Chicago
Architecture, deep-dish pizza, and Great Lakes culture
Best time: May-Sep · Typical stay: 3–7 days
Monthly overview
Each month classified using local weather, crowds, and prices.
Seasons
May-Sep
12-28°CBest time, outdoor festivals, Lollapalooza, Navy Pier alive, expensive
Oct-Nov
2-18°CFall foliage, Thanksgiving, windy city lives up to name, shoulder season
Dec-Apr
-10-12°CBrutal winter, polar vortex, extremely windy, cheap hotels, cozy restaurants
Top experiences
- Millennium Park & Cloud Gate — The Bean sculpture and gardens
- Architecture River Cruise — Historic buildings tour by boat
- Willis Tower Skydeck — 103rd floor glass ledge
- Art Institute of Chicago — World-class art collection
- Deep-Dish Pizza Experience — Lou Malnati's or Giordano's
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