As a lifelong Chicagoan I consider myself an expert in figuring out what to wear in Chicago. If you are visiting Chicago and don’t know what to wear, I’ve got you covered. I have all the packing essentials you will need in Chicago as well as outfit suggestions for every season.
Chicago Packing List Essentials
Below are the essential items you will need to pack for Chicago no matter what season you are visiting.
• Comfortable walking shoes – You will do a lot of walking in Chicago. Depending on the time of year you visit and what you plan to do, you can bring one of more pairs of comfortable shoes including: sneakers, boots, casual sandals and/or comfortable flats (see my shoe suggestions for each season).
• Dressier shoes – Bring a nicer looking pair of shoes that can be worn for dinner or drinks in the evening.
• Travel umbrella – It can rain in Chicago all year round. Although it is more likely to snow in the winter than rain, it does rain in the winter.
• Scarf – A scarf is essential most of the year.
• Hat – I wear a hat most of the year in Chicago. When the weather is hot, bring a sun hat or baseball hat to protect you from the sun. During the winter or cooler fall/spring days, a hat will keep you warm.
• Face mask – Masks are required in indoor places so pack a few face masks
• Day bag/purse – Bring a backpack/messenger bag/tote/purse for sightseeing in the day. Women might want to also bring an extra purse for going out in the evening.
• Reusable water bottle – It can be hard to find a water fountain so it is a good idea to have a reusable water bottle with you especially in the summer.
• Reusable bag – You might want to pack a reusable bag for grocery, drugstore and other purchases. Stores are required to charge you for bags in Chicago.
• External battery – You will use your smartphone a lot in Chicago (taking photos, using ridesharing services, looking up directions in google maps etc). It is a good idea to bring an external battery to recharge phone.
• Camera/photography gear – Chicago is a beautiful city so you will be talking a lot of photos! If you are a more serious photographer, bring your camera, portable tripod and extra memory card.
What to Wear in Chicago in the Fall
The weather is hard to predict in the fall. Early fall still tends to be very warm and does not feel that different from summer. Late fall can sometimes feel like winter. The temperature can change suddenly and drastically so be prepared for any type of weather. Layers are key!
Below are some fall outfit essentials for Chicago:
• Boots- In addition to sneakers or comfortable flats, fall is a great time to wear your cute fall boots.
• Jeans/pants
• Sweaters
• Long sleeved shirts
• Scarfs
• Vest/hoodie/fleece
• Jacket – You will probably need 1-2 jackets in the fall, depending on the temperature. You might need a light jacket and/or a warmer jacket depending on the temperature
What to Wear in Chicago in the Spring
Spring is similar to fall in that weather can be unpredictable and change quickly. However, it is more likely to rain in the spring. Be prepared to dress for any season. Just like fall, layers are key. Below are spring outfit essentials for Chicago:
• Rain boots- In addition to sneakers or comfortable flats, you might want to bring your cute rain boots
• Umbrella – An umbrella is a must in the spring. I like small travel umbrellas that you can keep in your purse or day bag
• Rain jacket
• Warmer jacket – In addition to a rain jacket, you might want to bring a warmer jacket for colder spring days.
• Jeans/pants
• Sweaters
• Long sleeved shirts
• Vest/hoodie/fleece
• Scarfs
• Hat – Spring can still be cold so bring a hat. It can also cover frizzy hair during a rainy day.
What to Wear in Chicago in the Summer
Summers in Chicago are hot and humid. Here are some outfit essentials for Chicago in the summer:
• Sandals/flip flops
• Sunglasses
• Hat – wear a proper sun hat or at least a baseball cap
• Swimsuit, sarong, beach bag and other beach/pool wear (if you are planning to spend time at the beach or if you have access to an outdoor pool)
• Shorts
• Dresses/skirts – I prefer maxi dresses since Chicago can be windy
• Lightweight pants
• Lightweight shirts/tops
• Light sweater or hoodie – For cooler evenings and indoor places with too much air conditioning
I also recommend packing these items if you are visiting Chicago in the summer:
• Waterproof phone case – If you plan to go kayaking or spend time at the beach
• Mosquito repellent – If will be spending time outside around dusk and in the evening.
• Sunscreen and lip balm (with UV) – essential if spending a lot of time outdoors!
What to Pack for Chicago in the Winter
Winter can be really cold and snowy in Chicago but not always! However you need to be prepared for the worse case scenario. Below are my Chicago winter essentials:
• Snow boots- These are essential for walking on snow or ice. When purchasing for snow boots, I focus on boots with rubber soles so that you do not slip. It is also a good idea to choose waterproof boots so your feet do not get wet. Even if there is no snow on the ground, snow boots can keep your feet warm on a cold winter day.
• Warm socks – wool socks are great for winter
• Warm coat
• Winter hat
• Scarf
• Gloves – If you use your phone a lot, I recommend a pair of gloves so that you don’t have to keep taking them on and off. Bring at least 2 pairs in case you lose a glove.
• Warm sweaters – I personally prefer turtlenecks because my neck gets cold easily
• Baselayer crew top – I wear a baselayer top under my sweaters. Not only do they keep me warmer but they are moisture wicking and breathable and absorb sweat.
• Jeans/thick pants
• Long underwear – I personally never wear long underwear under my pants, but if it is freezing and you will be outside a long time, consider wearing long underwear under your pants.
These are my outfit essentials for Chicago. Is there anything else I should add to my Chicago packing list?
