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Chicago City Stay - Mayflower Tours Tour
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Mayflower Tours Guided Tour

Chicago City Stay

5 Days 4 Departures
From $2,499 per person

Departure Dates & Pricing

4 departures available

Departure DateEnd DateStatusMayflower Tours Price Per PersonPavlus Discounted Price
Jun 18, 2028 Jun 22, 2028 Available $2,499per person Get Our Discounted Price
Jul 9, 2028 Jul 13, 2028 Available $2,499per person Get Our Discounted Price
Jul 23, 2028 Jul 27, 2028 Available $2,499per person Get Our Discounted Price
Aug 6, 2028 Aug 10, 2028 Available $2,499per person Get Our Discounted Price

Day-by-Day Itinerary

5 days through your journey

Day 1

Day 1 - Arrive in Illinois and Dinner at Nitti’s Supper Club

Arrive at Chicago’s O’Hare International Airport and transfer to your hotel. Meet your tour manager and traveling companions in the lobby at 6:00 p.m. for a welcome dinner Nitti’s Supper Club. In a building once owned by Chicago Mobster Frank Nitti you will travel back in time for dinner and live interactive show filled with historical anecdotes, audience interactions and plenty of laughs. Tonight, a crime is committed, and you are tasked with cracking the case. Meal: D
Day 2

Day 2 - Chicago Sightseeing and Pope Leo XIV

This morning a local guide conducts a narrated tour of “The Windy City.” Discover the history, architecture and incredible stories that make up Chicago. See the “Loop” Chicago’s business and theatre district along with some of the most architecturally significant buildings in the world. Also see Millenium Park, home to Anish Kapoor’s sculpture Cloud Gate, affectionately known as “The Bean” and the beautiful rococo wedding cake-style Buckingham Fountain, inspired by the Latona Fountain at the Palace of Versailles. This afternoon, a local expert conducts a tour following in the footsteps of Pope Leo XIV. You will see the very site where he was born, his childhood home, the seminary where he trained for priesthood and his childhood church that influenced his philosophy. Meals: B, L
Day 3

Day 3 - Frank Lloyd Wright, Ernest Hemmingway and Architecture Cruise

After breakfast come to the Frank Lloyd Wright’s first Home and Studio in Oak Park. Considered the birthplace of an architectural revolution, Wright used his home to explore design concepts that contained the seeds of his architectural philosophy. In his adjacent studio, he developed a new American architecture – the “Prairie Style”. The historic district surrounding the Home and Studio has the greatest number of Wright-designed residences worldwide. Then, visit Ernest Hemmingway’s Birthplace Museum. Born here in 1899, the Queen Anne-style home is an ideal place to begin exploring the roots of the author’s life and works. Later, climb aboard your vessel for a narrated Chicago River Architecture Tour. As you float past more than 50 architectural icons like the Wrigley Building, Willis Tower, Tribune Tower, and Marina City, you’ll learn why one building looks like a Champagne bottle, another like a corncob, and how Chicago became the city that taught the world to build up. Then, enjoy free time for shopping and dinner on own along Chicago’s Magnificent Mile. Meals: B, L
Day 4

Day 4 - President Obama, 360 Chicago Observation Deck and Lake Michigan Fireworks Cruise

The day begins at the one-of-a-kind Barack Obama Presidential Library, a cultural institution that aims to inspire, empower, and connect people to bring change home. Learn about the Obama’s journey from the south side of Chicago to the White House. Then, you will be whisked away to the 94th floor at 360 Chicago for panoramic skyline and lake views. Tonight, dinner is at Gino’s East, one of the city’s most beloved pizzerias specializing in deep dish pizza. Then sail along the Chicago River through to Lake Michigan, where you’ll enjoy unobstructed 360-degree views of the Chicago fireworks display. Meals: B, D
 
Day 5

Day 5 - Travel Home

Today, your tour ends with a group transfer to Chicago’s O’Hare International Airport for flights out after 11:00 a.m. Meal: B

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