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  1. Feb 23, 2021 · May and September to October are times to enjoy culture without the crowds. Chicago has two shoulder seasons – in late spring and early fall – when the city is either shaking off the winter chill or getting ready for it. Both are excellent times to visit, particularly if you plan to explore the city's museums.

  2. Sep 12, 2024 · The average temperature ranges from 50ºF to 70ºF, making for a comfortable exploration of the Windy City before the arrival of the summer crowds. For those looking for a balance between nice weather and manageable tourist numbers, late spring in Chicago might just be your perfect time to visit.

  3. The best times to visit Chicago are April through May and between September and October, when the temperatures are warm, a variety of festivals take place and crowds are manageable.

  4. Oct 7, 2024 · If you warmer weather, September is a great month to visit. If you like more moderate and pleasant temperatures, October and early November are great times to visit. Spring (especially late April and early May) is also a good time to visit for more pleasant temperatures and pretty spring flowers.

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  5. Oct 21, 2024 · The best time to visit Chicago is between late spring and fall, specifically the months of April through October. These times of year offer ideal weather and local events, so you can see and experience Chicago at its best.

  6. Jan 6, 2023 · Chicago in May. May is the best time to travel to Chicago if you want to get ahead of the busy summer (June-September) travel season. The weather is warm--often in the 70s degrees Fahrenheit during the day--but rainfall is at its peak for the year.

  7. Is May a good time to visit Chicago? May is a favorable time to visit Chicago. The weather begins to warm, providing an ideal climate for exploring the city's attractions.

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