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Condo holiday rentals in South Side

Find and book unique condos on Airbnb

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Popular amenities for South Side condo rentals

Weekly condo rentals

Superhost
Condo in Chicago
4.83 out of 5 average rating, 18 reviews

1st Floor Condo Apartment Close to Midway Airport

MariaRating, 5 stars1 month ago
We enjoyed our stay at Mackson’s place. We were out and about the majority of the time during our stay, but were able to relax in the evenings in the condo. The condo is in close proximity to a local park which was nice. We traveled with a baby and brought our own pack-n-play for the baby to sleep in. There was plenty of room for the pack-n-play in the bedroom. If we have another event in that area, we’d book again.
Superhost
Condo in Chicago
4.87 out of 5 average rating, 52 reviews

Art Deco Inspired Designer 2 Bed Loft In West Town

EllenRating, 5 stars1 week ago
We booked David’s place for a last minute trip to the city. We were thrilled with how beautiful and spacious the apartment was. We felt right at home, the kitchen was well equipped and the apartment was comfortable. Parking and access to the building can’t be beat!
Top Guest favourite
Condo in Chicago
5 out of 5 average rating, 28 reviews

Quick Drive to Downtown Chicago & Early Check-In

RoopaRating, 5 stars6 days ago
Thomas is an amazing host! He was very proactive in communicating right from the start of the trip ,was very welcoming and warm. This Airbnb house is spic and span. It is very clean , beautifully decorated and has everything you need to be comfortable in a home. The Kitchen is stocked with all vessels , has basic pantry supplies and has a gas for cooking warm meals. Thomas and his wife were also very thoughtful and considerate and left us a basket full of snacks and coffee pods - that was a really sweet gesture from their end.The coat closet has umbrellas , incase you need one , which I thought was very considerate as well. Thomas also regularly checked in on us to ensure we had a smooth stay - his check in and checkout instructions were uber clear and made it possible to check in and check out without any hassles. There is a starbucks and a bunch of small restaurants on a 10 - 13 min walk from the house.Overall , I would highly recommend his house to other guests.
Guest favourite
Condo in Chicago
4.84 out of 5 average rating, 31 reviews

Condo off the lake

GabeRating, 5 stars6 days ago
This was the best property we've ever stayed at. Everything was as advertised or better. Darryl answered all our questions in a timely fashion and even had the place ready a little before our scheduled check-in to accomodate our flight schedule. The neighborhood is excellent, very safe and quiet. We never had to park more than 50 feet from the front door. Everyone's first impression was "This place is huge" and it was actually even better than the pictures indicated--and the pictures indicated it would be great. Absolutely would look to stay here any time we are in Chicago and looking for something south of downtown. Would recommend to anyone looking for a place in the area. Easy commutes to downtown or Hyde Park and ride shares always arrived within 10 minutes.
Guest favourite
Condo in Chicago
4.98 out of 5 average rating, 165 reviews

Spacious 4 Bedroom Condo

ScottRating, 5 stars4 weeks ago
We had a great stay for an extended wedding weekend with our entire family. Adrian's home was clean, modern, and well appointed. The beds were all very comfortable and linens were very soft. We felt very safe and the garage parking spot was a nice addition. I would highly recommend his home and would not hesitate to rebook there in the future.
Superhost
Condo in Chicago
4.88 out of 5 average rating, 17 reviews

Penthouse w/ Massage Chair Near McCormick.

Dimeress SRating, 5 stars3 months ago
Great quiet stay! After having another host cancel the day before checking in I found Keeva’s place and I must say I’m happy the other host cancelled because staying here was perfect! Also that massage chair was everything !
Superhost
Condo in Chicago
4.78 out of 5 average rating, 18 reviews

HUGE Modern, 1BD Home Office, Chef's Kitchen Patio

BrianRating, 5 stars2 weeks ago
Spacious with many amenities! Great place to relax with friends.
Guest favourite
Condo in Chicago
4.93 out of 5 average rating, 59 reviews

Luxury Penthouse w/ HOT TUB & Amazing Roof Deck

GreerRating, 5 stars1 week ago
Great experience and a flexible, highly communicative host. Would stay again in a heartbeat!

Pet-friendly condo rentals

Superhost
Condo in Chicago
4.84 out of 5 average rating, 134 reviews

816 PLZN Luxury Apt | Rooftop | Garage Parking

HasimeRating, 5 stars1 month ago
The host and team were very communicative. The space was beautiful with high ceilings , clean, spacious, and well equipped.
Top Guest favourite
Condo in Chicago
4.99 out of 5 average rating, 178 reviews

RockStar Pad W3A BoysTown/Wrigley Field/Parking

RonniRating, 5 starstoday
Beautiful, clean unit and Will was extremely responsive and helpful. Super clean, and the beds and furniture were soooooo comfortable! It looks exactly as it does in the photos and there are so many items included, in case you forgot something! A foot massager?! Amazing 🤣The location is perfect with lots to do close by and no shortage of options for places to eat. I feel extremely fortunate that I came across this one and will definitely book again in the future. Just perfect.
Top Guest favourite
Condo in Chicago
4.97 out of 5 average rating, 412 reviews

Lincoln Square Gem!

EvanRating, 5 stars1 week ago
Great location, and easy access to all main streets. The neighborhood is quiet, and very safe. The people in the neighborhood were very welcoming. The condo was nice, very spacious and a great value for the cost.
Top Guest favourite
Condo in Chicago
4.98 out of 5 average rating, 118 reviews

💥IN THE ACTION!💥 2 Bed, 2 Bath on Northalsted!

