Chicago has world-class architecture, museums, jazz and blues clubs and a long lakefront path that turns into a beach in summer. It is best from May to October, with a festive December.
Month by month
Best: April, May, June, July, August, September, October, November
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Avoid Poor OK Good Excellent Peak
Worth avoiding: January, February.
How long to stay
3–5 days is the sweet spot.
Flight time
About 2h from the US East Coast, 8.5h from Europe, 15.5h from South Asia.
Good to know
- The L train connects both airports to the Loop; a Ventra card works on trains and buses.
- Book the architecture river cruise early in summer; it is the best way to see the skyline.
- Winter wind is real; layers and hats are essential from December to March.
Plan a trip to Chicago
Pick your dates and Offdays builds a day-by-day itinerary from Chicago's best places.
Destination