20 days in Chicago & East Coast of USA Itinerary

20 days in Chicago & East Coast of USA Itinerary

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Route & dates

20 days in Chicago & East Coast of USA Itinerary

Start: New Delhi
Fly:  17​h 45​min
1
Chicago
— 2 nights
Fly:  5​h 45​min
2
Key West
— 1 night
bus:  45​min
3
Big Pine Key
— 2 nights
Drive:  1​h 45​min
4
Key Largo
— 2 nights
Drive:  1​h 15​min
5
Miami
— 3 nights
Fly:  5​h 30​min
6
New York City
— 2 nights
Drive:  5​h 30​min
7
Eastham
— 3 nights
Fly:  25​h
End: New Delhi

2
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
On the 12th (Wed), make a trip to Skydeck Chicago - Willis Tower. On the 13th (Thu), you'll have a packed day of sightseeing: contemplate in the serene atmosphere at Fourth Presbyterian Church, then admire nature's wide array of creatures at Lincoln Park Zoo, then appreciate the extensive heritage of Millennium Park, and finally explore the world behind art at The Art Institute of Chicago.

For reviews, more things to do, photos, and tourist information, read our Chicago day trip website .

New Delhi, India to Chicago is an approximately 18-hour flight. You can also do a combination of train and flight. The time zone difference moving from India Standard Time (IST) to Central Standard Time (CST) is minus 11 hours. When traveling from New Delhi in June, plan for cooler days in Chicago, with highs around 32°C, while nights are little chillier with lows around 20°C. Finish your sightseeing early on the 14th (Fri) to allow enough time to travel to Key West.

Things to do in Chicago

Museums Parks Childrens Museums
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
The Field Museum ©
The Field Museum
Museum of Science and Industry ©
Museum of Science and Industry

1
night
Key West

Located just 140 km (90 mi) from Cuba, Key West is an island only about 6.4 km (4 mi) long and 1.6 km (1 mi) wide.
Start off your visit on the 15th (Sat): get up close to creatures of the deep with a dolphin and whale watching tour, identify plant and animal life at Key West Butterfly & Nature Conservatory, then view the masterpieces at 7 Artists & Friends, and finally glide through the air with a parasailing or paragliding tour. Here are some ideas for day two: glide peacefully along the water with some of the best stand-up paddleboarding in the area, cast your line with a fishing tour, and then explore the different monuments and memorials at Key West Cemetery.

To see where to stay, reviews, more things to do, and other tourist information, use the Key West visit planner .

Fly from Chicago to Key West in 6 hours. Alternatively, you can drive; or do a combination of bus and shuttle. The time zone difference when traveling from Chicago to Key West is 1 hour. In June, Key West is a bit warmer than Chicago - with highs of 36°C and lows of 30°C. Wrap up your sightseeing on the 16th (Sun) early enough to take a bus to Big Pine Key.

Things to do in Key West

Tours Outdoors Wildlife
Highlights from your plan
Stand-Up Paddleboarding
Dolphin & Whale Watching

2
nights
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. On the 17th (Mon), identify plant and animal life at National Key Deer Refuge and then take a memorable tour with Tours. Get ready for a full day of sightseeing on the 18th (Tue): find your balance on the water with some of the best stand-up paddleboarding in the area and then tour the pleasant surroundings at Bahia Honda State Park.

For other places to visit, maps, ratings, and more tourist information, read Big Pine Key driving holiday planning tool .

Traveling by bus from Key West to Big Pine Key takes an hour. Alternatively, you can drive. June in Big Pine Key sees daily highs of 38°C and lows of 30°C at night. Wrap up your sightseeing on the 18th (Tue) to allow time to drive to Key Largo.

