New York to Chicago Road Trip

18-to-Thirtysomethings, New York City to Chicago

Image by G Adventures

Tour description provided by G Adventures

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

  • 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 to the joining hostel at any time. Welcome meeting at 7:00pm. From the Statue of Liberty to Ground Zero to Chinatown, New York City is full of things to do and see. We recommend spending extra time here; please speak to your sales agent to book pre-trip accommodation. Included Activities: Arrival Day and Welcome Meeting
Day 2 New York City/Newburgh (1D) Dive into the hustle and bustle of NYC on a brief orientation to the city with the CEO, then trade in the big city for a campfire. Additional Notes: This tour departs New York City mid-day on Day 2. Transport: Private Vehicle (3.00 hour(s), 112km)
Day 3 Newburgh/Finger Lakes (1B, 1L, 1D) Discover one of the highest waterfalls east of the Rocky Mountains, Taughannock Falls. Take a hike to explore this beautiful area on foot, rent a kayak or paddleboard, or just relax by the lake. Opt to taste wine from one of the local vineyards. Included Activities: Taughannock Falls Visit Transport: Private Vehicle (6.00 hour(s), 375km)
Day 4 Finger Lakes/Niagara Falls (1B, 1L, 1D) An exciting adventure awaits in Niagara Falls. Feel the rushing waters of the falls taking the famous "Maid of the Mist Boat Tour." Return after darkness settles over the Niagara region and witness the Falls illuminated in a rainbow of colour! Included Activities: Maid of the Mist Tour Transport: Private Vehicle (4.00 hour(s), 190km)
Day 5 Niagara Falls/Sandusky (1B) Travel to Sandusky and opt to catch some thrills at a local amusement park. Transport: Approximate Distance to Sandusky: 430km (267 mi) Private Vehicle (6.00 hour(s))
Day 6 Sandusky/Chicago (1B) There's tons to do in the Windy City – walk along the river to Millennium Park, enjoy dazzling music, and stroll the boardwalk of the Navy Pier. Opt to ride to the top of the Willis (formerly Sears) Tower, or hit the town for a final night out with the group. Additional Notes: Please note this trip ends on arrival to Chicago. We recommend booking post-tour accommodation if you would like to enjoy more of the city. Included Activities: Amish Community Visit Departure Day (Activities) Transport: Private Vehicle (4.00 hour(s), 275km) Private Vehicle (3.50 hour(s), 240km)