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Family Vacation - Driving from Chicago to Washington D.C.

Updated on April 10, 2018

Driving Vacation from Naperville, Illinois to Washington D.C.

When my kids were younger, we would take the kids on road trips that brought us to and through through Washington D.C. We have been to Washington D.C. many times when my dad lived in Silver Springs, Maryland. I have chronicled one two week driving trip we took and some of the great places to visit.

The drive from Chicago to Washington DC is only 12 hours long, but what's the fun in driving straight thru? On this particular trip, we stopped in Sandusky, Ohio, Niagara Falls, New York, Hershey, Pennsylvania, and Gettysburg, Pennsylvania. And on the way home, we drove through Assateague Island, Maryland, Williamsburg, Virginia, West Virgina, and finally Louisville, Kentucky.

My Dad lived in Maryland for over twenty years, so we have visited a lot of the Washington D.C. sites. Just a word of caution when you get to the Washington D.C. section of this page, you can not visit everything on this list in a week or probably two weeks, so don't even try. Plan ahead and pick the ones you want to see and enjoy the day there. And when you're done seeing the monuments during the day, don't forget to go back and see the monuments and memorials lit up at night.

I hope you enjoy the page and my usual ramblings along the way.

Plan your Stops and Overnight Stays

Determine what you want to see before you go...

This takes quite a while to get through all the things that you could do on a driving vacation. The first thing is to determine what is between your home and destination. Don't just look along the direct route, look at alternate routes that may take a few hours more and take you through an interesting place or a city you have never visited.

Think about old friends, neighbors, and relatives that are near your route, that you would like to visit and that may be willing to put you up overnight. These are usually the best of both worlds.

When you stop overnight, will you have time to relax or is it just for sleeping purposes? My kids love the whole hotel/swimming experience, so we are always looking for places with pools and stopping early enough in the evening to get some dinner and relax by the pool.

Do you have hotel points that can be used for a free night, and are where are there hotels / motels in the area? What about your final destination, in this case Washington D.C.? There are many great hotel sites to find a great hotel, like this one which lists Washington D.C. hotels from multiple providers.

Bottom line, it's a vacation, if your rushing, you will be stressed and not able to enjoy the family time you want from this vacation.

Planning your Route

Sometimes the most direct route is not the best

Driving from Chicago to Washington DC, there are so many things to do on the way if you don't go direct. What you need to think about are your interests and kids interests.

  • Do you like history? - Gettysburg, PA .
  • Do you like Baseball? Check out the MLB Hall of Fame in Cooperstown, NY or the Louisville Slugger Bat Factory in Louisville, KY.
  • Do you like nature? All the mountain ranges from New York to the Great Smoky Mountains and don't forget about Niagara Falls, NY.
  • Are you a chocolate lover? Hershey, PA is your stop.
  • How about theme parks and roller coasters? Cedar Point in Sandusky, OH, Hersheyland in Hershey, PA, and Williamsburg, VA.
  • Are you a Music Lover? Check out the Rock and Roll Hall of Fame in Cleveland, Ohio, or the Country Hall of Fame in Nashville, Tennessee

Eat Local not National

We love taking the not so direct route. A 2-lane road through the mountains or along a river is much more fascinating than those super expressways.

When you are on those two-lane road, stopping at local dining establishments or even a small fruit stand for a break is one of our favorite past times. We always look for places that are crowded or with a unique name, especially if it's named after one of our kids. That local ice cream shop in the middle of West Virginia that you know makes there own out of local ingredients is fantastic. It's always a goal of ours to not eat somewhere that you could eat at home. However, there is the occasion, where a Big Mac just hits the spot.

Places to visit between Chicago and Washington DC

show route and directions
A markerHome -
Naperville, IL
get directions

B markerGreat Wolf Lodge and Cedar Pointe -
Sandusky, OH
get directions

C markerHorseshoe and Wedding Viel Falls -
Niagara Falls, NY
get directions

D markerHome of the Hershey Bar -
Hershey, PA
get directions

E markerHistoric Civil War Battlefields -
Gettysburg, PA
get directions

F markerMonuments, Museums, and other Historical Sites -
Washington DC
get directions

G markerYorktown, Jamestown, and Colonial Williamsburg -
Williamsburg, VA
get directions

H markerLouisville Slugger Bat Factory -
Louisville, KY
get directions

Entertaining your kids during a road trip.

