Road Trips

New York City to Chicago Road Trip: Itinerary/Map

New York TO Chicago Road Trip
Written by Town & Tourist

New York City to Chicago Road Trip – New York City and Chicago have always had a rivalry. Some say New York is just Bigger & Badder, while others point out that the Chicago people are just more friendly & laid back!

Me & my girlfriend were having this same dispute…so to settle any arguments we decided to to a road trip be New York City & Chicago and of course head past some great cities on the way!

New York City to Chicago Road Trip Stops:

  1. New York City 
  2. Philadelphia
  3. Baltimore
  4. Washington D.C
  5. Pittsburg
  6. Cleveland
  7. Detroit
  8. Chicago

You can also head to Chicago via Finger Lakes & Niagara Falls which is a great option.

Map of New York to Chicago Road Trip: 

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Is it cheaper to fly or drive?

It’s not always cheaper to drive, but in many cases it be less than half the cost of flying to drive and alot more fun! 

New York City to Chicago Road Trip Itinerary:

1. New York City

Drive/walk over Brooklyn Bridge

Brooklyn Bridge is one of the most iconic places in New York City. Either drive straight over or take the subway to Downtown Brooklyn then take a walk over.

Insider Tip:

The is the perfect place to capture some iconic New York City photos, great for instagram, facebook or just good old fashioned memories!

brooklyn-bridge-1791001_640

brooklyn-bridge-

Best Viewpoints:

  • Empire State Building
  • Rooftop Cocktails at Pod 39 – a Great Empire State Alternative!
  • Top of the Rock Viewpoint, Rockerfella Centre.

New Yorker Highlights:

    • Central Park – Give you a real feel for New York City!
    • Grand Central Terminal – A Vibrant place to visit.
    • Time Square (Busy but FREE!)
    • Ground Zero: 911 Museum – An Emotional Place
    • Bryant Park – Watch the Ice Skaters during the winter.
    • Queens (Flushing Area) – Great local foods/Cultural Hub.
    • Bronx (Arthur Avenue) – Great Italian Food (Better than little Italy!)
    • Intrepid Air & Space Museum (See the Enterprise Space Shuttle!)
Intrepid-sea-air-museum

Intrepid-sea-air-museum

Insider Tip:

Check out John Lennons Strawberry Fields at Central Park. This is where his ashes were scattered after his fatal assassination in New York City!

2. Philadelphia 

Road Trip Route: New York to Philadelphia Drive: Hop on I-95 S & take the short 1hr 34min drive (94.6 miles) to Philly!

Philadelphia is Pennsylvania’s largest city, famous for it’s rich history, tasty foods and vibrant culture! Historically, Philadelphia was the inception point for the United States of America.

philadelphia-1740685_640

philadelphia-1740685_640

Philadelphia Museum of Art – Run up those famous steps from Rocky!! 

Philadelphia is famed that Iconic scene in the Rocky movies where he runs up the steps of the Philadelphia Museum of Art! This is a great area for a selfie, “Yo Adrian, we did it”.

After you get to top, be sure to head inside the Museum of Art, which is one of the best in the U.S.A. Here you will find works by Van Gogh, Picasso and many more!

There is also monuments and structures from around the world such as the 16th-century Indian temple hall, a Japanese teahouse and even a 17th-century Chinese Palace hall!

Liberty Bell Center

This is a MUST SEE attraction for all Americans! Just opposite Independence Hall, you will discover the Liberty Bell Center located in Independence National Historical Park.

Protected in Glass gazebo, this historical Bell weighs over 2000 pounds and was previously mounted on Independence Hall.

This was used to mark events of great significance such as the first public reading of the Declaration of Independence.

Liberty Bell, Philadelphia Road trip

Liberty Bell, Philadelphia Road trip. Source: getty Images

Independence Hall

If you want to delve deeper into the history of the USA. Check out Independence Hall. Where the Declaration of Independence & American Constitution were debated & signed!

Hungry? Head to Reading Market Terminal!

Previously included in our: Ultimate Foodie Road Trip: East Coast Maps!and Epic Food Hall Road Trip USA: 21 Best Food Halls!

