The Magnificent Second City

Best of Chicago

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Postponed to Fall 2020

Hold onto your hats during this springtime visit to Chicago, known as both The Windy City and the Magnificent Second City. The wind won’t sweep you away, but the city’s many exciting highlights will! Welcome to Chi-Town! 

Day 1 – Westward Bound (D)
Journey westward through four states today while meeting new friends and getting to know your Upper Class Tour Director! Check into the Fairfield Inn in Youngstown before enjoying some good ole’ home cookin’ at Cracker Barrel. 

Day 2 – Hello Windy City! (D)
Check into your home for four nights, The Hampton Inn Downtown, in the center of the city’s biggest attractions and just half a block from the famous Magnificent Mile! With modern amenities and an ultra-convenient location, you’ll be easy walking distance from Lake Michigan, Navy Pier, Lake Shore Park, shopping, restaurants and more! Enjoy a group welcome dinner at the iconic Lawry’s Prime Rib Restaurant located inside the historic McCormack Mansion, one of the city’s great architectural landmarks!

Day 3 – Hold Onto Your Hats! (B, L)
See the Windy City in all its glory today, beginning with a guided tour. Your expert guide will share stories and places that even the locals don’t know! There will be several stops on this driving tour during which you’ll see the Magnificent Mile, the historic Water Tower, State Street, the historic Printer’s Row District, early skyscrapers of downtown, the lakefront beaches and a stunning view of the city skyline from Museum Campus! Take a different look at the city during a classic Chicago River cruise aboard a Europeaninspired, glass enclosed vessel. With panoramic views and lunch served onboard, float through the city with unmatched views of world-renowned architectural feats!

Day 4 – Art, Sky and Pizza (B, D)
Did you know Chicago is home to one of the finest art museums in the world? At the Art Institute of Chicago, take a guided tour of the main galleries that feature one of Monet’s famous Water Lilies and six of his Haystacks! See Grant Wood’s American Gothic, Sunday in the Park by Georges Seurat and more masterpieces by Cassatt, Van Gogh, Picasso, Renoir and Cezanne. This afternoon, feel like you’re on the top of the world at the one and only John Hancock Tower. Visit the observation deck 1,000 feet above the city, with clear skies, you’ll see for miles! No trip to Chicago is complete without a taste of the city’s famous deep-dish pizza, and nobody does it better than Giordano’s! Named Chicago’s best pizza, dig into a delicious four-course dinner, with one course featuring three different varieties of deep dish! Yum!

Day 5 – Your Chicago with Tommy Gun’s Garage! (B, D)
You’ve gotten to know the city, now you can enjoy a day on your own re-visiting your favorite spots or finding more to explore. Stroll the Magnificent Mile, visit Buckingham Fountain, dip your toe into Lake Michigan – the day is yours! Or choose our optional morning excursion to tour Wrigley Field! Tonight, finish with dinner at Tommy Gun’s Garage, an interactive, speak easy and dinner theater. Be transported to 1920’s Chicago with Roaring 20’s music, gangsters, flappers, coppers, guys and dolls dance and sing with non-stop comedy and mafioso fun.

Enhance Your Trip - Wrigley Field
Join us for a behind the scenes tour of one of the oldest stadiums in the country. Home to the Chicago Cubs for 102 years, learn all about the “Friendly Confines,” a legendary, baseball cathedral!
Optional Tour - $45 per person

Day 6 – Rock On Cleveland (B, D)
Goodbye Windy City, hello Cleveland, the home of the Rock and Roll Hall of Fame! Arrive in time for a self-guided tour of the Hall of Fame’s seven floors, five theaters and exhibits including The Legends of Rock, British Invasion and Power of Rock, an adrenaline-fueled theater experience! Keep the beat going tonight with dinner and a live performance at the Music Box Supper Club. 

Day 7 – Homeward Bound (B)
After breakfast at the hotel, we’ll head home today. Use the travel time to connect with new friends - chat, share pictures and make plans for your next trip!

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  • $1,499 Triple
  • $1,599 Double
  • $2,149 Single
  • Wrigley Field Optional tour Day 5 - $45 per person
  • Travel Protection 10%


  • Downtown Hotel in Prime Location
  • Chicago River Cruise, Hancock Tower
  • Chicago City Tour, Deep Dish Pizza,
  • Chicago Art Institute Tour
  • Lawry's Prime Rib Dinner, Rock N' Roll Hall of Fame
  • Tommy Guns Garage, Music Box Supper Club
  • 6 Nights Hotel, 11 Meals
  • Upper Class Tour Director, Taxes & Gratuities


Saturday May 2nd, 2020

  • Mamaroneck 7:00 am
  • Yonkers 8:00 am


Friday May 8th, 2020

  • Yonkers 6:00 pm
  • Mamaroneck 6:45 pm