South Side Holiday Homes

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Featured Holiday Homes in South Side

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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.

South Side Holiday Homes essential information

Accommodation
97 Holiday Homes
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Popular accommodation
LakeHouse, Lux Home in Chicago 7mins Downtown, House with garage, outdoor dining and basement bar, Stay, Relax & Explore Chicago, Bronzeville Jazz Room. Beautiful, cozy, centered, relaxing, rustic., Charming house in amazing Chicago with WiFi and AC. Close to many restaurants., 1 #23 - 4 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown, A Home Away From Home!, Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!, Cheerful 4 bedroom smart home w/ indoor fireplace, Mayors Manor, Zen Garden Oasis, Hot Tub & Sauna in Central Chicago, 8-12 guests, Newly Revamped Home - For privacy lovers, Lakefront property , minutes from McCormick Place and Downtown Chicago. , “The Marlowe” A Couples Getaway, Renovated 6 Bedroom 5 Bathroom Home 10 Minutes from Downtown Chicago