“Everything was top notch on the Chicago trip.” Kay Klement – Gibbon
“What a great trip to see & learn about Chicago!” Linda – St. Francis
Day 1 – Home to Delavan, WI
Our adventure starts out as we make our way into Wisconsin, stopping for lunch on own, before checking into our hotel in Delavan. Tonight dinner is served at the Rosewood followed by their “America’s Bandstand” show. Nothing sets the stage for popular culture of a generation more than the music of the 1950’s. This show takes us back to the sock hops, spotlighting Rockabilly, Doo-Wop and Motown artists, songs and the history of early Rock and Roll. Enjoy songs by Chuck Berry, Elvis Presley, Roy Orbison, Diana Ross, Neil Sedaka, The Everly Brothers and many, many more!
Included Meals: Dinner
Hotel: Comfort Suites
Day 2 – Delavan to Chicago, IL
After breakfast we travel to the Windy City and explore Navy Pier where you will have time to have lunch on your own and do some shopping. After lunch we will board our Architecture Cruise boat for a cruise on the Chicago River. We’ll learn about Chicago’s historic role as the birthplace of modern American architecture and about more than 40 famous buildings along the scenic route. Then we check into the Hampton Inn in downtown Chicago for a three-night stay. You may wish to take a swim in the hotel pool or enjoy the sights and sounds of the city by going for a walk on the Magnificent Mile. Tonight, we will have dinner at a local Italian restaurant before we gather together to enjoy watching fireworks tonight at Navy Pier.
Included Meals: Breakfast, Dinner
Hotel: Hampton Inn on Illinois (3 Nights)
Day 3 – Chicago
Following breakfast, we’ll start our day with an interesting “Untouchable Tour” with the help of a local gangster guide who will take us through the 1920’s & 1930’s Prohibition Era of Chicago and show us the hot spots, hit spots, and hideouts made famous by Al Capone. Then a special lunch will be served at Macy’s on the historic 7th floor in the Walnut Room where Chicagoans have eaten for generations. This is truly a lunch to remember! After lunch we are off to the Skydeck, where we will travel 103 stories at the Willis Tower to experience grand views of the Chicago area. If you are brave enough you can step out on “the Ledge,” a glass box extending out 4.3 feet from the Skydeck and 1,343 feet off the ground and receive a souvenir picture of yourself too! Afterwards, we will return to the hotel. Then have dinner on your own before we’ll go to the Briar Street Theatre to see a performance by the “Blue Man Group.” We’ll experience brand-new moments featuring new instruments, technologies and audience interactions as we discover music, laughter, & surprises at every turn. By the end of this spectacular show’s journey, you’ll be saying, “I don’t even know what just happened, but I loved it!”
Included Meals: Breakfast, Lunch
Day 4 – Chicago
After breakfast we’re treated to a tour of Wrigley Field! We’ll see the Cubs’ dugout, field, upper deck, bleachers, & Outfield Ivy. After lunch on your own, a local step-on guide will take us on a highlights tour of the city. We’ll experience Chicago’s “Loop,” Buckingham Fountain, & Little Italy to name a few! We’ll also explore Millennium Park, a 24.5 acre rooftop garden built over an underground parking garage. Our farewell dinner will be a pizza party right at the hotel! We will order pizza & pop from a local pizzeria. It will be a great way to end the day and spend our last evening together.
Included Meals: Breakfast, Dinner
Day 5 – Chicago to Home
As we make our way back home, we will be thinking about all that we saw and enjoyed in the “Windy City.” Along the way we’ll have
a stop for lunch on your own in Mauston, WI.
Included Meals: Breakfast
Motorcoach Per Person Pricing Information
Motorcoach Travel Protection Per Person
Travel Bucks
Deposit Due
Passport Needed
Tour Pace
Price Includes
8 Meals, Hotels & Activities as stated in brochure, Luxury Motorcoach
07/15/2025 07/19/2025
Tour Map
Tour Highlights
* 3 Nights in Downtown Chicago
* Blue Man Group Performance
* “Untouchable Tour” - Chicago’s original Gangster tour
* Architectural Boat Cruise
* Skydeck
* City Tour with Step-on Guide
* Millennium Park
* Wrigley Field Tour
* Macy’s Walnut Room Lunch
* Magnificent Mile
* Fireworks at Navy Pier
* Rosewood’s “America’s Bandstand” Dinner Show
