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Monthly Rentals in Woodlawn, Chicago

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

Nearby monthly rentals

Guest favourite

Apartment in Woodlawn

5 out of 5 average rating, 7 reviews

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

Loft in South Shore

4.82 out of 5 average rating, 28 reviews

Historical Basement by Jackson Park; Metra/Parking

Guest favourite

Guest suite in Hyde Park

4.93 out of 5 average rating, 46 reviews

Classic Den @ U Chicago

Guest favourite

Private room in Chatham

4.96 out of 5 average rating, 46 reviews

Cozy 2 bedroom 2 bath home, near UC-Downtown-Lake

The comforts of home and great monthly rates

Fully furnished rentals

From peaceful mountain cabins to convenient urban apartments these furnished rentals have all the amenities of home.

Digital nomads & travelling professionals

Comfortable accommodation for nomadic and remote working professionals, with Wi-Fi and dedicated workspaces.

Delight included

Sometimes the destination is the accommodation. From cliffside cabins to tranquil houseboats, these rentals are full of unique features.

Pets welcome

Discover places to stay that accommodate pets, so you can bring your four-legged friend along.

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.

Popular amenities for monthly rentals

Laptop-friendly workspace

Free parking on premises

Corporate Housing

Stay near Woodlawn, Chicago's top sights

University of Chicago14 locals recommend

Museum of Science and Industry151 locals recommend

DuSable Black History Museum and Education Center31 locals recommend

Destinations to explore

*Some exclusions may apply in certain geographies and for some properties.