Reading Market Terminal is a Food Market which contains over 80 different food vendors! It’s the perfect place to try some local Philly foods and baked goods. In addition, to a variety of international foods such as Greek, Mexican, Indian and even Thai!

Reading Terminal Food Market

Reading Terminal Food Market, Philadelphia

Philadelphia is also a melting pot for some epic foods such as the mouth watering Philly cheese steak!

The Venue is located beneath the 1891 train station (a National Historic Landmark!)

3. Baltimore, Maryland 

Road Trip Route: Next hop onto I-95 S and take the 1 h 40 min (97.4 miles) to Baltimore, Maryland. Baltimore Marylands largest city, it’s colorful, diverse and famed for it’s scenic harbor, with up market crab shacks!

Viewpoints: 

401 E Pratt St 27th floor

Head to the Inner Harbor:

Alot of Balitmore famed attractions such as the USS Constellation, the National Aquarium and the Maryland Science Centre can be found at the historic inner harbor.

baltimore-4027194_640

baltimore-4027194_640

National Aquarium in Baltimore

(One of the best in the country, the National Aquarium houses more than 20,000 animals. Features include, an open pool with stingrays & fish, a Rainforest Replica and a gigantic shark tank!

Check out the “Blacktip Reef” exhibit, a $12.5 million area which models in the indo-pacific reef system.

This includes 20 blacktip reef sharks, 60 species of fish, zebra sharks and even a enormous sea turtle weighing 500 pounds named Calypso!

National Aquarium Baltimore

National Aquarium Baltimore

Insider Tip:

The National Aquarium can get very busy on the weekends! Your best bet is to attend on a weekday or before 11AM and after 3P.M on weekends

How much does the National Aquarium Cost?

Adult admissions costs $39.95; admission for children costs $24.95; and entry for seniors costs $34.95. It is open between 9 a.m. to 5pm but it can vary. See their website for further details website

Parking:

Parking at the National Aquarium is available at nearby garages.

USS Constellation:

Baltimore has attractions such as the Civil War–era warship the USS Constellation, see 15 Epic Maritime Museums: USA Navy!In addition to it’s National Aquarium which showcases thousands of marine creatures.

Parking:

There is on street parking close by.

Federal Hill – FREE

Federal Hill offers arguably the best views of Inner Harbor and the Baltimore Skyline. Historically it was used during the Civil war as a lookout point. For Families, the park offers a playground and when you get hungry there are plenty of restaurants nearby.

How to get to the top of Federal Hill? 

To get to the top of Federal hill you can take the stairs or the rolling hill.

You have two options for getting to Federal Hill’s summit: stairs or rolling hill. For the  stairs, walk up the 100 stairs on the Battery Avenue side.

Other Highlights:

4. Washington D.C

The Capital of the United States and home to many federal buildings & iconic landmarks such as the Whitehouse, Washington Monument and the capitol.

In addition, Washington D.C is also home to many iconic museums, war memorials and performing-arts centres, such as the Kennedy Centre.

There are lots of parking garages near the iconic landmarks. A good one is at 600 D St NW close to the Newseum. From there you can walk to alot of the major landmarks.

The Newseum

This is a really unique Museum, the idea of the museum is to capture the essence of free speech & expression.

It has a newspaper wall which contains headlines from some of the most iconic events in U.S history such as after 9/11.  Other highlights include, pieces of the Berlin wall and remains of the world trade center!

The Newseum Washington DC Road Trip

The Newseum Washington DC Road Trip

Hungry? Head to Capital Grille

After making headlines, head just across the street to The Capital Grille. Here you can find an array of delicious foods: from steaks to seafood, & soups.

Walk down to the National Mall

Next take a stroll down the National Mall, a park which stretches a couple of miles  from the Capital Building on the East to Lincoln Memorial on the west.

Washington Monument – The worlds tallest obelisk! 

Check out the Washington Monument, the worlds tallest obelisk which stands at 555 feet tall!

It was built in 1888 and was the worlds tallest structure before the Eiffel tower was built in 1889. For more info see: 10 Tallest Observation Towers in the USA

Martin Luther King Memorial

An historic place, close to the World War 2 Memorial. This wall is dedicated to late Martin Luther King. The civil rights leader who “Had a dream!”

