Rent a retreat space in South Side, Chicago, IL

Discover and book unique spaces directly from hosts in South Side, Chicago, IL

The scene depicts an open, industrial-style loft with a blue couch, a wooden table surrounded by black chairs, and large windows allowing natural light to fill the space.
from$100/hr
South Facing Windows

South Side, Chicago, IL

5.0(166)
Venue capacity icon30

Photo Studio

South Facing Windows. Beautiful natural light studio located in the historic Spiegel headquarters building in Bridgeport. 2,330 sqft space with 13 ft ceilings and beautiful south facing windows. Perfect for photoshoots, video production, conferencing and more. Open layout for you to utilize the space for your needs. 2...
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The interior features a lounge area with a basketball hoop, leather sofas, and a vibrant green wall, creating a relaxed atmosphere for socialization.
from$450/hr
Urban Event Lounge

South Side, Chicago, IL

5.0(2)
Venue capacity icon20

Event Venue

Discover the perfect place for birthday parties, graduation celebrations, family gatherings, and more! We offer a spacious and versatile environment designed to make every event unforgettable. Enjoy ample seating and multiple screens for seamless entertainment. Our unique cyc wall serves as both a photobooth and...
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Luxury Upscale Loft | Natural Light | MEETINGS | Gallery Image in South Side, Chicago, IL
from$375/hr
Luxury Upscale Loft | Natural Light | MEETINGS | Gallery

South Side, Chicago, IL

5.0(2)
Venue capacity icon200

Industrial Loft

...industrial charm with modern elegance. This gallary has high ceilings & large windows providing lots of natural light. Great for offsites, workshops, trainings, retreats, etc. The space is perfect for: • Award Ceremonies • Discussion Panels • Coffee Talks • Book Clubs • Game Night • Meetings • Q&As And any other...
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SouthSide Liberation Center Image in South Side, Chicago, IL
from$125/hr
SouthSide Liberation Center

South Side, Chicago, IL

Venue capacity icon90

Event Space

...Can sit 75 people seated. Space can be converted to fit whatever need i.e. Workshops, fundraisers, birthday and baby shower, yoga, spa retreat, repass, meeting space. Chair and tables provided. Ample public parking available and easily accessable by public transportation...
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Vesatile Luxury Spa Retreat Near South Lakeshore - Perfect for Events, Productions, Meetings, and Relaxation Retreats Image in South Side, Chicago, IL
from$195/hr
Vesatile Luxury Spa Retreat Near South Lakeshore - Perfect for Events, Productions, Meetings, and Relaxation Retreats

South Side, Chicago, IL

4.5(2)
Venue capacity icon40

House

...ranch home, just 5 minutes from Lakeshore! This luxurious and versatile space is ideal for a wide range of gatherings—from wellness retreats and intimate celebrations to corporate meetings and creative productions. Experience the serene ambiance of our spa-inspired retreat, designed with modern aesthetics...
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Charming Apartment near U of C Campus Image in South Side, Chicago, IL
from$50/hr
Charming Apartment near U of C Campus

South Side, Chicago, IL

5.0(1)
Venue capacity icon15

Apartment Home

...Welcome to your perfect city retreat! This charming, newly renovated apartment offers a blend of classic charm and contemporary comforts . The space features high ceilings, large windows for abundant natural light, and tasteful décor that adds to the apartment’s cozy vibe. With two private...
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near South Side, IL

A modern interior featuring a dining table with fruit, a pool table, and a staircase leading to an upper level.
from$85/hr
Urban Penthouse in Historic Bronzeville Neighborhood

South Side, Chicago, IL

Venue capacity icon10

Penthouse

...Welcome to the Urban Penthouse 44, your ideal setting for photoshoots, video productions, off-site meetings, retreats, and teambuilding events. Situated in the heart of historic Bronzeville, Chicago, our 4-bedroom, 2.5-bathroom duplex spans two floors, offering a versatile and dynamic environment. Our space...
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Stay Inn South Shore Image in South Side, Chicago, IL
from$50/hr
Stay Inn South Shore

