Taylor,
Chicago happens to have some amazingly great restaurants for V-Day options:
A great, fairly budget conscious option to start off with would be
Cafe Spiaggia. Sharing the same kitchen as Spiaggia, the cafe serves amazing Italian food, and the best tiramisu I've had in North America.
To go higher-end, my first suggestion would probably be
Spiaggia. Spiaggia features a higher-end dining room, larger menu, larger wine list, and I believe jackets are required. The views from the main dining room windows are also absolutely amazing.
For something different than Italian food, you should consider
Tizi Melloul. A Moroccan restaurant with one of the best interiors of any restaurant in the city, the food is sexy.
If you're not looking to go downtown,
Bistro Campagne serves great, bistro-style French food, in Lincoln Square. It's cozy and gives off the "small restaurant" feel. Honestly though, I like this place better when it's warm outside and they open their outdoor seating. Great beer selection here too.
Sola, on the northside, serves some really fun, again, sexy, food, but is possibly too loud for a good V-Day date. If you don't mind your restaurants bustling, this isn't a bad option at all.
If you're downtown for dinner and want to continue the evening,
Pops for Champagne recently moved to a downtown location, and is a fun Jazz and Champagne bar.
A great, and little known secret of downtown dining is
Tru's dessert-only option, which allows you to skip out on the 12 course dinner, and jump in on their menu for just the 5 course or so dessert by award winning dessert chef Gail Gand. (My gf's comment: "Oh, that's hot.") Not that going to Tru for a meal would be a bad thing, but the full menu at Tru will definitely leave you too full to do anything but nap after dinner.
Depending on how modern your food tastes and your ability to get reservations,
alinea is clearly one of the star restaurants of chicago, and the whole feel of dining there is amazing.
Downtown, I'm also a pretty big fan of
NoMI, but only if you can get a seat by the window.
Of course, depending on you and your date's tastes, one of the more frequent V-Day go-tos has become sushi.
Heat,
Sushi Wabi, and tons of others do high-end sushi very well, in a variety of atmospheres and locations.
In terms of non-dining, I find that non-roses work better than roses, and if you go early in the day to a good florist, you don't have to suffer through making a bouquet out of picked over remnants. Chicago is also a great chocolate city, with ethel'ses every 2 blocks and whatnot. While Godiva is certainly nice, I'd do something like Vosge, Ethel's, etc, I think are just nicer.
Of course a higher-work, lower-cost option is to prepare dinner at home. The reason this option can work, even for a novice cook, is that women love seared fish, and seared fish is insanely easy to prepare.
Anyway, hope that helps, and that you don't steal my reservations!
c
Oh, my worst Valentine's Day experiences have definitely centered around going places that suck: Bistro 110, Cheesecake Factory. Yuck. Also going out with a girl you're not really in to or isn't really in to you sucks too. I find that super-huge restaurants or venues of any type really just don't fly for me on Valentine's day. The smaller the place the more intimate of a feel to the whole date, I think.