8 days in Chicago & New York City Itinerary

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.

Chica-GO Off The Beaten Path Tours has been added to your itinerary. On the 8th (Thu), engage your brain at Museum of Science and Industry, then admire the local landmark of Buckingham Fountain, and then explore the world behind art at The Art Institute of Chicago. On your second day here, take in panoramic vistas at 360 Chicago Observation Deck, then savor the flavors at Chica-GO Off The Beaten Path Tours, and then take in panoramic vistas at Skydeck Chicago - Willis Tower.

For traveler tips, maps, and more tourist information, use the Chicago online road trip planner.

New York City to Chicago is an approximately 5-hour flight. You can also drive; or take a bus. The time zone difference when traveling from New York City to Chicago is minus 1 hour. Plan for a bit cooler nights when traveling from New York City in April since evenings lows in Chicago dip to 40°F. Wrap up your sightseeing on the 9th (Fri) early enough to travel to New York City.

Writer Pearl Buck once called New York City “a place apart,” and this giant urban center remains unlike any other in the world.

New York City is known for museums, nightlife, and shopping. Your plan includes some of its best attractions: go for a walk through Central Park, tour the pleasant surroundings at The High Line, take in nature's colorful creations at Brooklyn Botanic Garden, and pause for some photo ops at Statue of Liberty National Monument.

To see reviews, other places to visit, photos, and other tourist information, read New York City online driving holiday planner.

Traveling by flight from Chicago to New York City takes 5 hours. Alternatively, you can drive; or take a bus. Due to the time zone difference, you'll lose 1 hour traveling from Chicago to New York City. In April, daytime highs in New York City are 61°F, while nighttime lows are 45°F. Wrap up your sightseeing on the 14th (Wed) early enough to travel to Chicago.

On the 15th (Thu), engage your brain at Field Museum, observe the fascinating underwater world at Shedd Aquarium, and then don't miss a visit to Millennium Park.

To see traveler tips, reviews, maps, and tourist information, read our Chicago visit planner.

You can fly from New York City to Chicago in 5 hours. Other options are to drive; or take a bus. You'll gain 1 hour traveling from New York City to Chicago due to the time zone difference. Traveling from New York City in April, plan for slightly colder nights in Chicago, with lows around 40°F. Wrap up your sightseeing on the 15th (Thu) to allow time to travel back home.