Epic Journey: Train Travel from Chicago to Boston with Scenic Stops

Day 1: Chicago to Pittsburgh

Pittsburgh, PA on August 28, 2025

8:00 AM

Breakfast at Louisa's Cafe

Start your day with a hearty breakfast at Louisa’s Cafe, known for its delicious pancakes and fresh coffee. Be sure to try their signature omelet, made with locally sourced ingredients.
USD15, 1 hour

9:30 AM

Board Train to Pittsburgh

Embark on your scenic journey by taking a train from Chicago to Pittsburgh. Enjoy the views along the way as you transition from urban landscapes to the rolling hills of Pennsylvania.
USD60, 8 hours

5:30 PM

Arrive in Pittsburgh - Explore Strip District

Upon arrival, head to the Strip District, a vibrant neighborhood with market stalls and local shops. Don't miss the chance to taste some authentic Pittsburgh pierogies!
Free, 2 hours

7:30 PM

Dinner at Primanti Brothers

Delight in a classic Pittsburgh sandwich at Primanti Brothers, where the sandwiches come piled high with fries and coleslaw directly inside! A must-try that will fill you up for the night.
USD20, 1.5 hours
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Day 2: Pittsburgh to Niagara Falls

Niagara Falls, ON on August 29, 2025

8:00 AM

Breakfast at Pamela's Diner

Indulge in a delicious breakfast at Pamela's Diner, famous for its crepe-style pancakes and cozy atmosphere. This local favorite will provide you the perfect fuel for the day ahead.
USD15, 1 hour

9:00 AM

Explore the city of Pittsburgh - Visit Phipps Conservatory

Before boarding your next train, visit the beautiful Phipps Conservatory and Botanical Gardens to see a wide variety of plants and stunning floral displays.
USD20, 2 hours

11:00 AM

Board Train to Niagara Falls

Catch the train to Niagara Falls and take in the scenery as you cross into New York state and eventually into Canada. It's a short and picturesque ride.
USD40, 5 hours

4:00 PM

Arrive at Niagara Falls - Visit the Falls

Once you arrive, head directly to the iconic Niagara Falls to witness the breathtaking views and power of the rushing water. Don't forget your camera!
Free, 2 hours

6:30 PM

Dinner at Skylon Tower Revolving Dining Room

Enjoy dinner with a view at the Skylon Tower's revolving dining room, where you'll dine 775 feet above the falls, offering a 360-degree view of the falls and the skyline.
CAD75, 1.5 hours
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Day 3: Niagara Falls to Boston

Boston, MA on August 30, 2025

8:00 AM

Breakfast at The Flying Saucer Diner

Kick off your day with breakfast at The Flying Saucer Diner, a retro spot known for its hearty breakfasts and inventive eggs benedict options, great for getting energized.
USD15, 1 hour

9:30 AM

Explore the area - Maid of the Mist

Take a thrilling boat ride close to the falls on the Maid of the Mist. Get up close to experience the roar and splendor of Niagara Falls like never before.
USD30, 2 hours

11:30 AM

Board Train to Boston

Depart from Niagara Falls on your final train journey to Boston, enjoying picturesque landscapes along the way. Sit back, relax, and reflect on the experiences of your trip.
USD80, 10 hours

9:30 PM

Arrive in Boston - Dinner at Legal Sea Foods

Once you arrive in Boston, treat yourself to dinner at Legal Sea Foods, where you can enjoy fresh seafood from New England. Make sure to try their famous clam chowder!
USD40, 1.5 hours
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Day 4: Explore Boston

Boston, MA on August 31, 2025

8:00 AM

Breakfast at Tatte Bakery & Cafe

Start your day at Tatte Bakery & Cafe, where you can savor exquisite pastries and rich coffee in a charming ambiance. Their shakshuka is a must-try dish.
USD15, 1 hour

9:30 AM

Freedom Trail Tour

Join a guided tour of the Freedom Trail to explore Boston’s rich history. Visit iconic sites such as Boston Common and Paul Revere's House.
USD25, 3 hours

1:00 PM

Lunch at Quincy Market

Head to Quincy Market for lunch where you can choose from a variety of food stalls offering everything from clam chowder to lobster rolls, perfect for a quick bite.
USD20, 1 hour

2:30 PM

Visit Boston Tea Party Ships & Museum

Dive into interactive exhibits at the Boston Tea Party Ships & Museum, where you can learn about the events leading to the American Revolution.
USD30, 2 hours

5:00 PM

Dinner at The Capital Grille

Indulge in a fine dining experience at The Capital Grille, renowned for its dry-aged steaks and extensive wine list. A perfect treat after a day of exploring.
USD60, 2 hours
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Day 5: Boston to Chicago

Chicago, IL on September 1, 2025

8:00 AM

Breakfast at Flour Bakery

Start your day with a remarkable breakfast at Flour Bakery, known for its freshly baked goods and innovative breakfast sandwiches.
USD15, 1 hour

9:30 AM

Explore Boston - Visit Boston Common

Spend some time enjoying the beautiful Boston Common, the oldest park in the USA, perfect for a leisurely walk or a moment of relaxation.
Free, 1.5 hours

11:00 AM

Board Flight to Chicago

Head to the airport and board your flight back to Chicago, taking with you a wealth of experiences and memories from your journey.
USD200, Duration varies
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