I stood outside a Chicago bar at midnight in a t-shirt. June, so I thought I was safe. But the wind came off Lake Michigan and cut right through me. My friends laughed. They had jackets. I shivered for twenty minutes before the Uber came.
That is the thing about US cities. The weather plays by its own rules. You need a system, not just a packing list. This is your US Weekend Trip Packing Guide.
The real problem with US City Travel
You are walking through three different climates in one day.
The hotel lobby is fine. You step outside, and it is windy, get on the subway, and it is stuffy. You walk six blocks to a restaurant and sweat. Then you sit down, and the air conditioning is set to meat locker.
Your body cannot adjust that fast. Your clothes have to.
The fix is layers. Not complicated ones. Just a base, a mid, and a shell. You add. You remove. That is the whole game.
Only One Bag For A US City Weekend Trip Packing
Airlines now charge $35 to $45 for checked bags. Sometimes more. You wait at baggage claim for twenty minutes. For a weekend trip, that is just dumb math.
Use a carry-on. A backpack works better for cities because you take stairs and subways. A roller bag is fine if your back bothers you. Just make sure it fits the overhead bins on smaller planes.
If you cannot carry your bag up three flights of subway stairs, you packed incorrectly.
The stuff you cannot replace
Put these in one spot. Not scattered through your bag. Not buried at the bottom.
Your ID. Driver’s license or passport. If you fly domestically in the US, check if your license is Real ID-compliant. Some states are behind. Some airports check harder than others.
Two credit cards. Keep them separate. One in your wallet. One in your bag. If you lose one, you have a backup.
Hotel address saved offline. Screenshot it. Write it down. Phone batteries die at the worst times.
Cash. Twenty or forty dollars. Some places in cities are still cash only. Dive bars. Food trucks. That one pizza slice place opens at 2 AM.
Electronics you actually need
- A power bank is not optional. You will use GPS for hours and take photos. You will check maps. By 3 PM, most phones are at 20 percent. Then you panic. I watched a woman in Philadelphia sit on a curb outside a closed Starbucks, waiting for her phone to charge enough to call an Uber. Do not be that person.
- Headphones help. City noise is constant. Sirens. Subway brakes. Street musicians. Noise canceling is worth the space.
- Laptop if you need it for work. Kindle or iPad if you read. Leave the books at home. They are heavy.
- TSA makes you take laptops out of your bag. Pack it near the top.
- Phone. Cable. Wall plug. That is the minimum.
Clothes that do the work
Here is the rule. Pack for three days, even if you stay longer.
Wear one outfit on the plane. Pack two outfits in the bag. Mix and match them. Nobody notices if you wear the same jeans twice.
For the guys:
- Dark jeans that look fine at dinner
- One pair of comfortable pants for heavy walking days
- Two solid t-shirts in gray and navy or black (they go with everything)
- One long-sleeve shirt for layering
- A hoodie or light fleece
- A jacket that blocks wind and rain
For the girls:
- Dark jeans or comfortable pants
- Leggings for the flight if you want
- Two tops that work with both bottoms
- A cardigan or jacket that dresses up a casual outfit
- A scarf (city women wear them even when it is warm, it just works)
City by city guide
Different places need different stuff. Here is the short version.
New York or Chicago in winter. Cold and windy. Real coat. Thermal underwear if you run cold. Hat and gloves. The wind between buildings hurts your face.
Miami or New Orleans in summer. Humid. Your shirt sticks to you. Skip jeans. Shorts and linen pants. Light colors only. Dark colors soak up heat.
San Francisco, any time of year. Fog. Always fog. Bring a jacket every single month. Locals wear puffy coats in August. They are not wrong.
Las Vegas or Phoenix. Hot days. Cold nights. The desert drops forty degrees after sunset. That hoodie you packed? You will wear it at midnight.
Seattle or Portland. Rain. Not hard rain. Constant mist. Waterproof jacket. Water-resistant is not the same thing. You will learn the difference.
Washington DC in summer. Humid and hot. Walkable, but you sweat. Light clothes. Good walking shoes. Museums have strong AC, so bring a light layer inside.
Shoes make or break the trip
You will walk ten miles a day. Maybe more. I did fourteen in DC once. My feet hurt for two days after.
Bring shoes that are already broken in. Never bring new shoes on a city trip. Never.
One pair of walking sneakers. Real ones. Not fashion sneakers. Your feet do not care about fashion at mile eight.
One pair of evening shoes. Boots or loafers, or clean sneakers. Something that looks nice, but you can still walk in.
Wear your bulkiest shoes on the plane. Saves suitcase space.
Toiletries and the TSA rules
- Carry-on rules are simple. All liquids in 3.4 ounce bottles or smaller. All those bottles in one quart size clear bag. One bag per person.
- They check this. I have seen them make people throw away expensive shampoo. Do not risk it.
- Buy travel sizes or get refillable silicone bottles.
- Hotels give you shampoo and soap. You do not need to bring it unless you have specific hair or skin stuff.
- Solid deodorant and solid shampoo bars do not count as liquids. Pack as many as you want.
- Throw in four Band-Aids and three ibuprofen. Your feet will hurt. Your head might hurt. Be ready.
What people forget
- Phone charger. Everyone forgets this. Left in bathrooms everywhere.
- Chapstick. Plane air dries you out. City air dries you out.
- A pen. You need it for customs forms sometimes. Or for writing down directions when your phone dies.
- A reusable water bottle. Airports have filling stations. City water is fine to drink. Saves money.
- Small umbrella if you have room. But know that wind breaks them. A good jacket is better.
Mistakes I made, so you do not have to
Packed a suit once for a nice dinner. Never wore it. Ate at a place that did not care about suits.
Brought an umbrella to Boston. Wind snapped it in ten minutes. Bought a cheap one there. It also snapped.
Thought a light jacket was enough for San Francisco in August. Spent eighty dollars on a tourist sweatshirt. Still have it. Still mad about it.
Packed books. Heavy. Just use the phone app. Or buy a paperback there if you finish it.
Forgot my charger once. Paid forty bucks for a new one at a drugstore. Still mad about that too.
Packed for perfect weather. The weather is never perfect. Pack for rain, cold, and heat. All of them.
The five-second check
Before you walk out the door:
- ID in pocket?
- Cards in wallet?
- Phone charged?
- Power bank charged?
- Jacket that handles rain?
- Shoes comfortable?
Good. You are ready.
Questions people ask
No. TSA takes knives. Leave it at home. Even small ones.
Backpack is easier for cities with stairs. Roller is easier on your body. Pick based on your back, not fashion.
Yes. Your phone dies at 3 PM. You will stand in a coffee shop waiting. Just bring the battery.
3.4 ounce bottles. 1 quart bag. 1 bag per person. Memorize it. TSA asks.
Fold them inside those thin plastic bags from the dry cleaner. Reduces friction. Works okay. Or just accept wrinkles. Nobody cares.
Yes. Solid food is fine. Bring granola bars. Airport food is expensive.
Leave room for stuff
Here is the thing nobody tells you. You will buy things there.
Shirts from that concert. A mug from the museum. Hot sauce from that place you liked. A book from that indie store.
If you pack perfectly full, you have no space for memories. Pack light. Buy things. Come home with a full bag and empty laundry.
That is the goal. Not perfect packing. Just smart enough packing that you enjoy the trip.
Disclaimer: This is just advice from someone who travels a lot and makes mistakes. Check TSA rules before you go because they change. Have fun out there.