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Holiday rentals in South Side

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Top-rated holiday rentals in South Side

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

Superhost
Guest suite in Chicago
Bike the Lakefront from a Sleek Urban Retreat
Cook in a stainless-steel kitchen with granite countertops, gleaming utensils, and a well-stocked fridge. Black and gray accents and dark woods offset a muted palette at this open-concept home. Thoughtful details include 800-thread-count linens. A retreat designed to evoke relaxation through luxury and elements of the earth. Lush bath linens & robes, luxury body and hair care products, coupled with sleek design creates a spa bathroom retreat you're sure to enjoy. Full granite and stainless steel kitchen, with wine fridge, stocked with morning essentials and Bronzeville BNB staples to ease you into the day's adventure. Relax or be social in the open space living and dining area equipped with Amazon entertainment system and Wi-Fi providing up-to-date weather, sports, news, the latest movies and yes...sometimes...work. Retreat to one of three sleeping accommodations, each drept in 800 thread count, 100% cotton linens. You'll find Bronzeville BNB thoughtful touches around every corner. Enjoy! You'll have access to the full suite including open floor plan living room/dining room/kitchen, spa bathroom, bedroom with walk in closet, hall closet, rear mud room containing washer/dryer, mop/broom, garbage tray, and fire extinguisher. There is concrete patios at the front and the rear entrances also. The backyard, main property deck and garage are restricted areas. The suite is nestled in the historic Bronzeville-Hyde Park neighborhood. Rent a Divvy bike to explore the 18-mile lakefront recreation trail close by. Chicago’s main attractions are a short drive away. The most efficient way to get around the city is UBER offering door-to-door service to all of Chicago's top attractions. Claim your FREE Uber ride (up to $5) gift from the host by signing up using this link: https://www.uber.com/invite/zkyf4 Divvy bike rentals are an awesome way to explore Chicago's 18 mile lakefront trail. The Divvy Explorer Pass includes 24 hours of bike access, with unlimited trips up to 3 hours each for $15/day. Pick up and return bikes at the 575+ Chicago & Evanston Divvy stations. Download the Divvy app for station locations and ride pass purchases. Your safety is important. Please be safe and aware of your surroundings. In any huge city, things can happen. It is suggested to not walk at night, avoid public transportation outside of downtown, and use rideshare transportation apps to avoid exchanging currency.
16–23 Jan
₹8,262 per night
4.93 out of 5 average rating, 168 reviews
Guest favourite
Flat in Chicago
Your brand new Chicago suite (unit 1F)
Come stay in the home of an artist. Enjoy this comfortable eclectic apartment that's filled with great work from local artist. Enjoy the book collection while you relax on the tufted chaise or cozy up to the couch and enjoy netflix. You get the entire apartment to yourself. It has everything you need for a comfortable stay. The neighborhood is very quiet with multiple nearby transportation options. Surrounding neighborhoods just 10 min away offer many restaurant & entertainment options.
30 Aug – 6 Sep
₹7,906 per night
4.84 out of 5 average rating, 152 reviews
Guest favourite
Apartment in Chicago
Quiet, Modern, Convenient 2 bedroom condo
PLEASE READ DESCRIPTION PRIOR TO BOOKING* Stay at this quiet, charming, Chicago-themed garden unit suite, sitting in the heart of Chicago's historic Bronzeville neighborhood. This convenient location with 1000 sq feet of space is perfect for young professionals, student, small groups, families, and people traveling with children. Easy access to public transportation, downtown Chicago, the Museum of Science and Industry, the University of Chicago, downtown Hyde Park, and so much more.
26 Apr – 3 May
₹7,447 per night
4.87 out of 5 average rating, 116 reviews

Popular amenities for South Side holiday rentals

Other great holiday rentals in South Side

Guest favourite
Guest suite in Hyde Park
Convenient Hyde Park 2 Bedroom Apartment
11–18 Sep
₹9,867 per night
4.92 out of 5 average rating, 190 reviews
Guest favourite
Flat in Chicago
Amazing Location | Stunning Views | Free Parking
27 Nov – 4 Dec
₹30,932 per night
4.86 out of 5 average rating, 147 reviews
Guest favourite
Apartment in Woodlawn
A Stones Throw from U Chicago South Campus!
24–31 Oct
₹10,080 per night
4.9 out of 5 average rating, 184 reviews
Guest favourite
Guest suite in Bridgeport
Comfortable & Cozy in Bridgeport
8–15 Apr
₹6,884 per night
4.94 out of 5 average rating, 117 reviews
Guest favourite
Flat in Pilsen Historic District
Modern
28 Mar – 4 Apr
₹7,885 per night
4.89 out of 5 average rating, 239 reviews
Guest favourite
Guest suite in Chicago
Chicago Living: Your Home Away From Home
23–30 Jan
₹8,130 per night
4.9 out of 5 average rating, 167 reviews
Guest favourite
Holiday home in South Shore
UChicago Luxurious King Suite Lakefront
23–30 Oct
₹8,198 per night
5.0 out of 5 average rating, 39 reviews
Guest favourite
Flat in Chicago
Ground-Level Speakeasy: 1BR-1.5BA Near Everything!
30 Mar – 6 Apr
₹8,216 per night
4.94 out of 5 average rating, 63 reviews
Superhost
Flat in Woodlawn
Eclipse: Modern Apt. in Woodlawn
20–27 Apr
₹9,460 per night
4.89 out of 5 average rating, 55 reviews
Superhost
Guest suite in Bronzeville
Bronzeville Guest Suite - 1 Br
1–8 Jul
₹6,079 per night
4.84 out of 5 average rating, 90 reviews
Guest favourite
Apartment in Woodlawn
University of Chicago Condo-Upgraded and Spacious
22–29 Apr
₹11,860 per night
5.0 out of 5 average rating, 12 reviews
Superhost
Flat in South Shore
Taste the Best of Chicago
21–28 Apr
₹10,070 per night
4.83 out of 5 average rating, 12 reviews

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