Skylines & Signposts – Chicago, Route 66 & Milwaukee

Day 1 – Welcome to Chicago! (Friday, May 22)

Optional transfers from our departure points this morning will have us at LAX for our scheduled nonstop flight arriving at the Chicago O’Hare Airport this afternoon. Those guests making their own flight arrangements can request the group’s flight schedule (subject to change) to coordinate a flight arrival time that would allow them to be included on the complimentary transfer to the hotel. Upon arrival, we’ll board a deluxe motorcoach and continue to our stately, AAA Four Diamond, all-suites hotel conveniently located in the heart of downtown Chicago’s Magnificent Mile neighborhood. Enjoy the hotel’s nightly “happy hour” followed by some of Chicago’s famous deep dish pizza at a locals’ favorite. (Dinner)

Day 2 – Chicago (Saturday, May 23)

After an included, made-to-order breakfast, we’ll join a local guide for an immersive exploration of Chicago’s storied past and architectural marvels while on an in-depth driving tour with multiple stops. See the soaring skyscrapers and the historic Water Tower on The Magnificent Mile along Michigan Avenue. Savor the celebrated outdoor sculptures within The Loop and the stately water fountains along the scenic Lakefront. On a guided walking tour in Millennium Park we’ll stroll past the Frank Gehry-designed Pritzker Pavilion, the interactive Crown Fountain and the world-famous “Bean.” View Chicago’s striking skyline from Planetarium Point and see the iconic Buckingham Fountain within Grant Park. In Chicago’s historic South Side we’ll retrace the era of The Devil in the White City in Jackson Park when we pass the Griffin Museum of Science and Industry, the final vestige of the 1893 World’s Columbian Exposition. In Hyde Park we’ll see Frank Lloyd Wright’s Prairie-style Robie House and explore the prestigious University of Chicago, full of neo-Gothic grandeur like the Rockefeller Memorial Chapel. We’ll return to the hotel in the late afternoon with the balance of the evening at leisure. (Breakfast)

Day 3 – Celebrating the Route 66 Centennial (Sunday, May 24)

This morning we’ll join a local Route 66 guide and step back in time as we follow the “The Mother Road” from its start in downtown Chicago in to rural Illinois. As we travel the first 100 miles of Route 66 to small towns like Wilmington, Gardner and Dwight, we’ll discover the larger-than-life landmarks, quirky roadside attractions, charming towns and remarkable stories that made Route 66 the legendary “Main Street of America.” Savor the nostalgia of a simpler time as we cruise past rolling prairies, iconic neon signs and classic Americana where each stop offers a glimpse into a bygone era and America’s storied past. Enjoy an included lunch at a favorite Route 66-style diner. We’ll return to the hotel in the late afternoon with the balance of the evening at leisure. (Breakfast, Lunch)

Day 4 – Chicago (Monday, May 25)

Enjoy a full day in leisure in Chicago to explore as you please. Or, take advantage of one or both of our optional museum excursions with your tour director aboard our motorcoach, payable at time of booking. This morning, an optional excursion to the legendary Field Museum of Natural History is available for an additional $35 p.p. (including transportation, admission, taxes, fees; minimum of 10 guests required) providing approximately 2 hours at leisure to explore an extraordinary world of dinosaurs, glittering gemstones, and prehistoric North America. Enter a three-story replica of an ancient Egyptian tomb, see the 90% complete fossil skeleton of the Tyrannosaurus rex named “Sue” and view original objects from the 1893 World’s Columbian Exposition. This afternoon, an optional excursion to The Art Institute of Chicago is available for an additional $40 p.p. (including transportation, admission, taxes, fees; minimum of 10 guests required) providing approximately 2 hours at leisure to explore this world-renowned art museum that is home to the greatest collection of Impressionist paintings outside of Paris, including works by Monet, Renoir, Seurat, and Van Gogh. In addition, the Renzo Piano-designed Modern Wing features an extraordinary collection of works by Chagall, Dalí, Matisse, Picasso, and Pollock. Late this afternoon all guests will depart the hotel to enjoy a Chicago River architecture cruise, providing the best views of Chicago’s iconic architecture and a detailed narrative of Chicago’s architectural styles and stories of the legendary figures who designed and built this city. This evening we’ll enjoy an included dinner at a locals’ favorite. (Breakfast, Dinner)

Day 5 – Milwaukee (Tuesday, May 26)

This morning we’ll travel north to Milwaukee, Wisconsin, a big city with a small-town feel and an incredible mix of old and new. We’ll delve deep into Milwaukee’s brewing heritage and toast this remarkable city while on a beer history tour of the Pabst Brewery. Enjoy a classic Pabst or Schlitz draft beer as we are transported back in time while visiting the stunning 19th century offices, the Blue Ribbon Hall, and Captain Pabst’s former office. This nostalgic, charming and educational tour focuses on the brewery’s “German Renaissance” architecture and how the Best and Pabst families grew the brewery to become America’s largest by 1874! Following time at leisure for lunch on your own at the Milwaukee Public Market, a local guide will join us for a driving tour to showcase Milwaukee’s historic mansions, the Milwaukee Art Museum, outdoor sculptures, murals, a variety of neighborhoods and the Basilica of St. Josaphat – designed after St. Peter’s Basilica in Rome. This afternoon, we’ll tour the Pabst Mansion to discover the extravagant lifestyle of a Gilded Age beer baron. Built in 1892, the home is a masterpiece of Flemish Renaissance Revival style and features 66 rooms, 14 fireplaces, stunning woodwork, original furniture, stained glass, and a rare collection of fine art. We return to Chicago this evening with the balance of the evening at leisure. (Breakfast)

Day 6 – Wrigleyville, Journey Home (Wednesday, May 27)

This morning we’ll travel the short distance to Wrigleyville for a guided behind-the-scenes tour of Wrigley Field. The second oldest baseball stadium in the U.S., “The Friendly Confines” is famous for its ivy-covered brick outfield walls, manual scoreboard and historic charm. The tour involves a moderate amount of walking and includes both stairs and ramps. After time at leisure for lunch on your own in Wrigleyville, we’ll continue to O’Hare International Airport to board a scheduled, nonstop flight arriving in Los Angeles this evening. Those guests making their own flight arrangements can request the group’s flight schedule (subject to change) to coordinate a flight departure time that would allow them to be included on the complimentary transfer to the airport. Back in Los Angeles, those guests with pre-arranged transfers will be returned to their respective drop-offs. (Breakfast)

While we make every effort to operate our tours as outlined in the itinerary, we ask for your patience, understanding and flexibility and to retain a sense of adventure while traveling with us. Situations may arise that necessitate changes to the itinerary. Should we need to adjust the itinerary either prior to or while on tour, these changes will be communicated to you and only done when absolutely necessary.