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Chicago Short-Term Vacation Rentals

Find Short-Term Rentals near Chicago

About Chicago Short Term Stay on Rent By Owner

Discover more than 357 short term vacation rentals in Chicago. We have a huge number of short-term holiday rentals in or near Chicago. Whether you are traveling as a whole family, in groups, with friends, or solo, there are rentals that would suit your plans and budget. Short-term rental homes are perfect for those seeking to stay in Chicago for a short term or on a temporary basis. RBO short-term stays give you the luxury of enjoying all the benefits attached to having a home. A serene environment, spacious rooms, private pools, indoor/outdoor heated swimming pools, hot tubs, self-catering, spa, and gyms are examples of such benefits. Rent By Owner has plenty of vacation rentals that are available on a weekly or monthly basis in Chicago. A furnished short-term rental in Chicago comes with great amenities that would make you an unforgettable experience.

These short-term home rentals that are available in Chicago come in different sizes and vary according to your needs. Whatever your style or budget is, Rent By Owner has got you covered; all you have to do is use our search and filter tool to find the right rental in a matter of minutes.

Rent By Owner makes it easy to compare, discover and book short-term accommodations, including pet-friendly places to stay, in Chicago that is within your budget. RBO helps you save time, and gives you hassle-free booking for your favorite short stay home.

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Frequently Asked Questions About Chicago Short-term Rentals

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 Short Term Stays in Chicago:

At RBO short-term furnished accommodation in or near Chicago ranges from $7 to $24,240 per night.
We have 357 places to stay near Chicago. Check out the complete list of holiday rentals in Chicago to find what works for your next trip.
Yes, there are 357 self-catering short-term rental homes in Chicago that have hot tubs & other amenities The most popular self-catering top-rated rental homes are:
There are more than 357 luxury temporary places to stay near Chicago, with other amenities available according to 2025 data from Rent By Owner.