A Luxury Collection Destination, Illinois, United States
The birthplace of the skyscraper, and home to some of the most celebrated theaters, museums, and architectural landmarks in the United States, the city’s legacy merges with a stunning natural lakeside landscape. Dine at standout restaurants, explore innovative parks and green spaces, and get lost for hours wandering through the vibrant neighborhoods of Chicago.
Drink glogg (hot spiced wine) and shop for hand-carved toys and ornaments at this traditional German holiday market that pops up every year beneath the Chicago Picasso sculpture in Daley Plaza.
Smaller in scale and more low-key than the rock fest veteran Lollapalooza, this independant music and arts festival in Union Park is a favorite among locals and tapped-in visitors.
The neighborhood that was once Chicago’s bookmaking hub is now host to one of the country’s largest free outdoor book fairs with discussions, readings, and signings by big name authors.
Pack a picnic for the oldest outdoor music festival in North America. World-renowned opera, classical, country, and rock performers take the stage of the 1904 Prairie-style stage on summer nights. Set in a leafy suburb north of downtown, it’s an easy trip on the Metro train to the venue.
Irish or not, all wear green for the St. Patrick’s Day Parade down Michigan Avenue in Chicago. Even the Chicago River is dyed a shocking shade of green for the occasion.
This three-day celebration of live music is the largest free blues event in the world. The festival has been going strong for over three decades and shows no signs of slowing down.
Grab the popcorn for the country’s longest running international competitive film festival which screens films from around the world.
One of the six World Marathon Majors, Chicagoans cheer on runners from around the globe as they make their way from the Chicago lakefront through neighborhoods across the city.
Chicagoans take their baseball very seriously, and opening day on either end of the city — North Side for the Cubs or South Side for the White Sox — is something to celebrate.
Founded in 1980, this fair is the original food pop-up event showcasing Chicago’s established and emerging chefs and restaurants. The festival also hosts big name bands and performers on two stages along with the independent ChicagoMade market.
The elegant dining room and club-like lounge with 1930’s-inspired cocktail list gives a wink and and a nod to Chicago’s past, but the sophisticated menu is decidedly forward-thinking.
Make new friends Upstairs at the Gwen over a bowl of Prohibition Pomegranate Punch—a potent mix of pomegranate liqueur, raspberry vodka, fresh lime juice and crowned with a fruity ice mold.
Dine on locally sourced specialties—pan roasted Lake Michigan-caught whitefish and thick burgers made with Slagel Family Farm’s beef—from chef Oscar Hernandez’s innovative American menu at Circa.
Make like a rare bird and find your perch Upstairs at the Gwen, the hotel’s enviable outdoor patio. Raise a glass and nibble on small bites all with straight-on skyline views.
OPENED IN 1930, THE SHEDD AQUARIUM REMAINS AN INNOVATIVE CENTER FOR AQUATIC LIFE AND IS HOME TO 32,000 ANIMALS, INCLUDING BELUGA WHALES.
Following an inspirational visit to the Art Institute of Chicago, transform your guest room into an artist’s studio. A full-sized easel, canvas, paints, brushes, and pastels will be set-up in room, and your masterpiece will be shipped home when you check out.
Head out to a baseball game and cheer on the Chicago White Sox or the Chicago Cubs with an exclusive baseball package that includes tickets, train passes and a sports-themed welcome.
Take in million-dollar skyline views at rooftop bar and restaurant. Sip on craft cocktails paired with hearty small plates.
Join the Starwood Preferred Guest program and end every journey with a reward, including points for exclusive offers and free nights at exceptional hotels and resorts worldwide.