Of those 4, I'd do Tru--but you might want to check availability before you get too attached to any of them...

My experience at Tru was the staff was a bit formal and stiff. If you want fun, I'd go to Moto.

Everest might be the most romantic, but also the most conservative/old fashioned/formal of the bunch - great view though.

Tru/L20 would offer the best food (in my opinion), with L20 perhaps being more contemporary but also highly seafood focused, in case that matters.

Moto would be the most avant garde and fun, but I wouldn't expect the food quality would quite match that of Tru/L20.

Personally, I'd go to GNR El Ideas--Have you come across it in your research?
GNR El Ideas
http://elideas.com/

It would satisfy all of the components (fun, wonderful food, unique atmosphere, yet intimate) and it's BYO so you can bring whatever special bottle(s) you might enjoy. Plus, I bet they'd help you bring off a hell of a proposal.

If you are looking for something fun and not stuffy, I wouldn't go to Everest, L20 or TRU. They are all great places, but very stiff.

Blackbird is amazing food and a lot less stuffy (I got engaged there). Bavette's is also romantic and not stuffy and has great food. It would be a great place for a proposal.

chgoeditor wrote:

ReddiWhipSmart wrote:A proposal at Schwa has the potential to be the most epic thing ever.

Or go wrong in epic proportions...

There's a joke about closing due to plumbing problems in there somewhere, but my mind is drawing a complete blank.

That's probably a good thing.

I would steer away from places where the food and its presentation require all of your focus. While Alinea and the like are certainly great dining experiences, those type of scripted meals are very intense and demand your complete attention. Under the circumstances, you may want to spend more time concentrating on your dining companion, rather than the details of the meal itself. I would go with something more relaxed and accommodating with a cozy room and a nice view. I would throw North Pond back into the mix. It has an intimate and welcoming vibe in a one-of-a kind location. It is in an actual historical Prairie School Arts and Crafts style building on a pond in the heart of Lincoln Park overlooking the city skyline. The dishes themselves are upscale modern interpretations of Midwestern comfort food. Truthfully, I have not eaten at most of the other places mentioned, some are just not "my thing", however I have always found North Pond to be romantic in an elegant and charming way, maybe that is a little clichéd, but sometimes clichés do work.

Of the other places that were mentioned, that I have not dined at, El Ideas appeals to me the most. While it may not be trendy, it is certainly unique. The menu is fixed and changes every night as new dishes are added and others are retired. There is only one menu, and the entire room is served each course at the same time. Before each course is served, the chef who developed the dish announces it and explains his philosophy and intentions behind the design. Sharing a communal experience with a group of fellow culinary adventurers, has the potential for an interesting evening, if you are open to meeting new people. Again, it might not be the perfect environment for a proposal of marriage, however, celebrating the moment with a group of strangers has the potential for a memorable experience.