The Chicago to Washington D.C. is a long trip, so you do need to plan for more than a few hours of boredom. Here's a few ways to entertain your kids along the way.

  • The License Plate Game - Watching for different license plates (Hawaii, Alaska, and Canadian license plates are very rare. I've even seen one from Puerto Rico).
  • The ABC Game - Start with the letter A and find a word, then B, then C, etc. We always use the rule that the word has to be outside the car.
  • The I Spy Game - One person gives a clue on something they see, and others try to guess what it is.
  • The 20 Questions Game - One person thinks of an object, and everyone else asks up to 20 questions to determine what it is.
  • The Song Game - Ask the question, What if "singer" didn't "do what is in the song". For example, What if Garth Brooks didn't have friends in low places?
  • Car Bingo - Bingo cards for the car.
  • DVD Player - And if its raining or at night, a good movie always gets everyone to sleep.

Check out these places to stop between Naperville, Illinois and Washington DC

Sandusky, Ohio

Even though Cedar Pointe is in Sandusky, Ohio, we decided to stop at the Great Wolf Lodge and hang out at the water park and pool for a couple of days. What a great start to our vacation.

Niagra Falls from the US or Canada side

I never realized that Niagara Falls was about 20 minutes from Buffalo, NY. So as one of our stops prior to going to Washington DC, we decided to stop near Buffalo, NY and go to Niagara Falls.

We arrived about 5pm and took the Maid of the Mist boat to the falls. At 5pm, there were no crowds, there were about 50 people on the boat, and everyone had a front row view. And the view from the observation tower is just excellent.

I have friends that went to Niagara Falls recently and have been told that the Cave of the Winds is excellent as well.

Click the link to learn more about Niagara Falls State Park.

Hershey, Pennsylvania

Where they make Hershey Chocolate

If you've never been to Hershey, Pennsylvania, and are around the area, its worth the stop for a couple of hours. We stopped at Hershey's Chocolate World. Chocolate World is where you catch the trolley ride, buy souvenirs, and take the free Chocolate Tour Ride.

The Chocolate Tour Ride is about 5 minutes of how chocolate is made and where it comes from. My kids being pretty young, loved the ride, especially the singing cows. Can't beat the singing cows.

Other attractions in Hershey, PA include Hersheypark, think amusement park, and Hershey Gardens.

Gettysburg, Pennsylvania - Plan to spend the whole date and tour The Battlefields of Gettysburg

We didn't plan this stop very well as we arrived in Gettysburg about 5pm on our way from Hershey, PA and our stop in Maryland just outside of Washington DC. We stopped by a local visitor center and they gave us a map of the area. We toured The Soldier's National Cemetery at Gettysburg where Abraham Lincoln gave the famous Gettysburg Address during the Cemetery dedication on November 19th, 1863. There is a monument dedicated to Abraham Lincoln in the cemetery as well.

After leaving the cemetery, we drove around a couple of the battle fields and looked at all the monuments. The count for the number of monuments at Gettysburg is about 1320. We saw a near fraction in our time there.

Plan to spend a whole day in Gettysburg, the history just oozes out of the place. One of the things I learned about afterword is there are driving tours of Gettysburg. So be sure to pick up or borrow one of the many Gettysburg driving tours.

Assateague Island, Maryland on the Atlantic Ocean

If your looking for a beach on the Atlantic Ocean. The kids and I had a whole lot of fun here. For those not familiar with Assateague Island, it is on the southern tip of the strip of land between the Cheasapeake Bay and the Atlantic Ocean.

Assateague Island is home to a heard of wild ponies that roam the island, in fact driving in and out of the National Park there, we saw many ponies off in the distance.

Click here to learn more about Assateague Island, Maryland.

