Need help with a cool and cheap hotel in Chicago, suggestions? I'm meeting up my wife (who I will not have seen for 2 months) in Chicago for a romantic reunion, then a wedding of a buddy downtown. I'm looking for a cool and relatively cheap (trying to keep it under $150) hotel in a fun neighborhood in Chicago. It will the last 4 nights of June. I'd be willing to stay away from downtown the first couple nights, then switch to something closer for the wedding. I'm really hoping to have something special the first couple nights, I want to do something nice for the mrs when she comes in. Any suggestions would be much appreciated!