Food & Drink

Having just arrived to Chicago in a private jet, one of the best ways to learn about the heart and culture of a new place is to try the regional favorites in food and drink. For Chicago’s most beloved food traditions, that means Chicago-style pizza at Lincoln Park Chicago Pizza & Oven Grinder, and Chicago-style hot dogs at Portillo’s. If you are seeking something extraordinary, a dinner like no other, then reserve a table at the Michelin 3-Star restaurant that has been voted among the best in the world: Alinea. Reservations book at least two months in advance, so plan ahead for this singularly spectacular food experience. Dinner is multiple courses and around three hours. For an updated classic, visit RPM Steak, in the River North neighborhood. This modern steakhouse with an elegant sunken dining room boasts a curated craft cocktail list and chef-driven menu.

World Famous Art & Entertainment

Among the entertainment options in Chicago for theater and the performing arts are many Tony Award-winning theater companies, and the world-famous comedy club and school of comedic improv, The Second City. A rich musical history and seasonal festivals are something Chicago offers in spades, and will motivate you to book your private flight to Chicago as often as possible. Jazz and blues both have regionally specific forms developed in Chicago during the early to mid part of the twentieth century. The Green Mill Jazz Club in Uptown, first opened in 1907, still hosts incredible local and traveling musicians late into the night on weekends, while the annual Blues Festival in Millennium Park showcases the absolute best acts in music today. Chicago’s energetic Thanksgiving Day parade features giant inflatables, floats, marching bands, and artistic performances; this is one your family will not want to miss. Another famous parade heads through Chicago’s storied streets each year on St Patrick’s Day, and the entire Chicago river is turned green. When the crisp weather settles in, the authentic Chicago Christkindlmarket opens for around six weeks every year in November and December. Inspired by the German markets of Nuremberg that began centuries ago, featuring European delights and artisan creations, attendees delight in the unique gift shopping and enjoy the delicious seasonal food and drinks.

Michigan Avenue between the Chicago River and Oak Street is known as Chicago’s Magnificent Mile. Often compared to New York City’s Fifth Avenue or Paris’ Champs-Élysées, this famous boulevard is constantly bustling with crowds of visitors and locals enjoying the shopping, dining, and sightseeing. In the Michigan Avenue art galleries you can find a masterwork to add to your home gallery, and then relax with lunch at The Purple Pig where sharable plates and house-cured meats are the specialty, and the wine list is one of the best in the country. For a meal with a view, stop in at the Shanghai Terrace, known for exceptional upscale Chinese cuisine and located on a fourth-floor terrace overlooking the high-rises of Chicago. The Magnificent Mile is home to 19th century architecture, luxurious hotels, and fabulous upscale shopping at favorites such as Cartier, Prada, and Chanel.

Outdoor Activities & Landmarks

Jutting out into the sparkling turquoise waters of Lake Michigan, the Navy Pier is 50 acres of parks, attractions, restaurants, expo facilities, and more. Throughout the summer months there is a free fireworks show every Wednesday and Saturday night, and among the many attractions is the magnificent Centennial Wheel: a 196-foot Ferris wheel with unbelievable views. During the winter months, the fun is kept alive year-round with an indoor Winter Wonderfest and Wonder Market. When the weather warms up, seek out the Lakefront Trail for a waterfront jog, walk, or bike on the 18-mile long trail that winds along the shoreline of Lake Michigan. Or take a kayak out on the Chicago river, weaving your way downtown through the canyons of steel and concrete while soaking up sunshine. If sports are the motivator for your private charter flight to Chicago, then Chi-Town during baseball season will not disappoint. Whether rooting for the White Sox, or cheering on the Cubs at Wrigley Field, you’ll find yourself echoing Harry Caray: “it’s a bee-yooo-tiful day for baseball”.

Millennium Park is nicknamed “Chicago’s Front Yard” and is a can’t-miss spot for photo ops, as well as activities. Among the most recognizable landmarks in the city, the sculpture titled Cloud Gate (or colloquially called “The Bean”) is a favorite stop for pictures, while the numerous fountains and water features throughout the area provide relaxing, memory-making moments. The Crown Fountain is an interactive art piece with water and video elements, where water-spouting towers create a fun environment for children of all ages to cool off in summer heat. In winter months, try ice skating along the Ribbon at Maggie Daley Park, where the city skyline backdrop on one side is almost as breathtaking as Lake Michigan on the other. During the warm months, the Pritzker Pavilion bandshell is a premier outdoor amphitheater for numerous events, with seating for thousands. Completed in 2016, the Chicago Riverwalk is another wonderful waterfront path where you can grab a bite or sip local wine and enjoy the vibe of the city as you watch boats drift by.

Museums certainly top the list of favorite things to do in Chicago for tourists and locals. The Museum of Science and Industry is housed within the former Palace of Fine Arts from the 1893 World’s Colombian Exposition. It is the largest science center in the Western Hemisphere and just steps away from the Lake. Stretching along the glittering lakefront is Grant Park, where you’ll find the Art Institute of Chicago (one of the largest art museums in the country) and the Museum Campus. Sharing space in the Chicago Museum Campus with Adler Planetarium and Shedd Aquarium is the Field Museum, where you can seek out new adventures in natural history and world cultures. This museum famously houses the most complete and best preserved T. Rex ever discovered (named SUE). Or spend an afternoon walking through the Chicago History Museum, where you can learn all about the Great Fire, Chicago’s history as the railroad and transportation crossroads of America, Abraham Lincoln, and much more.

While certainly known for its historic architecture and impressive lakefront skyscrapers, Chicago has a few particularly significant buildings that are worth visiting when you charter in for vacation. As one of just a few structures that survived the Great Chicago Fire of 1871, the iconic Water Tower rises high above Michigan Avenue. It remains a testament to the strength and resilience of the city. The Willis Tower (formerly the Sears Tower) was once one of the tallest buildings in the world, still proudly standing at 110 stories, and is open year-round for tours. Its famous Skydeck at the top of the Tower offers views of four states on a clear day, and The Ledge (a glass balcony hanging out over the city at 1,353 feet up) is the perfect spot for a thrilling selfie.