Things to do in Big Pine Key

Outdoors Tours Wildlife
Highlights from your plan
Bahia Honda State Park ©
Bahia Honda State Park
Fishing Charters & Tours
Stand-Up Paddleboarding

2
nights
Key Largo

The northernmost island of the Florida Keys, Key Largo provides stunning scenery, a number of watersports opportunities, and plenty of areas to relax on vacation.
Start off your visit on the 19th (Wed): look for all kinds of wild species at Florida Keys Wild Bird Rehabilitation Center, get a new perspective on things with Boat Tours & Water Sports, and then get a new perspective on things with Boat Tours & Water Sports. On the 20th (Thu), you'll have a packed day of sightseeing: see the vivid underwater world at Spiegel Grove and then get a new perspective on things with Boat Tours & Water Sports.

For maps, where to stay, ratings, and other tourist information, you can read our Key Largo tour itinerary maker .

Drive from Big Pine Key to Key Largo in 2 hours. Alternatively, you can take a bus. In June, daily temperatures in Key Largo can reach 36°C, while at night they dip to 28°C. Finish your sightseeing early on the 20th (Thu) so you can drive to Miami.

Things to do in Key Largo

Wildlife Tours Outdoors

Side Trip

Islamorada
Highlights from your plan
Fishing Charters & Tours
Scuba & Snorkeling

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.
Step out of the city life by going to Shark Valley and Gumbo Limbo Trail. Relax by the water at South Beach and 12th Street Beach. Explore the numerous day-trip ideas around Miami: Everglades National Park (Slough Slog & Pineland Trail). Next up on the itinerary: get some thrills out on the water with a waterskiing or jet-skiing adventure and get a new perspective on things with Boat Tours & Water Sports.

For reviews, maps, more things to do, and other tourist information, go to the Miami route builder website .

Traveling by car from Key Largo to Miami takes 1.5 hours. Alternatively, you can take a bus. In June, daily temperatures in Miami can reach 37°C, while at night they dip to 29°C. Wrap up your sightseeing on the 23rd (Sun) early enough to travel to New York City.

Things to do in Miami

Outdoors Parks Trails

Side Trips

Everglades National Park, Miami Beach
Highlights from your plan
Shark Valley ©
Shark Valley
Gumbo Limbo Trail ©
Gumbo Limbo Trail
South Beach ©
South Beach

2
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.
Your cultural itinerary includes sights like The Metropolitan Museum of Art and Times Square. There's still lots to do: go for a walk through Central Park, see the interesting displays at New York Public Library, make a trip to Empire State Building, and pause for some photo ops at 9/11 Memorial.

For more things to do, traveler tips, and tourist information, refer to the New York City itinerary maker app .

You can fly from Miami to New York City in 5.5 hours. Alternatively, you can do a combination of flight and bus; or drive. Plan for slightly colder temperatures traveling from Miami in June, with highs in New York City at 31°C and lows at 21°C. Wrap up your sightseeing on the 26th (Wed) early enough to drive to Eastham.

Things to do in New York City

Museums Parks Historic Sites
Highlights from your plan
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art
9/11 Memorial ©
9/11 Memorial
American Museum of Natural History ©

3
nights
Eastham

Eastham ©
Eastham is a town in Barnstable County, Massachusetts, United States, Barnstable County being coextensive with Cape Cod. Get a sense of the local culture at Chatham Marconi Maritime Center and Salt Pond Visitor Center. Step out of the city life by going to Cape Cod National Seashore and Nauset Beach. There's much more to do: kick back and relax at Nauset Light Beach, stroll through Marconi Beach, and steep yourself in history at First Encounter Beach.

To see photos, more things to do, traveler tips, and other tourist information, read Eastham trip planner .

You can drive from New York City to Eastham in 5.5 hours. Alternatively, you can take a bus. Plan for little chillier temperatures traveling from New York City in June, with highs in Eastham at 26°C and lows at 16°C. On the 30th (Sun), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Eastham

Parks Beaches Outdoors

Side Trips

Chatham, Nauset Beach, Cape Cod National Seashore, Marconi Beach
Highlights from your plan
Chatham Marconi Maritime Center ©
Chatham Marconi Maritime Center
Cape Cod National Seashore ©
Cape Cod National Seashore
Nauset Beach ©
Nauset Beach

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