
Condo vacation rentals in South Side
Find and book unique condos on Airbnb
Top-rated condo rentals in South Side
Guests agree: these condos are highly rated for location, cleanliness, and more.

❤︎ 1,800ft² Parking ⎜ Workspace ⎜ W/D ⎜Full Kitch
• 1,800ft² | 167m² . My home is on the top floor of a four flat Itallian Brick Building . You have 3 flight of stairs to Climb to enter. • Walk Score 95 (walk to cafe's, bars, eating, nightlife, etc.) • Biker's paradise • Fully equipped + stocked kitchen • Extremely safe neighborhood • Onsite, secured parking • Onsite washer + dryer ➠ 5 min walk to the Lincoln Park ➠ 10 min drive to Downtown Chicago ➠ 30 min drive to O'Hare Chicago Airport Note: The fireplace is non working

10 Min 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.

Humboldt Park Traveler's Lodge
Come stay at my gorgeous condo! Featuring exposed brick, a private entrance, stainless steel appliances, and a queen bed --> all on a quiet tree lined street! It's a perfect place to re-energize between big city adventures. Free street parking, and a 5 min walk to some of the best independently owned shops, restaurants, and bars in the city. Also, the massive and incredible Humboldt Park is also just a 5 min walk away! Please reach out for recommendations - I love giving them to people!

The Oasis / Free street parking
Comfortable home in quiet, walkable, family-friendly neighborhood with quick access to downtown! 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*

Spacious 3BR/3BA Condo in Trendy Ukrainian Village
Welcome to our Cozy and luxurious three-bedroom, three-bath property in Ukrainian Village, Chicago. With a modern design, natural light, and a private patio, our home offers a comfortable and stylish stay. Enjoy a fully equipped kitchen, cozy living area, high-speed Wi-Fi, and laundry facilities. Explore the vibrant neighborhood with its unique shops and restaurants, visit nearby Smith Park or venture to the trendy Wicker Park area. Downtown Chicago's attraction are also easily accessible.

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.

Downtown Chicago - Spa Bath, Patio, 3 blocks to L
Explore Chicago's charm just moments from downtown! This Airbnb boasts a spa bath with a luxurious rain shower and jetted tub, a fully equipped kitchen for culinary adventures, comfortable reclining sofas for relaxation, and ample space to unwind. Sleep like royalty in the master bedroom's king bed, and a queen murphy bed in the living area ensures a comfortable stay for up to four guests. Step outside to the patio with a fire pit for cozy evenings. Your Windy City getaway begins here!

GLORIOUS GOLD COAST GETAWAY
Welcome! 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. We look forward to hosting you!

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!

MICH AVE #5|Safe DTown Grant Park, Museums 2bd/2ba
Feel at Home, Unwind, and Enjoy the amenities you deserve next to Grant Park! Most homes don’t provide professional service along with “local vibes.” Guests love staying with us because: ✅ Beautiful views of Chicago ✅ Central Location ✅ Parking garage attached to the building ($15-30 / night - Operated by LAZ) ✅ FAST WIFI ✅ Comfy KING beds ✅ Shared Rooftop Deck w Grills ✅ 1 block from Red "L" subway ✅ Close proximity to Grant Park, Soldier Field, Museums

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!

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!
Popular amenities for South Side condo rentals
Weekly condo rentals

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

The Upscale Getaway Near Downtown

Newly updated 1BD/1B in Old Irving Chicago!

Near Lake Michigan & Wrigley Field

The En Bronze ~ 7mins To Dining & Downtown Chicago

2BD/2BA MAG MILE MASTERPIECE (+Rooftop)

Modern Luxury In Old Town - Sleeps 4

Peaceful & Airy Modern-Chic Condo in Trendy Pilsen
Pet-friendly condo rentals

Chic and Charming Vintage Condominium in Lincoln Park

Wrigley Residence in Iconic Wrigley Rooftop

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

Convenient & Spacious 3BR Condo w/Free Parking

Luxuriously bright 3-bedroom condo: The Treehouse

NEW luxury Old Town 1-Bedroom condo

Can't Beat This 2min Walk to Wrigley!

Susie's Space. 2BR easy parking & pet friendly
Condo 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 Vacation rentals
- Platteville Vacation rentals
- Indianapolis Vacation rentals
- Downtown Chicago Vacation rentals
- Southern Indiana Vacation rentals
- Detroit Vacation rentals
- St. Louis Vacation rentals
- Columbus Vacation rentals
- Louisville Vacation rentals
- Cincinnati Vacation rentals
- Wisconsin River Vacation rentals
- Milwaukee Vacation rentals
- Rentals with a washer and dryer South Side
- Waterfront rentals South Side
- Rentals with a hot tub South Side
- Rentals with an EV charger South Side
- Rentals with a fire pit South Side
- Rentals with beach access South Side
- Rentals with outdoor seating South Side
- Rentals with a patio South Side
- Family-friendly rentals South Side
- Rentals with a fireplace South Side
- House rentals South Side
- Private suite rentals South Side
- Bed and breakfasts South Side
- Smoking-friendly rentals South Side
- Apartment rentals South Side
- Fitness-friendly rentals South Side
- Rentals with lake access South Side
- Rentals with pools South Side
- Rentals with breakfast South Side
- Pet-friendly rentals South Side
- Townhouse rentals South Side
- Condo rentals Chicago
- Condo rentals Cook County
- Condo rentals Illinois
- Condo rentals United States
- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Grant Park
- Navy Pier
- 875 North Michigan Avenue
- Six Flags Great America
- Humboldt Park
- Soldier Field
- Shedd Aquarium
- Guaranteed Rate Field
- The Field Museum
- Wicker Park
- Lincoln Park Zoo
- Oak Street Beach
- Garfield Park Conservatory
- Frank Lloyd Wright Home and Studio
- Brookfield Zoo
- Museum of Science and Industry
- Illinois Beach State Park
- Willis Tower
- Washington Park Zoo
- The 606




