Monthly Rentals in South Side
Discover long-term rentals that feel like home for stays of a month or longer.
Nearby monthly rentals
Top guest favourite
Private room in Chicago
4.91 out of 5 average rating, 238 reviewsFresh and Sunny Bed & Bath by UofC
Superhost
Private room in Chicago
4.67 out of 5 average rating, 3 reviewsliving room with twin sofa bed
Guest favourite
Flat in Chicago
5 out of 5 average rating, 5 reviewsLong Stay,The Jewels,2bd/2ba,UC 2mi,Pkg,DTWN 15mi
Superhost
Private room in Chicago
4.66 out of 5 average rating, 120 reviewsOne bedroom/semi-private bath in Hyde Park
The comforts of home and great monthly rates
Amenities and perks for longer stays
Furnished rentals
Fully furnished rentals include a kitchen and the amenities you need to live comfortably for a month or longer. It’s the perfect alternative to a sublet.
Flexibility you need
Choose your exact move-in and move-out dates and easily book online, without any additional commitment or paperwork.*
Simple monthly prices
Special rates for long-term holiday rentals and a single monthly payment without additional charges.*
Book with confidence
Reviewed by our trusted community of guests and 24/7 support during your extended stay.
Work-friendly spaces for digital nomads
Travelling professional? Find a long-term stay with high-speed wifi and dedicated working spaces.
Looking for corporate housing?
Airbnb has fully furnished apartment homes ideal for staffing, corporate housing and relocation needs.
Popular amenities for monthly rentals
Destinations to explore
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- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- West Side Holiday rentals
- North Side Holiday rentals
- South Bend Holiday rentals
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- Rentals with an EV charger South Side
- Rentals with a fireplace South Side
- Townhouse rentals South Side
- Pet-friendly rentals South Side
- Family-friendly rentals South Side
- Rentals with a firepit South Side
- Fitness-friendly rentals South Side
- House rentals South Side
- Bed and breakfasts South Side
- Family-friendly rentals South Side
- Apartment rentals South Side
- Flat rentals South Side
- Smoking-friendly rentals South Side
- Waterfront rentals South Side
- Rentals with beach access South Side
- Rentals with a washing machine and dryer South Side
- Rentals with a patio South Side
- Rentals with outdoor seating South Side
- Rentals with breakfast South Side
- Rentals with a hot tub South Side
- Rentals with pools South Side
- Rentals with lake access South Side
- Private suite rentals South Side
*Some exclusions may apply in certain geographies and for some properties.