21 days in Chicago, Florida & New York City Itinerary

21 days in Chicago, Florida & New York City Itinerary

Created using Inspirock United States trip planner

Plan created by another user.Make it yours

Route & dates

1
Chicago
— 3 nights
2
Big Pine Key
— 1 day
3
Marathon
— 1 night
4
Miami
— 2 nights
5
Orlando
— 5 nights
6
New York City
— 5 nights

3
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Get a sense of the local culture at The Magnificent Mile and Field Museum. Kids will appreciate attractions like The Art Institute of Chicago and Museum of Science and Industry. Next up on the itinerary: admire nature's wide array of creatures at Shedd Aquarium, stroll around Milton Lee Olive Park, stop by Wicker Park, and don't miss a visit to Millennium Park.

To see other places to visit, more things to do, ratings, and more tourist information, go to the Chicago online trip itinerary builder.

Manama, Bahrain to Chicago is an approximately 20-hour flight. You'll gain 9 hours traveling from Manama to Chicago due to the time zone difference. In March, Chicago is much colder than Manama - with highs of °C and lows of °C. Finish your sightseeing early on the 24th (Sun) to allow enough time to travel to Big Pine Key.

Things to do in Chicago

Museums Childrens Museums Shopping

Side Trip

Schaefer's Wines and Liquors
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Museum of Science and Industry ©
Museum of Science and Industry
Field Museum ©
Field Museum

1
day
Big Pine Key

Big Pine Key ©
Big Pine Key is a census-designated place and unincorporated community in Monroe County, Florida, United States, on an island of the same name in the Florida Keys. Kick off your visit on the 25th (Mon): enjoy the sand and surf at Calusa Beach and then enjoy the sand and surf at Bahia Honda State Park.

To find traveler tips, photos, maps, and more tourist information, refer to the Big Pine Key road trip planner.

You can fly from Chicago to Big Pine Key in 6.5 hours. Alternatively, you can drive; or take a bus. Traveling from Chicago to Big Pine Key, you'll lose 1 hour due to the time zone difference. Expect warmer temperatures when traveling from Chicago in March; daily highs in Big Pine Key reach °C and lows reach °C. Wrap up your sightseeing on the 25th (Mon) early enough to drive to Marathon.

Things to do in Big Pine Key

Outdoors Parks Beaches
Highlights from your plan
Bahia Honda State Park ©
Bahia Honda State Park

1
night
Marathon

Marathon ©
A tiny city just 16 km (10 mi) long, Marathon is spread across several islands in the middle of the Florida Keys.
Start off your visit on the 26th (Tue): enjoy the sand and surf at Anne's Beach, see the interesting displays at Crane Point Museum & Nature Center, thenkick back and relax at Sombrero Beach, and finally look for gifts at Bayshore Clothing.

For other places to visit, more things to do, maps, and more tourist information, read our Marathon day trip site.

Marathon is very close to Big Pine Key. In March in Marathon, expect temperatures between °C during the day and °C at night. Finish your sightseeing early on the 26th (Tue) to allow enough time to drive to Miami.

Things to do in Marathon

Parks Outdoors Beaches

Side Trip

Anne's Beach
Highlights from your plan
Sombrero Beach ©
Sombrero Beach
Crane Point Museum & Nature Center ©
Crane Point Museum & Nature Center
Anne's Beach ©
Anne's Beach

2
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.
Kick off your visit on the 27th (Wed): shop like a local with Aventura Mall and then wander the streets of Lincoln Road. Get ready for a full day of sightseeing on the 28th (Thu): get a taste of the local shopping with Collins Avenue, thenappreciate the extensive heritage of Art Deco Historic District, and then stroll through South Beach.

To see traveler tips, maps, reviews, and other tourist information, go to the Miami road trip website.

Traveling by car from Marathon to Miami takes 2.5 hours. Alternatively, you can take a bus; or fly. In March, plan for daily highs up to °C, and evening lows to °C. Finish up your sightseeing early on the 28th (Thu) so you can travel to Orlando.

Things to do in Miami

Shopping Neighborhoods Historic Sites

Side Trips

Miami Beach, Aventura Mall
Highlights from your plan
Lincoln Road ©
Lincoln Road
Art Deco Historic District ©
Art Deco Historic District
Aventura Mall ©
Aventura Mall

5
nights
Orlando

Orlando ©
For most people, any mention of Orlando immediately conjures up images of sprawling theme parks filled with characters plucked right out of popular animated movies.
Attractions like Walt Disney World Resort and Universal's Islands of Adventure make great kid-friendly stops. Have a day of magic on the 1st (Mon) at Magic Kingdom Park. Pack the 2nd (Tue) with family-friendly diversions at Universal Orlando Resort. Next up on the itinerary: make an unforgettable trip to Happily Ever After Fireworks and get in on the family fun at SeaWorld.

To find ratings, maps, other places to visit, and more tourist information, read our Orlando visit planner.

Traveling by flight from Miami to Orlando takes 3.5 hours. Alternatively, you can drive; or take a bus. Traveling from Miami in March, Orlando is a bit cooler at night with lows of °C. Finish up your sightseeing early on the 2nd (Tue) so you can travel to New York City.

Things to do in Orlando

Theme Parks Nightlife
Highlights from your plan
Magic Kingdom Park ©
Magic Kingdom Park
Walt Disney World Resort ©
Walt Disney World Resort
Universal's Islands of Adventure ©
Universal's Islands of Adventure

5
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.
Satisfy your inner culture vulture at The Metropolitan Museum of Art and Statue of Liberty National Monument. Attractions like Times Square and Central Park make great kid-friendly stops. There's still lots to do: admire the landmark architecture of Empire State Building, look for gifts at Tiffany & Co., learn more about the world around you at American Museum of Natural History, and don't miss a visit to Fifth Avenue.

To see ratings, traveler tips, maps, and more tourist information, read our New York City visit planner.

Fly from Orlando to New York City in 6.5 hours. Alternatively, you can drive; or take a bus. Traveling from Orlando in April, things will get much colder in New York City: highs are around °C and lows about °C. Finish your sightseeing early on the 8th (Mon) to allow enough time to travel back home.

Things to do in New York City

Museums Shopping Parks
Highlights from your plan
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art
9/11 Memorial ©
9/11 Memorial
Central Park ©
Central Park

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