My research shows that many hotels are sold out from Oct. 20th to 23rd. I believe there are several conventions in town. For example, the website of thehotel I'm staying in those dates, the Hyatt Regency McCormick Place, indicates no rooms are available...and this hotel is slightly south of downtown Chicago. My bid was accepted on PL at $88 per night, only after I had exhausted all possibilities in downtown Chicago. Good Luck!