The Vietnam Veterans Memorial

Just a short walk away is the Three Soldiers a Vietnam War memorial. There is also the Memorial Wall which names the soldiers who were killed or missing in action during the Vietnam war from 1959.

Vietnam Veterans Memorial

Vietnam Veterans Memorial. Source: Britannica.

The White House

Home of the President, head to the Iconic Whitehouse. For the best view take a walk down Pennsylvania Avenue.

The Lincoln Memorial

Take a walk up the steps to the famous gigantic statue of honest Abe Lincoln. This is an iconic place but it can get really busy during the afternoon!

Insider Tip:

Not many people know but It is possible to arrange a tour of the White House.(Public tour requests must be submitted through one’s Member of Congress. For more info see )

Insider Tip:

If your here during April, you HAVE TO VISIT THE CHERRY BLOSSOMS! These are captivating and offer fairytale beauty. For more info see: 21 Epic Flower/Garden Festivals: U.S.A

National cherry-blossom festival -tidal-basin-1

National cherry-blossom festival -tidal-basin-1

Other Highlights: 

If spending longer in D.C be sure to check out these other highlights.

  • Visit  Smithsonian Museums
  • Visit the International Spy Museum
  • Spend a day in Georgetown
  • Adventure at the National Zoo
  • Tour the Capitol Building (click For more  info)
  • Tour the US Holocaust Museum
  • Visit the Arlington National Cemetery
  • Visit the Washington National Cathedral
  • Day trip out to Mount Vernon
  • Visit the Library of Congress

5. Pittsburg, PN

Pittsburgh is known as “Steel City” due to it’s large Steel Industry, in addition it is known as the “City of Bridges” as it has over 446 Bridges which is greater than any other city in the world! In addition, Pittsburg is home to the worlds first T Rex Fossil.

Pittsburgh

Pittsburgh. Source: www.post-gazette.com

Things to Do in Pittsburg:

The Andy Warhol Museum

The Pop Art Legend Andy Warhol was Born in Pittsburg and is known as one of the greatest artists of all time. Thus to honour him this Museum was created. It is the largest Museum in North America dedicated to a single artist.

Did Andy Warhol Get Shot?

Like many great legends Andy Warhol was Shot! Valerie Solanas was a radical feminist, who thought Andy Warhol was stealing her work.

She then purchased a gun & shot at him 3 times with one bullet hitting him. It didn’t kill Warhol, buts it thought that the gunshot wound contributed to his death a few years later.

Andy Warhol Museum

Andy Warhol Museum. Source: www.warhol.org.

How much does it cost?

Museum parking is $8 (cash only) in The Warhol lot during normal museum hours (10 a.m.–5 p.m. Tuesday–Sunday; 10 a.m.–10 p.m. Fridays.

Where is it?

117 Sandusky St, Pittsburgh, PA 15212

Point State Park

Point State Park is the ideal place for hiking fun and all things nature. The 36 acres of lush greenery makes it great in the summer months, located in downtown Pittsburgh.

Kennywood Amusement Park

Kennywood is an amusement park is located in West Mifflin, this is the ideal place for some family fun!

Address:  4800 Kennywood Blvd, West Mifflin, PA 15122, United States

Carnegie Museum of Natural History 

Want to see a Fossilised T Rex? Head to the Carnegie Museum of Natural History . As one of four Carnegie Museums of Pittsburgh, the Carnegie Museum of Natural History is one most highly regarded Natural History Museums in the U.S.A. The Museums collection contains a large number of extraordinary artifacts.

Carnegie Museum of Natural History 

Carnegie Museum of Natural History Source: www.carnegiemnh.org

Phipps Conservatory & Botanical Gardens:

Phipps Conservatory and Botanical Gardens is in Schenley Park, was built in 1893 and is an historic landmark. It’s even listed on the National Register of Historic Places.

Insider Tip: 

Metered street parking available on either side of Schenley Drive is also free after 6 p.m. Monday – Saturday and all day on Sundays. Tel: +1 412-622-6914. 

Pittsburgh Zoo & PPG Aquarium

The Pittsburgh Zoo is one of only six major Zoo & Aquarium combos in the U.S.A. It sits on 77 acres of park area and has over 4,000 animals which represent of 475 species including 20 endangered species.

