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
4.67 out of 5 average rating, 3 reviews

living room with twin sofa bed

MadelineRating, 5 stars8 months ago
Thank you Aminata the stay was great! Glad it worked out well for us both!
Superhost
Apartment in Chicago
5 out of 5 average rating, 5 reviews

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

AvaRating, 5 stars4 days ago
Very clean, stylish, you have everything you need, peaceful, quiet neighborhood, especially good if you have a car because there is parking, great communication. Whole Foods, Trader Joes about a 10 min drive away. It's great if you're travelling to Chicago- I had a car so very optimal and easy. Thanks Jamal!
Guest favorite
Private room in Chicago
4.89 out of 5 average rating, 201 reviews

HydePark003, UC, NavyPier, Chinatown, freeparking

EleciaRating, 5 stars4 months ago
Enjoyed my time there. Private, clean, and extremely comfortable. The other guests were hard to run into, so it feels private. The only recommendation I have is to have more cookware. Granted, the listing does say to only do light cooking, but I could not fry eggs because there was only a very large pan in the kitchen. Overall, I would definitely stay again!
Superhost
Private room in Chicago
4.66 out of 5 average rating, 120 reviews

One bedroom/semi-private bath in Hyde Park

ZachRating, 5 stars6 months ago
I had a great stay in Hyde Park! Loved the neighborhood, and it was walking distance to UChicago hospitals, where I worked for the month. Very convenient for any person studying or working at University of Chicago.

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.

Destinations to explore

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