Heading to Chicago this fall? From the golden leaves in Lincoln Park to breezy walks along Lake Michigan and pumpkin spice lattes in The Loop, Chicago in autumn is magical—and unpredictable. This Chicago fall packing list covers everything you need to stay warm, dry, and stylish in the city’s ever-shifting weather.
Weather Overview 🌡️
Fall in Chicago (September–November) brings cool, crisp air, stunning foliage, and—you guessed it—wind.
- September: 14–24°C (57–75°F) – Mild, sunny, and breezy
- October: 8–18°C (46–64°F) – Cool, with occasional rain
- November: 1–10°C (33–50°F) – Chilly with chance of snow
➡️ Pro Tip: Layer like a local. Pack for wind, fluctuating temps, and a bit of rain or sleet, especially in November.
What to Pack for Chicago in Fall 🎒
Packing smart will help you make the most of your trip. Here’s everything you need to bring for a comfortable and stylish adventure.
Carry-On Suitcase / Travel Bag Duffle / Portable Steamer / Packing cubes / Luggage scale / Wireless Noise-Cancelling Headphones / Speaker / Portable Charger / Universal Travel adapter / Compact Hair Dryer / Eye Mask / Waterproof Toiletry Bag Hanging / Zipper Pouch / Water BOTTLE / Liquid I.V. Hydration Vegan
Dressing Etiquette:
Chicagoans are stylish but practical. Think smart-casual with city-chic outerwear, sleek layers, and comfortable shoes for lots of walking. You’ll want to balance cozy warmth with fashion-forward flair.
🧳 Luggage & Packing Tools
If you want more options to have everything organized and well packed, take a look at these suggestions.
1. Rolling Backpack / 2. Luggage (large) / 3. Luggage (small) / 4. Toiletry Bag / 5. Beach Bag / 6. Backpack / 7. Packing Cubes
🧳 Carry-on suitcase – Durable & city-roll-friendly
🧳 Checked luggage – Optional unless staying long
🎒 Daypack or tote – Great for museums, markets, or shopping
👜 Crossbody bag – Secure and stylish for city use
🧼 Packing cubes – Separate warm layers & citywear
👟 Shoe bags – Dirty boots stay separate
💄 Makeup bag – Windproof your routine
🛁 Hanging toiletry bag – Great for hotel vanities
📁 Document organizer – ID, tickets, train passes
🛍️ Collapsible tote – For local markets or bookstores
🧺 Laundry bag – Fall layers add up fast
⚖️ Luggage scale – Midwestern thrift shopping is real
🔒 TSA lock – If checking luggage
🧢 Zipper pouch – Lip balm, transit card, hand cream
🧖 Quick-dry towel – Optional, for fitness centers or Airbnb
💤 Neck pillow – For train, plane, or long Uber rides
😴 Sleep mask – Helpful if staying downtown
👗 Clothes
👕 Long-sleeve shirts / tops (3–4) – Base layers that mix & match
👚 T-shirts (2) – For warmer early-fall days
🧥 Lightweight sweater (2–3) – Cable-knit, fleece, or cashmere
🧥 Cardigan or blazer (1) – For city-smart dinners or work trips
🧥 Insulated coat or trench (1) – Windproof & water-resistant
🧥 Packable puffer (1) – Especially for November
👖 Jeans (2) – Classic and versatile
👖 Casual pants or leggings (1–2) – For walking or lounging
👗 Sweater dress / midi dress (1–2) – Pair with boots + tights
🧘 Activewear set (1) – For parks or travel days
🛌 Pajamas – Warm and cozy
🧤 Underwear (7+) – Pack extras in cooler months
👙 Bras (3–4) – Everyday + sports
🧦 Wool or thermal socks (5–6) – A must for cold feet
🧤 Tights / leggings (1–2) – Under dresses or as base layer
🧣 Gloves (1 pair) – Especially for October/November
🧣 Scarf (1–2) – Chunky or soft knit
🎩 Beanie / knit hat – Wind-chill defense
💆 Skincare
🧼 Cleanser – Deep cleanse for urban air
🌸 Toner – Optional, but refreshing
🧴 Moisturizer – Cream-based for colder air
🌞 SPF moisturizer – Sun still shines in fall
🧽 Makeup remover – Wipes or micellar
🌿 Exfoliator – Use 1–2x/week
👁️ Eye cream – Wind protection for delicate skin
💦 Facial mist – Rehydrating boost
🧖 Sheet masks (1–2) – For dry or tired skin
💄 Lip balm with SPF – Windy City = chapped lips
🩹 Spot treatment – For breakouts in dry air
💄 Makeup
🧴 Tinted moisturizer or foundation – With hydration
🖌️ Concealer – For tired eyes or redness
🌫️ Powder – Minimal, just for shine
🌺 Blush – Cream or powder
🌟 Highlighter – Light glow for golden hour
👁️ Eyeshadow palette – Warm tones for autumn
✒️ Eyeliner – Smudge-proof
👁️ Mascara – Windproof and waterproof
👁️ Brow pencil – Tame and define
💄 Lipstick – Rust, berry, nude or bold red