RebeccaRating, 5 stars2 weeks ago
One of my favorite Aibnbs of all time. The location is FUN - right in the center of the action in Northalsted. The space itself is beautiful and clean. The bedrooms are spacious, and the kitchen is well equipped. Allan was awesome and left us a bottle of prosecco to welcome us. Best part of the house is the huge covered front balcony - a front row seat to the joyous crowds, especially on the weekend. We saw a concert, walked to a Cubs game, spoiled the kids on Michigan Ave - and everyone agreed the balcony was our fave part of the trip. The rear deck is icing on the cake. We were in town so our kids could go to a concert and they also loved the area. If you're sensitive to noise, bring earplugs - all the action brings a bit of music - but really it's a steady din so super easy to tune out at bedtime. We love this place and can't wait to come back!
Guest favourite
Condo in Chicago
4.93 out of 5 average rating, 240 reviews

Cozy 1bdr Rogers Park, Loyola, Northwestern.

JenniferRating, 5 stars1 week ago
This is a WONDERFUL one bedroom apartment that is both private and spacious! The owner/host has the space fabulously decorated with an eclectic mix of original contemporary artwork and antiques. Nothing is generic about the space and it has been outfitted for guests with loving care. The host, Kaye, clearly puts much trust in her guests with her charming decor and furnishings. The amount of space, the privacy and the home-y feel make it a place we'd love to return to.
Superhost
Condo in Chicago
4.79 out of 5 average rating, 224 reviews

Modern Luxury In Old Town - Sleeps 4

AlexanderRating, 5 stars4 weeks ago
I had a great stay! The Airbnb was easy to get to and in a fantastic location within walking distance to restaurants, bars, gyms, and public transportation. The space was very clean and well-maintained. Would definitely recommend and stay here again!
Superhost
Condo in Chicago
4.88 out of 5 average rating, 154 reviews

Lincoln Park Hideaway - 5 Min Walk to the Park!

SydneyRating, 5 stars2 weeks ago
Cindy was a lovely and responsive host and the apartment was great. She was very responsive and let me adjust the booking without any hassle. There was plenty of towels and blankets, and the coffee area was well stocked. Location was in a great area of lincoln park very close to the zoo & actual park area and not a far walk to the cta/many bus stops. Would definitely recommend!
Guest favourite
Condo in Chicago
4.97 out of 5 average rating, 124 reviews

Large 2BR, 2BA, patio, sunroom, W/D, L-kitchen

SusanRating, 5 stars2 weeks ago
Pablo was an incredibly responsive and helpful host, even volunteering to have us check in early. His place was spacious (can accommodate 4-5 people) and comfortable. . . really a home away from home. Had everything we needed for a 5-day stay . . washer/dryer a plus! Parking can be a challenge, but using SPOT Hero helped us identify available spots. While next to the train, the train noise was more like white noise and did not disturb us. Would definitely stay again!

Condo rentals with a pool

Guest favourite
Condo in Downers Grove
4.92 out of 5 average rating, 63 reviews

Upscale, Washer Dryer, Smoke Free, Pet Free,

ChidoRating, 5 stars2 months ago
I really loved the place—it was cozy, soundproof, and felt just like home. It had a warm, inviting atmosphere and a great sense of comfort. Plus, the neighborhood felt very safe, which made our stay even better.
Guest favourite
Condo in Evanston
4.96 out of 5 average rating, 97 reviews

"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym

AaronRating, 5 stars1 month ago
I would highly recommend Michelle's listing! The listing is spacious and perfect for a couple or small family (we had our <1 year old). Michelle is communicative, all the instructions are clear, and the location is convenient.
Guest favourite
Condo in Evanston
4.95 out of 5 average rating, 107 reviews

"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux

RemiRating, 5 stars1 month ago
Our Stay at The Bliss of Evanston was great. The host is very responsive and was very accommodating of our requests. The location and view can not be beat.
Condo in Chicago
4.4 out of 5 average rating, 10 reviews

voco: Balcony & City View

BrookeRating, 5 stars3 weeks ago
Our stay here worked out perfectly. The host was nice, and the location was centrally located to great shopping and restaurants. Very private and safe. The view at night was beautiful.
Condo in Chicago
4.33 out of 5 average rating, 9 reviews

30 E. Huron #2603 Private Residence

Diego HernanRating, 5 stars25 months ago
Incredible experience. Kevin was very nice and helped us with everything. I would go back again to this amazing apartment and great location.
Guest favourite
Condo in Elk Grove Village
4.94 out of 5 average rating, 85 reviews

Just remodeled apartment close to airport and mall

MeagRating, 5 stars2 months ago
I am incredibly particular with places I stay. This place was simple, very clean, had everything you would need to be comfortable. Bed was great! ⭐️ ⭐️ ⭐️ ⭐️ ⭐️
Guest favourite
Condo in Evanston
4.91 out of 5 average rating, 126 reviews

Chicago's Treasure "Heart of Evanston" 2bdr +1 Ba

FeiRating, 5 stars2 days ago
可以步行到西北大学,周边环境整洁舒适宜人。屋内设施齐全,很喜欢在厨房cooking。我们全家在这里度过了愉快的一周。下次还会入住。
Guest favourite
Condo in Evanston
4.96 out of 5 average rating, 100 reviews

"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool

AileenRating, 5 stars1 week ago
Space was clean and in a charming, walkable city. The view in the living room was beautiful. The neighbors were quiet. The coffee in the condo and in the lounge was surprisingly delightful. Our group of friends had a great time, and this would be a perfect place for a family.

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