540 N State St. Chicago IL, Downtown Dreamer
Unit #4601 at 540 N State St. Chicago IL is also known as the Downtown Dreamer. The building is entirely rental apartments. The apartment complex is allowed to rent a portion of the building as short term. 
This unit can not be purchased, but there is a neighboring tower of condo units that are individually owned. They are very similar to the rental apartments.
Both the rental apartment portion and the condo units share the building amenities. Pet Friendly! Rooftop pool and lounge area! Fitness Center! Running Track! etc!
This property is a two bedroom, two bathroom apartment. I found and booked this property through VRBO and it is managed by Vacasa. I learned a lesson; my rental bill would have been a bit less if I had booked directly through Vacasa. Vacasa is a big enough management company that I did not need the added fees for added protection from VRBO. (The big vacation rental advertising sites currently keeps approx. 8% of the bill, most owners add that to the total rent.) Moving on…
The views from the 46th floor are spectacular! 
I have included links to the Vacasa listing for this property, their pictures are lovely. The apartment rental income generated can help offset HOA fees for the entire property.
I found similar condo properties in the neighboring tower for sale for approx. $500,000. Short term vacation rental is very restricted in Chicago. One Real Estate Agent said that the condo building is one of only 2 high rise buildings in Chicago that allow short term rental. These condos are allowed to rent at no less than 31 days.
VACASA
Working with Vacasa was fine. The VRBO posting said that the unit had two bedrooms and slept six. Booking through VRBO would only allow me to designate 4 people in my party. Vacasa said, “we know there is a glitch, don’t worry about it.” Vacsa required me to print out the contract, sign it, then fax, or scan and email it back to them. I don’t know how they new I put my signature on a screen rather than with pen and paper, but they did, and I had to print paper. As a rental gift, Vacasa provided a shopping bag and wine cork screw. There is a grocery store located next door to the entrance, so the gift was perfect.
Check in was at 4:00, we collected the keys and info from the doorman, and up we went. We like the added security of the doorman. Our ears popped in the elevator every time we went up or down. All the common area and amenities, other than the front lobby, are located on the 9th floor. The elevator conversation included other guests who were also happy with the location, units and amenities.
540 N State St. Chicago IL
After we got our things into the unit, we went to check out the 9th floor amenities. There were many people enjoying the outdoor common areas, visiting with friends and enjoying an afternoon drink in the lovely weather. Several owners and their dogs are enjoying the dog park.
We spent two nights in the unit. The unit has a balcony with wonderful views, but there is no patio furniture. The view down from the balcony made is a bit dizzy. We were surprised at the volume of city noise that drifted up to us while we were outside.
Downtown Dreamer
One bedroom has a king bed and the second bedroom has a queen bed. There was enough room in the second bedroom for a king, I would prefer both rooms to have king beds. I think a queen is only comfortable for 2 people who sleep together regularly. The listing said that it slept 6 and that the third bed was a futon. The futon was actually a foam pad stored in the closet that could be unfolded onto the floor. It is a bit tough for some people to get onto the floor like that, and unfortunately, the foam cushion had stains and did not look very nice.
The property location is great and this complex has great amenities. The fact that owning a condo in the second building, would allow some rental is very appealing. If you are interested in owning property in down town Chicago, it will be very important to work with a realtor who is familiar with the Chicago zoning laws and rental restrictions as well as the individual property HOA rules.
If you are traveling with family or a group, and prefer the residential type rental rather than a hotel room, this pace is great. We walked from Olgalvie Transportation center, Navy pier, and Millennial park. We could see the Chicago theater sign from the balcony. Fabulous restaurants, Macy’s, and gold coast shopping are also close.
Would you like to tour property during your next vacation? Please let me know if you have any further questions or comments!
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Thank you!