New York to Chicago Road Trip

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?

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

Day 2 New York/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.