Chicago’s handy grid system makes navigation a breeze and most downtown tourist attractions are within walking distance of each other. The CTA transit system is relatively straightforward and if you can’t face walking in that infamous wind, taxis are everywhere – just get your thumb ready to flag them down local-style. When it comes to weather, the spring (April - May) is a sweet spot. Clear skies are a common sight and there’s far less wind and rain than usual. Hotels are often cheaper then too, due to fewer crowds.