Colonial Williamsburg in Virginia

We spent a couple of hours roaming around Colonial Williamsburg not realizing how much there was to actually do and see. You could take a week and go to Williamsburg by itself. There's a huge amusement park, Yorktown Revolutionary War battlefields where the British surrendered, and historic Jamestown where John Smith landed in the seventieth century.

Not far from Williamsburg is Monticello, the home of Thomas Jefferson; Virginia Beach on the Atlantic Ocean, Jamestown, and Yorktown.

Louisville Slugger Bat Factory

The Louisville Slugger Bat Factory in Louisville, Kentucky is a great place for the baseball fan. They take you on a tour of where they make wooden bats. Bats are made here for Major League Baseball players. I even got to hold one of Jim Thome's bats, ok, it was probably one they didn't give him, but its fun to think about anyway.

There's a great movie about baseball that was playing when we were there, I think they have changed it now. And, there's the biggest bat in the world standing outside the building.

A great place to stop for a couple of hours.

What to do while in and around Washington D.C.

Sightseeing in Washington D.C.

The first thing you'll need to realize is that you can't do/see everything in Washington D.C. in a day and probably not even a week. You will need to plan your visit so that you don't become overwhelmed with the sheer magnitude of the area. The best way is to make a list of the places and monuments you would like to visit, pick the top 3 or 4 and then fill in with other monuments that are nearby the top places. For example, trying to visit all the museums in one day is nearly impossible since they don't open until 10am. You should pick a museum for the morning and then visit a couple monuments in the area in the afternoon. Visits to Mt. Vernon and Annapolis are pretty much a day trip so don't try to add in the National Zoo on the same day.

Washington DC has one of the best Metro's in the Nation if not the World. The Metro Stations go near (within 1/4 to 1/2 mile) of most of the main attractions in Washington DC.

Another great way is to board one of the many tour groups that go around Washington DC. There are a couple of tour groups that have a rotation and take you around to the various memorials, museums, and monuments. You get off, do your thing, and then wait for the next vehicle to go to the next stop.

And finally, walking around Washington is a lot of fun as there are many great sites to see on and off the beaten path. A word of warning, if you are on foot and exploring the National Mall area, the distance from the US Capitol to the Lincoln Memorial is over 2 miles (round trip over 4 miles). This is ok for adults, however, for small kids it is very tiring and in my experience, they become crabby when they are tired.

Washington D.C. Map of Attractions and Monuments

show route and directions
A markerWhite House -
1600 Pennsylvania Ave NW, Washington, DC 20500, USA
get directions

B markerUS Capitol Building -
100 East Capitol St NE, Washington, DC 20543, USA
get directions

C markerJefferson Memorial -
701 E Basin Dr SW, Washington, DC 20242, USA
get directions

D markerLincoln Memorial -
2 Lincoln Memorial Cir NW, Washington, DC 20037, USA
get directions

E markerFord's Theater -
511 10th St, NW, Washington DC
get directions

F markerMartin Luther King Jr. National Memorial -
1964 Independence Ave., SW, Washington, DC
get directions

G markerArlington National Cemetery -
Fort Myer, VA 22211, USA
get directions

H markerNational Zoo -
3001 Connecticut Ave NW, Washington, DC 20008, USA
get directions

I markerNational Archives -
700 Pennsylvania Ave NW, Washington, DC 20408, USA
get directions

See the US Constitution and the Declaration of Independence

J markerNational Mall (Museum Campus) -
Madison Dr NW & 12th St NW, Washington, DC 20560, USA
get directions

Museums located on the mall include Air and Space Museum, American History Museum, Museum of Natural History, and the Portrait Gallery.

K markerUS Capital Building -
East Capitol Street, NE and 1st Street, NE, Washington DC 20002
get directions

L markerNational Archives -
Constitution Ave NW between 7th & 9th St, Washington DC
get directions

M markerUS Navy Memorial -
701 Pennsylvania Ave NW # 123, Washington DC
get directions

Smithsonian and other Museums

The Smithsonian is a series of 19 museums, 9 research centers, and the National Zoo. In addition to the Smithsonian, the National Archives and the US Holocaust Museum are in Washington DC Below is a glimpse of the few I have been to.

