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Romantic Weekend in Chicago

Make it a weekend for the memory books, one to reflect on in days to come. Choose a gracious, historic hotel to set just the right vintage tone to accompany a handful of classic tidbits curated from Chicago’s long lists of romantic diversions.

Reflections of style

Alas, the Palmer House®, A Hilton Hotel was only 13 days old in 1871 when the property at the corner of State and Monroe streets was destroyed by the Great Chicago Fire. However, after rising from the ashes two years later, the sumptuous hotel has turned out to be America’s longest continually operating hotel. Hats off to this Beaux Arts grande dame and her younger Hilton Hotel sisters.

Half-a-century later, Chicago put the roar into the Roaring Twenties. The town was dry due to Prohibition, but that didn’t stop them from building fine hotels such as The Drake Hotel (1920), the Hilton Chicago (1927) and the North Shore’s Hotel Orrington (1925), named after the co-founder of Northwestern University, and now known as the Hilton Orrington/Evanston.

Reflections on the river

Grab your camera and your honey’s hand and get over to the river. From The Drake, it’s a gorgeous walk along Magnificent Mile. Hear fascinating skyline stories about Chicago and how it got that way from informed, enthusiastic docents aboard your Chicago Architecture Foundation River Cruise. If you both already love Chicago, you’ll love it double, seeing the skyline reflected on the water. P.S. Prohibition ended in 1933, so step right up to be served at the boat’s full bar.

Catch your own reflection

From the Chicago River to the Palmer House®, A Hilton Hotel is only a 13-minute walk. But, slow down — you don’t want to miss the entrance to Millennium Park. No trip to Chicago is complete without catching a fun, distorted reflection of yourselves cuddling under the Cloud Gate sculpture, a.k.a. "The Bean." The shiny sculpture is the original selfie station, creating a very 21st century souvenir.

Reflect on fine art

Stop to capture another Instagram moment in front of the stately bronze lions at the entrance to the Art Institute of Chicago. These handsome creatures predate ‘The Bean’ by more than a century. One of Chicago’s most captivating spots is the elegant, polished marble stairway inside America’s second-largest museum. Wander through the galleries, pausing to reflect on your own favorites displayed among the Romanticists, the Impressionists and the post-Impressionists.

A reflection on royalty

Traditional English afternoon tea accompanied by live harp music is served beside the sparkling fountain at The Palm Court at The Drake, as enjoyed by Queen Elizabeth II in 1958 and by Princess Diana in 1996. Your cozy tea for two is imported, properly prepared and politely served in a picture postcard setting to seal a memory of your own.

Speaking of romantic and royalty, remember to stop by The Drake’s Cape Cod Room to see the wooden bar where newlyweds Marilyn Monroe and Joe Di Maggio carved their initials in 1954.