Some info has been automatically translated. Show original language

Condo holiday rentals in South Loop, Chicago

Find and book unique condos on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for South Loop, Chicago condo rentals

Weekly condo rentals

Guest favourite
Condo in Chicago
4.93 out of 5 average rating, 68 reviews

Urban Oasis Getaway. 6 stops to downtown!

LydiaRating, 5 stars1 week ago
The hosts are great—very responsive and accommodating. It’s a lovely space, with a fully functioning kitchen and very walkable to a close cta stop that’s a quick 30 minutes downtown. Area around the place is lower income, so if you’re not used to being in a city, you maybe feel less comfortable. Would recommend if you’re comfortable with urban environments though!
Top Guest favourite
Condo in West Town
5 out of 5 average rating, 30 reviews

Private rooftop | Breathtaking skyline view

BrianRating, 5 stars1 week ago
The space was exactly as advertised, roof top patio was awesome. Location was great and Anna was easy to work with. Definitely recommend, we would stay here again.
Top Guest favourite
Condo in West Town
5 out of 5 average rating, 57 reviews

Sun-Soaked West Loop Penthouse - Private Rooftop

KendallRating, 5 stars2 weeks ago
We stayed at Reggie’s place for Memorial Day weekend as a family of 5 (2 Adults, a 4 year old, twin 2 year olds). Reggie was very easy to communicate with from the first booking request. He let us know that there couldn’t be loud noise after 10 am (no issue for us) before confirming the booking. We had no issues with check in or check out, and he was responsive to every question. The location was perfect and walkable to so many things, including all the restaurants in west loop and worked well for our family and dog.
Guest favourite
Condo in West Town
4.9 out of 5 average rating, 86 reviews

Welcome to the Chi! Close to Downtown

MartelRating, 5 stars1 month ago
Enjoyed my stay at Jasna's. Great unit in a great location
Top Guest favourite
Condo in Lake View
4.98 out of 5 average rating, 118 reviews

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

RebeccaRating, 5 stars1 week 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 Woodlawn
5 out of 5 average rating, 39 reviews

University of Chicago Condo-Upgraded and Spacious

TiaraRating, 5 stars4 weeks ago
I had a wonderful stay! The place was exactly as described—clean, cozy, and in a great location. The host was super friendly and responsive, which made the whole experience smooth and welcoming. I especially appreciated the thoughtful touches like I’d definitely stay here again and highly recommend it to others!
Top Guest favourite
Condo in Tri-Taylor
5 out of 5 average rating, 28 reviews

Quick Drive to Downtown Chicago & Early Check-In

RoopaRating, 5 stars5 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 South Side
4.78 out of 5 average rating, 37 reviews

Entire Cozy Home in the Heart of Bronzeville

NgocRating, 5 stars1 month ago
This is a beautiful Airbnb, everything was absolutely clean and spotless. Plentiful amenities. We loved our stay, thank you for having us!!

Pet-friendly condo rentals

Guest favourite
Condo in North Side
4.84 out of 5 average rating, 361 reviews

Chic and Charming Vintage Condominium in Lincoln Park

PatrickRating, 5 stars2 weeks ago
We had a terrific stay and would definitely recommend it to others. Great location, especially if you are doing anything around Lincoln Park, DePaul, etc. The dedicated parking space was really helpful (there are 2 of them, but we only had one car). We had six people and were very comfortable. Colin is very responsive as well.
Top Guest favourite
Condo in Lake View
4.99 out of 5 average rating, 177 reviews

RockStar Pad W3A BoysTown/Wrigley Field/Parking

BenjaminRating, 5 stars1 day ago
My dad and I were on a baseball road trip and this was a perfect place for a cubs game! About a 15 minute walk. Will was responsive and friendly, and the place might have been one of the coolest bnbs. Such a fun and relaxing spot. Would easily stay again!
Guest favourite
Condo in Humboldt Park
4.92 out of 5 average rating, 120 reviews

Luxuriously bright 3-bedroom condo: The Treehouse

RachaelRating, 5 stars1 week ago
Our stay was fantastic. We have three children and everyone was comfortable. The location was perfect, the hosts were clear communicators and quick to respond. We would stay here again in a heartbeat.
Top Guest favourite
Condo in Lincoln Square
4.97 out of 5 average rating, 412 reviews

Lincoln Square Gem!

EvanRating, 5 stars6 days 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 North Side
4.92 out of 5 average rating, 347 reviews

Susie's Space. 2BR easy parking & pet friendly

PennyRating, 5 stars2 weeks ago
Great neighbourhood! Susan was very communicative and a great host. Highly recommend.
Top Guest favourite
Condo in Edgewater Glen
4.97 out of 5 average rating, 117 reviews

Steps from the Lake, Lovely 3-Bedroom Condo

CherannRating, 5 stars2 weeks ago
Very close to public transit, grocery stores, and restaurants. Quiet neighborhood and comfortable sleeping.
Superhost
Condo in Lincoln Park
4.79 out of 5 average rating, 224 reviews

Modern Luxury In Old Town - Sleeps 4

AlexanderRating, 5 stars3 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 Old Town Triangle
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!

Condo rentals with a pool

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, 106 reviews

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

JasonRating, 5 stars1 month ago
Our stay in Evanston was great! The apartment is close to all of downtown Evanston, the Metra, and the L. Also easy access to NU. Everything was just as it says and the free underground parking is a HUGE plus!
Condo in River North
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 Lombard
4.84 out of 5 average rating, 56 reviews

Smoke & Pet Free, Washer Dryer, Fireplace, Balcony

LelandRating, 5 stars5 months ago
Briana was responsive before, during and immediately after our stay, always seeking to ensure our comfort and satisfaction. We would have no reservations about staying with them again if they have an opening during a future visit to the area.
Condo in Magnificent Mile
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 stars1 day ago
You can walk to Northwestern University, and the surrounding environment is clean, comfortable, and pleasant.The house is fully equipped, and I love cooking in the kitchen.Our whole family had a wonderful week here.Would stay again.
Guest favourite
Condo in Evanston
4.96 out of 5 average rating, 100 reviews

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

AileenRating, 5 stars6 days 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.

Quick stats about condo rentals in South Loop, Chicago

  • Total rentals

    50 properties

  • Nightly prices starting at

    $66 NZD before taxes and fees

  • Total number of reviews

    3.7K reviews

  • Family-friendly rentals

    30 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with a pool

    10 properties have a pool

Destinations to explore

  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Chicago
  6. South Loop
  7. Condo rentals