  • National Air & Space Museum
  • Dulles Air & Space Museum
  • National Archives
  • National Museum of American History
  • National Museum of Natural History
  • National Portrait Gallery
  • US Holocaust Museum
  • American Art Museum and the Renwick Gallery

Washington D.C. Monuments and Memorials

In between the Museums and Galleries, don't forget to visit all of the Monuments and Memorials. You can spend a long time going through them all. Here are some of the ones I have visited:

  • Abraham Lincoln Memorial
  • Thomas Jefferson Memorial
  • George Washington Monument
  • FDR (Franklin Delonar Roosevelt) Memorial
  • World War II Memorial
  • Iwo Jima Memorial also knows as the US Marine Corps War Memorial
  • Korean War Veterans Memorial
  • Vietnam Veterans Memorial
  • Theodore Roosevelt Memorial
  • US Navy Memorial
  • US Air Force Memorial
  • MLK (Martin Luther King Jr) National Memorial

White House

A visit to Washington DC is not complete without strolling by the White House. Or, if you are lucky enough to get tickets for a visit inside the White House. These days, they White House can only be seen through the fences.

US Capital Building

Another must visit is the place where all the laws of the United States are made, the US Capital Building. Tours of the capital building are free and last about 90 minutes. If not in session, you get to see the chambers of the Senate and House of Representatives.

While visiting Washington DC, be sure to contact the office of your Congressmen as there are sometimes special luncheons or breakfasts they have on a weekly or monthly basis to welcome their constituents to Washington.

Arlington National Cemetery

Arlington National Cemetery sits across the Potomac River from the Lincoln Memorial in Arlington, Virginia. You can easily spend 2-3 hours walking through Arlington National Cemetery. While there be sure to visit:

  • The Tomb of the Unknown Soldier and watch the changing of the guard.
  • The Eternal Flame which is the burial site of John Kennedy, Robert Kennedy, Jackie Kennedy, and Ted Kennedy.
  • President William Howard Taft Monument.
  • Kennedy and Taft are the only two Presidents buried at Arlington National Cemetery.

The Cherry Blossoms on the Mall

If you've never been to Washington D.C. while the cherry trees are blooming, it is a real treat. In late March or Early April for about two weeks the approximately 3,700 cherry trees located along the tidal basin, around the Washington Monument, in Hains Point (East Potomac Park), and West Potomac Park bloom with these magnificent pink and white blossoms.

The cherry trees were a gift of friendship from the people of Japan in 1912. First Lady Taft and the Viscountess Chinda, wife of the Japanese Ambassador, planted the first two cherry trees on the northern bank of the Tidal Basin near the John Paul Jones statue at the south end of 17th Street.

Mount Vernon, home of George Washington

Mount Vernon sits on the banks of the Potomac River and was the home of George Washington. I always love the peaceful setting of Mount Vernon and walking on the back porch.

It is about a 45 minute drive to Mount Vernon from Washington D.C. There is no Metro service to Mount Vernon, so driving is the only access.

Ford's Theater in Washington D.C. - where President Abraham Lincoln was shot by John Wilkes Booth

As a resident of the state of Illinois, I have never been to Ford's Theater to see where President Lincoln was shot, or the house across the street from Ford's Theater where he died. It's on my list the next time I am in D.C. On recent 8th grade trips to D.C., my daughters have both visited Ford's Theater and really enjoyed the experience.

The National Zoo

The main attraction at the National Zoo are the Panda Bears that were given to the United States by China. If your lucky they will be out and you will get to see them. And of course, a Bald Eagle or two. There are also Red Pandas, Lions, and Tigers, and Bears.

National Cathedral

Yes, there is a National Cathedral. For the religious folks on the trip, it is a great place to visit. It takes a couple of hours to walk through and look at all the beautiful stained glass windows, and alters.

