12 days in New York City, Chicago & Miami Itinerary

12 days in New York City, Chicago & Miami Itinerary

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Route & dates

12 days in New York City, Chicago & Miami Itinerary

Start: San Juan, Puerto Rico
Fly + bus:  4​h
1
New York City
— 3 nights
bus + Fly:  5​h
2
Chicago
— 4 nights
Fly:  5​h 30​min
3
Miami
— 4 nights
Fly:  5​h 30​min
End: San Juan, Puerto Rico

3
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.
New York City is known for parks, museums, nightlife, historic sites, and shopping. Your plan includes some of its best attractions: wander the streets of SoHo.

To see maps, reviews, more things to do, and other tourist information, go to the New York City online journey planner .

San Juan, Puerto Rico to New York City is an approximately 7-hour combination of flight and bus. You can also fly; or do a combination of car, flight, and bus. Due to the time zone difference, you'll gain 1 hour traveling from San Juan to New York City. Expect a bit cooler temperatures when traveling from San Juan in September; daily highs in New York City reach 31°C and lows reach 22°C. You'll have a few hours on the 1st (Tue) to wrap things up before traveling to Chicago.

Things to do in New York City

Neighborhoods Shopping
Highlights from your plan
SoHo ©
SoHo

4
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Chicago Riverwalk and Cantigny Park are good opportunities to explore the local culture. You'll explore the less-touristy side of things at Lakefront Trail and Chicago Cultural Center. You'll find plenty of places to visit near Chicago: South Bend (Grotto of Our Lady Lourdes & Basilica of the Sacred Heart), Silver Beach County Park (in Saint Joseph) and Geneva Lake Shore Path (in Lake Geneva). And it doesn't end there: immerse yourself in nature at Starved Rock State Park, explore the world behind art at The Art Institute of Chicago, paddle through the water with a kayaking and canoeing tour, and don't miss a visit to Millennium Park.

For other places to visit, photos, traveler tips, and more tourist information, use the Chicago tour planner.

You can do a combination of bus and flight from New York City to Chicago in 5 hours. Alternatively, you can fly; or drive. The time zone difference when traveling from New York City to Chicago is minus 1 hour. Expect little chillier temperatures when traveling from New York City in October; daily highs in Chicago reach 21°C and lows reach 11°C. Finish up your sightseeing early on the 6th (Sun) so you can travel to Miami.

Things to do in Chicago

Historic Sites Outdoors Parks

Side Trips

South Bend, Baha'i House of Worship, Cantigny Park, Geneva Lake Shore Path, Starved Rock State Park
Highlights from your plan
Lakefront Trail ©
Lakefront Trail
Starved Rock State Park ©
Starved Rock State Park
Chicago Riverwalk ©
Chicago Riverwalk

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.
Lincoln Road and St Patrick Catholic Church will appeal to history buffs. Visiting Bill Baggs Cape Florida State Park and Deering Estate will get you outdoors. Take a break from Miami with a short trip to Spiegel Grove in Key Largo, about 1h 20 min away. Next up on the itinerary: explore the world behind art at Wynwood Walls, zoom along the surf with a waterskiing or jet-skiing adventure, cast your line with a fishing tour, and wander the streets of Wynwood.

Take the guesswork out of planning a Miami vacation by using our trip itinerary maker.

You can fly from Chicago to Miami in 5.5 hours. Other options are to do a combination of flight and bus; or drive. Due to the time zone difference, you'll lose 1 hour traveling from Chicago to Miami. Traveling from Chicago in October, expect Miami to be much hotter, temps between 36°C and 27°C. Wrap up your sightseeing by early afternoon on the 9th (Wed) to allow time for travel back home.

Things to do in Miami

Museums Parks Outdoors

Side Trips

Bill Baggs Cape Florida State Park, Spiegel Grove, Lincoln Road
Highlights from your plan
Lock & Load Museum ©
Lock & Load Museum
Bill Baggs Cape Florida State Park ©
Wynwood Walls ©
Wynwood Walls

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