Condo vacation rentals in South Side

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Top-rated condo rentals in South Side

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Guest favorite

Condo in Chicago

4.96 out of 5 average rating, 114 reviews

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 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. Free parking on Lawndale Ave.

Guest favorite

Condo in Chicago

4.95 out of 5 average rating, 126 reviews

10 Mins Downtown Free Parking Ping-Pong Sleeps 10

ONE FREE INDOOR & SAFE PARKING SPOT INCLUDED! The building is next to a bus stop that brings you right into downtown! You would enjoy staying in the spacious 1800 sq ft with 10 ft high ceilings. 2 bedroom/2 bathroom apartment with ZERO STAIRS to get inside! It is an excellent solution for elder people and families with kids or maybe just a group of friends coming to have fun at the UNITED CENTER sports event or tourists as well as business folks or doctors to attend McCormick Place conferences.

Superhost

Condo in Chicago

4.85 out of 5 average rating, 149 reviews

Quiet, Modern, Convenient 2 bedroom condo

PLEASE READ DESCRIPTION PRIOR TO BOOKING* Stay at this quiet, charming, Chicago-themed garden unit, sitting in the heart of Chicago's historic Bronzeville neighborhood. This convenient location with 1000 sq feet of space is perfect for young professionals, student, small groups, families, and people traveling with children. Easy access to public transportation, downtown Chicago, the Museum of Science and Industry, the University of Chicago, downtown Hyde Park, and etc. Hotel style, no kitchen

Superhost

Condo in Chicago

4.87 out of 5 average rating, 119 reviews

Unique 2BR/2BA FREE Street Parking/WI-FI Near DT

Traveling to Chicago and looking for the PERFECT place to stay? This Cozy unit is PERFECT for Business trips, Romantic Getaways or just relaxing with family. Its located in the Pilsen/ChinaTown area just minutes from Downtown, the McCormick Place, United Center, Rush Hospital, West Loop,South Loop, Michigan Ave, and White Sox Stadium. This listing offers FREE street parking on both sides of the street and Not to mention, it’s near plenty of shopping, Dining and Fun. Can't wait to host you!

Guest favorite

Condo in Chicago

4.94 out of 5 average rating, 208 reviews

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.

Guest favorite

Condo in Chicago

4.87 out of 5 average rating, 127 reviews

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.

Guest favorite

Condo in Chicago

4.91 out of 5 average rating, 163 reviews

Ultra clean/cozy condo, 10 mins south of Downtown!

The space has been intentionally designed to offer a modern, yet comfortable feel for individual guests or families. Conveniently located just 6 miles south of Magnificent Mile, 5.6 miles from Navy Pier, 1 mile to Lake Shore Drive, 1.5 miles from the University of Chicago, 2 miles from Museum of Science and Industry, 1.2 miles from the many restaurants on 53rd Street in Hyde Park and close to many Chicago favorites! On-street parking available directly in front of the building.

Superhost

Condo in Chicago

4.86 out of 5 average rating, 118 reviews

Cabin 308 at 747 Lofts

This studio apartment is in the perfect location in Chicago for getting to Downtown via the Blue Line L or to the Hot West Loop and Randolph street restaurant row. Walk to bars, shops, restaurants, coffee liquor stores and transportation with ease! You will love our spa baths, in unit laundry and full modern kitchens to make it feel like a home away from home. One of the best pizza spots in Chicago is only steps away!

Guest favorite

Condo in Chicago

4.95 out of 5 average rating, 106 reviews

Modern Izakaya Studio in Wicker Park

Stay in a sleek underground izakaya themed studio in one of Chicago's most desirable neighborhoods. Relax and enjoy the quiet zen decor. Find our hidden Japanese whisky room. Kick back in our pillowy loungers and dig into our ramen selection... The Izakaya Studio in the heart of Wicker Park is about giving you a uniquely luxurious guest experience from which to begin your adventures in Chicago.

Guest favorite

Condo in Oak Park

4.94 out of 5 average rating, 239 reviews

Picture Perfect 3Bed Steps from Train and FLW

Welcome to your beautiful 3 bedroom home-away-from-home! From the Instagram-worthy forest room to the cozy fireplace reading nook to the modern ice crusher in the kitchen, we've put so much thought into this home that we're sure you won't ever want to leave. Welcoming and newly updated, this unit is close to restaurants, shopping, the best of Frank Lloyd Wright, and the train to the city.

Guest favorite

Condo in Chicago

4.87 out of 5 average rating, 237 reviews

A Stones Throw from U Chicago South Campus!

This 2 bedroom garden unit located in vintage World's Columbian Exposition era building, it's been renovated and updated. You can't get much closer to the University of Chicago campus. This quiet garden unit is within walking distance of lakefront beaches, golf courses, the Museum of Science and Industry, public transportation, and Jackson Park. No pets allowed.

Guest favorite

Condo in Berwyn

4.9 out of 5 average rating, 126 reviews

Picturesque Apartment in Berwyn

This stylish place to stay is perfect for group trips. 2 bedrooms with queen beds, spacious living room with a sofa bed and well equipped kitchen. The apartment is located in North Berwyn, 15 minutes drive from Downtown Chicago, walking distance to Roosevelt Road's bars and restaurants, 0.8 miles to CTA Blue Line rail line station.