Apartment vacation rentals in South Side

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Top-rated apartment rentals in South Side

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Guest favorite

Apartment in Chicago

4.91 out of 5 average rating, 170 reviews

Handicap accessible apartment w/Level-2 EV Charger

Just 12.5 miles from downtown in the extremely quiet Chicago neighborhood of Hegewisch. Walking distance to the South Shore train line, which can easily get you to Chicago museums and entertainment, or attractions in NW Indiana. Private parking in back also gives you the option of driving anywhere and then walking directly to your door, and outside cameras are present for security. Banks, restaurants, grocery, convenience, and liquor stores are all 1 block of the apartment for all your needs.

Guest favorite

Apartment in Chicago

4.95 out of 5 average rating, 124 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.

Superhost

Apartment in Chicago

4.84 out of 5 average rating, 131 reviews

Perfect Private Getaway in Perfect Pilsen

This quiet and cozy studio in Pilsen is the perfect place to rest your head after a long day of exploring the Windy City. With so much to do in the area and easy access to public transit, you won't run out of ways to spend your time! Close to Chinatown, the United Center, and the Medical District, and downtown is a quick train ride away on the Pink Line. Relax in this thoughtfully designed space, perfect for couples or business travelers. Book today! Please note: ceiling height is about 6'3"

Guest favorite

Apartment in Chicago

4.98 out of 5 average rating, 224 reviews

Ukrainian Village Garden Retreat

A newly updated 1 bedroom, 1 bathroom apartment in Chicago's historic Ukrainian Village. Located a few blocks from Wicker Park, Ukrainian Village is a small historic district of Chicago filled with historic architecture. Access the apartment via a smart lock, the apartment includes everything you need for a comfortable stay, including a queen-sized bed, full kitchen, fiber high-speed internet (100+ Gbps up and down), smart TV, modern bathroom, in-unit washer & dryer, and free garage parking.

Guest favorite

Apartment in Avondale

4.97 out of 5 average rating, 120 reviews

Designer Avondale Attic

Soak in the beauty of this professionally designed and newly-renovated minimalistic attic in the heart of Chicago's most hip neighborhoods! Every detail of this home was thought through extensively to provide the perfect experience for our guests. Designer furniture, luxury soaps and amenities, a smart TV, high speed wifi, free laundry on site! A quick walk brings you to amazing coffee shops, trendy restaurants, or hop on the Blue Line train to help you get to any part of the city with ease.

Guest favorite

Apartment in Chicago

4.85 out of 5 average rating, 162 reviews

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.

Guest favorite

Apartment in Chicago

4.96 out of 5 average rating, 265 reviews

Turquoise Wonder - Clean, Cozy & Stylish Apt

Clean, stylish & comfy apartment, perfect for 1 or 2 adults. 2 guest maximum, no children. Close to public transit (bus), wonderful restaurants & bars, gift shops, boutiques, coffee shops, parks, museums & more. Ukrainian Village/Humboldt Park area. King size comfortable Tempurpedic mattress. Central heat, A/C. Nice kitchen w/ stainless appliances, excellent bathroom, shower & tub. Free street parking. Relax in the comfort of the Turquoise Wonder! Enhanced cleaning protocols for COVID.

Guest favorite

Apartment in Chicago

4.91 out of 5 average rating, 112 reviews

NEW Modern 2BRD apartment| 5min to McCormick Place

Enjoy your stay at newly remodeled, spacious two-bedroom, lower level of 3 unit building apartment in the lovely city of Chicago. Free street parking. Couple blocks away from Illinois Institute of Technology, 7-8 mins walk to Green and Red lines, 15mins walk to White Sox stadium, 20mins walk to 31st street beach. 5 mins drive to McCormick. The apartment is comfortable for up to 4 people and has 2 private bedrooms. Full kitchen, work space,TVs,WIFi

Guest favorite

Apartment in Chicago

4.89 out of 5 average rating, 301 reviews

Vintage Bridgeport Apartment

This AirBNB is located within Bridgeport, on Chicago's South Side. You're only a short walk from grocery stores, restaurants, bars, cafes, and whatever else you may need on your trip. We welcome all with open arms. All religions, nationalities, genders. No smoking inside the building, including the back porch. We are no longer accepting new guests with pets. If you stayed with us in the past with a pet they are more than welcome back!

Guest favorite

Apartment in Cicero

4.98 out of 5 average rating, 204 reviews

COZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy

Quiet city side street. Walking distance to dozens of restaurants and stores. Walking distance to Public Transportation including Metra train, CTA Pink line, Direct CTA Bus to Midway Airport. You will be a short 20-minute drive to Downtown Chicago, 15 minutes to United Center or Soldier Field. Perfect for the quick getaway, the night before your flight, or even the long work assignment. Relax on the Patio with a fire pit and grill.

Guest favorite

Apartment in Blue Island

4.93 out of 5 average rating, 266 reviews

Charming Unique 2 Bdrm Apartment in Victorian Home

My place is close to the excitement and culture of the beautiful city of Chicago. It is a short walk to Metra trains with a 25 minute ride downtown. You’ll love my place because of the diverse, comfortable, quiet, tree lined neighborhood where you can relax and feel secure. It is close to expressways, golf courses and a local park with walking path. The apartment is not available to guests without previous positive reviews.

Superhost

Apartment in Chicago

4.84 out of 5 average rating, 176 reviews

The Cottage

Nice cozy and welcoming place. Easy access to public transportation. 10 to 15 minutes from downtown, museums, Sox and Bulls stadiums. Located in the colorful and lively neighborhood of Pilsen and close to Little Italy. Smart devices installed for easy check-in and safety (extremely accurate and sensitive smoke detector warning all occupants of possible problems). Guest wifi included with some feel home amenities.