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

4.93 out of 5 average rating, 168 reviews

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.

Jan 17 – 24

$100 per night
Guest favorite

Apartment in Chicago

4.96 out of 5 average rating, 121 reviews

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.

Jun 4 – 11

$144 per night
Guest favorite

Vacation home in Chicago

4.95 out of 5 average rating, 40 reviews

UChicago Luxurious King Suite Lakefront

Sink into a pillowtop king size bed in a sunny, spacious bedroom suite w/twin bed, his/hers closets and comfy love seat. Spacious 1,000 s.f. condo luxury, kitchens /bath with granite counters, office space, 3rd-floor unit, private entrance gated and on-street parking. Walk to beach, trails, golf course and bike rental. Located 1 blk from Express bus (15 minutes) to Univ of Chicago/Hyde Park and Museum of Science and Industry,(20 minutes) to Soldier Field, Grant Park, Downtown, Navy Pier

Oct 3 – 10

$99 per night

Popular amenities for South Side vacation rentals

Other great vacation rentals in South Side

Guest favorite

Guest suite in Chicago

4.93 out of 5 average rating, 40 reviews

Classic Den @ U Chicago

Aug 13 – 20

$95 per night
Superhost

Apartment in Woodlawn

4.89 out of 5 average rating, 57 reviews

Eclipse: Modern Apt. in Woodlawn

Nov 28 – Dec 5

$104 per night
Guest favorite

Apartment in Chicago

4.94 out of 5 average rating, 65 reviews

Ground-Level Speakeasy: 1BR-1.5BA Near Everything!

May 10 – 17

$115 per night
Superhost

Home in Washington Park

4.85 out of 5 average rating, 13 reviews

Cozy 2 bed Condo in Bronzeville!

Jun 9 – 16

$91 per night
Superhost

Guest suite in Bronzeville

4.85 out of 5 average rating, 92 reviews

Bronzeville Guest Suite - 1 Br

Jun 7 – 14

$79 per night
Guest favorite

Apartment in Chicago

5.0 out of 5 average rating, 16 reviews

Travel To Chicago New City

Dec 15 – 22

$89 per night
Guest favorite

Apartment in Bridgeport

4.87 out of 5 average rating, 31 reviews

Your Perfect Spot :)-With Memory Foam Mattress!

Sep 2 – 9

$92 per night
Guest favorite

Home in Chicago

4.92 out of 5 average rating, 84 reviews

Boho Chic Coach House 30Min to downtown W/ Parking

Jun 28 – Jul 5

$105 per night
Superhost

Apartment in South Shore

4.83 out of 5 average rating, 12 reviews

Taste the Best of Chicago

Nov 6 – 13

$122 per night
Guest favorite

Guest suite in Chicago

4.91 out of 5 average rating, 67 reviews

Cozy Eco-Friendly 2BD Lake Suite Near Downtown

Dec 15 – 22

$123 per night
Superhost

Apartment in Pilsen Historic District

4.91 out of 5 average rating, 22 reviews

15min/Loop, PilsenTreasure, Sunny1BR Apt w/Parking

Aug 28 – Sep 4

$112 per night
Guest favorite

Apartment in Bridgeport

5.0 out of 5 average rating, 14 reviews

Urban Cottage

Aug 20 – 27

$115 per night

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