STYLETHREAD -- LET'S TALK SHOP!

my bf and i always take visitors to cafe iberico on lasalle.  it's right downtown, it would be a $5 cab.  it's a tapas restaurant....my favorite.  the food is amazing, and it's fun for a group dining experience.  it's best to go early or late on friday or saturday night as the wait can be long during prime hours (if you have a group of more than 6 you can make an rsvp i think).  it's open for lunch too.  their sangria is amazing. 

another place that we like to take people is chicago pizza and grinder.  it's cash only, but it's amazing pizza (not chicago style, but better).  it comes in a bowl, and they flip over the bowl and it's like a pizza pot pie.  everyone we've taken asks to go back whenever they come.  it has some chicago history as the st. valentine's day masacre happened across the street.  this is another place that may be busy during prime hours.  i would suggest to go there for lunch (taking a $10 cab) and then walk two blocks (west) to the lincoln park shopping area.  they have the standard bebe, bcbg, banana, arden b, barney's co-op, club monaco, bluemercury (a great make-up place), and then a ton of little boutiques on a street called armitage. 

my plan would be shopping on michigan ave or state street during the day, then cafe iberico for an early dinner.  then the next day i would go to chicago pizza and grinder for lunch and walk to the lincoln park area and go shopping.  this always seems to work with my friends. you can then take the train back to the city to save money.    

pm me if you would like more specifics or recommendations.  i've decided to leave the city for new year's, but last year when i hit the town it was a lot of fun (expensive, but fun).