Chicago’s The Drake

Arrival/Check-In: While a plethora of high-end hotels exists in Chicago, when it comes to history, The Drake does not have much competition. The property joined the Historic Hotels of America in 2014; with a history dating to 1920, The Drake served as a high society favorite in the Roaring Twenties and continues to delight guests through the modern day. Marilyn Monroe and Joe DiMaggio even carved their initials into the hotel’s Cape Cod Room’s bar in the 1950s.

Stay & Meet with Confidence

Penha Longa Resort in Portugal

Arrival/Check-In: My TAP Portugal flight arrived in Lisbon early in the morning, which brought up some questions regarding hotel check-in. Although Penha Longa Resort is located in Sintra and check-in is in the afternoon, I was hoping to get into my room early and enjoy a little shuteye before exploring the property. The receptionist who helped me check in could see how tired I was. She kindly suggested I enjoy the breakfast at the resort while staff rushed to get my room ready. By the time I was finished with my meal, my room was waiting for me.