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What to Wear in Chicago?

by 陈菁 05 Jun 2025

Although it is not the capital of any state in the United States, Chicago has an economic and cultural status that is no lower than those of the capital. The location in the center of the North American continent provides favorable conditions for Chicago to become one of the world's financial centers and the largest commercial center in the United States.

In addition, Chicago, located in the southern part of Lake Michigan, also has rich tourism resources and is a world-famous tourist destination. Since Chicago is the largest air transport center and railway hub in the United States as well as the largest inland port in the world, it will never be inconvenient for you to travel to Chicago no matter where you come from. The most important thing you need to consider when packing for your trip to Chicago is what to wear so that you can stay comfortable while still looking very stylish. Do not worry! We will provide you with the fashion suggestions in different seasons respectively!

a lady in a green orange printed slip dress and an openwork cardigan
a lady in a brown tencel blend maxi dress

The Climate Features in Chicago

The climate of the four seasons is totally different in Chicago, which is due to its temperate continental climate. July is the hottest month of the year, while January is the coldest month. The significant continental characteristics lead to a large annual temperature difference in Chicago. In July, the highest temperature will reach about 30 degrees Celsius, while in January, the lowest temperature may drop below -10 degrees Celsius.

But at the same time, you will find that there is plenty of rainfall and it is often windy due to the influence of Lake Michigan. Summer is the season with the most precipitation, usually in the form of rain; while winter is the season with the least precipitation, with an average snowfall of about 70 inches per year. Because the lake has a certain regulating effect on the climate, the climate in the areas along the shore of Lake Michigan is milder. In the summer, the lake absorbs a lot of heat, making the lakeside area cooler than the inland area; in the winter, the lake releases heat, making the lakeside area relatively warm.

But it is worth noting that as the third largest city in the United States, Chicago has a significant heat island effect, which makes strong winds occur more frequently in Chicago. However, it is worth noting that as the third largest city in the United States, Chicago has a significant heat island effect, which makes strong winds appear more frequently in Chicago. Since the 1980s, due to global warming, extreme weather has also appeared more frequently. Therefore, please remember to check the weather forecast before traveling and try to choose a date with good weather.

The obvious seasonal differences also determine that Chicago has obvious tourist peak and off-peak seasons. Summer is the season with the most tourists in Chicago. Because in summer, Chicago is not only more comfortable in temperature, but also has many food festivals and music festivals to attract tourists. The spring and autumn in Chicago is also attracting. The temperature in these two seasons is relatively mild, and there are not as many tourists as in summer. The cold winter is the off-season for traveling in Chicago. The cold temperature discourages many tourists. However, the city covered with ice and snow has a unique flavor, and the special activities and celebrations will also attract some tourists.

a lady in a linen halter top and a pair of linen pants
a lady in a black slip dress with white polka dots and a black cardigan

What to Wear in Chicago in Different Seasons?

Although summer is the peak season for traveling to Chicago, you may not feel very comfortable. High temperatures and frequent precipitation are both challenges you need to overcome during your trip. Summer is a good time to wear all kinds of beautiful dresses and skirts, but at the same time you also need to consider whether these dresses and skirts are suitable for long-term outdoor walking. So, what are the suitable outfits for traveling to Chicago in summer that are both comfortable, practical and fashionable?

A short sleeve knit top + a denim slit skirt

This outfit is simple yet elegant, black is also versatile and suitable for more formal occasions. It is a perfect combination for museums and other attractions. In addition, you may have heard of Jay Pritzker Pavilion. An open-air concert hall does not require very formal dress like ordinary theaters, but it also expects relatively decent dress. The combination we recommend will be the perfect choice.

An off shoulder top in a light color + a pair of ripped jeans

Chicago is not a place where you need to dress conservatively. Every day, people from all over the world, all races and all professions come and go here. In this inclusive metropolis, you can fully show your fashion style. As long as it is not a formal occasion with strict dress code, you don't have to worry about being criticized for wearing some unique clothes. A colorful off shoulder top can show your vitality and uniqueness, and the off shoulder design can also increase breathability in the hot summer. A pair of ripped denim jeans can show a sense of fashion and casualness, suitable for wearing at lively music festivals or outdoor activities.

A chiffon shirt in a light color+ a pair of wide leg linen pants

Chiffon is both light and breathable, making it very comfortable in the hot summer. The light color will also give you a cooler visual effect. The loose fit of the wide-leg pants can not only make your legs more comfortable when walking, but also add a touch of retro charm and fashion taste to your look. In addition, linen fabric is also very breathable, which can give you a better wearing experience in summer. When you are walking on the lakeside, this outfit will fully show your elegant temperament.

Chicago in winter is definitely not warm, so you need to pay extra attention to keeping warm when traveling to Chicago in winter. And it should be noted that fashion and warmth are not contradictory. You can achieve a look through refined matching methods. Chicago is not only cold in winter, but also windy, so when traveling to Chicago in winter, you need to wear something that is not only warm but also windproof. The specific outfits you can refer to are as follows:

A wool sweater + a pair of straight leg jeans + a black down jacket

No matter how low the temperature is, a thick down jacket can bring you enough warmth. A wool sweater underneath can provide you with extra warmth. Don't underestimate a pair of ordinary straight jeans, they are the most versatile and best choice for shaping your legs.

a lady in a floral printed silk dress
a lady in a linen rose printed dress

Accessories Recommended for Your Chicago Tour

In winter, you might need some accessories that can both provide you with extra warmth and complete your outfits. For example:

🧀A knit hat. A knitted hat can protect your head in the cold winter temperature. In addition, you can also choose some styles with cute decorations, such as a knitted hat with a pom pom on the top, which will add a touch of cuteness to your look. In the snowy scene, you can try to choose a knitted hat in bright colors to create a sense of contrast and atmosphere.

🧀A checkered wool scarf. A checkered wool scarf can not only keep your neck warm, but also become the first choice for many women to go out in winter because of its classic pattern. In addition, the checkered scarf can also be used as a shawl to be wrapped around the upper body, and used as a prop when taking photos.

🧀A pair of gloves. While protecting your head and neck, don’t forget to keep your hands warm! If you prefer an elegant style, choose a pair of brown faux suede or wool gloves in a solid color! If you like a cute style, a pair of furry gloves with cartoon patterns is also a good choice.

In the rainy summer, you need to take some rain gear in case of emergency. In some scenes, rain gear can even be used as a prop for taking photos. On sunny days, you need to prepare for sun protection.

🧀Hats are also essential when traveling in summer, but you certainly can't wear a knitted hat in the hot summer. Instead, you can choose a bucket hat or a wide-brimmed straw hat to block the sun.

🧀A transparent umbrella. When it rains, a transparent umbrella certainly can play its practical function. In addition, you can also open the umbrella when taking pictures. Because it is transparent, it will not block the scenery behind it, and at the same time it can give your photos a refreshing atmosphere unique to the rainy season.

🧀A bracelet. When summer comes and ladies start to expose their beautiful arms, you can also wear bracelets! You can choose a gold carved bracelet, which looks gentle and elegant. Of course, if you don’t like this luxurious style and prefer a rustic style, you can also choose a nylon rope braided bead bracelet.

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