Best of Chicago
September 4 – 9, 2025
$3250 pp(Based Upon Double Occupancy) +$700 (Single Supplement)
Includes Roundtrip Airfare from Phoenix

DAY 1: ARRIVE CHICAGO
Arrive in Chicago and meet your Tour Director. Check in for a 5-night stay at the Palmer House Hilton, a historic hotel with modern amenities in the heart of downtown. Chicago, also known as “the Windy City” and “the Second City,” is the 3rd largest city in the U.S. Tonight join your fellow travelers for a Welcome Dinner. Meals: (D) Overnight: Chicago

DAY 2: CHICAGO CITY TOUR
Today join a local guide for your Chicago City Tour. Learn about the Great Fire of 1871, the World’s Fair of 1893, Prohibition gangsters and famous residents like George Pullman, Oscar Mayer, Sears & Roebuck, Carl Sandburg and Louis Sullivan. See the Loop, “L” trains, the Water Tower, the Bean, Navy Pier, Buckingham Fountain & 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. Be sure to sample Chicago’s famous deep-dish pizza and a Chicago-style hot dog during your stay. Meals: (B) Overnight: Chicago

Day 3: GANGSTER TOUR – OAK PARK
This morning embark on an Untouchables Tour to learn the story of Chicago’s notorious past including the “gangster” era of the 1930’s when Al Capone, Machine Gun Kelly and John Dillinger ruled the streets of Chicago. This afternoon, travel to the lovely suburb of Oak Park, famous as the home of architect Frank Lloyd Wright. Visit the Frank Lloyd Wright Home & Studio, where he lived and designed 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 dinner at a local Italian restaurant. Meals:(B,D) Overnight: Chicago

DAY 4: CHICAGO – MILWAUKEE, WI
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. In 1975, the mansion was placed on the National Register of Historic Places. Visit the Miller Brewing Company for a Brewery Tour & Tasting experience. Learn the history of Frederick Miller’s arrival in Milwaukee and the high-speed, 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-century buildings and enjoy some leisure time at the Milwaukee Public Market, inspired by Seattle’s Pike Place Market with local food vendors. Later return to your hotel to enjoy an evening at leisure in Chicago. Meals:(B) Overnight: Chicago

DAY 5: WRIGLEY FIELD – RIVER CRUISE
Today travel north along Lakeshore Drive past Lincoln Park. Stop in Wrigleyville and see famous Wrigley Field, built in 1914 and home of the Chicago Cubs. Later enjoy a narrated Chicago River Architecture Cruise to 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. Meals:(B,D) Overnight: Chicago

DAY 6: CHICAGO – FLY HOME
This morning visit Cantigny Park, the former 500-acre estate of Col. Robert McCormick, editor of the Chicago Tribune. Go inside the elegant mansion, walk the 10-acre garden or visit the 1st Infantry Division Museum. Later fly home with wonderful memories of your Best of Chicago experience. Meals: (B)