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Southwest Side Vacation Rentals
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Our top choices for Southwest Side vacation rentals
W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade
W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | ArcadeBrighton Park
9.4 out of 10, Exceptional, (9 reviews)
"Great location, spacious, and family friendly. Had cousins over and they had a blast playing the video games. "
Jessica H.
The price is ￥11,932
￥42,670 total
includes taxes & fees
Apr 21 - Apr 22
9.2 out of 10, Wonderful, (1,128 reviews)
"Clean spacious my go to vacation spot all year around "
xavier
The price is ￥21,383
￥29,774 total
includes taxes & fees
Apr 12 - Apr 13
Sunlit 1BR Apartment | Warm & Welcoming Space
Sunlit 1BR Apartment | Warm & Welcoming SpaceDowntown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Host was very friendly and informative. Place was clean and close to lots of fun. Trains loud and busy but knew that going in. "
Tyler B.
The price is ￥17,977
￥36,121 total
includes taxes & fees
Apr 29 - Apr 30
Modern Comfort: 1BR Unit w/ Laundry
Modern Comfort: 1BR Unit w/ LaundryDowntown Chicago
9.0 out of 10, Wonderful, (17 reviews)
"Great location, apt well equipped and host very responsive. Wonderful stay. "
Gina G.
The price is ￥11,454
￥28,480 total
includes taxes & fees
Apr 20 - Apr 21
Chic Studio in the Heart of the Gold Coast
Chic Studio in the Heart of the Gold CoastDowntown Chicago
10.0 out of 10, Exceptional, (5 reviews)
"The communication was really effective and made for a smooth check in and check out process. Host was friendly and made great recommendations, 10/10 would stay again!"
Seynabou
The price is ￥17,023
￥33,412 total
includes taxes & fees
Apr 30 - May 1
West Loop Living – Bright 1BR
West Loop Living – Bright 1BRDowntown Chicago
10.0 out of 10, Exceptional, (8 reviews)
"Great spot next to the green line train a few restaurants and a Starbucks right up the street I will book again for sure "
2k G.
The price is ￥15,608
￥33,363 total
includes taxes & fees
Apr 12 - Apr 13
River North Rooftop With In and Out Parking 3
River North Rooftop With In and Out Parking 3Downtown Chicago
9.6 out of 10, Exceptional, (4 reviews)
"We had a very comfortable stay here. The hosts are exceptionally communicative and helpful. Loved having a place to park my car, and the hosts set it up so my license plate was recognized at the gate so that parking was free. The unit was very clean and spacious. Note, the kitchen does not have pots or pans to cook, so plan on eating out!"
Jennifer M.
The price is ￥25,454
￥72,651 total
includes taxes & fees
Apr 15 - Apr 16
Premium Urban 4BR - Perfect Mix of Comfort & Location
Premium Urban 4BR - Perfect Mix of Comfort & LocationNear North Side
10.0 out of 10, Exceptional, (1 review)
"Nice place, clean property, great views "
Zach L.
The price is ￥19,727
￥67,142 total
includes taxes & fees
Apr 15 - Apr 16
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
Hotel Felix River North/Magnificent Mile
10/10 Excellent
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