Condo vacation rentals in South Side

Find and book unique condos on Airbnb

Top-rated condo rentals in South Side

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Guest favorite

Condo in Chicago

4.84 out of 5 average rating, 305 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.

Mar 2 – 9

G$29,461 GYD per night

Guest favorite

Condo in Chicago

4.93 out of 5 average rating, 187 reviews

Pvt 1bdr Rogers Park, Loyola, Northwestern.

Visiting Northwestern, Loyola University, Rogers Park or North Shore Evanston Hospital? This AirBnb is perfectly situated. An immaculately clean, private apartment 2 blocks from parks & sand beaches, walking distance to Loyola, short ride to Northwestern, steps to public transportation - red line "El" trains & bus routes. Apt has a private, queen bedroom with en suite full bathroom, living room with queen sofa bed, TV, dining table and kitchenette. Dogs allowed and Parking available for a fee.

Jan 25 – Feb 1

G$20,349 GYD per night

Guest favorite

Condo in Chicago

4.97 out of 5 average rating, 101 reviews

Stylish 3BR + Free Parking 10-15mins from Downtown

This apartment is located in Historical Humboldt Park, a residential area that is an easy 10-15mins drive to Downtown, Medical District, Wicker Park, West Town, Logan Square, and Ukranian Village. Due to the proximity, we host guests visiting for tourism, fests,concerts, sport events , work conferences, weddings, birthdays, and visiting family. There are grocery stores closeby. There’s street parking and a gated private parking available. Location wise, you are close enough to everything.

Sep 3 – 10

G$32,325 GYD per night

Guest favorite

Condo in Little Italy

4.96 out of 5 average rating, 120 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.

Jun 25 – Jul 2

G$59,328 GYD per night

Superhost

Condo in Chicago

4.9 out of 5 average rating, 136 reviews

East Garfield Park 2 Bedroom

Charming two bedroom, two bath Apartment. With washer/dryer.in Historic East Garfield Park beautiful block filled with old Mansions. Half a block to the Green line El Train.3 stops to Morgan street also known as the fulton market district and resturant row.5 stops to Downtown Chicago. Half a block from Garfield Park and it's Conservatory. Carroll street Artist district 3 blocks away Ukrainian. village, Logan square, wicker park a ten minute car ride away. Close to goose island brewery,

Nov 16 – 23

G$28,127 GYD per night

Guest favorite

Condo in Chicago

4.87 out of 5 average rating, 118 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.

Oct 16 – 23

G$24,779 GYD per night

Guest favorite

Condo in Chicago

4.92 out of 5 average rating, 100 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.

Dec 12 – 19

G$76,636 GYD per night

Guest favorite

Condo in Chicago

4.98 out of 5 average rating, 234 reviews

Urban Luxury 1BR/2BA Logan Square Condo w/Garage

Luxurious 1BR/2BA garden-level condo in vibrant Logan Square! Comfortably furnished with tons of light and amenities, conveniently located one block from the Logan Square Blue Line Station and located on a quiet street. Steps from all of the hip restaurants and nightlife in Logan Square. Huge back yard and patio with fire pit for guest use. Free on-site garage parking with remote. And, if using public transit, the Logan Square is 8 stops, ~15-20 minutes from the Loop downtown!

Mar 18 – 25

G$40,794 GYD per night

Guest favorite

Condo in Chicago

5.0 out of 5 average rating, 100 reviews

Spacious 4 Bedroom Condo

Located in West Town in the heart of Noble Square, just north of West Loop with access to all the best restaurants and only minutes away from River North and Old town, enjoy this 4 bedroom, 3.5 bath condo with private parking, 2 living spaces, heated floors throughout the entire lower level and steam showers. A gourmet kitchen stocked with everything you will need including an espresso maker. This home is perfect for families, couples, friends or traveling for business.

Feb 11 – 18

G$94,293 GYD per night

Superhost

Condo in Chicago

4.87 out of 5 average rating, 108 reviews

Spacious Duplex in Great Location

This below-grade unit has everything you want! Nestled on a quiet tree-lined street public transport is close by and downtown is a quick car ride away. The condo has lots of space and all the amenities you can ask for - plenty of parking, a King sized bed with premium linens, a luxury memory foam mattress, walk-in closet to store all your things, double spa shower, and a coffee bar stocked with top shelf Nespresso coffee. This unit books up quickly, so grab it today!

Oct 13 – 20

G$20,498 GYD per night

Guest favorite

Condo in Oak Park

4.88 out of 5 average rating, 164 reviews

Attractive Flat - Historic Oak Park

Attractive One Bedroom Flat for Rent in Historic Downtown Oak Park. Truly - one of the Best Locations in all of Chicago. Two Blocks from the Epicenter of this lovely city. Easy Access to Public Transportation to Downtown Chicago or the Greater Metro Area. The Elevated train -and- the Metra Train (15 Minutes by Train to Downtown) are each a quick walk. See “ property description “ For Important information for all perspective Guests:

Dec 22 – 29

G$28,322 GYD per night

Guest favorite

Condo in Chicago

4.86 out of 5 average rating, 125 reviews

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.

Nov 7 – 14

G$23,152 GYD per night