1. USA
  2. Illinois
  3. Chicago
  4. Monthly Stay

2418+ Chicago Monthly Rentals on Rent By Owner

Extended Stay Rental Homes By Owners Chicago

About Chicago Monthly Stay on Rent By Owner

Rent By Owner monthly rentals makes it easy to find, compare, and book vacation homes and condos for extended periods of time in Chicago. Whether you are looking for a weekly vacation rental, hotel suite, villa, cottage, or extended stays furnished apartment, there’s always a plan to suit your style and budget. RBO monthly holiday rentals is a great option for comparing places to stay for longer periods.

Chicago is popular for monthly stays. We list rentals that include full kitchenettes, dryers, air-conditioning & heating, indoor or private swimming pools, gyms, and hot tubs. So, whether you're looking for a luxury villa, condo, or cottage cabins that allow pets for a weekly or monthly stay in Chicago, with the entire family, working remotely, or an extended honeymoon in Chicago, you'll find a large selection of monthly furnished accommodation with top amenities to choose from.

Rent By Owner is a good option for executive traveler or those relocating for work or school. We connect you with property owners who are willing to have longer term, yet not permanent rentals. The Rent By Owner website makes it easy to filter options for guests wanting to find the best accommodation for groups, families, or solo travelers who need a place to stay for more than a few nights.

Show more
Show less

Chicago Monthly Stay Frequently Asked Questions

There are a lot of options in Chicago. If you plan on staying in the Chicago area, consider making a reservation for a few nights at one of these properties as these have been rated the top Monthly Stays in Chicago:

To book any amount of stay in Chicago visit RBO rental listings, click length of stay, choose the number of days, weeks, or months you want to spend, then enter the date and destination. Some properties may need you to inquire with the property prior to booking to learn more about extended or monthly stays.
We have many pet-friendly long-term rentals in or near Chicago. The top pet-friendly rentals in Chicago are:

See all pet-friendly monthly rentals in Chicago

Yes, there are more than 2418 vacation rentals in Chicago that have indoor and private swimming pools. Check out our filter option and find your best extended stay near Chicago.
Internet access is a requirement for most extended-stay travelers. Most of the holiday rentals we list have internet availability on premises.