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Southwest Side Vacation Rentals

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Check prices for these dates

Tonight
Nov 21 - Nov 22
Tomorrow
Nov 22 - Nov 23
This weekend
Nov 21 - Nov 23
Next weekend
Nov 28 - Nov 30

Vacation Rentals in Southwest Side

Indoor pool
Sentral Michigan Avenue

Sentral Michigan Avenue

4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (987)
"Loved my stay! Staff was amazing and the apartment had everything to make you feel like home. "
United States
Nicole
The price is ￥15,862
￥23,240 total
includes taxes & fees
Dec 7 - Dec 8
Sentral Michigan Avenue
49-inch Smart TV with digital channels, TV, streaming services
Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (625)
"Room was very nice, location was wonderful."
United States
Nicholas
Kasa Magnificent Mile Chicago
Front of property - evening/night
Level Chicago – Old Town

Level Chicago – Old Town

4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (384)
"Property was clean, centrally located with wonderful staff. Will definitely stay again."
United States
Michelle
Level Chicago – Old Town
Deluxe Apartment, 1 Bedroom, Non Smoking, Balcony (Self Check-in with Virtual Front Desk) | Balcony
Kasa South Loop Chicago

Kasa South Loop Chicago

4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (376)
"An excellent place to stay in Chicago downtown."
United States
ABDULHAFEEZ
Kasa South Loop Chicago
Front of property
The Neighborhood Hotel-Little Italy

The Neighborhood Hotel-Little Italy

4.0 star property
Near West Side
9.6 out of 10, Exceptional, (219)
"Staff was courteous. Great location."
United States
Pamela
The Neighborhood Hotel-Little Italy
Business center
Kasa River North Chicago

Kasa River North Chicago

4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (179)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Living area
Wrigleyville Suites

Wrigleyville Suites

2.0 star property
Lakeview
9.6 out of 10, Exceptional, (25)
"Excellent location and very clean! Would stay again!"
United States
Jacob
The price is ￥18,842
￥22,120 total
includes taxes & fees
Nov 24 - Nov 25
Wrigleyville Suites
Suite, 2 Bedrooms, Kitchen (Three Beds, Washer/Dryer) | Private kitchen | Full-size fridge, microwave, stovetop, dishwasher
The Gem Museum Suites

The Gem Museum Suites

3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (96)
"Great stay. The studio is small but has everything necessary."
United States
Julia
The price is ￥26,041
￥29,811 total
includes taxes & fees
Nov 30 - Dec 1
The Gem Museum Suites
Free WiFi, bed sheets
Chicago luxury home suites

Chicago luxury home suites

2.0 star property
Downtown Chicago
10.0 out of 10, Exceptional, (1)
"This was Amazing stay I have ever had in my life. Wonderful host, super clean. Stunning views, close to everything that you would needed. "
New Zealand
Moha
The price is ￥45,935
￥53,924 total
includes taxes & fees
Nov 25 - Nov 26
Chicago luxury home suites
Comfort Double Room | Desk, laptop workspace, blackout drapes, free WiFi
Comfort Inn Chicago Southland I-80 & I-294 Near Casino

Comfort Inn Chicago Southland I-80 & I-294 Near Casino

3.0 star property
Harvey
3.8 out of 10, (67)
"Good "
United States
Abel
The price is ￥11,413
￥12,896 total
includes taxes & fees
Nov 27 - Nov 28
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
1 bedroom, iron/ironing board, WiFi, bed sheets
Clean & Equipped 1BR Apt

Clean & Equipped 1BR Apt

Lakeview
9.2 out of 10, Wonderful, (35)
"Amazing location and even nicer place inside. Enjoyed my time there a lot!"
United States
Camron K.
The price is ￥8,658
￥25,046 total
includes taxes & fees
Nov 30 - Dec 1
Clean & Equipped 1BR Apt
Classic Apartment | Private kitchen
Stylish Apartment near Chicago Downtown

Stylish Apartment near Chicago Downtown

2.0 star property
Bridgeport
The price is ￥38,125
￥60,979 total
includes taxes & fees
Dec 8 - Dec 9
Stylish Apartment near Chicago Downtown
Fridge, microwave, oven, stovetop
Lakeview 2BR Apartment

Lakeview 2BR Apartment

Lakeview
9.4 out of 10, Exceptional, (26)
"The apartment was as described and the customer service was amazing! "
United States
Michael M.
The price is ￥9,422
￥28,457 total
includes taxes & fees
Dec 10 - Dec 11
Lakeview 2BR Apartment
Fridge, microwave, oven, stovetop
Stylish 1BR in West Loop

Stylish 1BR in West Loop

Downtown Chicago
10.0 out of 10, Exceptional, (9)
"We stayed for 4th of July weekend and had a wonderful time. Property is close to coffee shops, book stores, and within walking distance of nice restaurants. Easy paid parking nearby. The apartment was clean and everything we needed"
United States
Jacob D.
The price is ￥8,658
￥25,046 total
includes taxes & fees
Nov 30 - Dec 1
Stylish 1BR in West Loop
Outdoor dining
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place

3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place

Near West Side
10.0 out of 10, Exceptional, (268)
"Lovely place! Very clean and has all of the amenities necessary for a good stay. Lots of fresh towels, a fully stocked kitchen and the location is excellent. "
United States
Angela C.
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
Interior
Remodeled West Loop Apartment Near United Center

Remodeled West Loop Apartment Near United Center

Near West Side
9.0 out of 10, Wonderful, (56)
"This apartment is very close to downtown with easy parking right outside! The unit is very well maintained with spacious rooms and amenities! The host has thought of everything to make it feel like your own home! Would love to come back and stay here again!"
United States
kiran
Remodeled West Loop Apartment Near United Center
Interior
Art Villa

Art Villa

5.0 star property
West Town
10.0 out of 10, Exceptional, (2)
" "
United States
tomonobu
The price is ￥59,252
￥126,025 total
includes taxes & fees
Dec 22 - Dec 23
Art Villa
2 bedrooms, iron/ironing board, travel crib, WiFi
Charming 2BR in Vibrant Lakeview

Charming 2BR in Vibrant Lakeview

Lakeview
9.0 out of 10, Wonderful, (30)
"Great stay. Place was spic and span on arrival and host very easy to communicate with. "
United States
Lukas H O.
The price is ￥9,759
￥28,894 total
includes taxes & fees
Nov 30 - Dec 1
Charming 2BR in Vibrant Lakeview
Fridge, microwave, oven, stovetop
LakeHouse

LakeHouse

South Shore
9.4 out of 10, Exceptional, (24)
"Everything was perfect with the property and the host even came to help right away when we had one issue with the lights."
United States
Isaiah P.
LakeHouse
Fridge, microwave, oven, stovetop
Experience Chicago living near United Center

Experience Chicago living near United Center

Austin
9.2 out of 10, Wonderful, (28)
"We were in town with our rowing team for a regatta, and this was a perfect spot to stay! Amenities were perfect for our needs, the living room is super spacious for some morning yoga, and the owners were responsive to any questions we had. Will definitely be saving this location for our trip here next year?"
United States
McKenzie J.
Experience Chicago living near United Center
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

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

10/10 Excellent
"The room was spotless, gorgeous rooftop views, delicious food and room that over looks the river. Will stay here again! "
Chanelle 2-night trip
Posted 8 hours ago
LondonHouse Chicago, Curio Collection by Hilton

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