Monthly Rentals in Oak Park

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

Nearby monthly rentals

Guest favourite
Guesthouse in Oak Park
4.95 out of 5 average rating, 104 reviews

O'Malley Oasis!

AndreaRating, 5 stars4 months ago
Clean, beautiful space. Has everything needed and the most comfortable seating space to relax. Clear instructions, easy parking. Be aware that there are several stairs to enter as seen in the pictures. They are well maintained with a handrail. This was not an issue at all for us but could be for someone with mobility limitations. Otherwise one of the best places I have stayed in Oak Park. Hope it is available when I come back.
Superhost
Apartment in Austin
4.9 out of 5 average rating, 21 reviews

Modern NEW Deluxe Studio in Oak Park

JohnRating, 5 stars4 weeks ago
We moved from the Chicago area some years ago and have lived in 3 other states, always making trips back each year to see family. This time we decided we wanted to spend more time in the city so after looking in the western suburbs and not finding anything reasonable, I thought of Oak Park which is next to Chicago, giving us easy access while staying in a town that is as interesting as it is enjoyable. This place was perfect. I have stayed in a couple of places that have posted pictures that are not trying to be as accurate as they should be. Not here. Comfortable bedding, large bathroom and a cozy kitchen area. I did read comments about being on a busy street which is accurate. It’s just white noise and slows down as the night goes on. My wife and I barely noticed it. Besides having access to the city by car, you can also take the Metra train and be in the city in minutes, or take the CTA trains from downtown Oak Park (which has plenty of excellent restaurants).
Guest favourite
Condo in Oak Park
4.96 out of 5 average rating, 229 reviews

Picture Perfect 3Bed Steps from Train and FLW

DianaRating, 5 stars1 week ago
We had an amazing stay ! Lovely place , looks exactly like the pictures. The location is amazing, we felt very safe walking around outside. Very clear instructions , parking was easy to figure out :) We were able to check in an hour early through many texts and communicating with the host. Can’t wait to book again !
Guest favourite
Apartment in Oak Park
4.83 out of 5 average rating, 35 reviews

Urban oasis in Oak Park

AnnRating, 5 stars1 month ago
Jill’s place was our home base as we visited family in the Chicago area. The house is older with a lot of character and decorated very nicely. I am especially grateful that Jill allows dogs since we have to travel with ours. The backyard is fenced in so we could let her out without worrying about her running away. The neighborhood is very quiet and walkable with interesting architecture. You will hear “city noises” but we used fans in the house to create white noise when sleeping. There are many great restaurants and a couple of bakeries very close by. You can also walk to a shopping area with a Target, Old Navy, grocery store and many other restaurants a little further, but walkable. Public transportation is also close if you don’t have a car. We were not able to use the garage because our truck was too long, but Jill made sure we could park in the street in front of the house without any problems. She was very quick to respond to my questions. I would recommend staying at Jill’s.

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

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Simple monthly prices

Special rates for long-term vacation rentals and a single monthly payment without additional charges.*

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Work-friendly spaces for digital nomads

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Stay near Oak Park's top sights

Frank Lloyd Wright Home and Studio41 locals recommend
Classic Cinemas Lake Theatre17 locals recommend
Ernest Hemingway Birthplace Museum24 locals recommend
Maya Del Sol19 locals recommend
FitzGerald's25 locals recommend
Spilt Milk11 locals recommend

Destinations to explore

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