16 days in Miami, Chicago & New York City Itinerary

16 days in Miami, Chicago & New York City Itinerary

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Route & dates

16 days in Miami, Chicago & New York City Itinerary

Start: Buenos Aires
Fly:  12​h 30​min
1
Miami
— 3 nights
Fly:  5​h 30​min
2
Chicago
— 4 nights
Fly + bus:  4​h 45​min
3
New York City
— 7 nights
bus + Fly:  14​h 45​min
End: Buenos Aires

3
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.
On the 14th (Mon), take a stroll through Lincoln Road, then kick back and relax at South Beach, and then don't miss a visit to Ocean Drive. Here are some ideas for day two: don't miss a visit to Bayside Marketplace, get a taste of the local shopping with Espanola Way, and then kick back and relax at Fort Lauderdale Beach.

For maps, reviews, traveler tips, and more tourist information, refer to the Miami road trip planner.

Buenos Aires, Argentina to Miami is an approximately 12.5-hour combination of flight and tram. You'll gain 2 hours traveling from Buenos Aires to Miami due to the time zone difference. When traveling from Buenos Aires in May, plan for much warmer days and somewhat warmer nights in Miami: temperatures range from 36°C by day to 27°C at night. Finish your sightseeing early on the 16th (Wed) to allow enough time to travel to Chicago.

Things to do in Miami

Parks Outdoors Beaches

Side Trips

Miami Beach, Fort Lauderdale Beach
Highlights from your plan
South Beach ©
South Beach
Lincoln Road ©
Lincoln Road
Fort Lauderdale Beach ©
Fort Lauderdale Beach

4
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Step out of Chicago to go to Saint Joseph and see Silver Beach County Park, which is approximately 1h 40 min away. And it doesn't end there: take a stroll through The Magnificent Mile, don't miss a visit to Buckingham Fountain, stroll through Milton Lee Olive Park, and admire nature's wide array of creatures at Shedd Aquarium.

To find maps, more things to do, where to stay, and other tourist information, use the Chicago travel planner.

Do a combination of bus and flight from Miami to Chicago in 5.5 hours. Alternatively, you can do a combination of bus and flight; or drive. Due to the time zone difference, you'll gain 1 hour traveling from Miami to Chicago. When traveling from Miami in May, plan for a bit cooler days and colder nights in Chicago: temperatures range from 26°C by day to 13°C at night. On the 20th (Sun), you'll have the morning to explore before heading off to New York City.

Things to do in Chicago

Museums Parks Shopping

Side Trip

Silver Beach County Park
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
The Magnificent Mile ©
The Magnificent Mile
Silver Beach County Park ©
Silver Beach County Park

7
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.
Head to Fifth Avenue and Tiffany & Co.for plenty of shopping. Relax by the water at Gateway National Recreation and Jones Beach State Park. Explore the numerous day-trip ideas around New York City: Belmar Beach (in Belmar) and Ocean Grove Beach (in Ocean Grove). The adventure continues: wander the streets of Times Square, appreciate the history behind 9/11 Memorial, explore the world behind art at The Metropolitan Museum of Art, and take in panoramic vistas at Empire State Building.

For other places to visit, reviews, traveler tips, and more tourist information, read our New York City day trip planning website .

You can do a combination of flight and bus from Chicago to New York City in 5 hours. Other options are to do a combination of flight and train; or drive. The time zone difference moving from Central Standard Time to Eastern Standard Time is 1 hour. In May, daytime highs in New York City are 24°C, while nighttime lows are 15°C. Wrap up your sightseeing on the 27th (Sun) to allow time to travel back home.

Things to do in New York City

Parks Outdoors Beaches

Side Trips

Belmar Beach, Ocean Grove Beach, Gateway National Recreation, Jones Beach State Park
Highlights from your plan
Central Park ©
Central Park
Times Square ©
Times Square
Fifth Avenue ©
Fifth Avenue

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