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By Huuk Team

Road trip from Chicago to Philadelphia

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ITINERARY

14h 3m758 miles13 stops
1
Museum Of Illusions Chicago
25 E Washington St, Chicago, IL 60602-1708
2
The Chopping Block
4747 N Lincoln Ave Lincoln Square, Chicago, IL 60625-2026
The Chopping Block, Chicago's premiere recreational cooking school and gourmet retail store, offers demonstration and hands-on cooking classes, as well as wine classes, private cooking parties and corporate team building events. Classes at Lincoln Square cover subjects from cooking basics to intensive Boot Camps as well as seasonal, date nights, healthy and kids classes. We have a food-friendly wine selection so students can select beverages to pair with the menu of their class. Sorry, BYOB is not allowed.
3
Michigan Avenue Bridge
333 Michigan Ave, Chicago, IL 60601-3901
The view from the bridge is one of the best vistas the city has to offer.
4
Frank Lloyd Wright's Robie House
5757 S Woodlawn Ave, Chicago, IL 60637-1698
In accordance with CDC recommendations, the Frank Lloyd Wright Trust requests that both vaccinated and unvaccinated persons wear a face mask indoors at all Trust sites. (8/3/21) The Frederick C. Robie House on the University of Chicago campus is considered one of the most important buildings in the history of American architecture. This Prairie style masterpiece is now a UNESCO World Heritage Site on the 20th Century Architecture of Frank Lloyd Wright List. Discover the residence Wright described as “a cornerstone of modern architecture” on guided tours that take in both the exterior and interior of the building. Inspired by the expansive landscape of the Midwest prairie, Wright’s Robie House is the most famous of the architect’s groundbreaking Prairie houses. Public tours are available Thursday - Monday. The museum is closed Tuesday and Wednesday. Visit flwright.org to learn more.
5
Promontory Point
5491 S Shore Dr, Chicago, IL 60615-5983
6
Mr. Darby's Antique & Collectible Emporium
8574 Market St, Boardman, Youngstown, OH 44512-6726
7
Boardman Park
375 Boardman Poland Rd, Youngstown, OH 44512-4904
8
Vintage VanBlair Antiques and Oddities
11839 South Ave, North Lima, Youngstown, OH 44452-8558
Vintage VanBlair Antiques and Oddities has an eclectic mix of quality items ranging from mid century, industrial and oddities to primitives and antiques. We feature nine curated vendors each with their own unique aesthetic. We also carry Heirloom Traditions paint and hand-painted furniture.
9
Pennsylvania National Fire Museum
1820 N 4th St, Harrisburg, PA 17102-1501
Enter the 1899 Victorian Firehouse, Home of the Reily Hose Co. No. 10 and experience the sights and sounds of Firefighting History. The Pennsylvania National Fire Museum features fire apparatus from Handtubs and Steam Pumpers, hand drawn to horse drawn, to motorized Engines and a 1935 MACK tillered Ladder Truck. An outstanding and varied collection of artifacts are on display
10
Cathedral of Saint Patrick
212 State St, Harrisburg, PA 17101-1108
11
Pennsylvania State Capitol
Third Street ird Street d Street Street reet et, Harrisburg, PA 17101
Teddy Roosevelt declared that this Italian Renaissance-style building was “the handsomest building I ever saw”. Indeed, the State Capitol, with its vaulted dome and grand staircase and the murals and painted floors inside, is thing to behold.
12
Old City Hall
Independence Mall, Philadelphia, PA 19106
13
Philadelphia Distilling
25 E Allen St, Philadelphia, PA 19123-1753
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OVERVIEW

All aboard for an epic train adventure from the bustling streets of Chicago to the historic heart of Philadelphia! Get ready to witness breathtaking landscapes and experience the vibrant cultures that connect these two iconic cities. As the train glides through the vast countryside, you'll marvel at rolling hills, shimmering rivers, and picturesque towns. The journey itself becomes a destination, filled with moments of wonder and discovery.

As you approach Philadelphia, the landscape transforms into a tapestry of charming suburbs and urban excitement. The train pulls into 30th Street Station, a bustling hub that welcomes you to the City of Brotherly Love. From here, you'll step into the vibrant streets, ready to explore the rich history, iconic landmarks, and vibrant energy that make Philadelphia a captivating destination.

This train journey is more than just a mode of transportation; it's an adventure that unfolds with every mile. Whether you're a seasoned traveler or embarking on your first train expedition, this journey promises to create lasting memories and a deeper appreciation for the beauty and diversity of our nation. So, pack your bags, grab a good book, and let the rhythmic sound of the tracks carry you away on an unforgettable journey from the Windy City to the birthplace of American independence.

