Southwest Side Vacation Rentals
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Browse Select Southwest Side Vacation Homes

Cozy Room with Rooftop Lounge & City Views in River North
Cozy Room with Rooftop Lounge & City Views in River North
10.0 out of 10, Exceptional, (1)
The price is CA $215
CA $318 total
includes taxes & fees
Aug 25 - Aug 26

The One: A 1BR Stay That Feels Like Home
The One: A 1BR Stay That Feels Like Home
8.0 out of 10, Very good, (1)
The price is CA $144
CA $303 total
includes taxes & fees
Sep 2 - Sep 3

Stylish 1BR in West Loop
Stylish 1BR in West Loop
10.0 out of 10, Exceptional, (5)
The price is CA $148
CA $308 total
includes taxes & fees
Sep 2 - Sep 3

Sun-Drenched 1BR Apartment
Sun-Drenched 1BR Apartment
The price is CA $148
CA $308 total
includes taxes & fees
Sep 2 - Sep 3

2 Connecting Suites at a 4⭐️ Hotel
2 Connecting Suites at a 4⭐️ Hotel
The price is CA $757
CA $1,022 total
includes taxes & fees
Sep 1 - Sep 2

2 Connecting Suites at a 5⭐️ Hotel
2 Connecting Suites at a 5⭐️ Hotel
The price is CA $3,653
CA $4,930 total
includes taxes & fees
Sep 1 - Sep 2

Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
10.0 out of 10, Exceptional, (7)
The price is CA $198
CA $276 total
includes taxes & fees
Aug 28 - Aug 29

Cozy house in the city
Cozy house in the city
8.8 out of 10, Excellent, (3)
The price is CA $245
CA $551 total
includes taxes & fees
Aug 25 - Aug 26
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

The Royal Sonesta Chicago Downtown
10/10 Excellent
Find out more about Southwest Side
Find out more about Southwest Side
Southwest Side Vacation Homes information
Number of reviews | 383 |
---|---|
Accommodation | 431 Vacation Homes |
Lowest Price | CA $78 |
Highest Price | CA $310 |
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