Pack smart: bring layered clothing, a compact umbrella, and a light waterproof coat for Madrid's variable November weather. From Chicago O'Hare International Airport (ORD), expect potential winter delays—carry essential items in your carry-on (medications, chargers, a change of clothes) and enable mobile notifications with your airline for gate or delay updates. Consider travel insurance that covers weather cancellations, especially if traveling around Thanksgiving. Reserve airport transfers from Adolfo Suárez Madrid-Barajas Airport (MAD) in advance for late arrivals, and research local transit cards for cost-effective in-city travel. Finally, verify baggage allowances and bring printed or digital copies of your itinerary and accommodation confirmations to speed through immigration at MAD.