This is a walking city, familiarize yourself with the public transit system! it's worth it.
Glenn's Diner off the Brown Line leans slightly seafoodie but worth the trip out. Topolobampo was ok. Table Fifty-Two had that intimate, new American meal we were looking for. Ginos East for dd pizza, good but fair warning go hungry for lunch instead! The Signature Room- eh. Great view of the city but overly crowded - not into that.
Besides food, yes I'm a baseball girl so Wrigley Field for sure and I was surprised at how much i liked U.S. Cellular Field. Not very pretty but people were nice and I got the baseball experience we were looking for. Try the corn off the cob!
We watched the Blackhawks win the Stanley Cup from Mother Hubbard's Bar.The whole city erupted. Fun bar too!
Trip 2, 3 etc. Stayed at Longman&Eagle in Logan Square...unique 6 room B&B, great cocktails, brunch and Donuts on Sundays yum! If you stay in a room (#55) beware it's directly over bar open till 3am & VERY loud.
Cloud Gate, go. Architecture cruise, worth it. Buckingham fountain, eh. Giordano's for ddish pizza yes but prepare for a long wait! Cubby Bears bar, go. Goat & Girl- dinner reservations a must. Started out as a disappointment but redeemed itself. Will crave the pig face. The planetarium was a huge disappointment don't waste your money. The Chicago skyline is amazing from there though...