Between meals, Chicago still wants your attention. The river cruise really is worth it. The festival calendar runs hard from June to September. And winter, handled correctly, is a feature: holiday markets, steamed-up ramen counters and jazz sets that start when the lake wind gets serious.
This is where we compare the big-ticket experiences honestly, starting with which architecture boat tour to book and whether a food tour beats self-guiding, and where we keep the seasonal guides: summer festivals, Christkindlmarket, the green river in March.
