Monthly Rentals in South Side

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

Nearby monthly rentals

Superhost
Private room in Chicago
4.81 out of 5 average rating, 21 reviews

WP2S-Min away from U of C and Hyde Park 3a

RocioRating, 5 stars8 months ago
The place was clean, exactly like pictures and description. Infront, there is a park where you can run or walk. Also there is a bus stop across the street of the apartment and a metro station 4 blocks away. The neighborhood is safe, clean and beautiful.
Flat in Chicago
5 out of 5 average rating, 3 reviews

Sunny Penthouse - Oakwood Beach

DeannaRating, 5 stars3 days ago
Manny and Veronica have a beautiful apartment and were amazing hosts! They helped with any issues and were more than accommodating of me and the 3 other guests I booked with! Communication was quick and if I needed anything, they were more than ready to assist. The apartment is really spacious, supurb natural lighting, great appliances, and is decorated in such a way that it feels very homey. It's a 5 minute drive from a great grocery store and restaurants are not that far in a very comfortable and safe feeling area. It was a great place to come back to after spending the day out and about, I highly recommended staying here if you want a super nice and comfortable Chicago stay!
Guest favourite
Flat 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.
Flat in Chicago
4.67 out of 5 average rating, 3 reviews

Sunny Studio by UChicago, Walk to Campus & Museums

SadafRating, 5 stars1 week ago
Had a great stay! Very responsive host and easy check-in. The place was clean and had all the essentials

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.

Destinations to explore

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