Monthly Rentals in South Side

Discover long-term rentals that feel like home, for stays of a month or longer.

Nearby monthly rentals

Enter dates and number of guests to see the total trip price including additional fees and taxes, and rounded up to the nearest integer.

Guest favourite
Apartment in Chicago
5 out of 5 average rating, 5 reviews

Modern 2Bdrm Condo w Private Deck

DavidRating, 5 stars2 weeks ago
Perfect location for me. 20 minutes from the U of C campus. Very walkable area with good grocery stores nearby and Hyde Park Produce. Neighborhood has character. The apartment is very pleasant, spacious, fully updated with high ceilings. Very usable kitchen.
Guest favourite
Apartment in Chicago
5 out of 5 average rating, 6 reviews

Long Stay,The Jewels,2bd/2ba,UC 2mi,Pkg,DTWN 15mi

EricRating, 5 stars2 weeks ago
Stayed here for a month while waiting to move into our apartment. Place was clean and spacious. Even when we found there wasn't a can opener, Jamal was responsive and purchased and delivered it to us. Only hesitation I would have is if you are trying to work remotely with more than one person, the halls can echo and there are not work spaces in the rooms.
Apartment in Chicago
4.67 out of 5 average rating, 3 reviews

Sunny Studio by UChicago, Walk to Campus & Museums

SadafRating, 5 stars5 days ago
Had a great stay! Very responsive host and easy check-in. The place was clean and had all the essentials
Loft in Chicago
4.82 out of 5 average rating, 28 reviews

Historical Basement by Jackson Park; Metra/Parking

SahityaRating, 5 stars3 days ago
Andy's basement studio was exactly what I needed during my 4 week stay. it had everything I needed. though it's in the basement of a home with other rental units, you get the whole basement sized suite to yourself, with great vintage decor. It's quite a charming place to come back to from work and you feel safe and secluded It stays relatively cool compared to outside so it's comfortable in the warm seasons. Andy was great as well, very communicative and accommodating.

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 Wi-Fi and dedicated working spaces.

Looking for corporate housing?

Airbnb has fully furnished apartment homes ideal for staffing, corporate housing and relocation needs.

Destinations to explore

*Some exclusions may apply in certain geographies and for some properties.
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  2. United States
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  4. Cook County
  5. Chicago
  6. South Side
  7. Monthly Rentals