Even looking at the full side of the glass, it's getting harder to justify buying rentals in Chicago. This Alderman is going to present yet another tenant friendly regulation.
There are a lot of reasons why this is tenant friendly, but one of them is you can no longer end month-to-month, even with 30-day notice, unless there's a "good cause," which is described here.
Also, now the tenants could have a longer period to pay back the rent and stay in the property. In other words, even if you pay the eviction attorney, and start the eviction process, if the tenants pay pack all the money by certain time, you have to keep them.
The above is just a proposal at this point, but I'm not surprised if this pass. Obviously this involves legal matter, so read the above with that in mind.
This website summarizes prety well.
I believe Portland and other cities are considering similar measures wherein you must have very, very good reasons for not renewing a tenant. In other words, the State will decide what you can do with your property. It's a classic move of leftist government, always reaching for more control.
I think investors of large, liberally run cities would be wise to consider selling off their investments in these Tenant-friendly cities while the market is still hot. There are many cities and states that are fair to Landlords. Just the lower tax rates alone would pay for property management and still give you a better return.