Chicago – Hamilton tickets included!

June 30, 2019 thru July 4, 2019

Book Now

As the weather in Tucson heats up, escape to the world-class city of “Big Shoulders” – Chicago – for an Independence Day getaway. Situated on Lake Michigan, Chicago is the third largest city in the U.S. and summer is the perfect time to visit. We stay at the historic, comfortable and perfectly-sited Palmer House Hilton Hotel, in the heart of the city, while experiencing the fabulous architecture, parks, history and cuisine that makes Chicago a truly special city. Join us for an astounding Architectural Boat Tour, in-depth Frank Lloyd Wright Home & Studio Tour, Lake Michigan Fireworks Dinner Cruise, and for a performance of Hamilton, an 11-time Tony winner.


Air included


Motorcoach included


5 days, 4 nights

Activity Level


There is bit of walking in larger cities.


8 (4 breakfasts, 1 lunch, 3 dinners) included


Sold out. Call us to be added to the waiting list.


Livery service to/from your home included

Tour Highlights

  • Architectural Boat Tour
  • See Hamilton
  • Millennium Park
  • Frank Lloyd Wright Home and Studio Tour
  • Landmarks city tour
  • Lake Michigan Fireworks dinner cruise
  • Chicago Art Institute
  • Chicago Botanic Gardens
  • Lincoln Park


  • Roundtrip air transportation from Tucson to Chicago
  • Motorcoach transportation in Chicago
  • Pickup/livery service
  • 4 nights lodging
  • 8 meals (4 breakfasts, 1 lunch, 3 dinners)
  • Admissions and tickets as described
  • Baggage handling
  • Bus refreshments
  • Services of a tour director
  • Driver tips

Day 1

We take an early flight from Tucson to Chicago, we then start right way with a city tour. This gives a fantastic overview of many of Chicago’s unique neighborhoods, each with their own history, flavor, smells and characters. After lunch at one of the many local restaurants, we see historic and vibrant neighborhoods, including visiting Buckingham Fountain – dedicated in 1927, it is one of the largest fountains in the world – before we wind our way down to to the Magnificent Mile to see local landmarks and – and Millennium Park – Chicago’s premier green space – 25 acres of awe-inspiring landscape, breathtaking architecture and an iconic collection of public art. Late afternoon we check in to the Palmer House Hilton for our 4-night stay, and have a welcome dinner at the hotel.

Day 2

This morning we have a late start, where you can enjoy the wonderful breakfast at the hotel, use the many hotel amenities, or sleep in, and then we walk over to the Art Institute of Chicago for a guided tour of this incomparable art museum.  The Art Institute of Chicago, founded in 1879 and located in Chicago’s Grant Park, is one of the oldest and largest art museums in the United States. Recognized for its curatorial efforts and popularity among visitors, the museum hosts approximately 1.5 million guests annually. After our visit to the museum, we embark on an architectural boat tour, which takes on tour of the city from a different perspective – from the Chicago River and Lake Michigan. CAC-certified volunteer tour guides interpret more than 50 buildings along the Chicago River. You’ll find out how Chicago grew from a small settlement into one of the world’s largest cities in less than 100 years. In 90 minutes, get the real story on Chicago architecture and its history. Tonight, you are free to enjoy the city on your own.

Day 3

The Chicago-area is notable for its Prairie-style architecture, and today we travel west to leafy Oak Park, which is home to the world’s largest collection of Frank Lloyd Wright-designed buildings. We tour the Frank Lloyd Wright Home and Studio – his first home to experiment with design concepts that contain the seeds of his architectural philosophy. In his adjacent studio, Wright and his associates developed this new American architecture. We then have a local expert guided tour to visit other Wright masterpieces in Oak Park and River Forest. We then make the short trip back into Chicago, where you have free-time to explore until dinner and enjoy 11-time Tony Award-winning musical Hamilton. This show has been sold out since day 1, and we have lower mezzanine and center orchestra seats that provide a great view to see all of the stage and enjoy a wonderful performance.

Day 4

This morning we head north, taking in Lincoln Park, the Lincoln Park Zoo, Wrigley Field and other gems along the Lake Michigan coast north of Chicago, until we end up at the world-renowned Chicago Botanic Garden for a tour of their Japanese Gardens. After lunch at the Gardens we head back into Chicago to relax and get ready for our Independence Day Eve Fireworks Dinner Cruise on Lake Michigan – a wonderful 3-course meal with prime fireworks viewing overlooking the water and city.

Day 5

Happy Independence Day! Today, we fly back to Tucson with terrific memories of our extended stay in Chicago.

