Chicago (2025)

September is perhaps the best time

to visit Chicago. Winters can be

brutally cold and August can be hot

and humid.

September marks the end of the summer. There’s the jazz festival, Chicago Live! on the pier, the start of the Chicago Symphony Orchestra season and much more. The weather is warm and sunny. Places are not busy. Flights are less expensive. There are few queues and shops are not crowded. We stayed at the Thompson. It is in a good place, surrounded by many of the best Chicago restaurants. A 7 day travel pass is just $20, a real bargain. The boat trips were doing good business, especially in the evenings. Getting tables in restaurants was no problem. The people areas lovely as ever. We tried to do different things, and that was very easy.