42 days in New York City, Chicago & Indianapolis Itinerary

42 days in New York City, Chicago & Indianapolis Itinerary

Created using Inspirock United States tour planner

Plan created by another user. Make it yours

Route & dates

1
New York City
— 16 nights
2
Chicago
— 14 nights
3
Indianapolis
— 10 nights

16
nights
New York City

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.
Give yourself a bit of retail therapy at Fifth Avenue and SoHo. Your inner history buff will appreciate 9/11 Memorial and Ellis Island. You'll find plenty of places to visit near New York City: Shinnecock East County Park (in Southampton), Cloverdale Farm County Park (in Barnegat) and Edwin B. Forsythe National Wildlife Refuge (in Oceanville). Next up on the itinerary: wander the streets of Times Square, pause for some serene contemplation at St. Patrick's Cathedral, enjoy the sand and surf at Cupsogue Beach County Park, and stroll through Ponquogue Beach.

For ratings, photos, more things to do, and more tourist information, use the New York City trip itinerary planning site.

Lagos, Nigeria to New York City is an approximately 15.5-hour flight. Due to the time zone difference, you'll gain 6 hours traveling from Lagos to New York City. July in New York City sees daily highs of 35°C and lows of 26°C at night. Wrap up your sightseeing on the 30th (Thu) early enough to travel to Chicago.

Things to do in New York City

Parks · Outdoors · Museums

Side Trips

Southampton, Westhampton Beach, Ocean Grove Beach, Bliss Price Arboretum and Wildlife Sanctuary, 8th Ave Jetty
Highlights from your plan
Central Park ©
Central Park
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art
9/11 Memorial ©
9/11 Memorial

14
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Let the collections at The Art Institute of Chicago and Chicago Cultural Center capture your imagination. The Magnificent Mile and Illinois Holocaust Museum & Education Center are good opportunities to explore the local culture. Explore Chicago's surroundings by going to Atwater Park & Beach (in Shorewood), Weko Beach Park (in Bridgman) and Grant Park (in South Milwaukee). There's still lots to do: get a taste of the local shopping with Ernest Hemingway Birthplace, enjoy the sand and surf at Kathy Osterman Beach, get curious at Museum of Science and Industry, and stroll through Rosewood Beach.

To see other places to visit, more things to do, and other tourist information, go to the Chicago day trip planning app.

Fly from New York City to Chicago in 5 hours. Alternatively, you can drive; or take a bus. Due to the time zone difference, you'll gain 1 hour traveling from New York City to Chicago. Traveling from New York City in July, you can expect nighttime temperatures to be slightly colder in Chicago, with lows of 22°C. Finish your sightseeing early on the 13th (Thu) so you can drive to Indianapolis.

Things to do in Chicago

Parks · Outdoors · Beaches

Side Trips

Saint Joseph, Highland Park, Skokie, Oak Park, Oak Savannah Trail
Highlights from your plan
The Magnificent Mile ©
The Magnificent Mile
The Art Institute of Chicago ©
The Art Institute of Chicago
Museum of Science and Industry ©
Museum of Science and Industry

10
nights
Indianapolis

Indianapolis ©
Indiana's capital and most populous city, Indianapolis is best known for its racecar events and impressive museums, and as the hometown of Kurt Vonnegut.
Satisfy your inner culture vulture at Spring Mill State Park and Mallow Run Winery. Take a break from the city and head to Exotic Feline Rescue Center and Mary Gray Bird Sanctuary. Explore the numerous day-trip ideas around Indianapolis: Dayton (Dayton Dragons Baseball & America's Packard Museum - The Citizens Motorcar Co.), Starve Hollow State Recreation Area (in Vallonia) and Goose Pond Fish and Wildlife Area (in Linton). There's still lots to do: contemplate the waterfront views at Sodalis Nature Park, identify plant and animal life at Lilly Nature Center, get outside with Morgan's Outdoor Adventures, Inc., and stroll through Monon Trail.

To find out how to plan a trip to Indianapolis, use our trip itinerary maker.

Traveling by car from Chicago to Indianapolis takes 3.5 hours. Alternatively, you can fly; or take a bus. You'll lose 1 hour traveling from Chicago to Indianapolis due to the time zone difference. In August, daily temperatures in Indianapolis can reach 34°C, while at night they dip to 21°C. Cap off your sightseeing on the 23rd (Sun) early enough to travel back home.

Things to do in Indianapolis

Parks · Outdoors · Wildlife

Side Trips

Brookville, Dayton, Cardinal Greenway, Donaldson's Finer Chocolates, Lilly Nature Center
Highlights from your plan
Exotic Feline Rescue Center ©
Exotic Feline Rescue Center
Starve Hollow State Recreation Area ©
Starve Hollow State Recreation Area
Spring Mill State Park ©
Spring Mill State Park