Arrive in Chicago, the largest city in Illinois and the third most populous city in the United States, often called “The Windy City.” After landing at the airport, take a taxi or Uber to your hotel. Once you have checked in, you can choose to explore the area around your hotel, depending on your arrival time. In the evening, dine at one of Chicago’s many restaurants, then return to your hotel to relax and prepare for the days ahead.

Chicago’s nickname, “The Windy City,” is thought to reference both its weather and its history of political debate, dating back to the late 19th century.

Begin your day by visiting Millennium Park, where you can see notable buildings, public art, and landscaped gardens. The centerpiece is Cloud Gate, often called “The Bean,” a silver sculpture known for its curved, reflective surface. While in the park, you can also stop by Crown Fountain, Wrigley Square, Lurie Garden, and the Jay Pritzker Pavilion open-air theater.

Next, head to the nearby Art Institute of Chicago, housed in a Beaux-Arts building dating to 1893. Founded in 1879, the museum features over 300,000 works and hosts exhibitions of artists such as Vincent van Gogh, Claude Monet, Pablo Picasso, and Andy Warhol.

In the evening, consider visiting the Green Mill, a lounge bar over a century old that was frequented by Al Capone. The venue is known for live jazz and poetry slams. Other nightlife options include searching for the hidden entrance to The Violet Hour, where you are asked to turn off your phone to enjoy the atmosphere, or visiting Blue Chicago for blues music, Jazz Showcase for jazz performances, and Chicago Magic Lounge for magic shows.

Millennium Park’s Cloud Gate, created by artist Anish Kapoor, has become one of Chicago’s most recognized landmarks since its installation in 2006.

Start your day at Navy Pier, a one-kilometer-long destination featuring shops, parks, restaurants, museums, and attractions. While at the pier, you can explore the Crystal Gardens botanical courtyard, visit the Shakespeare Theater, tour the Chicago Children’s Museum, or ride the Ferris wheel.

After your time at Navy Pier, head to Lake Michigan, which borders Illinois, Wisconsin, Indiana, and Michigan. You have the option to relax on the shoreline, swim, or visit one of Chicago’s beaches such as North Avenue Beach in Lincoln Park, Oak Street Beach, or Ohio Street Beach. You can also choose to take a boat tour for panoramic views of Chicago’s skyline and the lake.

Lake Michigan is one of the five Great Lakes of North America and is the only one located entirely within the United States.

Begin your day with an Architecture River Cruise, boarding at Michigan Avenue or the Chicago Riverwalk. During this 75-90 minute cruise, you will pass over 40 notable sights as a guide shares information about Chicago’s architectural styles, the city’s history, and the Great Chicago Fire. Landmarks along the route include the Wrigley Building, Marina City, and the Tribune Tower. The cruise also highlights Chicago’s many moveable bridges, a feature dating back to the city’s first such bridge in 1834.

After the cruise, walk along Michigan Avenue to explore the “Magnificent Mile,” home to more than 450 retailers, including popular brands, luxury labels, department stores, and boutiques. This area offers a wide range of shopping opportunities.

In the evening, attend a show at The Second City, a renowned comedy club that opened in 1959. The venue is known for its Chicago-style sketch and improv comedy and has featured many famous performers over the years.

Chicago’s network of moveable bridges is one of the largest in the world, with dozens still operating and contributing to the city’s unique urban landscape.

Today you travel to Oak Park, a suburb of Chicago known for its concentration of Frank Lloyd Wright buildings. During your visit, you will tour Frank Lloyd Wright’s Home and Studio, where the architect lived and worked for the first 20 years of his career. Oak Park contains more Wright-designed buildings than anywhere else, and you will also have the opportunity to see the Unity Temple, another of his significant works. The tour provides insight into Wright’s innovative Prairie Style and highlights how he experimented with design ideas in his own home.

Frank Lloyd Wright is widely regarded as one of the most influential architects in American history, with his Prairie Style emphasizing horizontal lines and integration with the landscape.

Today you visit the Museum of Science and Industry, one of the world’s largest science museums, which opened in 1993. Inside, you will find a wide range of interactive exhibits covering topics from history to technology. Explore the U-505 submarine, experience a simulated coal mine, see what Chicago looked like at the start of the 20th century, and visit the simulation lab to consider Chicago’s energy future.

In the evening, stroll along the Chicago Riverwalk. This riverside promenade offers views of passing boats and the city’s architecture. Along the way, you can stop at restaurants and bars for a drink or dinner, making it an enjoyable setting for your final night in Chicago.

The Museum of Science and Industry is housed in the former Palace of Fine Arts, one of the few remaining structures from the 1893 World’s Columbian Exposition.

On your final day, check out of your hotel. If Chicago is your only destination, arrange a taxi or Uber to O'Hare International Airport for your flight home. If you are continuing your travels elsewhere, check out and either pick up your rental car or take a taxi or Uber to the airport for your next flight.

O'Hare International Airport is one of the busiest airports in the world and has served as a major transportation hub for Chicago since opening in 1955.