Chicago Highlights: My Kind of Town

Duration: 7 Days | Meals Included: 6 Breakfasts, 3 Dinners

 

Trip Highlights:

 

Rock & Roll Hall of Fame

Discover the world’s premier museum celebrating the history, impact, and enduring spirit of rock and roll music. Designed by renowned architect I. M. Pei, this striking glass pyramid rises along the shore of Lake Erie at Cleveland’s North Coast Harbor. Inside, immersive exhibits bring music history to life through film footage, legendary performances, rare memorabilia, photography, interviews, and interactive multimedia displays honoring some of rock’s greatest artists and moments. Guests may also enjoy light refreshments and casual dining at the onsite café.

 

 

Obama Presidential Center

Set on the historic South Side of Chicago, the Obama Presidential Center is poised to become a vibrant destination for culture, community, and inspiration. Nestled within the beautiful surroundings of Jackson Park, this visionary campus honors the legacy of President Barack Obama and First Lady Michelle Obama while encouraging visitors to imagine and shape a brighter future.

 

More than a traditional presidential museum, the center will feature immersive exhibits, a world-class library, public gathering spaces, and beautifully landscaped grounds designed to inspire connection and conversation. Guests will explore powerful stories of leadership, hope, civic engagement, and change that helped shape a generation.

 

Blending history, architecture, and forward-thinking innovation, the Obama Presidential Center promises to be one of Chicago’s most significant new cultural landmarks, welcoming visitors from around the world to reflect, learn, and be inspired.

 

Untouchable Tour - Chicago's Original Gangster Tour

Step into the underworld of Prohibition-era Chicago with the Untouchables Tour - Chicago's Original Gangster Tour.

 

Explore the city's most infamous locations where Al Capone and his associates once ruled. Delve into the stories of Capone, Moran, Dillinger, and other notorious figures as you visit iconic sites like the St. Valentine's Day Massacre, the Biograph Theater, and Holy Name Cathedral. Led by knowledgeable Gangster Guides, this tour offers a blend of education and entertainment, providing insights into Chicago's dark and thrilling history.

 

 

Navy Pier

Since its construction in 1916, Navy Pier has stood as a cherished Chicago landmark. This iconic destination boasts dozens of restaurants, shops, special exhibits, entertainment options, and scenic gardens. Visitors can enjoy riding the impressive fifteen-story Ferris Wheel for unparalleled views of the Chicago skyline and experience the turn-of-the-century style carousel adorned with 36 hand-painted animals.

 

Field Museum of Natural History

Discover the Field Museum of Natural History, a revered Chicago institution and one of the world's foremost museums dedicated to natural history.

 

Dive into immersive exhibits that span ancient cultures to cutting-edge scientific discoveries, showcasing over 24 million objects. Journey into an ancient Egyptian tomb, encounter the planet's largest creature, marvel at insects up close, explore ancient civilizations, and much more. Our visit includes entry to all permanent exhibitions and After the Age of Dinosaurs special exhibitions, plus a thrilling 3D movie experience.

 

Lake Michigan and Chicago River Boat Cruise

Experience Chicago from a whole new perspective on the city’s most comprehensive boat tour, cruising both Lake Michigan and the scenic Chicago River. This signature journey takes you through the historic Chicago Lock, offering a unique transition between the river and the lake. Along the way, enjoy engaging live narration that brings Chicago’s rich history and world-renowned architecture to life, showcasing the skyline’s most iconic landmarks.

 

Comfortable vessels feature both open-air and covered seating, as well as onboard restrooms and a snack and cash bar.

 

 

Magnificent Mile

Stretching through the heart of downtown Chicago, the Magnificent Mile is one of the most iconic shopping and cultural destinations in the world. This vibrant boulevard along Michigan Avenue offers an unparalleled blend of luxury boutiques, popular retailers, acclaimed restaurants, and architectural landmarks. From historic treasures like the Wrigley Building and Tribune Tower to modern skyscrapers and scenic river views, every step along the Magnificent Mile delivers energy, elegance, and excitement.

