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Chicago Proposal


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Hi there,

I've been reading some of the great advice posted on buying diamonds and I was hoping that some of you might also be able to help me with my proposal.


Basically I am flying into the US for work in mid-jan and staying for two weeks. At the end of that time my girlfriend is flying out so that we can spend a couple of days together. She has never been to Chicago and I am planning on staying at a nice hotel (thinking about the Drake - any views?), enjoying some good meals and popping the question while we are over there.


My problem is that I would like to propose somewhere very romantic and preferably outdoors. However I believe it will be very cold and this really limits my options.


Can anybody recommend a good park/setting in Downtown Chicago that would be suitable for asking the question?


Any advice would be appreciated.

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  • 4 weeks later...

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.

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