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

4.9 out of 5 average rating, 100 reviews

Unique 2BR/2BA FREE Parking/WI-FI Minutes From 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 area, ChinaTown area just minutes from Downtown and the McCormick Place, United Center, Rush Hospital, West Loop,South Loop, Michigan Ave, 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

4.86 out of 5 average rating, 347 reviews

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.

Guest favorite

Condo in Chicago

4.96 out of 5 average rating, 158 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

4.85 out of 5 average rating, 141 reviews

Quiet, Modern, Convenient 2 bedroom condo

PLEASE READ DESCRIPTION PRIOR TO BOOKING* Stay at this quiet, charming, Chicago-themed garden unit suite, 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 so much more.

Superhost

Condo in Chicago

4.81 out of 5 average rating, 139 reviews

Cabin 207 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! Early Check-Ins and Late Check-Outs are difficult to accommodate.

Guest favorite

Condo in Chicago

4.92 out of 5 average rating, 135 reviews

Modern designed 2bed/2bath | Heart of Bronzeville!

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.

Guest favorite

Condo in Chicago

4.88 out of 5 average rating, 105 reviews

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!

Guest favorite

Condo in Chicago

4.9 out of 5 average rating, 220 reviews

A Stones Throw from U Chicago South Campus!

This 2 bedroom condo has entirely new EVERYTHING! Located in vintage World's Columbian Exposition era building, it's been newly renovated and updated. You can't get much closer to the University of Chicago campus. This quiet condo 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 Chicago

4.97 out of 5 average rating, 376 reviews

Lincoln Square Gem!

Very nice and updated condo in the heart of Lincoln Square! Lots of fun design elements and artwork await. This sunny condo is in the 2nd floor of a 2-flat building with friendly neighbors. My partner and I live on the first floor. You can walk to all that Lincoln Square has to offer! The Brown Line (Western stop) is just 2.5 blocks away for an easy commute to downtown!

Guest favorite

Condo in Chicago

4.97 out of 5 average rating, 760 reviews

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, cable TV, dvd/Blu-ray, 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.