6. Pack mindfully. The seasonal range in Chicago runs from bone-chilling winters to sweltering summers. Other than maybe the mildest of transitional spring and fall days, packing for Chicago is not a no-brainer. In winter, hat and boots are a must. Ditto sunhat and sun block in summer. Complicating generalizations, the vast Lake Michigan holds sway over the local climate in ways visitors don't expect, often producing days cooler near the lake in summer and warmer in winter. You can't predict a 60-degree August afternoon, but the best way to plan for it is to pack layers.
7. Show-go. Chicago's renowned for its sports and restaurants and music. But I'd argue the liveliest entertainment quarter is in the theater. Chicago sends hits to Broadway (Steppenwolf Theater's August: Osage County this year) and keeps Broadway playing here indefinitely (Wicked and Jersey Boys will stay as long as demand holds). And it's not just the big stages (Goodman, Court, Chicago Shakespeare, Lookingglass, Victory Gardens, Second City and Steppenwolf), but the little ones – the off-Loop storefront theaters with a coupla dozen seats – where creativity is nurtured as in few other cities. Top choices include Actor's Workshop Theatre, House Theatre, Lifeline Theatre, Profiles Theatre, Redmoon Theater, Steep Theatre, Timelineand dozens of others whose artistic directors will now flame me for not including them.
8. Plan ahead. Anything worth doing in Chicago is worth booking ahead. That goes for hot tables – give Alinea and Charlie Trotter's a call a month in advance of your visit; others like Blackbird and Sepia aren't as punishing but reservations are an unspoken essential, especially on weekends. This advice also applies to popular activities such as the Chicago Architecture Foundation's architectural boat tours, which allow you to book ahead (tip: avoid Sunday post-hotel-checkout noon-hour tours in summer which are the Foundation says are the most crowded). Even the Field Museum and the Museum of Science and Industry allow you to pre-order tickets online, which can save you the aggravation of standing on line with the crowds.
9. Ask directions. Downtown Chicago is laid out on a grid, with the epicenter being Madison St., which runs east-west, and State St., which runs north-south. Street numbers then escalate in any direction 100 per block (10 N. State St., for example, would be on the block just north of Madison, 300 S. Dearborn would be three blocks south of Madison, and 215 W. Randolph St. would be two blocks west of State). Still confused? Ask a local. Chances are if you stand on a street corner with a map and a perplexed look someone will offer their help. It's that kinda town, Chicago is.