The month of September is ideal for a trip to Chicago because of the pleasant and moderate weather.

The city looks magnificent.

Rainfall is also expected in Chicago in September as sometimes the weather can be unpredictable.

One of the major events in Chicago in September is Labor Day.

Additionally, many other festivals and events also take place during this time of the year.

These events include:

  • Arts Week and Arts Festival
  • Boat Tours
  • Sports events
  • Music festivals, including live music
  • Jazz festivals

You can also explore various museums, take a few shots at a rooftop bar, and enjoy riverwalk strolls with your family or friends.

September is tourists’ favorite month since the weather is still nice and you can enjoy various outdoor activities throughout the month.

Chicago during this time is jam-packed with tourists.

Hence, September in Chicago is the ideal month for a trip, with so many events and festivals taking place, delicious food, diversity, and much more. 

Chicago’s Weather In September:

In September, Chicago, Illinois, has nice and pleasant weather. During this month, there are many days when the temperatures are a little low and only a few days with rain.

Daily high temperatures vary from 79 °F to 69 °F (26 °C or 20 °C), with temperatures rarely falling below 59 °F (15 °C).

Daily low temperatures vary from 67°F (19 °C)  to 56°F (13 °C), with temperatures rarely falling below 46°F (7 °C).

What To Wear For Daytime Activities In Chicago?

In September, Chicago offers a number of festivals and events, including live music festivals, arts festivals, sports events, and other such outdoor activities and events.

Some festivals are well-known and draw large crowds and tourists, but there are numerous smaller outdoor festivals and events in Chicago that are largely attended by locals.

You can also explore the Chicago Riverwalk, which is one of the best areas in Chicago, and it also has many elite eateries, bars, stores, and places to sit.

The Riverwalk is less crowded in September than it is in the summer, making it a terrific time to visit.

If you are a sports enthusiast, you can also attend various sports events as September is the month when the regular baseball season comes to an end.

Now, deciding what to wear for such activities can be a little difficult, as the weather in September in Chicago can be a little unpredictable, so make sure you dress accordingly.

When days are warm and cozy during this month, especially in the early days of September, make sure to bring comfortable, light clothes with you, such as loose tees, shorts, skirts, tights, floral dresses, sandals, and sneakers. 

The weather begins to get a little colder in the evenings and later in the month, so make sure you also bring layers with you.

When you go out in the daytime, it’s very important that you apply sunblock evenly and wear comfortable walking shoes, since there are many wonderful outdoor activities and gorgeous parts of the city to discover on our walking tours.

Additionally, bring a water bottle with you so you can keep hydrated on your trip to Chicago.

What To Wear For Nighttime Activities In Chicago?

Because of the pleasant and moderate weather, September is an excellent month to visit Chicago.

The city appears to be lovely. In September, rain is forecasted in Chicago, since the weather can be unpredictable at times.

Labor Day is one of the most important events in Chicago in September.

You can take a lake cruise if you enjoy being on the water.

You will be able to observe the amazing architecture of Chicago during your river tour, and it’s possible that you might be able to catch a glimpse of the skyline. 

Other than that, you can also see various live performances, attend comedy shows, and live music concerts, or take a night tour with your friends. 

You can also pay a visit to various historic museums, and for such detours, you should dress nicely. You can wear good-looking jeans and a semi-formal shirt with sneakers. 

Since it is usually cold at night, make sure you wear long-sleeve shirts with extra layers.

One of the most significant pieces of clothing to wear in Chicago in September is a long sleeve shirt. 

At night, the weather is mostly windy, so you can also enjoy the famous lakes. 

Other Things You Should Pack For A September Holiday In Chicago:

In September, especially early in the month, Chicago can still be hot after the summer, and later this month, the weather begins to get a little colder in the evenings, so make sure you bring layers with you.

Pack your clothes according to the weather and your length of stay. Bring nice and comfortable tees, long-sleeve shirts, jeans, shorts, skirts, dresses, sandals, sneakers, and scarves.

Also bring toiletries, your important documents, your phone, camera, charger, an umbrella and a raincoat with you.


Kristen Cavanaugh is a fashion author and blogger; she has been preparing fashion articles for different magazines over the years and apart from writing about contemporary fashion, Kristen also runs a clothing store that offers massive discounts on Name brands. She does agree that there is a big problem with how people dress, as people simply don’t know how to pair clothes to achieve the perfect look. According to Kristen putting on the right kinds of clothes will not only boost your confidence but will also enhance your personality, and for people to achieve the above they need information, the reason why she came up with the extensive and comprehensive excerpts on the different aspects as concerns fashion.