One of the most visited and highly regarded cities in the U.S., Chicago is definitely worth visiting at least once in your lifetime.

Chicago is bursting at its seams with countless museums. There is a rich history that the city enjoys.

Chicago is home to stunning skyscrapers, outstanding theatrical productions, a vibrant musical and art scene, famous restaurants, and majestic waterfronts.

All of these attributes combined make Chicago an ideal place for a vacation.

If you plan to visit the city around August, you should keep in mind a couple of things.

Check the weather to pack accordingly and hold the essentials with you.

This article will discuss the weather in Chicago around August and what you can wear during this trip.

How is Chicago’s Weather in August?

In August, Chicago mainly comprises warm afternoons, with mornings and nights comfortable and not too hot.

The first half of the month can be humid, but it gets better as the month progresses.

The early mornings and late nights are more relaxed.

Early in the month, the daytime temperature will usually fall between 85-90°F (27-28°C).

However, as the month proceeds, the end of August comprises temperature in the upper 70s F (26°C).

The majority of the month observes sunny days, and only a handful will see rain.

What to Wear During Daytime Activities in Chicago?

Take an Architecture River Cruise

Chicago has a wide range of majestic skyscrapers that can be seen all around the city.

However, the best way to experience the architecture of Chicago is by taking a river cruise to look over the towering buildings.

Since it is expected to be windy at the river, wear a flowy maxi dress with a cardigan so that you don’t feel cold.

For guys, wear a white tee with Bermuda shorts to match the vibe.

Watch the Chicago Air and Water Show

The free annual show held every August in Chicago is an attraction for tourists coming to Chicago.

One of the most popular festivals in the city, the show offers a Dubai-inspired exhibition of water fountains, lights, and fireworks.

You can be highly casual during this festival.

Wear a pair of jeans with a crop top or a button-down shirt. You can also wear a full-sleeved shirt with slacks.

Attend a Baseball Game

Chicago is popularly known for its love for sports.

Around August, the atmosphere in Chicago will compel you to attend a baseball game even if you are not a fan of the sport.

Plus, it will allow you to dress up in cute athletic wear.

Going to a baseball game wearing a cute white polo, tennis shorts, and baseball cap is a fun experience.

You can also wear Bermuda shorts or anything similar.

What to Wear for Nighttime Activities in Chicago?

Take a Lake Cruise

If being on the waters is relaxing for you, you would love a lake cruise.

Departing from Navy Pier or Michigan Avenue bridge, a lake cruise overlooks the water bodies in Chicago.

While it won’t let you enjoy the fantastic skyscrapers up close like on an architecture cruise, it is a fun activity.

You can wear a blouse, nice jeans, or a skirt or slacks. Since this cruise is not as formal as usual cruises, you can dress up casually.

See the Bean at Millennium Park

If you have never been to Chicago, you must have seen the gigantic silver mirror sculpture that is the landmark of Chicago.

This bean is located next to the Jay Pritzker Pavillion in Millennium Park.

People dress up casually here too.

Wear jeans and a tank top or a cute summer dress with floral patterns. Wear a hat and click photos at the best photo spot in Chicago.

Attend the Grand Park Music Festival

Music is Chicago’s best attribute.

Go to Millennium Park and enjoy the free outdoor classical music concert.

You can listen to emerging artists or those reiterating classical music for free.

Wear something chic like a short black dress with fabulous jewelry or an all-black outfit for guys.

Other Things You Should Pack for an August Holiday in Chicago

Along with the clothes you have picked out to wear during the holidays, you should also pack some other items to make your trip better. Here are some things you should carry:

  • Comfortable walking shoes: Chicago gives you plenty of walking opportunities, so having comfortable shoes is essential to exploring the city.
  • Stainless steel water bottle: When tired, water bottles will save your day by storing water for you.
  • Light sweater/cardigan: Early mornings and late nights in Chicago can be chill, so a light sweater is good.
  • Powerbank/external battery: Keeping your phone charged is necessary on any trip.
  • Selfie stick/tripod: Going to Chicago and not keeping photography essentials? That’s a big no! Make sure to carry all your cameras and accessories. You will want to capture every moment while in Chicago!

Final Word

Happy vacations! Chicago is one of the best tourist cities in the U.S., and august is a fun time to visit this place.

Always keep your essentials in one place so that you don’t have to worry about losing them and maintain clothes that you can comfortably pair with other dresses.



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.

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