1
Start:Museum Of Illusions Chicago
Chicago, Illinois·
4.5
(97) review
25 E Washington St, Chicago, IL 60602-1708
2
The Chopping Block
Chicago, Illinois·
4.5
(98) review
The Chopping Block, Chicago's premiere recreational cooking school and gourmet retail store, offers demonstration and hands-on cooking classes, as well as wine classes, private cooking parties and corporate team building events. Classes at Lincoln Square cover subjects from cooking basics to intensive Boot Camps as well as seasonal, date nights, healthy and kids classes. We have a food-friendly wine selection so students can select beverages to pair with the menu of their class. Sorry, BYOB is not allowed.
4747 N Lincoln Ave Lincoln Square, Chicago, IL 60625-2026
3
Michigan Avenue Bridge
Chicago, Illinois·
4.5
(985) review
The view from the bridge is one of the best vistas the city has to offer.
333 Michigan Ave, Chicago, IL 60601-3901
4
Frank Lloyd Wright's Robie House
Chicago, Illinois·
4.5
(869) review
In accordance with CDC recommendations, the Frank Lloyd Wright Trust requests that both vaccinated and unvaccinated persons wear a face mask indoors at all Trust sites. (8/3/21) The Frederick C. Robie House on the University of Chicago campus is considered one of the most important buildings in the history of American architecture. This Prairie style masterpiece is now a UNESCO World Heritage Site on the 20th Century Architecture of Frank Lloyd Wright List. Discover the residence Wright described as “a cornerstone of modern architecture” on guided tours that take in both the exterior and interior of the building. Inspired by the expansive landscape of the Midwest prairie, Wright’s Robie House is the most famous of the architect’s groundbreaking Prairie houses. Public tours are available Thursday - Monday. The museum is closed Tuesday and Wednesday. Visit flwright.org to learn more.
5757 S Woodlawn Ave, Chicago, IL 60637-1698
5
Promontory Point
Chicago, Illinois·
5.0
(9) review
5491 S Shore Dr, Chicago, IL 60615-5983
6
Mr. Darby's Antique & Collectible Emporium
Boardman, Youngstown, Ohio·
4.5
(34) review
8574 Market St, Boardman, Youngstown, OH 44512-6726
7
Boardman Park
Youngstown, Ohio·
4.5
(60) review
375 Boardman Poland Rd, Youngstown, OH 44512-4904
8
Vintage VanBlair Antiques and Oddities
North Lima, Youngstown, Ohio·
4.0
(6) review
Vintage VanBlair Antiques and Oddities has an eclectic mix of quality items ranging from mid century, industrial and oddities to primitives and antiques. We feature nine curated vendors each with their own unique aesthetic. We also carry Heirloom Traditions paint and hand-painted furniture.
11839 South Ave, North Lima, Youngstown, OH 44452-8558
9
Pennsylvania National Fire Museum
Harrisburg, Pennsylvania·
5.0
(77) review
Enter the 1899 Victorian Firehouse, Home of the Reily Hose Co. No. 10 and experience the sights and sounds of Firefighting History. The Pennsylvania National Fire Museum features fire apparatus from Handtubs and Steam Pumpers, hand drawn to horse drawn, to motorized Engines and a 1935 MACK tillered Ladder Truck. An outstanding and varied collection of artifacts are on display
1820 N 4th St, Harrisburg, PA 17102-1501
10
Cathedral of Saint Patrick
Harrisburg, Pennsylvania·
4.5
(64) review
212 State St, Harrisburg, PA 17101-1108
11
Pennsylvania State Capitol
Harrisburg, Pennsylvania·
4.5
(977) review
Teddy Roosevelt declared that this Italian Renaissance-style building was “the handsomest building I ever saw”. Indeed, the State Capitol, with its vaulted dome and grand staircase and the murals and painted floors inside, is thing to behold.
Third Street ird Street d Street Street reet et, Harrisburg, PA 17101
12
Old City Hall
Philadelphia, Pennsylvania·
4.5
(99) review
Independence Mall, Philadelphia, PA 19106
13
Philadelphia Distilling
Philadelphia, Pennsylvania·
5.0
(98) review
25 E Allen St, Philadelphia, PA 19123-1753

CHECKLIST

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FAQ
Frequently Asked Questions
What's the driving distance between Chicago and Philadelphia?
The distance is 758 miles
What's the travel time between Chicago and Philadelphia?
The driving time can vary depending on traffic conditions, but it is typically 14h 3m mins in normal traffic
What are some of the best cities to visit between Chicago and Philadelphia?
Some popular stops include
Are there any cool sights or attractions I shouldn't miss on my drive to Philadelphia?
There are plenty! Here are some stops you shouldn’t miss on your way to Philadelphia
What’s the weather like in Philadelphia?
The weather in Philadelphia is generally mild year-round, with warm, dry summers and cool, wet winters. See the links below for more information
Weather in Philadelphia in January
Weather in Philadelphia in February
Weather in Philadelphia in March
Weather in Philadelphia in April
Weather in Philadelphia in May
Weather in Philadelphia in June
Weather in Philadelphia in July
Weather in Philadelphia in August
Weather in Philadelphia in September
Weather in Philadelphia in October
Weather in Philadelphia in November
Weather in Philadelphia in December
Interested in a detailed plan for your time in Philadelphia?
Plan your dream Philadelphia trip with our daily itineraries featuring must-see attractions! See them here!
A 1-day itinerary in Philadelphia
A 2-day itinerary in Philadelphia
A 3-day itinerary in Philadelphia
A 4-day itinerary in Philadelphia
A 5-day itinerary in Philadelphia
A 6-day itinerary in Philadelphia
Where else can I travel to if I'm starting my trip in Chicago?
We have a lot of great trip options for Chicago! See the links below for all the itineraries we created for you
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