New York to Chicago Road Trip

18-to-Thirtysomethings, New York City to Chicago
Image by G Adventures

Information from G Adventures

Tour description

The Big Apple, Finger Lakes, a Windy City, and some waterfalls that are so famous they don’t need a nickname – welcome to the most jam-packed week-long road trip in America. Experience skyscrapers, music, and street life in two of the coolest cities in the US and breathe in the fresh air in upstate New York. We’ll even throw in Niagara Falls for good measure. You’ll stay in the heart of the cities, and camping will keep you snug in the region's wild heart. Quick and affordable – how’s that for a great deal?

What's included

  • Your Welcome Moment: Meet Your CEO and Group
  • Entrance fees to all state parks
  • Maid of the Mist boat tour (Niagara Falls)
  • Amish community visit
  • Self-inflating mattresses and dome tents while camping
  • All transport between destinations and to/from included activities


  • See the sights in new york city
  • Feel the spray of niagara falls
  • Revel in the beauty of the finger lakes
  • Sample chicago-style deep-dish pizza.


Day 1: New York City Arrive at any time. Consider arriving a few days early to see more of this famous city.

Day 2: New York City/Newburgh Spend the morning exploring the Big Apple before heading to Newburgh.

Day 3: Newburgh/Finger Lakes Enjoy a day out in nature taking in the natural beauty of the Finger Lakes region. Visit towering Taughannock Falls, cool off in the lake, or sample wine from a local winery.

Day 4: Finger Lakes/Niagara Falls Get wet on the Maid of the Mist boat tour, and be sure to check out the falls illuminated in the evening.

Day 5: Niagara Falls/Sandusky Travel to Sandusky and opt to catch some thrills at a local amusement park.

Day 6: Sandusky/Chicago Stop for lunch in the Amish community of Shipshewana before continuing on to Chicago. Trip ends upon arrival to Chicago.