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.
A defunct elevated train rail line has been reinvented as a park and trail system connecting neighborhoods and reviving communities with much-needed green space. Hope on and off and several stops to bike or stroll the 2.7-mile recreational and cultural pathway lined with art exhibitions and distinctive landscape architecture.Learn More
Stroll the skybridge from Millennium Park which connects to the Art Institute of Chicago’s glassy Modern Wing, designed by prize-winning architect Renzo Piano. At this renowned museum, contemporary work, European art, African sculpture, Islamic ceramics, and Chinese stoneware are displayed alongside American masters like Whistler, Homer, and O'Keeffe. As well, a distinctive series of miniature interiors depicting a Shaker living room, a Louis XV-era boudoir, and a traditional Japanese home are on view.
One of the most scenic ways to explore the Windy City is on two wheels. Pedal the 26-miles of dedicated bike paths along Lake Michigan’s sparkling shoreline, and stop by the Museum Campus to stretch legs and take in the sites. Ditting this 57-acre museum park is North America’s first planetarium, the Field Museum of Natural History, Shedd Aquarium and Soldier Field which is the home stadium of the Chicago Bears.Learn More
Board Chicago’s First Lady for a leisurely architecture-geared boat cruise down the Chicago River. Knowledgeable docents from the Chicago Architecture Foundation impart the story, building by impressive building, of how this humble town rose from the prairie to become one of the world’s most architecturally daring cities.Learn More
Renowned architect and designer Frank Lloyd Wright established his first studio in his home just west of Chicago in the suburb of Oak Park. Take the comprehensive tour of Wright’s home and personal effects-packed studio for an intimate glimpse into the life and work of the influential Prairie School Movement leader.Learn More
Capture your reflection in Anish Kapoor’s polished, bean-shaped “Cloud Gate” sculpture known locally as “The Bean,” and splash in the puddles created by Jaume Plensa's innovative “Crown Fountain” within Millennium Park. The open-air Jay Pritzker pavilion undulates with architect Frank Gehry's signature brushed steel ribbons and is host to free concerts from a range of musicians from the Chicago Symphony Orchestra to Wilco. Once a neglected industrial patch of parking lots and defunct railyard, its been transformed into 24-acres of green space, gardens and world-class architecture.
Spend a few hours kayaking along the south bank of Chicago River before tieing up and coming on land to refuel. This lively pedestrian pathway has several dining and cocktail options, including a tiki-themed bar and the City Winery which also hosts live music, for a bite to eat with wonderful water views.
Catch comedy’s next-big-star at the legendary Second City Theater. Established in 1959, this performance space, acting and writing school for improvisational theater is where Bill Murray, John Belushi, Tina Fey, Amy Sedaris and a list of who’s-who of comedy got their start. Stay up late for the second performance of the mainstage sketch revue, which is followed by an outlandish improv session based on help from the audience.Learn More
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.Learn More
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.Learn More
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.Learn More
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.Learn More
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.Learn More
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.Learn More
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.Learn More
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.Learn More
Take in million-dollar skyline views at rooftop bar and restaurant. Sip on craft cocktails paired with hearty small plates.Learn More