🖌️ Brushes / sponge – Compact kit
🌟 Setting spray – Optional, for all-day museum-hopping
💇 Hair
💇 Hairbrush / comb – Anti-static preferred
🧷 Hair ties, bobby pins – Fall breeze = updos
🧴 Shampoo & conditioner – Hydrating formulas
🧴 Dry shampoo – For wind-blown refresh
💧 Hair oil / serum – Tame flyaways
🔥 Heat protectant – Flat iron must-have
💇 Blow dryer – Most hotels provide
💇 Flat iron or curling wand – Optional
🎀 Hair accessories – Berets, clips, or scrunchies
👠 Shoes & Accessories
👟 Sneakers – Stylish + supportive for long walks
👢 Ankle boots – Weatherproof & chic
🥿 Flats or loafers – For dinners or museums
🥾 Waterproof boots – Optional but useful for November
🧢 Hat or cap – Early-fall accessory
🧣 Scarf – Add warmth + fall flair
🧤 Gloves – Leather or knit
🕶️ Sunglasses – Fall sun is still bright
⌚ Watch – Classic or fitness
💍 Jewelry – Simple gold, hoops, or bold earrings
👜 Handbag – Secure with zippers
☔ Travel umbrella – Wind-resistant preferred
🧾 Documents & Essentials
🛂 ID / passport – Required for flights
📄 Copy of ID – Always wise
🪪 Driver’s license – Needed for car rentals
📃 Travel insurance – Smart for fall flights
📲 Boarding passes – Paper + digital
🏨 Hotel / Airbnb details – Keep address on hand
🚗 Car rental info – Optional for day trips
🎟️ Event tickets – Museums, concerts, architecture tours
🗺️ Offline maps – In case signal cuts out
💳 Credit / debit cards – Apple Pay is common
💵 Cash – For tips or small businesses
📇 Emergency contact list – Just in case
🖊️ Pen + notepad – Notes or journaling
📘 Chicago guidebook – For cool neighborhoods
🔑 House keys – In secure pocket
👛 RFID wallet – For L train + city streets
🩹 First Aid
🩹 Bandaids – For blisters from city shoes
🧴 Antiseptic wipes – For small cuts
🩺 Neosporin / cream – Wind-chafed skin
✂️ Small scissors – TSA-friendly
🦶 Blister pads – Required for all that walking
🌡️ Thermometer – Optional
✂️ Tweezers – Useful for anything
💊 Health & Hygiene
💊 Medications – Bring all you need
💊 Pain relievers – For weather headaches
🤧 Allergy meds – Fall allergens
💊 Motion sickness – If heading out to Lake Michigan
💊 Vitamins – Travel support
🩸 Feminine hygiene – Always bring what you prefer
🧴 Hand sanitizer – City essential
🧻 Wipes – For on-the-go refresh
🦟 Bug spray – Only needed if hiking
💊 Birth control – Pack it
👁️ Eye drops – For windy, dry eyes
🪥 Toothbrush + toothpaste – Don’t forget
🧴 Mouthwash + floss – Optional
🧴 Deodorant – Long-wear
🪒 Razor + shaving cream – Optional
💅 Nail kit – File, clippers
🌸 Perfume – Rollerball for daytime
🧻 Pocket tissues – For wind-runny noses
📱 Tech & Electronics
📱 Phone + charger – Must-have
📸 Camera – Cityscape photo ops
🔋 Power bank – For full day exploring
🔌 Charging cords – With backup
🔊 Bluetooth speaker – For your hotel room
🔌 No adapter needed (U.S. standard)
📶 SIM / data plan – Not needed for domestic travel
📖 Kindle / e-reader – Lakeside reading
🎧 Headphones – Noise-canceling for CTA trains
🎧 Entertainment
📚 Book / Kindle – Autumn reads
🎧 Podcasts – Perfect for walks or rain days
🎬 Downloaded shows – In case you stay in
📓 Journal – Chicago sparks creativity
🃏 Travel games – Optional
📰 Local paper or zine – Explore neighborhoods
🎒 Extras
🥜 Snacks / bars – Cold-weather munchies
💧 Reusable water bottle – Stay hydrated
🛍️ Foldable shopping bag – Eco & farmer’s markets
🧴 Laundry soap – For midweek rinses
🧵 Mini sewing kit – Coat button drama? Solved
📢 Safety whistle – Solo travelers
🧼 Lint roller – City wear fix
🦶 Inflatable footrest – Plane & hotel comfort
👟 Odor-fighting inserts – Damp boots relief
💤 Sleep aid – Jet lag = real in fall darkness
✈️ Travel Tips
✔️ Layer everything—weather flips by the hour
✔️ Download the CTA app for buses and L trains
✔️ Wear comfy shoes—you’ll walk a lot
✔️ Book museum passes in advance
✔️ Don’t underestimate windchill, especially near the lake
✅ Must-Haves for a Smooth Trip
🧥 Windproof jacket or coat
👢 Waterproof boots or sneakers
🧣 Scarf & gloves
👖 Jeans + warm base layers
👜 Crossbody or backpack
🧴 Lip balm + hand cream
📱 Phone + charger + maps
💳 Credit cards + backup cash
👍 Good-to-Have Items
💧 Liquid IV / hydration packs
🎧 Noise-canceling headphones
🛌 Blanket scarf
😴 Sleep mask
☔ Windproof umbrella
📶 Offline maps or Chicago city guide
🧼 Portable stain remover
📸 Phone tripod or wide-angle lens
