I will be going to Chicago toward the end of October and plan on proposing to my girlfriend. Thus far I have decided on Geja's for dinner and the Signature Room for drinks afterwards. I need help on everything in between. When and How should I propose to her? How should we get from Geja's to the Signature room? I thought about a carriage ride but her sister was proposed too during a carriage ride, would that be bad to do the same? Any help is greatly appreciated!