Road Trip

5 min read

Chicago to Cooperstown Road Trip Itinerary via Niagara Falls!

Explore the ultimate road trip from Chicago to Cooperstown, hitting iconic spots like Niagara Falls! Perfect guide for travelers seeking culture, baseball, and breathtaking views.

Tobi Miles
July 1, 2022
Chicago to Cooperstown Road Trip Itinerary via Niagara Falls!

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 its tasty foods from Chicago style pizza (Deep dish) & mouth watering Chicago hot dogs.

In addition, Chicago is know for its Jazz and of course the Notorious 1920s gangster Al Capone!

Cooperstown in Ostego County is quite the opposite! Cooperstown is a quaint village area with a charming main street, where you will find plenty of vintage shops & great restaurants.

Baseball fans will know the town as home of National Baseball Hall of Fame which celebrates the legendary players & managers from yesteryear. This is a great place to bring the kids!

Many choose to head down to Doubleday Field, to watch a ball game!

Should you take a road trip between Chicago and Cooperstown?

A road trip between Chicago and Cooperstown will take you through some of the most incredible natural wonders in the USA! We stopped off at Niagara Falls and the glorious Finger Lakes region for some wine tasting!

We also passed, "Motor city" Detroit, Cleveland and many memorable little towns in Ostego county.

How long is the drive from Niagara Falls from Chicago?

Driving direct Niagara Falls is 525 miles from Chicago! This will take you around 8 hours via I-69 N and I-94 E.

I recommended stopping in Detroit to break up the road trip like we did!

When is the Best time of year to visit Niagara falls?

Peak flow at Niagara falls is in the daytime during peak tourist season (June, July, and August). If you want less tourists you can head an alternative time of year.

New York City to Niagara Falls road trip

Which is better New York side or Canada side of Niagara falls?

The Canada side (Ontario) of Niagara falls (Horseshoe falls) is the best. It is the largest of the three waterfalls and has the majority of hotels, restaurants & attractions in the town of Niagara.

Insider Tip:

Take a drive along the scenic Niagara Parkway.

(For more on Niagara Falls check out our, New York City to Niagara falls Road trip!)

How long is the drive to Finger Lakes from Chicago?

Driving direct to Finger Lakes region, New York would take you approximately 10 h and you will cover 649.0 mi, (travelling via I-90 E).

How long is the drive from Niagara Falls to Finger Lakes?

The great news is Finger Lakes is just 2 hours 15 mins (133 miles) from Niagara Falls!

How long is the drive from Cooperstown from Chicago?

Driving direct to Cooperstown from Chicago would take you 12 hours and you will cover 765 miles via I-90 E

This can be a long drive, that's why its great stop off at some amazing wonders enroute like Niagara Falls!

Interactive Road Trip Map: Chicago to Cooperstown

Dive into our interactive road trip map below!

User Guide:  Simply Click the +/- buttons to zoom in & out,  Click on a favourite attraction, and click directions symbol to give you the driving or walking route directly there!

(Many visitors choose to share our map on Facebook by clicking the link below:


Road Trip Itinerary (Chicago to Cooperstown):

  1. Chicago, IL
  2. Detroit, MI
  3. Cleveland, OH
  4. Buffalo, New York
  5. Niagara Falls
  6. Seneca County, NY
  7. Finger Lakes, NY
  8. Gilbertsville, NY
  9. Milford, NY
  10. Cooperstown, NY

1. Chicago, IL

Here are my top 5 unique things to do in Chicago before you hit the road!

5 Unique Things to do in Chicago?

1. Visit the 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.

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

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

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!

chicago-view from willis tower

3. 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

How much does it cost?

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

4. Green Mill Lounge – Can you spot Al Capone's ghost??

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

5. 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

2. Detroit, Michigan

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

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.

Henry Ford Museum | Wikimedia Commons

  • 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!

  • 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 deer encounter where you can feed the deer.

  • 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!

Where to eat??

Chicago's 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!

3. Cleveland, OH

Cleveland can be a good city to visit. Attractions include, the Rock and Roll Hall of Fame, Cleveland Metro Parks nature reserve, Emerald Necklace and the Museum of Art,.

A little known national park is located just south of Cleveland (Cuyahoga NP).

Is Cleveland Dangerous!?

While Cleveland does have a very high homeless population which does result in crime, travel during the day is fine and just be cautious at nighttime. Or just carry on driving! haha

4. Buffalo, NY

Drive up the shores of Lake Erie to arrive at Buffalo, New York. Some popular attractions here include:


If your feeling hungry you have to try some of the spicy buffalo wings from Duffs. If your into spicy wings, this is the place. There medium is boiling, and they even have “death sauces” which are only for those which want a real spicy challenge.

