Day 1 - Thursday, 9/4/2025 - Dinner
Fly to Chicago
Arrive in Chicago, meet your Tour Manager and transfer to your downtown hotel. Tonight, enjoy your Welcome Dinner.

Day 2 - Friday, 9/5/2025 - Breakfast
City Tour / Sky Deck Tower
Join a local guide for a City Tour of the “Windy City.” Learn about the Great Fire of 1871, the World’s Fair of 1893, Prohibition gangsters, and such famous residents as George Pullman, Oscar Mayer, Sears & Roebuck, Carl Sandburg, and Louis Sullivan. See the Loop, the “L” trains, Chicago Water Tower, the Bean, Navy Pier, Buckingham Fountain, and Magnificent Mile. Later, ascend up 1,450 feet to Skydeck Chicago, the top of Willis Tower (formerly Sears). From 1974-1998 it was the tallest building in the world while today it is second tallest tower in North America. Your evening is at leisure. Be sure to sample Chicago’s famous deep dish pizza and a Chicago style hot dog during your stay.

Day 3 - Saturday, 9/6/2025 - Breakfast - Dinner
Gangster Tour / Oak Park
Embark on your “Untouchables” Tour, the story of Chicago’s notorious past. Learn about the “gangster” era of the 1930’s when Al Capone, Machine Gun Kelly, and John Dillinger ruled the streets of Chicago. This afternoon, motor west to the lovely suburb of Oak Park, famous for architect Frank Lloyd Wright. Tour the Wright Home & Studio, where the architect lived and worked from 1889-1909. Next, drive by to see Wright’s greatest public building of his Chicago years, Unity Temple. Nearby see Ernest Hemingway’s birthplace home, a restored Victorian where the famous writer was born in 1899. This evening, enjoy an included dinner at a local Italian restaurant.

Day 4 - Sunday, 9/7/2025 - Breakfast
Milwaukee, Wisconsin
Enjoy a full day trip north to Milwaukee, the largest city in Wisconsin, and historically known as the “Beer Capital of the World.” Enjoy a Pabst Mansion Tour, a gilded age mansion and architectural landmark built in 1892 for Captain Frederick Pabst, founder of the Pabst Brewing Company. Visit the Miller Brewing Company for a Brewery Tour & Tasting experience. Learn the history of Frederick Miller and the highspeed, high-tech production used in brewing today. Drive by Miller Park, home of the Brewer’s baseball club & see the Bronz Fonz, a statue of Happy Days’ cool guy Fonzie located in the scenic Riverwalk District. Travel to the Historic Third Ward to see meticulously renovated 19th c. buildings and enjoy some leisure time at the Milwaukee Public Market, inspired by Seattle’s Pike Place Market. Later return to your hotel to enjoy an evening at leisure in Chicago.

Day 5 - Monday, 9/8/2025 - Breakfast - Dinner
Wrigley Field / River Cruise
This morning, motor north along Lakeshore Drive, past Lincoln Park, to famous Wrigley Field, built in 1914 and home of the Chicago Cubs. Later, enjoy a narrated Architectural Cruise of the Chicago River. Learn about such landmarks as the Wrigley Building, Tribune Tower, and Merchandise Mart. Enjoy free time this afternoon to explore at your own pace. Perhaps visit the famous Art Institute of Chicago, the Field Museum, or explore Navy Pier. Tonight, reminisce with your fellow travelers during your Farewell Dinner at a fine local restaurant.

Day 6 - Tuesday, 9/9/2025 - Breakfast
Fly Home
Transfer to the airport for your return flight home.