9 reviews)
"A nice house that easily slept 4 kids and 4 adults. There were ants in the house, then than that it was very nice, it was easy to get to the train into Chicago from here."
United States
Ryan S.
The price is ￥32,426
￥82,700 total
includes taxes & fees
Oct 19 - Oct 20
5-minute walk to the largest old school arcade in America! Family friendly.
A circular fire pit with chairs around it, string lights overhead, and a house in the background.

17. 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 ￥34,347
￥163,942 total
includes taxes & fees
Oct 28 - Oct 29
Sleeps 18 • 7BR • Gym • Game Room • Theater
A white two-story house with a porch, steps, and a small table with chairs.

18. Oak Park Victorian by FLW Studio

Oak Park Victorian by FLW Studio
Oak Park
10.0 out of 10, Exceptional, (33 reviews)
"Would stay there again"
United States
Margaret L.
The price is ￥35,555
￥91,357 total
includes taxes & fees
Oct 27 - Oct 28
Oak Park Victorian by FLW Studio
A two-story house with a garage, solar panels, and a red car parked in front.

19. Lombard 1BR & 1BH Suite Close to freeway & Mall

Lombard 1BR & 1BH Suite Close to freeway & Mall
Lombard
The price is ￥19,626
￥60,825 total
includes taxes & fees
Oct 22 - Oct 23
Lombard 1BR & 1BH Suite Close to freeway & Mall
A modern living room with a grey sofa, a black coffee table, and a large window with a view of a house and greenery.

20. Entire home in Lockport, Illinois

Entire home in Lockport, Illinois
Lockport
8.8 out of 10, Excellent, (5 reviews)
"The house is very clean. The host was very kind and responsive. "
United States
Susan B.
The price is ￥30,910
￥67,258 total
includes taxes & fees
Oct 25 - Oct 26
Entire home in Lockport, Illinois
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 Southwest Side Hotel Reviews

River Hotel

River Hotel

8/10 Good
"The room had a great view of the river, but there was 2 things that didn’t work for me, the first one the AC unit, the first day that we arrived it was hot, we turned on the AC unit and it didn’t cool enough the room, so that night we had a hard time trying to sleep, the day after I report the issue and they fix it, the second one was the tv, half screen had a blue stain like the tv was damaged"
jose 4-night trip
Posted less than an hour ago
River Hotel

Find out more about Southwest Side

Southwest Side Vacation Homes information

Number of reviews
272
Accommodation
330 Vacation Homes
Lowest Price
￥32,938
Highest Price
￥154,700

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