I stumbled across this website by doing a search for proposal ideas in Chicago. I also am in the process of throwing around ideas of how to pop the big question. I am from the Cincinnati area and will be in Chicago the last weekend of next month. Maybe we can help each other with some ideas until other people chime in. I want to make this something really special. My girlfriend's father passed away unexpectedly 2 weeks ago and she really needs something to lift her spirits. I have brought up the idea of going out of town for a weekend next month to just get away for a few days. We have talked in the past about marriage and I had planned on doing it later this summer. I was able to work a lot of overtime shifts at the firehouse and picked up a part time job so I was able to save the money to pay off the ring quicker. She should be totally suprised. I just need to come up with something good. I have thrown around a lot of ideas. Here are some of the things I can come up with. 1. Asking on the observation deck of the Sears tower or the Hancock building. 2. Taking a horse drawn carriage ride around downtown and stopping and doing it somewhere. 3. Somewhere on Navy pier. There are many possibilities here. 4. Take one of the boat dinner cruises on the lake and ask there. 5. Take a limo ride around the city and stop somewhere and ask. These are just a few of my ideas, but all seem kinda cheesy. I wanna do something personal and very memorable. Anybody have any ideas on how to personalize these? I hate to hijack your original thread but I need the same info and maybe we can work together.