The Pentagon

US Military Headquarters

Military enthusiasts will want to visit the Pentagon in Washington DC. This amazing structure houses over 23,000 employees of the Department of Defense.

Visitors to the Pentagon can sign up for a guided tour of the building, but be prepared to walk up to two miles on the guided tour.

Annapolis, Maryland

Annapolis is the home of the Naval Training Academy and a great little town along the Chesapeake Bay to do some shopping and dining.

What was your favorite place to visit in or near Washington DC

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    • profile image

      Juntak 3 years ago

      That is amazing! One of my faritove teachers in college regaled us with tales of Boom Boom Smith every time we were near Devil's Den. Gettysburg is well worth the visit if you've never been there. I have been following this story ever since the damage happened. The monuments were one of the things that made me fall in love with the battlefield in the first place, I love the stories they tell us. But I also have a very special connection to the monument that stands only a few yards from this one. I did not have any family fight in the war (I'm the product of more modern waves of immigration); however, the regiment local to my area in New York was the 124th NY Orange Blossoms. Every time I visited the 124th monument I could see the empty pedestal for the 4th NY. It made me sad to think that the damage could have happened to our monument, and I knew that if that was the case I would want it fixed as quickly as possible. I am very glad that the monument is finally back in its proper place.

    • Charito1962 profile image

      Charito Maranan-Montecillo 4 years ago from Manila, Philippines

      In 1987, my family and I were in L.A.-California for a vacation. If I do visit the United States again, I'd like to see Chicago and Washington D.C.

    • profile image

      Eddie-N 5 years ago

      If there is one thing out capital does well, itâs providing a lot of things for free. The capital is awesome because you can spend a whole day or 2 just looking at free stuff. My favorite of all is the Smithsonian National Zoo: www.triposs.com/dc/national_zoo, where the in the world would you find a free admission for a zoo?

    • katprice lm profile image

      katprice lm 5 years ago

      Great lens! Next time you're out this way, visit Colonial Beach! The site where John Wilkes Booth was captured is not far from CB. (I saw that you had a segment on Ford's Theatre.)

    • profile image

      dcjourney 5 years ago

      Definitely the attractions in the National Mall: http://dcjourney.com/outdoors/nat-mall

    • CanadaRed LM profile image

      CanadaRed LM 6 years ago

      Yes you definitely need to plan before you go on a road trip. So many sights to see, it's hard to do it all. Nice lens.

    • profile image

      anonymous 6 years ago

      enjoyed your write up version of this, enjoyed my reading today, thank you indeed.

    • zimbali2011 profile image

      zimbali2011 6 years ago

      I love to travel. Good lens :)

    • justholidays profile image

      justholidays 6 years ago

      I love anything as much as travelling from the comfort of my house! Thanks for sharing your journey from Chicago to Washington DC!

      Blessed by an angel since I can't travel for the moment but spent a good time travelling through this page.

    • profile image

      trippste 6 years ago

      Awesome lens, I live near Washington DC and have been to most of these places.

    • LiquidGranite1 profile image

      LiquidGranite1 6 years ago

      A great trip and a great experience. Thanks for sharing it.

    • profile image

      Pete Schultz 7 years ago

      There was so much, and you are right, you can't wee it all in two weeks. I believe I enjoyed a trip over the Chesapeake to a small bayside restaurant where I enjoyed a delicious soft-shell crab sandwich. Later, I leanred it was the whole crab...eyeballs and all, breaded and deep fried, and I started wondering if I would ever eat that treat again. (I would) .

    • ZenandChic profile image

      Patricia 7 years ago

      I went to D.C. as a teenager on a family vacation. I enjoyed seeing the Vietnam wall and the statue of the soldiers because my father, no longer alive was in the Vietnam War. Wonderful lens!

    • Faye Rutledge profile image

      Faye Rutledge 8 years ago from Concord VA

      The National Air & Space Museum was our favorite. There's so much to do and see in Washington DC, it's hard to pick a favorite. Nice lens.

    • profile image

      anonymous 8 years ago

      Thanks for the lens. Been to Washington D.C. twice and visited a lot of these places. Very interesting.

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