Food and a flick might be a safe bet, but there are so many more unique, romantic outings in the city.
Chicago’s Gold Coast
Ambassador Chicago is the city’s original boutique hotel, located in the heart of the Gold Coast.
Built in 1926, the hotel has played host to the who’s who of the 20th and 21st centuries, attracting legends from Frank Sinatra to Bill Murray. There are countless iconic stories found in its stunning walls, like Dustin Hoffman goofing around with bell staff, or Elizabeth Taylor lounging in her self-named suite, even Marilyn Monroe dazzling guests in the Hotel Restaurant, and David Bowie getting glam before his gigs with the Spiders from Mars.
If walls could talk, the hotel would narrate stories of guests like celebrated Chicago sportscaster Harry Carry, a permanent resident of the hotel for years, rubbing elbows with the Rolling Stones while reveling outside his guest room.
Ambassador Chicago continues to host some of the most esteemed names in entertainment, as it makes its indelible mark on Chicago.
5 Next Level Date Nights in Chicago
5 Fitness Finds in the Windy City
Chicago offers so many cool fitness options, there’s no need to clock time on the treadmill while you’re in town.
Set Your Sights on Some of Chicago’s Best Views
With a skyline as gorgeous as Chicago’s, it’s no wonder residents and visitors are constantly seeking out the best views.