Southwest Side Vacation Rentals

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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 Southwest Side vacation rentals

Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,163 reviews)
"Spacious apartment with stunning view. A great stay!!"
United States
Tina
The price is NT$4,794
NT$6,553 total
includes taxes & fees
May 27 - May 28
Sentral Michigan Avenue
Dining room

Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (755 reviews)
"Great location"
United States
Alex
The price is NT$11,087
NT$15,235 total
includes taxes & fees
May 17 - May 18
Kasa Magnificent Mile Chicago
Seasonal outdoor pool, open 7:00 AM to 10:00 PM, pool umbrellas

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (477 reviews)
"Beautiful clean place. Great safe location within proximity to restaurants and transportation around the city with fantastic views. Would recommend and stay here again. "
Canada
Lissa
The price is NT$5,666
NT$7,428 total
includes taxes & fees
May 26 - May 27
Level Chicago – Old Town
Lounge

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (192 reviews)
"Great property - would come back. Decent size rooms and generally good all around"
United States
Suyash
Kasa River North Chicago
Breakfast, lunch, dinner served; Greek cuisine

The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (119 reviews)
"Perfect place to stay!"
United States
Anton
The price is NT$4,509
NT$5,161 total
includes taxes & fees
May 20 - May 21
The Gem Museum Suites
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

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

10/10 Excellent
"Stayed three nights, room was spotless, comfortable, roomy, well-equipped, perfect heating and cooling, quiet. Pool and gym were very nice. Loved the hotel cafe. Valet staff very attentive. Highly recommend "
Maria 3-night trip
Posted 1 hour ago
Hilton Chicago/Magnificent Mile Suites

Find out more about Southwest Side

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