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Chicago Highlights: My Kind of Town

Chicago Highlights: My Kind of Town

Discover the best of Chicago with Eyre Tours. Explore iconic landmarks, enjoy world-class dining, and experience the vibrant culture of the Windy City on this immersive tour.

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Chicago Highlights: My Kind of Town

Trip Duration: 7 Days

 

 

Trip Inclusions:

  • Meals: 6 Breakfasts, 3 Dinners

  • Tour Director 

  • Overnight accommodations

  • Deluxe motorcoach transportation

  • Baggage handling and related gratuities

  • Taxes

 

 

Trip Highlights:

 

Rock 'n Roll Hall of Fame

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 onsite cafe serves light refreshments and food.

 

Chicago Botanic Gardens Grand Tram Tour

Explore the expansive beauty of the Chicago Botanic Garden 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.

 

Untouchable Tour - Chicago's Original

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.

 

The All Access Pass grants entry to all permanent and special exhibitions, plus a thrilling 3D movie experience.

 

Lake Michigan and Chicago River Boat Cruise

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.

 

Magnificent Mile

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.

 

Skydeck Chicago

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.

 

Gino's East

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.

 

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 at Callahan's on Day 2 will include the following menu choices:

  • Fettucine Alfredo

  • NY Strip

  • Chicken Parmigiano

Meal includes a salad, chef's choice of vegetable, with a scoop of ice cream for dessert and soft drinks/coffee.

 

Dinner at Gino's East on Day 5 will be a pizza buffet with family style entrees featuring:

Homemade Spinach Sticks, Jumbo Buffalo chicken Wings, a variety of pizzas, salads, pasta, with brownies & chocolate chip cookies for dessert. Unlimited nonalcoholic drinks are also included.

 

Dinner at Grand Concourse on Day 6 will include the following menu choices:

  • Sirloin Steak: grilled, warm bleu cheese butter

  • Salmon: mango salsa, sriracha glaze

  • Roasted Vegetable Ravioli: provencale tomato cream, parmesan, basil chiffonade.

Meal includes salad & cheesecake.

 

Menus are subject to change.

 

 

Need to Know:

 

 

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 Accessibility Note: 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.

 

Eyre Tours 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:

Shuttle to meet Starr Bus
Travel to Independence, OH
Lunch on own
1 overnight at Doubletree Hotel
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 at the Hall of Fame
Travel to Chicago, IL
(Time change one hour behind to Central Time)
Dinner included at Callahan's Family Dining, Elkhart, IN
4 overnights at the Fairfield Inn Chicago Downtown

Day 3:

Breakfast included at hotel
Admission to the Field Museum of Natural History and one special exhibit
Return to hotel
Lunch on own
Sightseeing Untouchables Gangster tour
Dinner and evening on own at Navy Pier

Day 4:

Breakfast included at hotel
Travel to Glencoe, IL
Admission and Tram Tour through the Chicago Botanic Gardens
Lunch on own at the Gardens
Return to Chicago
Remainder of day on own to explore Chicago
Dinner on own

Day 5:

Breakfast included at hotel
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

Day 6:

Breakfast included at hotel
Check out and travel to Pittsburgh, PA
Lunch on own
(Time change one hour ahead to Eastern Standard Time)
One overnight at Double Tree Pittsburgh/Greentree
Dinner included at Grand Concourse Restaurant in Station Square

Day 7:

Breakfast included at hotel
Check out
Admission and guided tour of the Nationality Rooms
Lunch on own
Travel home

Subject to Change

Itinerary subject to change

Accomodations Day 1: Doubletree Hotel, Independence, OH

 

The Doubletree Cleveland South hotel offers Doubletree's world famous "Sweet Dreams" Bedding which includes a pillow top mattress, down comforter and down pillows. Enjoy a famous Doubletree chocolate chip cookie at check in. The hotel also offers a full-service restaurant and bar, fitness center, and indoor/outdoor pool.

 

Accommodations Days 2, 3, 4 & 5: Fairfield Inn Chicago Downtown

Enjoy the Fairfield Inn Chicago Downtown located 1 1/2 blockes from Chicago's famed Magnificent Mile. The hotel features a fitness center Breakfast is served each morning and the hotel is located steps from area local restaurants Guestrooms include refrigerator, coffee maker, hairdryer, iron/board & complimentary WiFi

 

Accommodations Day 6: Doubletree Pittsburgh/Greentree

Set on the south side and only 3 miles from downtown, this hotel features a restaurant and lounge, indoor/outdoor pool and fitness center. Guestrooms are well appointed and include a Sweet Dreams by Doubletree bed, hair dryer, iron/board, and coffee maker.

Below is a list of pick-up points available on this tour.

Below is a list of pick-up points available on this tour.

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Name Address
Ellicott City Long Gate Park and Ride
Meadowbrook Ln, Ellicott City, MD 21043
Leisure World Leisure World - Club House II (Residents ONLY)
3300 N Leisure World Blvd, Silver Spring, MD 20906
Silver Spg/Rockville, MD Georgia Ave Park & Ride
16000 Georgia Ave, Rockville, MD 20853
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Jul 19 2025 $2,349.00 Loading
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