Location:  Highland Park, 7370 Baker St, Pittsburgh, U.S.A

Pittsburgh Zoo & PPG Aquarium 1

Pittsburgh Zoo & PPG Aquarium. Source: Pittsburgh Zoo & PPG Aquarium

6. Cleveland, OH

Located just 2hrs (133 miles) from Pittsburgh is Cleveland Ohio. Cleveland is a great place for sightseeing and watching some of their local sports teams…which had a reputation of being very bad & had was known as the Cleveland Sports curse! 

What is the Cleveland sports curse? 

The Cleveland sports curse was a sports superstition, it stemmed from the fact that Cleveland failed to win a championship in any major league sport for a period of 52 years, from 1964 to 2016. 

Cleveland, OH 1

Cleveland, Ohio was named one of the best place to live if your after a new Job! Source: liveability.com/theiscleveland.com

Things to Do in Cleveland:

Rock & Roll Hall of Fame

The Rock and Roll Hall of Fame has to be one of the best places to visit in Cleveland. Here you will find a heap of Rock music history, artifacts and memorabilia from many Iconic artists lives and performances. From the Rolling stones, to Elvis, the Beatles and many many more.

rock-and-roll-hall-of-fame

rock-and-roll-hall-of-fame. Source: Rock & Roll Hall of Fame.

Cleveland Museum of Art – FREE activity. 

The Cleveland Museum of Art is an art museum in Cleveland, Ohio, located in the Wade Park District, in the University Circle neighborhood on the city’s east side.

The museum’s collections are FREE of charge to visit!

Cleveland Metro Parks Zoo:

The Cleveland Metroparks Zoo is a 183-acre zoo with over 3,000 animals representing over 600 species! The zoo is split into many areas & habitats from Australian Adventure to  African Savanna; Asian Highlands, Rainforest and even a Cat & Aquatics Building!

Location: 900 Wildlife Way, Cleveland, Ohio, U.S.A

Where to Eat?

West Side Market – Food Hall! 

The West Side Market is the oldest operating indoor/outdoor market space in Cleveland, Ohio. It offers a variety of local produce and gourmet food vendors. For more info see: Epic Food Hall Road Trip USA: 21 Best Food Halls!

West Side Market, Cleveland, Ohio.

West Side Market, Cleveland, Ohio.

7. Detroit 

Detroit is the largest city in Michigan, birth place of Motown and an Icon of the automotive industry, “Motor City”.

Is Detroit Safe?

The crime rate in Detroit has declined in recent years, but it’s still one the most dangerous cities in the U.S.A. However, that doesn’t mean everywhere is dangerous and the “Bad areas” are localised to a certain zone like many other big cities.

Detriot USA

Detriot USA

Things to do in Detroit:

Henry Ford Museum:

The Henry Ford Museum of American Innovation is the largest indoor-outdoor museum complex in the United States and is visited by over 1.6 million people each year.

It was founded in 1929 and documents the development of ford motor cars and the motor car industry as a whole. 

Henry Ford Museum

Henry Ford Museum. Source: www.fox47news.com

Fun Fact: The first mass produced motor car was the Model T Ford, produced in 1908.

Comerica Park

Comerica Park is an open-air ballpark located in Downtown Detroit. It serves as the home of the Detroit Tigers of Major League Baseball. This is a great place to watch a classic open air baseball match.

Outdoor Adventure Center

The Outdoor Adventure Center  is the perfect place to sample the “Great Michigan Outdoors”. Here you will find many interactive activities and experiences from cycling to viewing waterfalls, fishing and many more!

How much does it cost?

Children under two are free, children up to 12 are $3 and adults are $5.

Outdoor Adventure Center detriot

Outdoor Adventure Center Detroit. Source: OAC

Belle Isle Nature Center

The Belle Isle Nature Center promises to bring the wildlife of Michigan to Detroit.  Here you can find a variety of animals, and plant species. Be sure to try the dear encounter where you can feed the dear.

How much does it cost? 

It costs $11 for the Recreation Passport; otherwise, it’s free.

The Detroit Institute of Arts

One of the top rated Museums in the U.S.A, the Detroit Institute of Arts offering art, music, film gallery games and art making!

How much does it cost?