 

Skydeck Chicago

Take your Chicago experience to new heights at Skydeck Chicago, where breathtaking panoramic views stretch across the city skyline and into four surrounding states.

 

Ride the elevator up to the 103rd floor of Willis Tower and prepare for an unforgettable adventure.

 

Step out onto The Ledge—glass balconies extending 1,353 feet above the bustling streets below—for a thrilling, once-in-a-lifetime perspective overlooking Wacker Drive and the Chicago River. Capture incredible photos and test your sense of adventure as you stand suspended high above the city.

 

Your visit also includes engaging interactive exhibits that bring Chicago’s rich history and vibrant culture to life, making this an iconic, must-see attraction.

 

 

 

Nationality Rooms

The Nationality Rooms at the University of Pittsburgh's Cathedral of Learning showcase 27 unique classrooms depicting and gifted by ethnic groups integral to Pittsburgh's history. These rooms, designated as a Pittsburgh History and Landmarks Foundation Historical Landmark, are situated on the 1st and 3rd floors of the Cathedral of Learning, itself a National Historic Landmark on the university's main campus. While maintaining museum-quality exhibits, twenty-five of these rooms serve as active classrooms for University of Pittsburgh faculty and students. The remaining two rooms are designated as display areas accessible exclusively through guided tours.

 

Meal Information:

 

Dinner on day two is included at Rulli's Italian Restaurant. Choices are:

• Chicken Parmigiana

• Cheese Tortellini (vegetarian)

• Cajun Shrimp Alfredo

Dinner is served with a salad and a cannoli for dessert. Non-alcoholic drinks are included.

 

Dinner on day five is included at Giordano's.

Dinner is served family-style and features pasta with marinara sauce, and a mix of thick & thin crust pizza. Dinner is served with salad and dessert. Soda is included.

 

Dinner on day six is included at Grand Concourse. Choices are:

• Sirloin Steak: grilled with warm bleu cheese butter

• Bronzed Salmon: topped with mango salsa and sriracha glaze

• Lemon Chicken: served with mushrooms and artichokes with lemon butter

• Seasonal Vegetable Ravioli: topped with provencale tomato cream, parmesan, basil chiffonade

Dinner is served with salad, bread & butter, and dessert. Iced tea, coffee, and hot tea are included.

 

Menus are subject to change.

 

Need to Know:

• Lake Michigan and Chicago River Boat Cruise: The boat is cashless, credit cards are accepted for purchases at the snack bar.

• Every Starr trip includes deluxe round-trip motorcoach transportation from one or more of our departure locations.

• A Starr Tour Director will accompany you on this trip.

• Baggage handling at hotels is included.

 

Accessibility:

• This tour involves extensive walking. Please be aware that Chicago is a sprawling metropolitan city, and participants will need to walk more than 2-3 blocks at a time during the trip.

• Chicago Boat Tour: The boat is wheelchair accessible; however, there are approximately 60 easy steps down to reach the dock. This may pose difficulty for individuals with walking disabilities.

• Starr has a select quantity of wheelchair accessible motorcoaches available; therefore, we suggest you contact a Travel Advisor to discuss any needs you may have before reserving your trip.

Day 1: Drury Inn Cleveland Beachwood (Orange Village, OH)

The hotel features an indoor pool, whirlpool and fitness room. Guest rooms include a mini-fridge, microwave, hair dryer, and iron/board.

 

Days 2-5: Fairfield Inn Chicago Downtown (Chicago, IL)

The hotel is located 1 1/2 blocks from Chicago's famed Magnificent Mile and close to local restaurants and boutiques. The hotel features a fitness room. Guest rooms include a coffee maker, mini-fridge, hair dryer, and iron/board.

 

Day 6: DoubleTree Pittsburgh/Green Tree (Pittsburgh, PA)

The hotel is conveniently located just 3 miles from Downtown Pittsburgh. The hotel features a restaurant/lounge, indoor/outdoor pool, and a fitness room. Guest rooms include a coffee maker, mini-fridge, hair dryer, and iron/board.