This is a very last min trip just for one night. My friend has offered to pay for the room so we are looking for a cheap hotel, with a pool, for us..It may be up to 3 adults and my son who's 21 months..I haven't been down to the heart of Chicago in 10+ years so I have no clue where I'm heading into..Hoping we can stay under $100, is that even possible in Chicago on a week night? We were considering going Friday night but I figured due to crowds we might pay A lot more..I have a friend who works on S. Michigan Ave and want to sorta surprise him so I would like to stay sorta near there if possible..Any advice would be great!

but thank you for the helpful tips...If I'm able to make it down there I will for sure use them..thanks again!