28 days in Chicago, Washington DC & New York City Itinerary

28 days in Chicago, Washington DC & New York City Itinerary

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Route & dates

28 days in Chicago, Washington DC & New York City Itinerary

Start: Sydney
Fly:  23​h
1
Chicago
— 6 nights
Fly:  3​h 45​min
2
Washington DC
— 10 nights
Fly:  3​h 30​min
3
New York City
— 9 nights
bus + Fly:  26​h
End: Sydney

6
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Get outdoors at Jasper-Pulaski Fish and Wildlife Area and Potato Creek State Park. For shopping fun, head to The Magnificent Mile or South Bend Farmer's Market. Explore Chicago's surroundings by going to Starved Rock State Park (in Utica), Garwood Orchards (in LaPorte) and Baker Lake Park (in Peru). There's much more to do: stroll through Silver Beach County Park, look for gifts at The Olive Cart, identify plant and animal life at Sarett Nature Center, and hike along Grand Mere State Park.

To see more things to do, other places to visit, traveler tips, and more tourist information, refer to the Chicago route planner.

Sydney, Australia to Chicago is an approximately 23-hour flight. You can also do a combination of train and flight. You'll gain 16 hours traveling from Sydney to Chicago due to the time zone difference. Prepare for somewhat warmer weather when traveling from Sydney in July: high temperatures in Chicago hover around 33°C and lows are around 22°C. Cap off your sightseeing on the 7th (Sun) early enough to travel to Washington DC.

Things to do in Chicago

Parks Outdoors Nature

Side Trips

Saint Joseph, Grand Mere State Park, Potato Creek State Park, Baker Lake Park, South Bend Farmer's Market
Highlights from your plan
Starved Rock State Park ©
Starved Rock State Park
The Art Institute of Chicago ©
The Art Institute of Chicago

10
nights
Washington DC

Washington DC ©
The capital of the United States, the District of Columbia contains the lion's share of the country's most treasured monuments, memorials, and public museums.
Bring the kids along to Smithsonian National Museum of Natural History and National Zoological Park. Step out of the city life by going to Skyline Drive and Antietam National Battlefield. Change things up with these side-trips from Washington DC: The Christmas Haus (in New Oxford), Gettysburg (Gettysburg Museum & Visitor Center & Gettysburg National Military Park) and Harpers Ferry National Historical Park (in Harpers Ferry). And it doesn't end there: view the masterpieces at R.H. Ballard Shop & Gallery, look for all kinds of wild species at Elizabeth Furnace Recreation Area, stroll the grounds of Arlington National Cemetery, and examine the collection at United States Holocaust Memorial Museum.

For where to stay, photos, reviews, and other tourist information, use the Washington DC trip maker .

Traveling by flight from Chicago to Washington DC takes 4 hours. Alternatively, you can do a combination of flight and train; or drive. The time zone changes from Central Standard Time to Eastern Standard Time, which is usually a 1 hour difference. Traveling from Chicago in July, things will get somewhat warmer in Washington DC: highs are around 37°C and lows about 26°C. Finish your sightseeing early on the 17th (Wed) to allow enough time to travel to New York City.

Things to do in Washington DC

Parks Historic Sites Nature

Side Trips

Gettysburg, Strasburg, Shenandoah National Park, Moving Meadows Farm, Orr's Farm Market
Highlights from your plan
Skyline Drive ©
Skyline Drive
Antietam National Battlefield ©
Antietam National Battlefield
Gettysburg National Military Park ©

9
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.
Explore hidden gems such as Sam's Point Preserve and Quogue Wildlife Refuge. Museum-lovers will get to explore The Metropolitan Museum of Art and 9/11 Memorial. Get out of town with these interesting New York City side-trips: Ponquogue Beach (in Hampton Bays), Alex Ferrone Gallery (in Cutchogue) and Golden Fish Gallery (in Milford). There's still lots to do: take a stroll through Fifth Avenue, get a new perspective on nature at American Museum of Natural History, make a trip to Empire State Building, and examine the collection at New York Public Library.

To see photos, ratings, maps, and more tourist information, use the New York City road trip site .

Getting from Washington DC to New York City by flight takes about 3.5 hours. Other options: do a combination of flight and bus; or drive. In July, daily temperatures in New York City can reach 35°C, while at night they dip to 26°C. Finish your sightseeing early on the 26th (Fri) so you can travel back home.

Things to do in New York City

Parks Shopping Museums

Side Trips

Quogue Wildlife Refuge, Sam's Point Preserve, St. James General Store, Golden Fish Gallery, Cupsogue Beach County Park
Highlights from your plan
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art
9/11 Memorial ©
9/11 Memorial
New York Public Library ©
New York Public Library

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