Package Pricing

$2,298 per person

Double occupancy

Deposit: $200

$2,615 per person

Single occupancy

Deposit: $200

Price Includes

• Roundtrip air transportation from Tucson to Chicago
• All transfers and motorcoach transportation
• Pickup/livery service
• 4 nights lodging
• 8 meals (4 breakfasts, 1 lunch, 3 dinners)
• Admissions and events as described above
• Baggage handling
• Bus refreshments
• Services of a tour director
• Driver tips

Booking Policy

We pride ourselves on great service and an enjoyable experience for all, and will go over our booking policies after you make your request for booking. If you’d like to learn more about our booking policies before your trip, give us a call at (520) 325-8839, or visit our Booking Policies page. Click here for more information on our booking policies.


For your reference, we send to you a detailed itinerary approximately 3-4 weeks prior to the scheduled tour departure. This has day-by-day times and events, hotel information where you can be reached in case of an emergency, and airline information.

The times listed on the itinerary are all approximate. We cannot be held responsible for schedule changes due to unforeseen circumstances with weather, transportation agents, highway conditions, hotels or contracting agents.


You will be issued your boarding pass the morning of our departure, after your arrival at the Tucson International Airport. If you have a frequent flyer number, or a TSA number, please call our office at least 3 days prior to the tour to ensure we can note these in your reservation.

If you are joining the tour from locations other than Tucson, we make other arrangements for you to join the tour. Please call our office for more details.


Do not forget to bring your government issued picture ID to show at the airport. A Driver’s License or Passport is preferred. If you do not have proper ID, the airline will turn you away.


We have arranged for handling for one piece of luggage per person regarding the skycaps (where available) and hotels. If you check through luggage note that the maximum weight for the checked piece of luggage is 50 pounds and maximum size is 62 inches (length + width + height). If your bag weighs over 50 pounds the airlines will levy an extra fee that you will be responsible to pay. If you feel the need to lock your checked through luggage and your bag is searched, your lock could be damaged in the process. You can purchase a TSA (Transportation Security Administration) accepted and recognized lock at any luggage store. Make sure you ask for a TSA approved lock. These locks are the kind that TSA screeners can open by using a special tool without breaking. Passengers can carry-on 1 bag (dimensions are limited to 10x16x24 inches), plus a personal type bag, like a purse. We advise that you pack your carry-on lightly. There are restrictions regarding your carryon baggage and contents due to enhanced security measures. Attached find a list regarding commonly asked about items as well as an update. If you have further concerns, please visit the TSA's Web-site at There is room inside the motorcoach for your hand carried bag.


On our airline for this tour, passengers may be assessed a $25 fee per checked in bag, by the Airlines, upon checking in for the flight.


It is always a good idea to carry on your person a list of medications that you are taking and an emergency contact phone number while you are traveling. And we suggest making a copy of the itinerary and provide it to a friend or family member.


The traditional end-of-tour gratuity to your tour director is not included. If you feel your Tour Director helped you enjoy your tour, we suggest you enclose a gratuity in an envelope and present it individually at the end of the tour. Simply as a guideline, one may consider a per person, per day gratuity of $8.00 per tour guide as an average to be modified by one’s own personal experience. All hotel porterage and airport sky cap (when available) fees are included. We also include the gratuities for the coach/livery drivers. Maid tips are not included.


For your convenience we have a (round-tour) door-to-door pickup service with each multi-day tour. (This service is not available to all clients depending on your location.) Approximately 2 to 3 days prior to the departure date you will receive a call from our office and we will tell you your assigned pickup time. (These times can vary up to 15 minutes depending on traffic.)


If you would like to request special accommodations at the hotel(s) where we are lodging, please call us as soon as possible and we will forward these requests for you. The phone numbers of the hotel(s) where we are staying are listed on the itinerary.

Many hotels around the country have instituted a "reconditioning fee" of $300 or more that is levied upon a guest that smokes in a non-smoking room. If this occurs during our tour you will be responsible for paying this fee to the hotel prior to check-out.


We pay close attention to your requests but please realize that these are merely requests and cannot be guaranteed.


Pleasurebent Tours acts solely as agent in arranging hotels, transportation, sightseeing, baggage-handling and other services and does not assume any liability for injury, damage, loss or delay due to any act or default of any company or person. We, along with our subcontractors, reserve the right to make changes to an itinerary if it is necessary for the proper handling of a tour.


Typically, the air is much more humid than in Tucson and we can expect some Spring storms. Please be sure to bring a sweater and / or rain jacket, along with good walking shoes and a hat. There are no dress codes for the areas we take you to on this tour.

Inquire About This Tour

  • This field is for validation purposes and should be left unchanged.

Call 520.325.8839 to Book Today!

If you aren't ready to inquire by email, or would rather call and speak to a team member, we look forward to hearing from you.

Not done exploring?

We have plenty of tours to choose from, so take a look around!