Vacation rentals in South Side

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Top-rated vacation rentals in South Side

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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.
Aug 29 – Sep 5
$112 per night
4.93 out of 5 average rating, 168 reviews
Guest favorite
Apartment 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!
Dec 17 – 24
$353 per night
4.86 out of 5 average rating, 148 reviews
Guest favorite
Apartment in Bronzeville
Cozy 2 bdrm near McCormick Place & Wintrust Arena
Come enjoy Chicago via our cozy apartment in the quiet yet friendly Historical Bronzeville community. We are nestled between Hyde Park and South Loop, where you will find plenty of restaurants, theaters, and nightlife. Only steps away from McCormick Place, 10-15 min drive from downtown and 3-12 miles from all the sports arenas and airports. You can bike or walk to the nearest grocery store, park, gym, and beach. The nearest bus and/or train is 2-3 blocks away for your convenience as well.
May 9 – 16
$127 per night
4.96 out of 5 average rating, 121 reviews

Popular amenities for South Side vacation rentals

Other great vacation rentals in South Side

Guest favorite
Loft in Chicago
Lovely Garden Studio in Chicago
May 1 – 8
$95 per night
5.0 out of 5 average rating, 67 reviews
Superhost
Apartment in Chicago
McCormick Place Studio/parking/sleeps up to 4
Feb 9 – 16
$80 per night
4.81 out of 5 average rating, 58 reviews
Superhost
Apartment in Chicago
Taste the Best of Chicago
Sep 1 – 8
$122 per night
4.83 out of 5 average rating, 12 reviews
Superhost
Home in Chicago
Cozy 2 bed Condo in Bronzeville!
Nov 20 – 27
$84 per night
4.79 out of 5 average rating, 14 reviews
Superhost
Apartment in Chicago
Eclipse: Modern Apt. in Woodlawn
Jan 1 – 8
$101 per night
4.89 out of 5 average rating, 57 reviews
Guest favorite
Vacation home in South Shore
UChicago Luxurious King Suite Lakefront
Jul 23 – 30
$98 per night
5.0 out of 5 average rating, 39 reviews
Guest favorite
Guest suite in McKinley Park
1 bed apartment + futon room bridgeport
Mar 29 – Apr 5
$81 per night
4.9 out of 5 average rating, 71 reviews
Guest favorite
Apartment in Chicago
Travel To Chicago New City
Nov 20 – 27
$78 per night
5.0 out of 5 average rating, 16 reviews
Guest favorite
Guest suite in Chicago
Classic Den @ U Chicago
Aug 13 – 20
$95 per night
4.93 out of 5 average rating, 40 reviews
Superhost
Guest suite in Chicago
Bronzeville Guest Suite - 1 Br
Mar 26 – Apr 2
$72 per night
4.85 out of 5 average rating, 92 reviews
Guest favorite
Apartment in Chicago
Ground-Level Speakeasy: 1BR-1.5BA Near Everything!
Jun 5 – 12
$121 per night
4.94 out of 5 average rating, 65 reviews
Guest favorite
Apartment in Chicago
Urban Cottage
Jul 7 – 14
$109 per night
5.0 out of 5 average rating, 13 reviews

Destinations to explore

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  6. South Side