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 “The itinerary was spot on with all the activities to acquaint us with Chicago. What fun! Restaurants were good and the hotels were excellent – centrally located with good amenities.”  Jeneann Oppedahl Chicago 2023 R&J Traveler 



Day 1 – Home to Delavan, WI 

Our adventure starts out as we make our way into Wisconsin, stopping at Randy’s Restaurant for lunch, before checking into our hotel in Delavan. Tonight dinner is served at the Rosewood followed by their “The Beat Goes On” show. Rhythm is at the heart of swing, R & B, and popular music. This upbeat show will have us tapping our toes to hits by Glen Miller Band, Chuck Berry, The Andrews Sisters, Elvis, Ray Charles, Carl Perkins, The Monkees, Jerry Lee Lewis, Frankie Valli and the Four Seasons, The Jackson Five, Johnny Cash & more! 

Included Meals: Lunch, 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 at the hotel 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! Afterwards, we will experience Teatro ZinZanni, an original form of entertainment combining a unique fusion of cirque, comedy, cabaret, spectacle, and live music all the while serving up a multi-course feast.

Included Meals: Breakfast, Lunch, Dinner 


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. We will return to the hotel and dinner and the evening will be on your own to explore and experience some great restaurants. Maybe enjoy a Chicago favorite…deep-dish pizza! 

Included Meals: Breakfast 


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

Double: $1,999
Single: $2,399
Triple: $1,879
Quad: $1,799

Motorcoach Travel Protection Per Person

Double: $116
Single: $149

Travel Bucks

$30 Travel Bucks per person earned with this tour

Deposit Due

$100 deposit per person due at time of reservation. Full payment due 30 days prior to depart.

Passport Needed


Tour Pace

Moderate to Extensive Walking

Price Includes

9 Meals, Hotels & Activities as stated in brochure, Luxury Motorcoach

The average temperature while R&J is visiting is 86°
Travel with R & J Tours to a warm destination where it is...
Minneapolis, Mn
Chicago at Its Best
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Tour Map

Tour Highlights

3 Nights in Downtown Chicago
“Teatro ZinZanni” Dinner Show
“Untouchable Tour” - Chicago’s original Gangster tour
Architectural Boat Cruise
City Tour with Step-on Guide
Millennium Park
Wrigley Field Tour
Macy’s Walnut Room Lunch
Magnificent Mile
Fireworks at Navy Pier
Rosewood’s “The Beat Goes On” Dinner Show

Travel with R & J Tours to a warm destination where it is...
Minneapolis, Mn
Chicago at Its Best
The average temperature while R&J is visiting is 86°
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