What To Wear in Chicago in the Summer: Chicago Outfit Ideas

Are you looking for suggestions on what to wear in Chicago in the summer?

Then, don’t worry because I have the perfect summer day outfits for you to wear in Chicago!

Chicago is a popular Midwestern city for vacation and is also known as the Windy City.

Located along Lake Michigan, the city offers everything from cultural diversity to fun festivals to amazing attractions.

That being said, it can also become quite hot as the summer progresses so you must pack the right Chicago summer outfits for your vacation.

Not sure how to dress for summer in Chicago? Don’t worry!

With these outfit ideas and tips, you’ll be ready to explore the city in all kinds of weather while staying comfortable.

So, just keep reading my blog post on What to Wear in Chicago in the Summer to learn more!

What To Wear in Chicago in the Summer: Chicago Outfit Ideas

Chicago Weather in Summer

I feel that summer is the best time to visit Chicago as the days are long and sunny with pleasant temperatures.

Yes, there are occasional rain showers and humidity but nothing that makes it unbearable.

Are you planning a summer vacation to Chicago? If yes, then here is what you can expect to find in each of the summer months here:

• June: If you want to visit Chicago in good temperature, especially to explore around the city, then June is a great time to visit. The temperatures range from 60°F to 80°F (16°C-27°C) and you can enjoy cool evenings near the lake.
• July: For those who love the warmer weather, July is the perfect time to make the most of Lake Michigan and don your bathing suit. This is undoubtedly the hottest month as the temperature averages around 70°F to 85°F (21°C-29°C). That’s not all, it is more humid as well which is why you should wear lightweight clothing this month.
• August: Although August is still hot in Chicago the evenings are slightly cooler. The average temperature ranges from 68°F to 83°F (20°C-28°C) and there are occasional thunderstorms.

Due to the varying temperatures, dressing in layers and packing versatile Chicago outfits is essential.

Tips for Packing Outfits for Chicago in Summer

1. Pack Comfortable Clothes: Since summers in Chicago can be hot and humid, I recommend wearing clothes made out of breathable and lightweight fabrics such as cotton.
2. Be Resourceful: You can wear a mix of casual and dressy pieces that will work both during the day and night.
3. Always Be Rain Ready: It can rain anytime in Chicago so it is always a good idea to carry a compact umbrella or a lightweight rain jacket.
4. Protection From The Sun: Since the sun can be a little harsh during the summers, keep sunglasses, hats, and sunscreen for your Chicago vacation.

What to Wear in Chicago in June

Okay, let’s talk a little about what to wear in Chicago in June.

Since this is the beginning of summer in Chicago, you can expect warm days and cool evenings.

The temperature ranges between 60°F and 80°F (18°C – 27°C) with a few rain showers throughout the month. Plus, a light breeze tends to blow near the lake in June.

This is why I highly recommend layering so that you can easily adapt to the temperature changes throughout the day.

Chicago Outfit Ideas for June

• Tops: Make sure to pack light and breathable fabrics like cotton and linen for your June vacation. I feel tank tops, t-shirts, and short-sleeved blouses are the perfect way to enjoy your summer vacation here.
• Bottoms: For bottoms, you can never go wrong with denim shorts, midi skirts, or lightweight trousers.
• Outerwear: A light cardigan or denim jacket is a must to stay warm during the cool evenings.
• Shoes: Yes, this is the perfect time to flaunt your sandals and loafers as you explore around the city.
• Accessories: Don’t forget to wear sunglasses and a wide-brimmed hat. Carry a small backpack or tote bag to keep the summer essentials such as water bottle and sunscreen.

Did you know that you can also attend the Chicago Blues Festival if you visit in June?

This is a free outdoor festival where you will celebrate the city’s rich blues heritage.

For this casual and vibrant event, you can wear a cute sundress or jumpsuit with comfortable sandals and a light jacket for the evening.

If you are planning to just explore the attractions in Chicago like the Millennium Park or Chicago Skydeck, then you can wear High-waisted denim shorts with a pastel tank top.

Include sneakers for walking comfortably along with sunglasses and a hat for a chic look.

What to Wear in Chicago in July

One of the hottest months to visit Chicago, July means lots of hot and humid days.

