They are both good hotels. The Wit has a younger, hipper crowd. There are so many restaurants you need to give us some specifics. Do you want romantic or the latest in place?
You could propose at Buckingham Fountain, the Signature Room at the top of the Hancock Building, out on Olive Park, just North of Navy Pier where it sticks out over the water with a great view, or rent bikes and ride south where there are city views, take a horse carrage ride on Michigan Ave.
Also try running a search on this forum for proposal ideas. IIRC, there was a thread on the topic not too terribly long ago.
IMHO, a good location for a proposal depends on your girlfriend, frankly. For example, would she like, or hate, being proposed to in public? One friend received a proposal at the Bean in Millenium Park, and another at Buckingham Fountain in Grant Park. Obviously those are both a bit weather dependent, but great locations. Another idea is proposing on the big Ferris wheel at Navy Pier, which would be "private". The downside to that is that you only go around once (although slowly), so you'd have to get to the question fairly quickly!
Good luck, and congratulations!
If you like the Beach ....try Oak Street Beach for the proposal...
OR... Buckingham Fountains at night is a beautiful sight.....
I proposed to my wife in the couyrtyard of the Fourth Prez church on Michigan Ave. on the Magnificent Mile. It's "open" to the public but also sort of secluded and private. I had planned for the Signature Room but it was too crowded that evening so I had to come up with a Plan B. But that was twenty-plus years ago.
I like the Buckingham Fountain idea also, but there's liable to be a lot of "witnesses" there.
I did it back in July. Was perfect.
Dinner at the Signature room, window seat. Incredible view.
Cab ride to grant park.
Slow walk to Buckingham fountain
10pm fountain show was where I popped the question with the skyyline in the background. She cried, didn't see it coming. Was perfect.
Then had a horse and carriage waiting to take us back to the hotel.
Was a moment both of us will never forget.
Cubs home season ends 9/21.
thanks for all your help.
I've booked the wit hotel and a dinner at the signature room. won't be proposing there however
Darn, thought I had something with that Cub's thing...hmmm. Your proposal place could be someplace sort of elegant, or Chamber of Commerce-y, or it could be the basis of a story to enjoy for the rest of your lives. I would put the ring in my pocket, and then while walking on Michigan Ave on Sat afternoon I would declare "time for a cheeseburger" and drop down under Michigan Ave to the Billy Goat and ask her right at the bar with a cheeseburger and an Old Style.