Chicago: My Kind of Town

May 25, 2021 thru May 29, 2021

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Escape the Tucson heat and travel with us for a getaway to the world-class city of “Big Shoulders” – Chicago. Situated on sparkling Lake Michigan, Chicago is the third largest city in the U.S., and late spring is an ideal time to visit. We stay at the comfortable and perfectly situated Embassy Suites Chicago Downtown, in the heart of the city, while experiencing the fabulous architecture, parks, history and food that make Chicago truly special.


Air included


Motorcoach included


Architectural boat tour included


5 days, 4 nights

Activity Level 3


There is bit of walking in larger cities.


7 (4 breakfasts, 1 lunch, 2 dinners) included




Livery service to/from your home included


All taxes and tips (for tour guides and drivers too) included (

Tour Highlights

  • Landmarks City Tour
  • Art Institute of Chicago
  • Architectural Boat Tour
  • Frank Lloyd Wright tour in Oak Park
  • Authentic Italian, Steakhouse and Chicago Deep Dish dining experiences
  • Chicago Cubs Game
  • Live Theatre Performance
  • Driehaus Museum
  • Optional: Chicago 360 Observatory


  • Roundtrip air transportation from Tucson to Chicago*
  • Transfers & motorcoach transportation
  • Pickup/livery service
  • 4 nights lodging
  • 7 meals (4 breakfasts, 1 lunch, 2 dinners)
  • Admissions & tours as described
  • Services of a tour director
  • Baggage handling
  • Motorcoach refreshments
  • Taxes & tips for included items (except hotel housekeeping)
  • Tour director, driver & local guide tips


Tour Map    Print Tour

Day 1 – Arrive in Chicago & City Tour

We travel to Chicago and upon arrival we depart in our deluxe motorcoach for a city highlights tour. We see landmarks such as Buckingham Fountain, one of the largest fountains in the world. Then we check in to the Embassy Suites Chicago Downtown for our 4-night stay in the River North section of the city. A plethora of restaurants, bars, galleries and shopping is all close by. Included with the hotel stay is a nightly reception including drinks and snacks. Our welcome dinner will be at the renowned onsite restaurant Osteria Via Stato. (D)

Day 2 – Art Institute & Architectural Boat Tour

We start our day at the Art Institute of Chicago – founded in 1879 and one of the oldest and largest art museums in the United States – and Millennium Park – Chicago’s premier green space – 25 acres of awe-inspiring landscape, breathtaking architecture and an iconic collection of public art. After a can’t-be-missed lunch of deep dish pizza from Lou Malnati’s, we embark on an architectural boat tour, which shows us the city from a different perspective – from the Chicago River and Lake Michigan. Freshen up and then get ready for a night out at one of Chicago’s many theatres* (pending schedule announcements; may be substituted with an alternate special activity). (B,L)

Day 3 – Frank Lloyd Wright & the Chicago Cubs

The Chicago-area is notable for its Prairie-style architecture, and today we travel 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 guide our tour to other Wright masterpieces in Oak Park and River Forest. Returning to Chicago, we see a Cubs game live at Wrigley Field* (pending schedule announcement; may be substituted with an alternate special activity). (B)

Day 4 – Driehaus Museum & Free Afternoon

This morning we take a quick walk to The Richard H. Driehaus Museum, which explores the art, architecture, and design of the late 19th and early 20th centuries with a focus on the Gilded Age. The Museum is located just steps from the Magnificent Mile within the meticulously restored Nickerson Mansion, renowned as Gilded Age Chicago’s “Marble Palace.” Afterwards, you have the afternoon free to visit the many museums, parks and shopping destinations in the city, or join your Tour Director on a visit to the 360 CHICAGO observation deck. Located 1000 feet above the famed Magnificent Mile in the iconic John Hancock Building, it offers breathtaking 360 degrees views of the city skyline and Lake Michigan. an enclosed moving platform that literally tilts you out over Michigan Avenue from the 94th Floor. Tonight, we get back together for an unforgettable farewell dinner at Steak 48 just one block from the hotel. (B,D)

Day 5 – Travel Home

After a relaxing morning, we fly back Tucson with terrific memories of our wonderful stay in Chicago. (B)

Itinerary subject to change.

Package Pricing

$2,259 per person

Double occupancy

Deposit: $200

$2,646 per person

Single occupancy

Deposit: $200

Price Includes

Roundtrip air transportation from Tucson to Chicago*
Transfers & motorcoach transportation  
Pickup/livery service
4 nights lodging
7 meals (4 breakfasts, 1 lunch, 7 dinners)
Admissions & tours as described
Services of a tour director
Baggage handling
Motorcoach refreshments
Taxes & tips for included items (except hotel housekeeping)
Tour director, driver & local guide 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.


Level 3: Moderate

Expectations: Expect a moderate amount of walking. There will be time to rest on the coach and between attractions. To enjoy this tour, you should be prepared to walk slightly longer distances, climb stairs and tolerate periods of standing, for example on city walks, sightseeing stops or ship excursions. The daily pace and timing can fluctuate significantly between longer and shorter travel days, with additional activities possibly occurring in the early morning or evening. There may be some changes in altitude or temperatures.

Appropriate for: Most travelers beginning with those who are moderately fit, lead semi-active lives, are comfortable participating in long days of activities and expect some physical exertion.


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 $30 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 included. All step-on guide gratuities are included. 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.

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