Holiday rentals in South Side

Find and book unique accommodation on Airbnb

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.
13–20 MarProfessional Host,
£122 per night
4.93 out of 5 average rating, 168 reviews
Guest favourite
Flat in Chicago
Amazing Location | Stunning Views | Free Parking
You will feel on top of the world as this luxury property truly has it all. With a 24 hour doorman, heated parking in the building, hot tub, workout and rec rooms, and views not to be beat, this property is in a beautiful and safe neighborhood in Chicago. Be at Mccormick place in under five minutes or dash off to all Chicago has to offer from our perfectly located condo in our Luxury South Loop flat. Close to public transport and an easy cab ride to the airports, we look forward to your stay!
5–12 MarIndividual Host,
£396 per night
4.86 out of 5 average rating, 148 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.
2–9 MayProfessional Host,
£106 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 Bridgeport
Comfortable & Cozy in Bridgeport
10–17 MayIndividual Host,
£103 per night
4.94 out of 5 average rating, 117 reviews
Superhost
Flat in Woodlawn
University Retreat
21–28 JulIndividual Host,
£130 per night
4.83 out of 5 average rating, 150 reviews
Guest favourite
Flat in Bronzeville
Cozy 2 bdrm near McCormick Place & Wintrust Arena
11–18 MayIndividual Host,
£163 per night
4.96 out of 5 average rating, 121 reviews
Guest favourite
Flat in Cicero
COZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy
8–15 JulIndividual Host,
£112 per night
4.98 out of 5 average rating, 182 reviews
Guest favourite
Flat in Pilsen Historic District
Modern
13–20 JulIndividual Host,
£114 per night
4.89 out of 5 average rating, 239 reviews
Guest favourite
Flat in Chicago
Hyde Park 5 Bed/3 Full Bath Condo- Travelers Only!
25–30 AugIndividual Host,
£226 per night
4.94 out of 5 average rating, 432 reviews
Guest favourite
Home in Bridgeport
Cozy & Modern Chic Full House in Trendy Bridgeport
16–23 DecIndividual Host,
£132 per night
4.95 out of 5 average rating, 106 reviews
Guest favourite
Holiday home in Chicago
UChicago Luxurious King Suite Lakefront
2–9 OctIndividual Host,
£128 per night
5.0 out of 5 average rating, 39 reviews
Guest favourite
Flat in Chicago
Ground-Level Speakeasy: 1BR-1.5BA Near Everything!
1–8 AprIndividual Host,
£118 per night
4.94 out of 5 average rating, 63 reviews
Superhost
Home in Chicago
Cozy 2 bed Condo in Bronzeville!
13–20 JulIndividual Host,
£113 per night
4.9 out of 5 average rating, 10 reviews
Superhost
Guest suite in Chicago
Bronzeville Guest Suite - 1 Br
16–23 JunIndividual Host,
£98 per night
4.85 out of 5 average rating, 91 reviews
Superhost
Flat in Hyde Park
Great Location! 15 Min from DT -Historic Hyde Park
6–13 MarIndividual Host,
£138 per night
4.95 out of 5 average rating, 43 reviews

Destinations to explore

  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Chicago
  6. South Side