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Demand For Chicago Vacation-Home Units On Rise This Summer

After a year-long year battle against the effects of the COVID-19 virus on Chicago’s vacation-home and shared-housing industry, travel volume and bookings for units are rapidly returning, analysts say.

Nearly half of Chicago Airbnb hosts delisted their property as COVID-19 lockdowns surged in 2020, and inventory of available rentals fell to about 5,400 units from about 10,600 listings.

However, demand for vacation-home units apparently is skyrocketing back to 2019 levels this summer, according to industry sources.

Old Town living room listed on Airbnb

“Many Chicago vacationers are choosing private homes and well-appointed apartments over downtown hotels as the travel industry rebounds,” noted Realtor Sara E. Benson, president of Chicago-based Benson Stanley Realty, who works with owners of income properties.

In Old Town and Lincoln Park, some Airbnb rental rates for upscale two-bedroom units with private outdoor space and in-unit washer/dryer are running more than $300 per night, Benson said.

In the summer of 2020, the Chicago City Council approved regulatory measures to combat use of short-term rentals as “party houses” or hubs of prohibited activities.

Old Town bedroom listed on Airbnb

New amendments to Chicago’s policy on vacation-rental homes and short-term rentals include a ban on single-night stays. There also are tougher rules on excessive loud noise and/or vibrations generated from within the rental unit, in any private open space adjoining the rental, or on the adjacent public way.

Property owners who list homes as vacation rentals on popular booking sites such as Airbnb and VRBO must submit their registration information with the city and not only with the home-sharing platforms. Changes also increase the annual owner license fee to $125 per unit from $60.

This change should help the Department of Business Affairs and Consumer Protection track violations. Owners who violate the law will face fines of between $5,000 and $10,000.

An industry survey of Chicago vacation-home and shared properties shows the following trends in the marketplace:

  • Summer bookings are currently running 40% or more over 2019 levels, the last normal summer before COVID.

  • Larger home and apartment properties offering three or more bedrooms are seeing the most significant increases in demand.

  • Many properties are being booked at record-high average-daily rates for the months of August through November of 2021.

  • Average length of stay continues to trend upward and significantly exceeds pre-2020 levels.

If you are a property owner thinking about joining the booming shared-housing and vacation-home industry, it is important to remember there are some drawbacks even for well-managed units.

“We had a long-term vacation-home visitor from New York who apparently did not read our rules on garbage-can use,” said one irate owner. “They repeatedly tossed their kitchen garbage bags out on the rear deck, creating a buffet for rats.”

For more housing news, visit Don DeBat is co-author of “Escaping Condo Jail,” the ultimate survival guide for condominium living. Visit


“The book is Escaping Condo Jail by Sara Benson and Don DeBat. I would say that anybody thinking about buying a condo, or even anybody serving on a condo board, or anybody who has any connection to a condo, this is must reading—all 600 and something pages. Thanks a lot for a great book!”


Steve Sanders, “Your Money Matters” WGN TV, December 22, 2014

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