I first went to Chicago on my 8th grade class field trip and have been back a bazillion times since for work and fun and sometimes both. If Chicago could be moved about 10 hours south, I'd live there in a heartbeat. But I'm pretty much over northern winters.
These images are from a work trip extended into a fun weekend. It's the first time I've been on an architectural boat tour which I can't believe I'd never done before because it was such a great tour (Chicago Architecture Foundation Tours).
WHERE TO STAY Anywhere near Michigan Ave. > there's a variety of affordable places that are close to the action
WHAT TO EAT Chicago Pizza and Oven Grinder > my absolute fav - must get the mediterranean bread The Purple Pig Taste of Randolph (Street) Lawry's Garrett Popcorn (try to walk by their door and ignore the tantalizing aromas...try) Yolk Glazed and Infused (bacon on a donut!) Beatrix River North (lemon souffle pancakes with lemon syrup - ridic) Obviously this list could be crazy long but these were favorites from this particular trip
WHAT TO DO Architecture tour Shopping Michigan Ave. Shopping Halstead St. Museums Art Institute (this was also a first on this trip!) Soldier Field Seriously too much to list here too!