I'm not sure if they do the Wrigley Field tours in the offseason, but if they don't, you'd still want see Wrigley. There are some good places to grab a bite and a drink in the area and surrounding neighborhoods.
For steaks, I like Gene & Georgetti's, which is an old-school institution. Others might recommend Gibson's, Ditka's, Keefer's, Chicago Chop House, Michael Jordan's, to name a few.
For museums, I highly recommend the Science and Industry Museum along with the Field. If you're going to the Field, you should also see the aquarium and planetarium. They're all part of the museum campus on the south end of Grant Park, next to Soldier Field.
I'm not big on art museums, but I do recommend the Art Institute.

Hi, llbergkamp.
The Amalfi is a great choice for location and (hopefully) price.

For steak/seafood: I don't know anything about the Metropolitan club-sorry. May be nice for views, but the Signature Lounge at the John Hancock Building would probably be a nicer view and you can go there for just a drink and not shell-out for a big dinner. For V-day, I second Gibson's, and add Joe's Steak and Seafood. For other nights: Tejas de Brazil and Brazzazz are both popular with big-meat-eaters. Joining the Tejas de Brazil "e-club" gets you a coupon right away, I believe. Definitely check reviews on yelp.com or chowhound.

One suggestion I have may be for your Monday night. The improvolympic theater is 2 minutes away from Wrigley Field and they have a great improv show Mondays at 8:30 called 'The Armando Diaz Experience.'
http://chicago.ioimprov.com/io/shows/3
I think it would be a fun Chicago experience to get your pics in front of Wrigley, grab dinner in the neighborhood (at Vines, or Chen's, or Goose Island Brewery) and head over to the IO. These are the best improv actors in the city. I think they're more interesting than the Second City troupes.

Shopping: Anthropologie on State Street or Chicago Avenue would be nice for a 20-30-something. Akira has boutiques on State Street and Diversey. P+L at 2956 N. Clark is a cute boutique if you find yourself in the Lakeview neighborhood. Bucktown and Wicker Park has a slew of indie boutiques, but I can't speak to them. Maybe someone else can.

I hope you two have a great weekend in Chicago. I'd prepare yourself to hop in taxis to get around at night, and even during the day. February is cold. Personally, I'm always reluctant to shell out cash for cabs in a strange city. But using a cab to get around and inuring yourself to those 7-8-12 dollar fares before you get here is a good idea. Luckily, your hotel is very well-located, but there will be times that waiting for a bus or train just isn't worth it when you're on vacation.

You sound like a nice girlfriend! I hope you two have a great time.

Thank you so much to ChGogal and andrews98682! You did such a nice job of helping me wrap my mind around a few places. I will research your suggestions. I welcome any and all suggestions. I hope to have the trip pretty well planned for my boyfriend or at least be prepared to give him some choices!!! Looking forward to a fun four days.

Anyone know anything about www.tastebudtours.com or the Chicago Beer Experience? Curious if it was even worth our time.

Thanks so much to all who take the time to reply!

For steaks and sea food, definitely Gibson's on North Rush, a truly Chicago experience. http://www.gibsonssteakhouse.com/

Another truly Chicago experience - Italian beef sandwich and one of the best is Al's #1 Beef on west Taylor Street, right next to UoI. Great for lunch and not far from downtown area. http://www.alscatering.com/

96th Signature Lounge in the Hancock building is a wonderful way to waste some time, have a drink and enjoy the beautiful city and lake views from? 96th floor.... Make sure it's a clear, sunny day. Drinks are on the expensive side but it's no more expensive then taking the elevator to the Hancock observatory which is just 1 or 2 floors higher. The lounge elevator ride is free.

Enjoy your trip to the best city in US!