Condo holiday rentals in South Side

Peaceful & Airy Modern-Chic Condo in Trendy Pilsen

Brand New Private Modern 2 bd 2bth apt for your stay in Chicago. We are located 2 blocks form the CTA line in the heart of Pilsen, a neighborhood Time Out labeled the 10th coolest in the world. Newly renovated, hardwood tiled floors throughout, chefs kitchen, toiletries, brand new furnishings including 2 queen beds, 1 twin sleeper, fresh linen, smart TV (HBO, Netflix, Hulu) wifi, tons of books,coloring books,board games & puzzles! We truly want you to feel like this is your home away from home.

Convenient & Spacious 3BR Condo w/Free Parking

Get cozy in this spacious 3-bedroom condo, conveniently located 3 blocks from the Halsted Orange Line overlooking Palmisano Park and only 5 minutes' drive to McCormick Place. Clean, neat, modern and comfortable, the condo offers spacious living space with an open kitchen, washer/dryer, and an outdoor balcony perfect for families and groups. Hungry? Our complex offers a few delicious high rated yelp restaurant options to fulfill your appetite. We look forward to hosting you and your guests!

3-bedroom exposed brick in Chicago's Wicker Park

Welcome to Wicker Park - one of Chicago's coolest walkable neighborhoods with endless restaurants, bars & shops. 2 blocks from the famous "L" train with access to the city & O'Hare airport. This 1893 vintage apartment has been freshly renovated and professionally designed blending historic details with a clean and modern aesthetic. The instagrammable one of a kind space has beautiful hardwood floors, soaring 10ft ceilings, exposed brick in all rooms, curated decor and a cozy private deck.

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.

Charming Condo near U.C./Loop/McCormick Place

Our spacious 3-bedroom, 2-bathroom condo is designed for comfort and convenience. Perfect for extended stays, it features a dedicated workspace with a desk and office chair, plus an in-unit washer and dryer. Two bedrooms offer cozy queen beds, while the third has a comfortable futon. The master bath is large enough for multiple people to get ready at once, and the fully stocked kitchen is ready for your culinary creations. Enjoy extra privacy in your secluded space within the building.

Lovely top floor 2BR/2BA, steps from everything!

BEST LOCATION IN LOGAN SQUARE/AVONDALE! 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.

The Oasis / Free street parking

Nothing beats summertime in Chicago! Explore downtown, recharge at the Oasis! Recently rehabbed 1st floor unit. Plentiful free street parking, well-stocked kitchen, lush backyard. Walk to parks, coffee shops, grocery store, restaurants, White Sox. Access to red & orange line trains to downtown and tourist attractions. Quick drive to Midway Airport & McCormick Center. No dishwasher Free washer dryer No chores at checkout =) Free early check in/late checkout *if available*

Chicago Oasis | Spa Bath, Patio & Fireplace

Experience the best of Chicago from this centrally located retreat just minutes from Downtown, top restaurants, shopping, and iconic attractions. Relax in a spa bathroom with a jetted tub and rain shower, cozy up by the fireplace, and enjoy a fully equipped kitchen. A king bedroom and queen Murphy bed comfortably accommodate up to 4 guests. Finish your evenings on the private patio gathered around the fire table.

A Stones Throw from U Chicago South Campus!

This spacious 2 bedroom garden unit is located in a lovely renovated vintage World's Columbian Exposition-era graystone. Located across the street from the University of Chicago campus, this comfortable and quiet unit is also within walking distance of the Obama Presidential Center, lakefront beaches, golf courses, the Museum of Science and Industry, public transportation, and Jackson Park. No pets allowed.

Modern Izakaya Studio in Wicker Park

The Izakaya Studio is a sleek, design-forward space in the heart of Wicker Park, with a secret whisky room inside. Inspired by the intimate atmosphere of a Japanese izakaya: warm, curated, a little unexpected. The kind of place where you settle in, pour something good, and stop thinking about your plans for a while. Spacious for a studio, and comfortable enough for a longer stay in Chicago.

Great location. Free parking.

Great location in Chicago's Wicker Park/Bucktown community. Fully furnished living room, bedroom with queen bed and bathroom. Internet, central heating/ac, small refrigerator, microwave, coffee maker. Small safe. Private free parking. One block from blue line (Division). From O’Hare via train – 35 min. 10 min to the city via blue line.

Comfy 2 Bedroom Apartment w/ Office

Located a few blocks from the University of Chicago and 1 mile west of Chicago's beautiful lakefront, this 1st floor Condo offers plenty of comfort and space. 2 Bedrooms include firm Queen-size mattress and plenty of space. Dedicated office space