The "Windy City" is just bursting with breathtaking architecture, wonderful museums, fantastic restaurants, a beautiful lakefront, and world-class shopping. Experience all this and more in Chicago, Illinois with Starr Tours!
View Dates & BookDuration: 7 Days | Meals Included: 6 Breakfasts, 3 Dinners
Explore the world's only facility dedicated to the living legacy of rock and roll music. Designed by I.M. Pei, this impressive $92 million structure towers above Lake Erie's shore at North Coast Harbor. Inside, the Hall of Fame wows visitors with a dynamic multimedia experience, blending film footage, music, interviews, animation, and photography to narrate the stories of rock and roll's iconic legends. An on-site cafe serves light refreshments and food.
Explore the expansive beauty of the Chicago Botanic Gardens aboard their tram tour. Covering 385 acres, the garden boasts 23 stunning display gardens and three native habitats spread across nine islands nestled among picturesque lakes. Enjoy a fact-filled, 45-minute narrated tour for an overview of the garden's diverse landscapes. Highlights include the tranquil Japanese Garden, expansive 100-acre oak woodland, and the vibrant native prairie.
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.
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.
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. The All Access Pass grants entry to all permanent and special exhibitions, plus a thrilling 3D movie experience.
Experience Chicago's premier boat tour offering unparalleled views of Lake Michigan and the Chicago River. This signature tour includes a trip through the Chicago Lock and a live narration featuring an overview of architecture and history. The boat features both open-air and covered seating options, restrooms, and a convenient snack bar. Rain or shine, this tour promises an unforgettable adventure along Chicago's iconic waterways.
Take a magnificent vacation in just eight spectacular blocks. Explore over 400 exclusive stores and boutiques, and indulge in fine dining at more than 200 restaurants.
Experience unparalleled views of Chicago and four surrounding states at Skydeck Chicago. Ride an elevator to the 103rd floor and see the breathtaking panorama. Challenge yourself with "The Ledge," a unique Chicago experience where you can stand on a glass platform extending over Wacker Drive and the Chicago River, 103 floors above ground. Admission includes access to interactive exhibits and signature photo opportunities.
For 50 years, the original Gino's East has been offering the best deep dish pizza experience in Chicago. Since they opened their doors in 1966, they've shared millions of their signature golden-crust Chicago-style pizzas with Chicagoans, celebrities, and visitors from all over the world.
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.
Chicken Parmigiana
Cheese Tortellini (vegetarian)
Cajun Shrimp Alfredo
The meal also includes a salad, non-alcoholic beverages, and cannoli for dessert.
Dinner will feature a variety of pizzas served buffet-style with family-style entrees including homemade spinach sticks, jumbo buffalo chicken wings, salads, pasta, with brownies & chocolate chip cookies for dessert. Unlimited non-alcoholic drinks are also included.
Sirloin Steak: grilled, with warm bleu cheese butter
Salmon: with mango salsa and a sriracha glaze
Roasted Vegetable Ravioli: provencale tomato cream, parmesan, and basil chiffonade.
Meal includes salad & cheesecake.
Menus are subject to change.
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.
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 and related gratuties are included.
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:
Travel to Independence, OH
Lunch on own
Check in for one overnight at Wyndham Independence
Dinner on own
Day 2:
Breakfast included at hotel
Check out and travel to Cleveland, OH
Admission to the Rock n' Roll Hall of Fame; lunch on own here
Travel to Chicago, IL
(Time change one hour behind to Central Time)
Dinner included at Rulli's Italian Restaurant in Elkhart, IN
Check in for four overnights at the Fairfield Inn Chicago Downtown
Day 3:
Breakfast included at hotel
Admission to the Field Museum of Natural History; includes 3D movie and special exhibit
Return to hotel
Lunch on own
"Untouchables Tour" gangster sightseeing tour
Dinner and evening on own at Navy Pier
Return to hotel
Day 4:
Breakfast included at hotel
Travel to Glencoe, IL
Admission and tram tour through the Chicago Botanic Gardens; lunch on own here
Return to hotel
Remainder of day on own to explore Chicago
Dinner on own
Day 5:
Breakfast included at hotel
Admission to Skydeck Chicago
Free time and lunch on own at "The Magnificent Mile"
Boat Cruise of Lake Michigan and the Chicago River
Return to hotel
Dinner included at Gino's East
Return to hotel
Day 6:
Breakfast included at hotel
Check out and travel to Pittsburgh, PA
Lunch on own
(Time change one hour ahead to Eastern Time)
Check in for one overnight at DoubleTree Pittsburgh/Green Tree
Dinner included at Grand Concourse Restaurant in Station Square
Return to hotel
Day 7:
Breakfast included at hotel
Check out
Admission and guided tour of the Nationality Rooms at University of Pittsburgh's Cathedral of Learning
Travel home
Lunch on own en route
Please note:
Itinerary subject to change
The hotel features a full-service restaurant and lounge, indoor/outdoor pool, and fitness room. Guest rooms include coffee maker, mini-fridge, hair dryer, and iron/board.
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 coffee maker, mini-fridge, hair dryer, and iron/board.
Conveniently located just 5 miles from Downtown Pittsburgh. The hotel features a restaurant/lounge, indoor/outdoor pool, and fitness room. Guest rooms include coffee maker, hair dryer, and iron/board.
Below is a list of pick-up points available on this tour.
Below is a list of pick-up points available for this tour. Pick up points vary by departure date so to see which date(s) your preferred location(s) is available, click “view” below.
Note: Not all pick-up points are available for all tours or all departure dates. Also, with less than 3 people booked from a pick-up point, that pick-up point may be changed or eliminated. If so, we will alert you approximately 30 days prior to departure.
City, State | Address |
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Bensalem, PA (MAIN/HUB) | Spark by Hilton Bensalem Phila (MAIN/HUB) 3499 Street Rd Bensalem, PA |
Cherry Hill, NJ (MAIN) | Cherry Hill Train Station Parking Lot (MAIN) Next to ShopRite at 2240 W Marlton Pike |
Chester, PA (SHUTTLE) | Harrah's Philadelphia Casino, Chester PA (SHUTTLE) 777 Harrah's Blvd |
Hamilton, NJ (MAIN/HUB) | Hamilton Station Park & Ride Garage (MAIN/HUB) 800 Sloan Avenue |
Iselin, NJ (SHUTTLE) | APA Hotel Woodbridge (SHUTTLE) 120 S Wood Ave Iselin, NJ |
Phila (NE), PA (SHUTTLE) | Phila (NE) KleinLife (SHUTTLE) 10100 Jamison Ave (at Red Lion Rd) Philadelphia PA |
Phila(South), PA (SHUTTLE | Oregon Diner 302 W Oregon Ave (at 3rd St) (SHUTTLE Philadelphia, PA |
Toms River, NJ (SHUTTLE) | Toms River Park & Ride (SHUTTLE) 400 Highland Parkway S. Toms River, NJ |
Wall Twnship NJ (SHUTTLE) | Judy Blume Service Area (SHUTTLE) 100 Garden State Parkway Wall, NJ |
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Jul 19 2025 | $2,049.00 | ![]() | Request a Call Back | Contact Us About This Tour | Add to Favorites ![]() |
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