By Huuk Team

Road trip from Chicago to Boston

All Category

Concerts & Shows

Food & Drink

Fun & Games

Sights & Landmarks

Shopping

Museums

Nightlife

Show more (4+)

ITINERARY

18h 49m993 miles16 stops

1

Paladin Brewing

6520 Mahoning Ave, Austintown, Youngstown, OH 44515-2012

2

The Comedy Cellar at Mojo's Pub-n-Grill

6292 Mahoning Ave, Austintown, Youngstown, OH 44515-2003

The Comedy Cellar at Mojo's located in the lower level of Mojo's Pub -n- Grill offers up the best national touring comics every Friday and Saturday.

3

Hollywood Gaming Mahoning Valley Race Course

655 N Canfield Niles Rd, Youngstown, OH 44515-1102

4

Steamtown National Historic Site

350 Cliff St, Scranton, PA 18503

This small museum is all about steam engines and their contribution to America's economy in the 19th century.

5

Museum Of Illusions Chicago

25 E Washington St, Chicago, IL 60602-1708

6

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.

7

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.

8

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.

9

Promontory Point

5491 S Shore Dr, Chicago, IL 60615-5983

10

Corby's Irish Pub

441 E Lasalle Ave, South Bend, IN 46617-2723

11

Basilica of the Sacred Heart

114 Coleman Morse Ctr University of Notre Dame, South Bend, IN 46556-4617

12

O'Rourke's Public House

1044 E Angela Blvd, South Bend, IN 46617-1374

13

DCU Center

50 Foster Street, Worcester, MA 01608-1305

14

Commonwealth Avenue Mall

484 Commonwealth Ave, Boston, MA 02215-2737

15

Boston Public Garden

4 Charles St, Boston, MA 02114-4602

This Frederick Law Olmsted-designed park, famous for its Swan Boats, has over 600 varieties of trees and an ever-changing array of flowers. It is America's first public garden.

16

Boston Children's Museum

308 Congress St, Boston, MA 02210-1016

Highlights of this interactive museum include the "Science Playground," featuring giant soap bubble-making tools and the "New Balance Climb," which teaches kids the laws of physics while navigating through a two-story-high maze.

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OVERVIEW

Get ready for an epic adventure, where skyscrapers meet cobblestone streets, and the shores of Lake Michigan give way to the Atlantic Ocean. Embark on a journey that will connect you with the vibrant heart of the Midwest and the historic charm of New England. Allow yourself to be swept away by the whirlwind of discovery as you explore two iconic American cities, each with its unique story to tell. This journey promises an unforgettable tapestry of experiences, leaving you with memories that will last a lifetime.

Prepare to be amazed by the architectural grandeur of Chicago, a city that reaches for the sky with its towering skyscrapers and captivates with its vibrant energy. Immerse yourself in the cultural mosaic of Boston, where history whispers through cobblestone streets and academic excellence thrives in hallowed halls. Discover the hidden gems waiting to be uncovered in these two metropolises, where art, music, and culinary delights converge to create a symphony of urban experiences.

As you make your way from the bustling streets of Chicago to the charming allure of Boston, marvel at the transformation of the landscape. Witness the serene embrace of rolling countryside, where nature's beauty unfolds in endless vistas. Gaze upon the vast expanse of Lake Michigan, glistening like a jewel under the sun's caress. Allow the rhythm of the train to carry you through picturesque towns and enchanting villages, each with its own captivating tale to share.

1

Start:Paladin Brewing

Austintown, Youngstown, Ohio·

4.5

(9) review

6520 Mahoning Ave, Austintown, Youngstown, OH 44515-2012

2

The Comedy Cellar at Mojo's Pub-n-Grill

Austintown, Youngstown, Ohio·

4.5

(11) review

The Comedy Cellar at Mojo's located in the lower level of Mojo's Pub -n- Grill offers up the best national touring comics every Friday and Saturday.

6292 Mahoning Ave, Austintown, Youngstown, OH 44515-2003

3

Hollywood Gaming Mahoning Valley Race Course

Youngstown, Ohio·

3.5

(83) review

655 N Canfield Niles Rd, Youngstown, OH 44515-1102

4

Steamtown National Historic Site

Scranton, Pennsylvania·

4.5

(902) review

This small museum is all about steam engines and their contribution to America's economy in the 19th century.

350 Cliff St, Scranton, PA 18503

5

Museum Of Illusions Chicago

Chicago, Illinois·

4.5

(97) review

25 E Washington St, Chicago, IL 60602-1708

6

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

7

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

8

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

9

Promontory Point

Chicago, Illinois·

5.0

(9) review

5491 S Shore Dr, Chicago, IL 60615-5983

10

Corby's Irish Pub

South Bend, Indiana·

3.5

(9) review

441 E Lasalle Ave, South Bend, IN 46617-2723

11

Basilica of the Sacred Heart

South Bend, Indiana·

5.0

(700) review

114 Coleman Morse Ctr University of Notre Dame, South Bend, IN 46556-4617

12

O'Rourke's Public House

South Bend, Indiana·

4.5

(9) review

1044 E Angela Blvd, South Bend, IN 46617-1374

13

DCU Center

Worcester, Massachusetts·

3.5

(93) review

50 Foster Street, Worcester, MA 01608-1305

14

Commonwealth Avenue Mall

Boston, Massachusetts·

4.5

(94) review

484 Commonwealth Ave, Boston, MA 02215-2737

15

Boston Public Garden

Boston, Massachusetts·

4.5

(9979) review

This Frederick Law Olmsted-designed park, famous for its Swan Boats, has over 600 varieties of trees and an ever-changing array of flowers. It is America's first public garden.

4 Charles St, Boston, MA 02114-4602

16

Boston Children's Museum

Boston, Massachusetts·

4.5

(994) review

Highlights of this interactive museum include the "Science Playground," featuring giant soap bubble-making tools and the "New Balance Climb," which teaches kids the laws of physics while navigating through a two-story-high maze.

308 Congress St, Boston, MA 02210-1016