Residents of Wayne, Oakland and Macomb Counties and children five and under receive free, unlimited general museum admission, but children over five are $6 and adults are $14.

Eastern Market – Foodie Favourite.

Eastern Market has to be one of my favourite places to visit in Detroit. Founded back in 1891 here you will find one the largest outdoor farmers markets in the country.

In addition to local produce you will find, hip cafes offering a range of foods from Tacos to Coney Island Hot Dogs. Head to Berts Warehouse Theatre for some live Jazz & Motown…of course!

Eastern Market detroit

Eastern Market detroit. Source; The great www.curbed.detroit.com

Insider Tip: 

Head Down on a Sunday to check out the arts & crafts from local artists.

How much is it?

It is FREE Entry and you just pay for what you eat or do inside.

For more info check out: Epic Food Hall Road Trip USA: 21 Best Food Halls!

8. Chicago

Starting in the Windy City, Chicago, Illinois is a large metropolis on the Scenic Lake Michigan. The Skyline is punctuated with vast skyscrapers, such as the Willis Tower (Former Sears Tower) and the Legendary John Hancock Center at over 1,451ft high.

Chicago is also known for Chicago style pizza (Deep dish) , and Chicago hot dogs in addition to Jazz and of course the Notorious 1920s gangster Al Capone.

chicago-1870010_640

chicago-1870010_640

5 Unique Things to do in Chicago: 

1. Millennium Park – FREE! 

Millennium Park  is not just a public park, its a true expression of the Chicago experience! It is the largest public space inside the 319 acres of Chicagos Grant Park, located downtown. This area includes, gardens, sculptures and attractions.

Cloud Gate (The “Bean”)

A Large public sculpture weighing in at over 110tones and is over 66 feet long and 33 feet high. This is an astonishing sculpture to see and was designed by British Artist Anish Kapoor.

Cloudgate Chicago Bean

Cloudgate Chicago Bean

Crown Fountain: 

Crown Fountain was designed by Spanish artist Jaume Plensa the fountain is made up of two 50 foot glass block towers which of display rotating images of over 1000 Chicago residents.

The fountain fires water out of the giant mouth and is really popular with kids during the summer months.

Crown Fountain Chicago

Crown Fountain Chicago

Other highlights at Millennium Park include, Lure Garden and Maggie Daley Park. A large 20 acre adventure park which includes rock climbing, slides and mirror walks.

Where is it?

201 E Randolph St, Chicago, IL 60602, United States

2. Willis Tower (“Sears Tower”) 

The Willis Tower is a 110-story, 1,450-foot skyscraper in Chicago. When it was completed in 1973, it surpassed the World Trade Center in New York to become the tallest building in the world!

3. Green Mill Lounge – Can you spot Al Capone?? 

Head back to the 1940s at Chicagos Green Mill Lounge. Here you can find local Jazz Musicians, poets and was once a hangout for the Notorious Gangster Al Capone.

Green Mill Lounge Chicago Al Capones hangout

Green Mill Lounge Chicago Al Capones hangout

4. Relax at the Lakefront Promenade 

As Lake Michigan spans across the entire length of Chicago, you should really take advantage of these glistening waters! Head down to the The Lakefront Trail where you will find 18 miles of biking & walking with scenic lakefront views.

Best Summer Spot:

Beach? If you fancy a beach head to Oak Street Beach, which is on North Lake Shore Drive.

Oak Street Beach Chicago 1

Oak Street Beach Chicago 1

This is a hidden gem popular with the locals during the summer months. Relax on the sands, overlooking glistening lake Michigan, while admiring the Skyscrapers in the distance!

5. Navy Pier

Navy Pier is a 3,300-foot-long pier on the shoreline of Lake Michigan. Here you will find many fairground rides & attractions including a 360 Chicago, (A Premiere observation deck), Centennial Wheel (Observation Wheel)  Museum of Contemporary Art, the Childrens Museum, River Cruises and many more!

Navy Pier Chicago

Navy Pier Chicago

How much does it cost? 

It is FREE to enter Navy Pier, each attractions or  show has it’s own admission price.

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About the author

Town & Tourist

A travel resource guide that has been carefully crafted and curated by travel bloggers to help you find the best places to travel to in the USA.