5. Niagara Falls - New York

You've made it to Niagara Falls, a raging wonder of the world! Fun facts about Niagara Falls:

  • Niagara Falls is over 15,000 years old, formed just the last Ice age
  • The Largest Fall (Horse shoe falls) is on the Canadian side 176 feet / 53.6 meters high.
  • 600,000 U.S. gallons / 2,271,247 litres per second flow over Horse shoe falls.
  • The first person to go over the Falls in a barrel and survive was a 63 year old female schoolteacher.
  • 30 Million Visitors come to Niagara falls each Year
  • 20% of the worlds freshwater lies in the Great Lakes and most flows over Niagara Falls.
  • In 2012 Nik Wallenda was the first person to cross the Niagara Falls by tightrope in 116 years. (He even had to present his passport at the border despite being on a tightrope!)

6. Go wild at Seneca County

Drive west into New York’s Seneca County, and be sure to check out Montezuma National Wildlife Refuge an area which offers of 10,000 acres of swampland and has been a national landmark since 1973.

7. Finger Lakes

Take the short drive to the Finger Lakes Regions where I suggest you spend a few days.

Fun Fact: The name “Finger Lakes” comes from the finger shape of two lakes Seneca and Cayuga, which are some of the deepest in the US.

The area is also famed for its wine vineyards, with over 100 in the area! You will also find boat cruises, farmers markets and a variety of Museums.

If you need some driving inspiration head to Watkins Glen International racing circuit

Finger Lakes New York

8. Gilbertsville (Otsego County)

With a population of just 399 people, according to a 2010 census, Gilbertsville is a tiny village located in the scenic Butternut valley, just a short drive from Unadilla, NY.

The village of Gilbertsville was added to the National Register of Historic Places in May 1983, making it a unique district to visit. Be sure to check out:

The Major’s Inn, a medieval English Tudor & Gothic Building, which is open seasonally & hosts many special events.

Wagner Farm State Forest offers over 450 acres, with hunting & trapping allowed during appropriate seasons.

9. Milford (Otsego County)

Just nine miles south of Cooperstown and just a 20 minute drive from Oneonta, NY, you will find Milford. Attractions here include:

  • Cooperstown Brewing Company

Cooperstown Brewing Company is one of many great craft breweries in the Cooperstown area. Here you will find english ales such as Old Slugger, Nine Man Ale and Benchwarmer,

  • Cooperstown & Charlotte Valley Railroad

After a few drinks, you can hop on board the Cooperstown & Charlotte Valley Railroad  for a scenic train ride along the Susquehanna River Valley.

Cooperstown & Charlotte Valley Railroad

  • The Murdock & Murdock Gallery

Here you will find artwork from old legends to modern contemporaries. They also sell American, European paintings, bronze, marble and even Tiffany lamps!

  • Raspberry picking at Middlefield Orchard

Pick apples, apples, pears, strawberries, blueberries & sweet corn at Middlefield Orchard, just a short 10 miles north in Middlefield, NY.

10. Coopers town (Otsego County)

Cooperstown in Ostego County is a quaint village area which packs a big punch in New York state. Baseball fans will know the town as home of National Baseball Hall of Fame which celebrates the legendary players & managers from yesteryear.

Many choose to head down to Doubleday Field, to watch a ball game!  Head along the charming main street to find plenty of quaint shops & great restaurants.

If your into some culture why not check out the world renowned Fenimore Art Museum and The Farmers’ Museum.

Winter Festivals?

If your here during the winter time be sure to check out seasonal performances at The Glimmerglass Opera Festival

Outdoor activities:

If you fancy heading outdoors then head to Glimmerglass State Parka 593 acre which offers year round activities including swimming and camping on the wood lined shores.

Hyde Hall:

Hyde Hall, is 50-room mansion which acts as a 19th century museum, of a bygone era when powerful english families had vast estates in their former colonies. The house is considered one of the finest examples of neoclassic country mansions anywhere in the United States.

Essential Road Trip Tips:

Make sure you are equip with some great Photography Gear![/caption]

How to get the best car rental Deals?

Check out: Ultimate Car Rental Travel Hacks!

For RV Rentals we always use: RV Share

Bring your RV to Tiden Park.

Want more info on Otego County & Niagara falls?

Check out: New York City to Niagara falls Road trip!

Tobi Miles
Article updated:
March 28, 2024
A nomadic wordsmith savoring the world's flavors and penning stories that turn every journey into an epic.
Find me on Twitter

Win a $500 Flight!

Thank you! Your submission has been received!
Oops! Something went wrong while submitting the form.
*Terms apply. To participate, enter your email to sign up for the newsletter . You must be 18+ and be a resident of the US. No purchase necessary. Begins January 1st  and ends February 28th, 2024. Winner announced on March 31st. For full rules and regulations, visit our Terms & Conditions page. Data  processed according to our Privacy Policy.
Enter Sweepstakes

You may also like...


Win a $500 Flight!

Thank you! Your submission has been received!
Oops! Something went wrong while submitting the form.
*Terms apply. To participate, enter your email to sign up for the newsletter . You must be 18+ and be a resident of the US. No purchase necessary. Begins January 1st  and ends February 28th, 2024. Winner announced on March 31st. For full rules and regulations, visit our Terms & Conditions page. Data  processed according to our Privacy Policy.
Enter Sweepstakes