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Vacation rentals in South Side

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Top-rated vacation rentals in South Side

Guests agree: these stays are highly rated for location, cleanliness, and more.

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SUPERHOST
Private room · Chicago
BRONZEVILLE OASIS I - Mins to UChicago & The Loop
Perfect oasis for STUDENTS, PROFESSIONALS and VACATIONERS. 5-7 Mins to UofC & IIT. 15 minutes to downtown Chicago & main attractions on Lakeshore Drive such as, McCormick Place & Soldier Field. This will be your home away from home.
$44 per night
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SUPERHOST
Entire rental unit · Chicago
1bed/1bath !Location! Steps to South Loop Apt
Please make sure to review "Getting Around" details within the "Neighborhood" section. Nearest building intersection is 28th Place & Canal St to map transit options Newly remodeled 1br with modern finishes, smart tech & security, in a hip, central neighborhood minutes from downtown Chicago & steps from all that trendy Bridgeport has to offer. Managed by a seasoned team specializing in monthly furnished rentals Per the City of Chicago ordinances, 31 night minimum on all stays
$25 per night
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SUPERHOST
Entire rental unit · Chicago
Bridgeport LR Renovated Loft Studio MONTHLY
Please make sure to review "Getting Around" details within the "Neighborhood" section. Nearest building intersection is 32nd Pl. & Carpenter St. to map transit options Newly remodeled loft-style apartment with modern finishes, smart tech & security, in a hip, central neighborhood minutes from downtown Chicago and part of all that trendy Bridgeport has to offer Managed by a seasoned team specializing in monthly furnished rentals Per the City of Chicago ordinances, 31 night minimum on all stays
$40 per night

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Stay near South Side's top sights

Photo of Museum of Science and Industry, Chicago
Museum of Science and Industry, Chicago185 locals recommend
Photo of Frederick C. Robie House
Frederick C. Robie House32 locals recommend
Photo of McCormick Place
McCormick Place62 locals recommend
Photo of University of Chicago: Hyde Park
University of Chicago: Hyde Park5 locals recommend
Photo of South Shore Cultural Center
South Shore Cultural Center9 locals recommend
Photo of McCormick Place
McCormick Place62 locals recommend

Other great vacation rentals in South Side

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Private room · Chicago
Luxury BR w/private bath 4mins to Univ & Hospital
$50 per night
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SUPERHOST
Private room · Chicago
SELF CHECK IN Downtown Chicago 8 minutes away
$36 per night
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SUPERHOST
Entire rental unit · Chicago
Pilsen HofC Deluxe 2bed/1bath Apt MONTHLY
$41 per night
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Private room · Chicago
Room B6
$24 per night
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Private room · Chicago
Room T6
$35 per night
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SUPERHOST
Entire rental unit · Chicago
Bridgeport 2R Renovated 2bed/1bath Apt. MONTHLY
$40 per night
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Private room · Chicago
Room B2
$25 per night
1 of 1 item showing
Private room · Chicago
5min walk to UnivOfChgo. MODERN Luxe
$49 per night
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Private room · Chicago
Homey, Energy Efficient 3 & Separate Laundry Room.
$36 per night
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SUPERHOST
Entire guest suite · Chicago
Bridgeport LF Renovated Loft Studio MONTHLY
$40 per night
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SUPERHOST
Private room · Chicago
Downtown Chicago 8 minutes away SELF CHECK IN
$46 per night
1 of 1 item showing
Private room · Chicago
Room 9 Pershing Inn
$48 per night
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