South Side, Chicago, IL

5.0(3)
Venue capacity icon20

Single-Family Home

...large tulip dining table seats eight, making it an ideal spot for dinner parties or group scenes. Bedrooms: Bedroom One: A chic retreat with a queen bed, alabaster sconces, and a desk, offering a stylish setting for any scene. Bedroom Two: Featuring a twin trundle...
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The living room features two blue sofas with decorative pillows, a glass coffee table, and large windows covered with light blue curtains.
from$30/hr
Urban Southside Cozy Apartment

South Side, Chicago, IL

4.9(15)
Venue capacity icon20

Apartment

Our aesthetically pleasing and cozy 1 bedroom apartment is perfect for your next small event or creative project! Within our 500 sq. ft space, we offer a vibrant swanky living room area, complete with a plush sofa set, sleek coffee table and Instagram-worthy fireplace along...
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An indoor studio space with wooden floors, a large mirror on one wall, and a prominent flat-screen TV mounted above a white stone feature wall.
from$200/hr
Chicago Southside luxury Hidden Gem

South Side, Chicago, IL

Venue capacity icon75

Event Space

...and nonprofit businesses. We have had guest that have done photo shoots, game nights, Zumba classes, dance classes, release parties,movie sets, retreat, meditation, school classes and cooking classing in our chef kitchen. We have about 1300 open square feet inside and about 1200 square...
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A meeting room with a large wooden table surrounded by chairs, two windows providing natural light, and a decorative fireplace.
from$100/hr
Victorian House Located in Chicago

South Side, Chicago, IL

Venue capacity icon30

Victorian House

...We can host holistic activities such as, yoga, sound therapy and other similar activities. The space is also ideal for team meetings, retreats and small social gatherings. There are several spaces available for use including individual meeting rooms, small prep kitchen, a large open living/dining...
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Cozy and spacious 4 bedroom house, 3 floors, fireplace, with pond in the back yard Image in South Side, Chicago, IL
from$60/hr
Cozy and spacious 4 bedroom house, 3 floors, fireplace, with pond in the back yard

South Side, Chicago, IL

Venue capacity icon13

House

...room with a charming fireplace, three inviting bedrooms, and a bathroom. This layout is perfect for families or groups needing a comfortable retreat. **Unique Features:** Our home is equipped with modern amenities, including high-speed Wi-Fi, smart TVs, and a serene yard with...
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Lakeside Charm: Two-Story Home Minutes from Downtown Chicago and Lake Michigan Image in South Side, Chicago, IL
from$150/hr
Lakeside Charm: Two-Story Home Minutes from Downtown Chicago and Lake Michigan

South Side, Chicago, IL

Venue capacity icon20

House

...Welcome to our charming two-story home, perfectly situated near the lake and just minutes from downtown Chicago. This spacious retreat offers a versatile layout, ideal for gatherings, events, photo shoots, and more. Inside, you’ll find generous living areas filled with natural light, stylish...
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A dining area with a dark wooden table surrounded by upholstered chairs, a chandelier overhead, and an open view into a kitchen with modern appliances and decor.
from$125/hr
Chic Urban Residence with basement bar and games

South Side, Chicago, IL

Venue capacity icon25

Residence

...and stylish residence provides the perfect setting for any occassion. Anything from photoshoots, baby showers, family game nights, prom send off, business retreats, girls night, and pop up shops. Contemporary large dining room table that seats up to 6 , and an open kitchen which is...
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A modern salon interior with black leather chairs, a green plant wall, and hooded hair dryers on stands.
from$30/hr
Urban , south side , roomy

South Side, Chicago, IL

5.0(2)
Venue capacity icon3

Hair Salon

Looking for a Clean, Bright, Airy and Welcoming Suite with plenty of sunlight. This 70sq.foot storefront office space is located Morgan Park Area . It is the perfect location for your next meeting, study space , Work space , Creative thinking , Photo Shoot...
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Frequently Asked Questions

