
Apartment holiday rentals in South Side
Find and book unique apartments on Airbnb
Top-rated apartment rentals in South Side
Guests agree: these apartments are highly rated for location, cleanliness and more.

Marvelous Condo w/ Pri Prkng Cls to Transit &Beach
Our 3 bedroom and 2 bathroom condo has a perfect open layout for any size group that is traveling together. You'll love the natural light. You'll have a ton of open space to share and feel at home, while also choosing from 3 bedrooms to get some privacy as well. Each bedroom has a queen size bed, while the master bedroom also has its own full size private bathroom. Feel free to stay in and cook with a fully equipped kitchen, enjoy the 55 inch Sony TV and/or gather around the very large island.

Tri-Taylor/Medical Dist. near West Loop
Enjoy this stylish Newly Rehabbed condo equipped with 3 bedrooms and 2 bathrooms. Modern kitchen with stainless steel appliances. ~UNITED CENTER home of the Chicago Bulls and Blackhawks located within 2-3 min walk *2 blocks*. 4-7 min drive to little Italy restaurants/Tri Taylor/Medical District. Near Downtown (5-7min drive). 2 Blocks from the blue line ~Free street parking ~Washer Dryer ~Dishwasher ~spacious Back patio Parties are restricted due to COVID guidelines for the city of Chicago.

Lovely top floor 2BR/2BA, steps from everything!
BEST LOCATION IN LOGAN SQUARE/AVONDALE with garage parking! Brand new stylish TOP floor 2 bed/2 bath located in the heart of the highly desirable Avondale neighborhood. This luxurious space is situated 15 minutes drive to Wrigley Field, 7 minutes walk from the CTA Belmont Blue Line, only minutes away from O'Hare airport, downtown Chicago and The Loop. Conveniently close to expressway. Steps from award winning restaurants, popular bars, great coffee shops, clubs, galleries and exclusive shops.

CHIC DOWNTOWN PENTHOUSE w/ private roof +parking
Escape into this spacious, Chicago Penthouse! Guests love this home because: - Surrounded by top-notch restaurants/retail - Close to all popular attractions that make Chicago so great - Luxurious, newly-renovated interior filled with natural light - Open-floor plan for entertaining! - Private, spacious roof deck viewing the entire Chicago skyline! - Fast WiFi (600 mbps) - Master en-suite w/ separate walk-out - Designated parking spot! - Steps away from blue line Damen station (800 feet)

The Urban Oasis | Outdoor Lounge • Sleeps 10+
Luxury 4BR/2.5BA residence featuring 3 private bedrooms and an open-concept bonus room with a queen bed and full-size bunk beds—perfect for upscale families or executive groups. The spa-inspired primary suite offers a soaking tub and rain shower with multiple settings. Enjoy a modern kitchen, stylish living room with a 76” smart TV, and a large covered patio. Located near UIC, West Loop, Chinatown, McCormick Place, the lakefront, and some of Chicago’s best dining and cultural attractions.

Private hot tub - King bed suite - Free parking
Welcome to this urban retreat in the heart of Chicago's Little Italy neighborhood. Conveniently located adjacent to Chicago's downtown Loop and West Loop neighborhoods, you will find endless opportunities to experience the best of Chicago. At the end of your day, enjoy a relaxing soak in your private outdoor hot tub (open year-round) before sinking in to your Tempur-Pedic king bed for a restful night's sleep. Complimentary off-street parking provides rare convenience near the city center.

Newly updated 1BD/1B in Old Irving Chicago!
Welcome to your home away from home in the heart of one of Chicago's safest and quietest neighborhoods! This beautifully updated 1 bedroom apartment offers everything you need for a comfortable and convenient stay. It is perfect for couples, solo travelers, and business visitors. Book now for a truly unforgettable experience in the Windy City! - 1 free parking spot - 400 MB Wifi - 2 smart T.V. with access to Netflix, Hulu, Amazon and more! - Desk - Easy app paid laundry in the building.

Downtown Park #11 - Mich Ave PH | gym+rooftop
Feel at Home, Unwind, and Enjoy the amenities you deserve when you come to Chicago! Guests love staying with us because: -Central Location on Grant Park (no car needed!) -FAST WIFI -En-suite Laundry -Did we mention the Lake & Park are outside our front door? -Comfy Queen bed -Loft style bedroom -Shared Rooftop Deck stunning views -Gym -3 blocks from Red "L" subway -Close to Grant Park, The Bean, Soldier Field, Museums If you are looking for a special place, you've found it!

