14 days in Chicago, New York City & Miami Itinerary

14 days in Chicago, New York City & Miami Itinerary

Created using Inspirock United States holiday planner

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Route & dates

14 days in Chicago, New York City & Miami Itinerary

Start: Sydney
Fly:  23​h
1
Chicago
— 3 nights
Fly + bus:  4​h 45​min
2
New York City
— 4 nights
Fly:  5​h 45​min
3
Miami
— 4 nights
Fly:  25​h
End: Sydney

3
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
On the 12th (Sun), pause for some photo ops at Cloud Gate and then explore and take pictures at Millennium Park. On your second day here, take a stroll through The Magnificent Mile, then explore the world behind art at The Art Institute of Chicago, and then tour the pleasant surroundings at Ohio Street Beach.

Plan a trip to Chicago easily and quickly by telling Inspirock to suggest an itinerary.

Sydney, Australia to Chicago is an approximately 23-hour flight. You can also do a combination of train and flight. The time zone changes from Australian Eastern Standard Time (New South Wales) to Central Standard Time, which is usually a -16 hour difference. Traveling from Sydney in August, things will get a bit warmer in Chicago: highs are around 33°C and lows about 22°C. Finish your sightseeing early on the 15th (Wed) so you can travel to New York City.

Things to do in Chicago

Parks Beaches Outdoors

Side Trip

Whihala Beach
Highlights from your plan
Millennium Park ©
Millennium Park
The Art Institute of Chicago ©
The Art Institute of Chicago
The Magnificent Mile ©
The Magnificent Mile

4
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.
Appreciate the collections at The Metropolitan Museum of Art and 9/11 Memorial. Head to Fifth Avenue and Economy Candyfor plenty of shopping. Venture out of the city with trips to Gateway National Recreation (in Sandy Hook) and Bronx Zoo (in Bronx). Next up on the itinerary: wander the streets of Times Square, contemplate the long history of Ellis Island, pause for some serene contemplation at St. Patrick's Cathedral, and tour the water at your own pace with Narwhal Yacht Charters.

To see ratings, more things to do, maps, and more tourist information, read New York City journey maker site .

Traveling by combination of flight and bus from Chicago to New York City takes 5 hours. Alternatively, you can fly; or drive. The time zone difference when traveling from Chicago to New York City is 1 hour. In August, plan for daily highs up to 34°C, and evening lows to 25°C. Wrap up your sightseeing on the 19th (Sun) early enough to travel to Miami.

Things to do in New York City

Museums Parks Historic Sites

Side Trips

Bronx Zoo, Gateway National Recreation
Highlights from your plan
Fifth Avenue ©
Fifth Avenue
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art
9/11 Memorial ©
9/11 Memorial

4
nights
Miami

Miami ©
Florida’s mecca of fun in the sun, the lively tropical metropolis of Miami is one of the world’s top vacation spots.
For shopping fun, head to Lincoln Road or Aventura Mall. Get a sense of the local culture at Art Deco Historic District and Ocean Drive. You'll find plenty of places to visit near Miami: Fort Lauderdale Beach (in Fort Lauderdale) and Everglades National Park (Shark Valley & Anhinga Trail). The adventure continues: kick back and relax at South Beach, see the interesting displays at Vizcaya Museum and Gardens, explore the world behind art at The Wolfsonian - Florida International University, and shop like a local with Bayside Marketplace.

To find where to stay, maps, traveler tips, and more tourist information, refer to the Miami trip itinerary planner.

Traveling by combination of bus, flight, and tram from New York City to Miami takes 6 hours. Alternatively, you can do a combination of flight and tram; or drive. Traveling from New York City in August, things will get somewhat warmer in Miami: highs are around 38°C and lows about 30°C. On the 23rd (Thu), you'll have the morning to explore before heading back home.

Things to do in Miami

Parks Outdoors Wildlife

Side Trips

Miami Beach, Everglades National Park, Aventura Mall, Fort Lauderdale Beach
Highlights from your plan
Shark Valley Visitor Center ©
Shark Valley Visitor Center
Anhinga Trail ©
Anhinga Trail
Lincoln Road ©
Lincoln Road

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