Manhattan

Three nights in the West Village.

One night is for Westville Cafe.

Recommendations for the remaining two nights?

Are you looking for places with the same pricepoint as Westville? Do you need to stay in the W. Village? There's Pearl's (for seafoody things), and the Spotted Pig(sometimes billed as a gastropub) both in the village, but more $ than Westville. I'm always up for Blue Ribbon-not exactly in the Village, and again more $. A ton of possibilities-if you could set the parameters.

A few superb (to my mind; i lived in Manhattan for ten years) suggestions:

Balthazar 80 Spring St (btwn B'way and Crosby) French brasserie

Lupa 170 Thompson St (btwn Bleecker and Houston) Italian osteria

Tocqueville 1 E 15th New American

Craft 43 E 19th St (btwn B'way and Park) One of NYC's best

Eleven Madison Park
Gramercy Tavern

And so many, many more...

Upscale dinner in the WV - Here are the two best places:
Blue Hill
Annisa

At either place, get the tasting menu. Blue Hill is my favorite.

Sushi:
Hop on the subway and go to Sushi Yasuda. Best sushi in NYC, hands down. You won't ever get to do this in Chicago.

Eleven Madison is also terrific - order the souflee. Brunch at Balthazar is hard to beat for people watching and the food is good too. Personally, I'm not a fan of Craft but my wife is. However, I do like Witchcraft, their sandwich shop if you want to grab a quick lunch near union square.

Above all else, I recommend hopping the F train to Carroll street to eat at The Grocery on Smith Street in Brooklyn. See if you can get a reservation. Most restaurants in the west village/union square area are overrated, overpriced or touristy, and Smith Street and the Cobble Hill area are more "west villagey" then the west village itself these days. When Grocery opened the property values in Carroll Gardens went up. It's one of the best restaurants in all of new york and singly turned Smith Street into a "Restaurant Row." Most visitors to NYC stay out of Brooklyn and miss out big time.

I agree with thereminjames, Annisa and Blue Hill are great choices (I would reverse the order). Also, Perry Street one of Jean-Georges restaurants or Wallse for Austrian food. You might also consider at a lower price point Fatty Crab. Although it is not at the top of my list, one should note that Babbo is in the Village as well. Pearl Oyster Bar is quite good (as in Mary's Fish Camp).

I do not recommend Lupa.

I've been waiting for someone to mention Blue Hill. I had a fantastic meal there just after Christmas. While it doesn't compare to Blue Hill at Stone Barns, up in Tarrytown for location, it's very special. Two amuses - one apple juice and a little beet sandwich, the best sturgeon I've ever had, wonderful hake, tender lamb, and a couple of nice deserts including a quince granita and a 'cheesecake' pudding type thing made up the tasting menu when I was there. Excuse the photos, it was dark in our corner.

I'm a fan as well. Great value.

I'll be in the West Village in a couple of weeks, too. I have some favorites down there (or within walking distance):

Moustache on Bedford Street is a friendly little Middle Eastern place with great food and decent prices. It's tiny, but often not too crowded.

Marinella on Carmine Street is a cozy Italian restaurant with excellent pasta dishes and terrific wines.

Focacceria on MacDougal Street is "our" place (my GF and I go there every time we are in NYC). It's a small, intimate spot with nice people, excellent Italian food, great wines, and outstanding desserts. And no one seems to know about it, so it's usually easy to get in.