Situated on the shore of sparkling Lake Michigan, Chicago shines from more than just the sun reflecting off skyscraper windows. America’s third-largest city is a cultural hub, known for its innovative architecture, distinct culinary scene, and fascinating history (Prohibition-era gangster tour, anyone?). We’ll explore all this and more during a five-night stay at the Palmer House Hilton, built in 1871 and a landmark in its own right. Plus, spend a day in Milwaukee — once touted as the Beer Capital of the World — with visits to Pabst Mansion, Miller Brewing Company, and the Milwaukee Public Market.
June 4-9, 2026
Itinerary Highlights:
Chicago city tour- Skydeck Chicago
- Untouchable gangster tour
- Chicago River architecture cruise
- Frank Lloyd Wright Home & Studio
- Wrigley Field
- Pabst Mansion
- Miller Brewing Company
- Milwaukee Public Market
Chicago city tour
Package Includes:
- Round-trip airfare from Raleigh-Durham International Airport or Charlotte Douglas International Airport
- Five nights’ hotel accommodations
- Eight meals: five breakfasts and three dinners
- All sightseeing and admissions per itinerary
- Deluxe motor coach transportation
- Professional tour director
- Our State host
- Two wine and beer receptions
- Hotel transfers
- Baggage handling at hotels
Accommodations:
- Five nights in Chicago: Palmer House Hilton
Note: Hotels are subject to change.
Detailed Itinerary:
Day 1: Arrival
Thursday, June 4, 2026
Arrive in Chicago and meet your tour director, then check in for a five-night stay at the 1871 Palmer House Hilton, the longest-operating hotel in the country. Tonight, enjoy a wine and beer reception followed by a welcome dinner with your fellow Our State travelers.
Meals: Dinner
Overnight: Palmer House Hilton in Chicago
Day 2: Chicago City Tour
Friday, June 5, 2026
Join a local guide for a tour of the city, where you’ll learn about the Great Fire of 1871, the World’s Fair of 1893, Prohibition-era gangsters, and famous residents like industrialist George Pullman, Oscar Mayer, Sears and Roebuck, poet Carl Sandburg, and architect Louis Sullivan. See the Loop central business district, “L” trains, the 1869 Water Tower, the Bean, Navy Pier, Buckingham Fountain, and the Magnificent Mile commercial district. Later, ascend 1,450 feet to Skydeck Chicago, the top of Willis Tower (formerly Sears). From 1974 to 1998, it held the title of the world’s tallest building, and today it is the second-tallest in North America. Be sure to sample Chicago’s famous deep-dish pizza and a Chicago-style hot dog during your stay.
Meals: Breakfast
Overnight: Palmer House Hilton in Chicago
Day 3: Untouchables Tour • Frank Lloyd Wright Home & Studio
Saturday, June 6, 2026
This morning, embark on the Untouchable Tour to learn the story of Chicago’s “gangster” era in the 1930s, when Al Capone, Machine Gun Kelly, and John Dillinger ruled the streets. Today you’ll also 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 to 1909. Next, pass by Unity Temple, considered Wright’s greatest public building from his Chicago years. Nearby, see the restored Victorian home where Ernest Hemingway was born in 1899. This evening, enjoy dinner at a local Italian restaurant.
Meals: Breakfast, Dinner
Overnight: Palmer House Hilton in Chicago
Day 4: Pabst Mansion • Miller Brewing Company • Milwaukee
Sunday, June 7, 2026
Enjoy a day trip north to Milwaukee, Wisconsin, historically known as the Beer Capital of the World. Take a tour of Pabst Mansion, a Gilded Age architectural landmark built in 1892 for Capt. Frederick Pabst, founder of Pabst Brewing Company. Then, during a tour and tasting at Miller Brewing Company, learn the history of Frederick Miller’s arrival in Milwaukee and the high-speed, high-tech production used in brewing today. Drive by American Family Field (formerly Miller Park), home of the Milwaukee Brewers Baseball Club, and see the Bronze Fonz, a statue of Happy Days’ 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 to browse the vendors at the Milwaukee Public Market. Later, return to your hotel to enjoy an evening at leisure in Chicago.
Meals: Breakfast
Overnight: Palmer House Hilton in Chicago
Day 5: Wrigley Field • Architecture Cruise
Monday, June 8, 2026
Today travel north along Lakeshore Drive past Lincoln Park. Stop in Wrigleyville and see the 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. This afternoon, enjoy free time to visit the renowned Art Institute of Chicago, the Field Museum, Navy Pier, or other city landmarks. Tonight, reminisce with your fellow travelers at a wine and beer reception followed by a farewell dinner.
Meals: Breakfast, Dinner
Overnight: Palmer House Hilton in Chicago
Day 6: Departure
Tuesday, June 9, 2026
Today, fly home. Want to share your memories with other travelers? Post your favorite pictures in the Our State Travel Club Facebook group!
Meals: Breakfast
Tour Rates:
Discounted rate*: $3,399 per person (based on double occupancy)
Regular rate: $3,499 per person (based on double occupancy)
Single rate: $4,149 ($4,049 with booking discount*)
Click here for information on payment schedule, cancellation policy, and trip insurance.
*Make your final payment by check and receive a booking discount of $100 per person.
For Reservations & More Information:
Premier World Discovery
Melissa Grant
(877) 953-8687, ext. 238 (Pacific Time)
mgrant@premierworlddiscovery.com
Online booking option: Click here and use booking number 204991 to make your deposit online.
This tour is Activity Level 3 of 4 — Active. For more information on physical requirements and what to expect on an Our State trip, click here.
