How to Pack for a Trip to Chicago

Last Updated: February 21, 2021

Chicago is an interesting city, filled with many things to see and do. A certain amount of trip planning must be done ahead of time, particularly in regard to packing. Airlines limit the amount of luggage you can take, plus no one wants to spend a trip to Chicago struggling with a lot of bags. Knowing how to pack for a trip to Chicago will make your trip much more enjoyable.

Steps

1
Make a list of what to pack for a trip to Chicago.
- Check the weather. Remember that Chicago has earned the title of "Windy City."
- Also know that Chicago weather is notorious for changing.
- Clothing items that you can layer works well for Chicago's unpredictable weather.
- Bring winter gear (coat, hat, gloves, and scarf) if you plan to travel to Chicago from late autumn to early spring.
- Thermal underwear makes chilly winter days easier to withstand.
2
Choose mix-and-match clothing items for greater versatility and to save space when packing.
- Plan to do laundry during if your trip to Chicago will last three weeks or more.
3
Roll or bundle clothing instead of folding.
- This provides more room in a suitcase and clothes are less wrinkled.
- Another trick to limit wrinkles is to roll clothing in tissue paper.
- Stick shoes, belts and other rigid items in the outer edge of the suitcase.
- Let no space go unused.
4
Pack for a trip with a backpack if you want your hands free.
- Packing heavier things on top and lighter things on the bottom allows the backpack to rest on your lower back, which is much more comfortable than having it cut into your shoulders.
- Place items that you need most often at the top of a backpack or in one of the zippered pockets so they are most accessible.
5
Limit toiletries to what is truly needed.
- Ask yourself what you know you will need, not what you think you might need.
6
Pack items like shampoo in small containers.
- Trip planning should always include plastic bags, such as Ziplocs. This keeps toiletries from leaking onto clothing. Plastic bags can later be reused for dirty clothes or garbage.
7
Split your group's clothing between various suitcases if travel to Chicago means flying with family.
- Everyone still has clothing if one suitcase is lost.
8
Remember to pack a carry-on bag for important papers, valuables and can't do without items. Diaper bags are usually a safe place for important items. Things to keep with you might include:
- Electronic items.
- Visa or passport if you're coming from outside of the U.S.
- Chewing gum may help your ears if you're flying.
- Change of clothes for long flights.
- Jewelry.
- Identification, credit cards.
- Prescription medication in original containers.
- Tickets, travel itinerary and trip planning notes.
- Important contacts and phone numbers.
9
Take no more than two pairs of shoes to save space when you pack for a trip.
- Make one pair of shoes fancy and the other casual.
- Save even more space by wearing one of the two pairs of shoes and packing the other.
10
Place a business card with a cell phone number in the baggage label.
- You don't want anyone to know that your house will be empty, so a business card is a better choice than a home address.
- Write your cell phone number and destination address on a self-adhesive label to stick inside your suitcase. This is helpful to the airline in case the baggage label comes off.
11
Consider extra items like guidebooks and maps. Other items you might need when you travel to Chicago include:
- Camera with additional memory, and if you're coming from outside the U.S., you may need an electrical adapter and plug converter.

Community Q&A

Question

What should I bring if I am going in October?

Community Answer

Pack warm clothes, food, water, a heavier coat, mittens and boots.
Question

What should l bring if I am going in March?

Community Answer

Chicago is usually chilly in the winter/spring months. You should bring warmer clothes and dress in layers so that you are not too hot or cold.
Question

What should I bring if I'm going in May?

Community Answer

Pack clothes for warmer weather, but also bring rain gear if you do not want to get wet, as it is often very rainy in May.
Question

Should I still bring warm clothes (scarfs, jacket, gloves, etc.) if I go in April?

Community Answer

Yes. Not a large coat, but a jacket, thin gloves, hat, scarf. You never know what might happen.
Question

What should I pack if I go in mid-April?

Community Answer

In April the weather can be chilly or warm, so pack clothes you can layer in order to deal with whatever weather occurs.
Question

What is the weather in Chicago?

Community Answer

This depends on what month. March - May can be very rainy, while June - August is usually really hot. October and November is usually sweater weather, 50ish. End of November through February is usually cold and snowy.
Question

What should I bring if it's mid June?

Community Answer

Bring warm weather clothing. Usually by the beginning of June the weather is 70-80 degrees.
Question

What should I bring in August? I am assuming it will be hot.

Community Answer

It is very hot in August so you should bring shorts, a pair of jeans, as the weather can unexpectedly change, and short sleeve shirts. You can also bring a lightweight long sleeve shirt in case it gets a little cooler at night.
Question

How is the weather in May?

Community Answer

It totally varies. It should be more or less warm (60s-70s F), but it might get chilly some days or at night, so bring some things you can layer, like a sweater, jacket, etc.
Question

What should I bring if I am going in December?

Community Answer

Ear muffs, scarves, gloves, snow jacket, snow boots and anything that will keep you warm. Bring clothing you can layer: sweaters, long-sleeved t-shirts, vests, etc.