Cozy 1bdr Rogers Park, Loyola, Northwestern.
Visiting Northwestern, Loyola University, Rogers Park or Evanston? This cozy AirBnb is perfectly situated. A beautifully clean, private apartment 2 blocks from parks & sand beaches, walking distance to Loyola, short ride to Northwestern, steps to public transportation & restaurants, red line "El" trains & bus routes. Apt has private, queen bedroom, en suite full bathroom, living room w/queen sofa bed, TV, dining table, & partial kitchenette. NOTE: No full kitchen.

MARVELOUS MAG MILE 2BD/2BA (+Rooftop)
Amazing Gold Coast/Streeterville location SECONDS from the LAKE and MAGNIFICENT MILE. Located on a quiet street, this apartment is tucked in between Michigan Ave and Lake Michigan. Steps away from the famous Drake Hotel, yet closer to the lake and Oak Street Beach. This spot is considered the best location in the city-- steps away from the best stores/restaurants in the world located on Michigan Ave (Mag Mile) and just north of Navy Pier.

3D Tour! Designer Condo near Logan Square
Scan QR code in photos for a 3D Tour! What you’ll love: - Totally renovated garden unit, completed in 2021. Everything new. - Upscale furnishings & decor. - Gourmet, fully equipped kitchen w/ new appliances, coffee maker and spices. - Remote work station w/ super fast Wi-Fi (600mb). - Serta queen mattress in master. - Bunk beds w/ full and twin sized memory foam mattresses. - Heat & A/C.

Urban Comfort in the Heart of Chicago
This is the PRIVATE first floor of our duplex condo, with your own entrance/exit, 75" flatscreen TV, central heat/air, and a newly remodeled en-suite bathroom. We are in the middle of Chicago's vibrant Northside while still having the benefit of coming home to a tree lined one lane residential street. Please contact us with any questions at all before you book your stay.
Popular amenities for South Side apartment rentals
Weekly apartment rentals

Modern Izakaya Studio in Wicker Park

South Shore Dr Retreat

2BR Chicago Escape | 20 min DT, Parking, Laundry

Beautiful Condo in North Kenwood with Parking

1st Floor Condo Apartment Close to Midway Airport

Rustic Cozy Haven in West Town

University of Chicago Condo-Upgraded and Spacious

The ModernFarmhouse Chicago-Near Downtown Chicago
Pet-friendly apartment rentals

Spacious 3BR/3BA Condo in Trendy Ukrainian Village

Spacious 3BR • Great for Groups • Fast WiFi • Pets

Wrigley Residence in Iconic Wrigley Rooftop

💥IN THE ACTION!💥 2 Bed, 2 Bath on Northalsted!

Lincoln Park Hideaway - 5 Min Walk to the Park!

MICH AVE #5|Safe DTown Grant Park, Museums 2bd/2ba

Large 2BR, 2BA, patio, sunroom, W/D, L-kitchen

Petfriendly Condo in Bucktown near blue line
Apartment rentals with a pool

"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym

"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux

Smoke & Pet Free, Washer Dryer, Fireplace, Balcony

Just remodeled apartment close to airport and mall

Chicago's Treasure "Heart of Evanston" 2bdr +1 Ba

Pond View, Washer Dryer, Non Smoking Community

"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool

Iconic Style, Charming Lake View
Destinations to explore
- Chicago Holiday rentals
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- Rentals with a hot tub South Side
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- Rentals with a patio South Side
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- Pet-friendly rentals South Side
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- Apartment rentals Chicago
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- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Six Flags Great America
- 875 North Michigan Avenue
- Humboldt Park
- Shedd Aquarium
- Guaranteed Rate Field
- Oak Street Beach
- The Field Museum
- Garfield Park Conservatory
- Wicker Park
- Lincoln Park Zoo
- Frank Lloyd Wright Home and Studio
- Brookfield Zoo
- Museum of Science and Industry
- Willis Tower
- The Beverly Country Club
- Illinois Beach State Park
- Washington Park Zoo
- The 606
- Raging Waves Waterpark




