12 days in Chicago, Boston & New York State Itinerary

12 days in Chicago, Boston & New York State Itinerary

Created using Inspirock United States travel route builder

This plan was created by another user.  Make it your plan

Route & dates

12 days in Chicago, Boston & New York State Itinerary

Start: Auckland
Fly:  20​h 15​min
1
Chicago
— 3 nights
Fly:  4​h
2
Boston
— 5 nights
Fly + bus:  5​h 15​min
3
Niagara Falls
— 2 nights
bus + Fly:  23​h 15​min
End: Auckland

3
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Visiting Lakefront Trail and Starved Rock State Park will get you outdoors. Chicago Riverwalk and Milwaukee Art Museum are good opportunities to explore the local culture. When in Chicago, make a side trip to see Harley-Davidson Museum in Milwaukee, approximately 1h 45 min away. There's still lots to do: explore the activities along Chicago River, admire the local landmark of Crown Fountain, and don't miss a visit to The Magnificent Mile.

To find where to stay, more things to do, and more tourist information, use the Chicago vacation maker app .

Auckland, New Zealand to Chicago is an approximately 20.5-hour flight. You can also do a combination of bus and flight. The time zone difference when traveling from Auckland to Chicago is minus 18 hours. When traveling from Auckland in September, plan for much warmer days and somewhat warmer nights in Chicago: temperatures range from 30°C by day to 19°C at night. Finish your sightseeing early on the 20th (Fri) to allow enough time to travel to Boston.

Things to do in Chicago

Parks Trails Outdoors

Side Trips

Milwaukee, Starved Rock State Park
Highlights from your plan
Chicago Riverwalk ©
Chicago Riverwalk
Starved Rock State Park ©
Starved Rock State Park
Lakefront Trail ©
Lakefront Trail

5
nights
Boston

Boston ©
Rich in museums, restaurants, shops, and historical sites, Boston attracts over 16 million visitors each year. New England's largest and most influential city, Boston ranks among the world's major centers of education and culture.
Get some cultural insight at Old North Church & Historic Site and Waterfront. Eschew the tourist crowds and head to Beacon Hill and The Elms. Get out of town with these interesting Boston side-trips: Newport (Cliff Walk, The Breakers, & more), Purgatory Chasm (in Middletown) and Ogunquit (Perkins Cove & Marginal Way Walkway). And it doesn't end there: enjoy the sea views from Nubble Lighthouse, explore the different monuments and memorials at Granary Burying Ground, indulge your thirst for a good beer at Samuel Adams Brewery, and get engrossed in the history at USS Constitution Museum.

To see more things to do, reviews, other places to visit, and more tourist information, refer to the Boston trip planner.

You can fly from Chicago to Boston in 4 hours. Other options are to do a combination of flight and bus; or drive. The time zone difference when traveling from Chicago to Boston is 1 hour. In September, plan for daily highs up to 28°C, and evening lows to 17°C. Finish your sightseeing early on the 25th (Wed) so you can travel to Niagara Falls.

Things to do in Boston

Historic Sites Neighborhoods Museums

Side Trips

Newport, Ogunquit, Nubble Lighthouse, Purgatory Chasm
Highlights from your plan
Waterfront ©
Waterfront
Perkins Cove ©
Perkins Cove
The Elms
The Elms

2
nights
Niagara Falls

Niagara Falls ©
The city of Niagara Falls houses the U.S.
Kick off your visit on the 26th (Thu): contemplate the long history of Frank Lloyd Wright's Darwin D. Martin House Complex, then Head underground at Cave of the Winds, and then take in the dramatic scenery at Niagara Falls.

To see traveler tips, reviews, ratings, and more tourist information, go to the Niagara Falls trip itinerary builder website .

You can do a combination of flight and bus from Boston to Niagara Falls in 5.5 hours. Alternatively, you can do a combination of flight and train; or drive. September in Niagara Falls sees daily highs of 28°C and lows of 15°C at night. Wrap up your sightseeing on the 27th (Fri) to allow time to travel back home.

Things to do in Niagara Falls

Parks Nature Historic Sites

Side Trip

Frank Lloyd Wright's Darwin D. Martin House Complex
Highlights from your plan
Cave of the Winds ©
Cave of the Winds
Niagara Falls ©
Niagara Falls

Similar Plans

16 days in United States BY A USER FROM UNITED STATES September, culture, beaches, historic sites, museums, shopping, wildlife, popular sights PREFERENCES: September, culture, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 15 days in Massachusetts & Maine BY A USER FROM FRANCE August, teens, kids, popular sights PREFERENCES: August, teens, kids ATTRACTION STYLE: Popular sights PACE: Medium 15 days in United States BY A USER FROM UNITED KINGDOM July, teens, kids, popular sights PREFERENCES: July, teens, kids ATTRACTION STYLE: Popular sights PACE: Medium 15 days in New York State & Washington DC BY A USER FROM UNITED KINGDOM July, teens, kids, popular sights PREFERENCES: July, teens, kids ATTRACTION STYLE: Popular sights PACE: Medium 16 days in United States BY A USER FROM UNITED STATES April, teens, kids, popular sights PREFERENCES: April, teens, kids ATTRACTION STYLE: Popular sights PACE: Medium 13 days in Chicago & New Orleans BY A USER FROM NEW ZEALAND October, outdoors, museums, shopping, popular sights PREFERENCES: October, outdoors, museums, shopping ATTRACTION STYLE: Popular sights PACE: Medium 15 days in Chicago BY A USER FROM BELGIUM July, teens, popular sights PREFERENCES: July, teens ATTRACTION STYLE: Popular sights PACE: Medium 15 days in Iowa, Wisconsin & Chicago BY A USER FROM UNITED STATES August, kids, popular sights PREFERENCES: August, kids ATTRACTION STYLE: Popular sights PACE: Medium 13 days in Huntsville, Chicago & South Haven BY A USER FROM INDIA September, culture, beaches, museums, shopping, wildlife, popular sights PREFERENCES: September, culture, beaches, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 15 days in New York City, Boston & New Orleans BY A USER FROM NEW ZEALAND September, kids, popular sights PREFERENCES: September, kids ATTRACTION STYLE: Popular sights PACE: Medium
View more plans