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 favorite
Private room in Chicago
4.91 out of 5 average rating, 238 reviewsFresh and Sunny Bed & Bath by UofC
Superhost
Private room in Chicago
4.5 out of 5 average rating, 4 reviewsPrivate living room with sofa bed available.
Guest favorite
Apartment in Chicago
5 out of 5 average rating, 5 reviewsLong Stay,The Jewels,2bd/2ba,UC 2mi,Pkg,DTWN 15mi
Guest favorite
Private room in Chicago
4.89 out of 5 average rating, 66 reviewsHyde Park / Kenwood, U of Chicago. Free bike.
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 vacation 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
Traveling 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 Vacation rentals
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- West Side Vacation rentals
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- Rentals with breakfast South Side
- Condo rentals South Side
- Bed and breakfasts South Side
- Waterfront rentals South Side
- Rentals with a washer and dryer South Side
- House rentals South Side
- Family-friendly rentals South Side
- Rentals with lake access South Side
- Rentals with a hot tub South Side
- Rentals with pools South Side
- Rentals with beach access South Side
- Private suite rentals South Side
- Rentals with outdoor seating South Side
- Apartment rentals South Side
- Rentals with an EV charger South Side
- Kid-friendly rentals South Side
- Smoking-friendly rentals South Side
- Rentals with a patio South Side
- Townhouse rentals South Side
- Rentals with a fire pit South Side
- Pet-friendly rentals South Side
- Fitness-friendly rentals South Side
- Rentals with a fireplace South Side
*Some exclusions may apply in certain geographies and for some properties.