This is why you must dress for comfort and wear Chicago outfits made out of breathable fabrics only.

You can expect the temperature range from 68°F to 85°F (20°C – 29°C) with lots of humidity and a few thunderstorms.

Chicago Outfit Ideas for July

• Tops: As it gets more hotter and humid in Chicago in July, then one of the best summer day outfits would be sleeveless tops, tank tops, and crop tops with bottoms. Make sure the tops are made out of lightweight materials like linen or moisture-wicking fabrics else you will be drenched in sweat.
• Bottoms: To combat the summer heat, I would suggest high-waisted shorts, flowy skirts, or culottes which will keep you cool while making you look chic.
• Dresses: I love wearing maxi dresses and wrap dresses in Chicago in July as they are comfortable and cool.
• Shoes: To complete the look while staying comfortable, you can wear open-toed sandals or lightweight sneakers.
• Accessories: Do pack a reusable water bottle, sunscreen, and a sun hat for your summer vacation. You can keep these in a crossbody bag or daypack.

Don’t forget to watch a free movie under the stars in the Millennium Park Summer Film Series that is held every year.

For a casual look, you can wear high-waisted denim shorts with a relaxed-fit graphic tee. Complete it with sporty sneakers and a lightweight hoodie to stay warm if it gets cool at night.

If you plan to take an architectural boat tour in Chicago, then you can wear a flowy maxi dress with flat sandals and a light jacket.

What to Wear in Chicago in August

Finally, August in Chicago means slightly cooler evenings although the daytime temperatures remain warmer.

The temperature in Chicago in August ranges from 65°F to 83°F (18°C – 28°C) which is still quite hot but thankfully, there is less humidity to endure now.

There are still occasional thunderstorms so, always be prepared for it.

However, overall, it is a great month to enjoy outdoor events and activities. with lots of humidity and a few thunderstorms.

Chicago Outfit Ideas for August

• Tops: As I have mentioned several times, stick to breathable fabrics like cotton and chambray for the summer day outfits in Chicago. You can wear short-sleeved button-ups for a trendy look.
• Bottoms: This month is great for wearing a variety of bottoms such as capri pants, midi skirts, and even shorts.
• Dresses: If you are looking for some summer dresses to wear in Chicago in August, then choose A-line dresses or shirt dresses that will not only look stylish but be comfortable too.
• Shoes: For footwear, I feel stylish flats, strappy sandals, or sneakers are perfect for exploring around the city.
• Accessories: Finally, do layer your outfit and include a lightweight scarf or jacket to stay warm in the evenings.

To make the most of the last summer month in Chicago, I would suggest hitting the beaches here in a one-piece swimsuit with a kaftan, a straw hat, a beach tote, and comfortable yet cute flip-flops.

In July, you can also attend the famous Lollapalooza music festival that attracts tourists from around the world.

You can wear a cute co-ord set or a sexy bralette/crop top with a midi skirt. Add a crossbody bag and sunglasses with a comfortable pair of sneakers to have the time of your life at this music event.

What To Wear In Chicago In Summer Packing List

If you will be traveling, either by plane or by car to Chicago, here are some tips on how to pack lightly.

This unisex RFID-blocking concealed travel pouch is lightweight and comes in several colors.

These RFID sleeves are another solution.

This Anker high-speed phone charging battery is the exact one I carry with me on all of my trips.

My daughter gifted me this FugeTek selfie stick and tripod setup for my birthday. It is made of lightweight aluminum and so easy to use.

I never leave home on a trip without my Bobble filtration bottle. The 18.5-ounce size is perfect for when exploring.

And the replacement carbon filter ensures fresh clean water whenever you fill the Bobble.

Then this collapsible silicone foldable water bottle would work well for you as well.

This foldable water-resistant backpack would be great.

Not all beaches are created equally and these quick dry slip-on Aqua shoes will come in handy for pebbly Chicago beaches.

These men’s quick dry trunks are essential.

For women, this one-strap one-piece bathing suit is amazing.

Consider bringing along quick-dry super-absorbent microfiber towels.

This wet-dry bag with handles is a good option.

These unisex polarized sunglasses come in a lot of lens colors and frame designs and are extremely affordable too.

If you are fond of aviator-style sunglasses these polarized aviators may interest you.