Chicago Proposal

[level22go]

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!

 

[MaddyRock]

Geja's and the Signature Room are both great choices. I think if her sister was proposed to on a carriage ride, you should come up with a different idea. As far as transportation you could just hail a cab, or arrange for a car service/limo to take you. The ride is very short, only a few miles, so it will only be about 5 or 10 minutes depending on traffic.

Here are my suggestions:
1. Propose at Geja's - it is a very quiet and intimate place so things wont be too public
2. Propose at the Signature Room - the lounge is open though, so this will be more public
3. Arrange for a limo after Geja's and drive around the city. You could stop at a few landmarks for pictures and could propose at one of them, or inside the limo at some point.