Loading...
📅 Sep - Nov
🌡️ 17°C / 8°C
☁️ Cool and colorful, great for walking
Fall in Chicago demands layers as temperatures swing from 17°C to 8°C. Pack a versatile jacket, comfortable walking shoes for exploring the Magnificent Mile and lakefront trails, and don't forget a windbreaker—Lake Michigan's breezes can catch you off guard.
Passport
Visa / entry documents
Travel insurance certificate
Flight & hotel confirmations
Driver's license
International driving permit
Credit / debit cards
Cash (local currency)
Emergency contact card
Underwear ×7
Socks ×7
Comfortable walking shoes / sneakers
Light cardigan / layer
Pyjamas / sleepwear
Casual t-shirts ×3
Jeans / trousers ×2
Belt
Hiking boots
Merino wool t-shirts ×3
Moisture-wicking hiking socks ×5
Zip-off hiking trousers
Lightweight fleece
Toothbrush + toothpaste
Shampoo + conditioner
Body wash / soap
Deodorant
Razor / shaving supplies
Moisturiser
Lip balm
Hair brush / comb
Nail clippers
Prescription medications
Pain relief — ibuprofen / paracetamol
Antihistamines
First aid kit
Band-aids / plasters
Antiseptic cream
Motion sickness tablets
Eye drops
Altitude sickness medication
Consult a doctor before visiting high-altitude destinations
Smartphone + charger
Universal power adapter
Portable battery pack
Headphones / earbuds
Camera + charger + memory cards
Daypack / backpack 20L
Packing cubes
Luggage lock
Luggage tags
Reusable water bottle
Travel pillow (neck)
Eye mask + earplugs
Money belt / hidden wallet
Sunglasses
Reusable tote bag
Compact umbrella
Quick-dry microfibre towel
Headlamp + spare batteries
Multi-tool
Waterproof dry bags
Trekking poles
Water purification tablets
Emergency whistle
Blister treatment kit
Planning your Chicago itinerary? Browse our free 3-day Chicago itinerary to see the full day-by-day plan. You can also use our free collaborative travel itinerary planner to build, map, and share your own custom trip.