Reviews for retreat spaces

Christine A.
Bright And Sunny Open Loft With Exposed Brick Walls
Beautiful, cozy, high vibe place and space that was perfect for our day long leadership retreat. Easy to have lunch delivered. Good amount of space for an intimate group. Beautifully curated and cultivated. thank you...
Jamiece A.
Bright & Airy Gorgeous Loft | Meeting Ready
The space was just what we needed for our work retreat. Brett was very communicative and helpful. Our team would recommend and use this space again...
Randy B.
Boardroom in West Loop Business Center
The space was great for my department's offsite retreat. The outdoor space was a great area to step out and get some fresh air or a nice outdoor lunch break. Sarah was very responsive and accommodating. We would definitely book again...
Tamara E.
Bright And Sunny Open Loft With Exposed Brick Walls
LOVEDDD this space!! So perfect for our personal branding retreat where folks can feel comfortable and relax
Marissa F.
Bright And Sunny Open Loft With Exposed Brick Walls
We hosted a staff retreat and this was the perfect aesthetic to have a creative incubator space for planning. We had everything we needed...
Ava F.
Bright And Sunny Open Loft With Exposed Brick Walls
the necessary instructions and shared her cellphone number for easy communication. Her space was spacious, clean, beautiful, and provided the essentials for a great retreat . I would definitely book this space again...
Pedro G.
Minimalist Speakeasy located in the West Loop
The space was terrific for our work retreat, and Adam was a wonderful host. I would definitely recommend for small gatherings whether for work or personal events...
Karla G.
Sacred Work Space- beautiful, sunny, modern in the heart of Wicker Park
We used the space for our leadership retreat. It's a great space and is perfectly set-up for yoga followed by lunch and a long meeting. We'd definitely book again...
Katlyn H.
West Loop Loft with Skyline View & Rooftop
Melissa was an excellent host and the space was absolutely perfect for our team retreat. We couldn't have asked for a better experience! Thank you so much...
Katlyn H.
West Loop Loft with Skyline View & Rooftop
This space worked perfectly for our team retreat! Melissa is a wonderful host. She provided coffee, snacks and water to accommodate our group. This was our second time utilizing this space, and we'll certainly be booking again soon. Thank you so much, Melissa...
Zane H.
Spectacular Corner 3BR Loft In Fulton Market, Newly Renovated
Todd was great to work with for our organization’s retreat! We’d love to stay here again
Lauren Michelle J.
Sacred Work Space- beautiful, sunny, modern in the heart of Wicker Park
This space was amazing, beautiful and perfect for hosting our staff retreat! I will definitely be using them again
Krista K.
Bright And Sunny Open Loft With Exposed Brick Walls
Absolutely gorgeous and cozy space, perfect for our staff retreat! Great WiFi and sound system. Super helpful host. We are so excited to book again in the future...
Rose L.
Bright And Sunny Open Loft With Exposed Brick Walls
my event and will definitely book again! Thank you for being an amazing host with an amazing space! So peaceful and perfect for our retreat...
Christine M.
West Loop Loft with Skyline View & Rooftop
The space itself was gorgeous - more spacious than I anticipated and very comfortable. This met all of my needs for a work related committee retreat; the amenities provided and cleanliness of the space were exemplary. I and everyone on my team said that we would absolutely book again! Thanks to...
Simone M.
A Bright White Box: Converted Storefront in the Industrial West Fulton Market
Andrew was super helpful and communicative. The space was perfect for the retreat, highly reccomend
Cecily M.
Hip West Loop loft production and meeting space
AMAZING SPACE held a company retreat here and the hosts were hands on, attentive, helpful and even chatted with the group if you’re thinking of booking don’t think about it go for it it’s absolutely the best choice to make...
Leona Q.
Bright And Sunny Open Loft With Exposed Brick Walls
My team had an incredible time for our annual retreat! This was the perfect place for a change of pace, with gorgeous plants, decor, and a very different feel than a 9-5 office. We were a group of 10 and were very comfortable. Shannon was an incredible host...
Ted T.
High-end bohemian oasis. Large open floor plan, high ceilings, concrete floors and features.
my day! The space is calming and live enriching. Highly recommended for personal and professional needs. I may book again to have a meditation retreat for a few hours...
Raina V.
Bright & Airy Gorgeous Loft | Meeting Ready
Brett’s space was perfect for our work retreat. He was very responsive and set up an extra table at my request. Everyone loved it - would use this space again...

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