Gayle,
Will you be in the city? Assuming you will, these are all within an easy cab ride/walk:
Pops for Champange: Pre or post dinner. The food is tasty but it's small plates. You go here for the bubbly.
NOMI: If it's a nice evening, go to the rooftop outdoor lounge for a cocktail. Celeb-spotting alert: David Schwimmer this past Saturday night...looking so Ross it was funny.
BOKA: A little away from downtown in our 'hood, Lincoln Park. Ask for Daniel at the bar or Adrian, a waiter. Tell them Dennis and Lisa sent ya.
Spiaggia and Cafe Spiaggia: will knock your socks off. Cafe Spiaggia will just untie your shoes for half the price but with equally great views.
North Pond: Again, in Lincoln Park but an amazing setting and awesome food. Difficult to get a reservation.
Salpicon: Interior of Mexico mexican food with an huge wine list.
Old Town Brasserie: Good French Bistro style.
Shaw's Crab House: (Hubbard location) Walk in, go up the steps and go to the right, to the Oyster Bar side. Sit at the bar and slurp oysters. Excellent for a nice lunch.
David Burke's Primehouse: If you want steak, go here. They sometimes have a 78 day dry-aged ribeye available. They also make a tasty leather-infused Manhattan.
one sixty blue: Modern French. A favorite of mine but, Lisa, not so much. So I don't get to go here anymore. It's great.
Of course there are the top tables in the city:
Charlie Trotter's, Alinea, Tru, Moto, etc. Break the bank expensive for sure. L20 is a new seafood place that just opened up with Laurent Gras as chef. I hear it's out of this world.
Let me know if I can help with anything else and enjoy Chicago!