58 days in Key West, New York City & Chicago Itinerary

58 days in Key West, New York City & Chicago Itinerary

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Route & dates

58 days in Key West, New York City & Chicago Itinerary

Start: Anaheim
Drive:  48​h
1
Key West
— 2 nights
Drive:  25​h
2
New York City
— 28 nights
Drive:  13​h 15​min
3
Chicago
— 22 nights
Drive:  32​h
End: Anaheim

2
nights
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.
On the 15th (Thu), see the interesting displays at The Ernest Hemingway Home and Museum, look for all kinds of wild species at Key West Butterfly & Nature Conservatory, get interesting insight from Tours, then take a leisurely stroll along Mallory Square, and finally pause for some photo ops at Florida Keys Historical Military Memorial. Keep things going the next day: get a new perspective on things with Boat Tours & Water Sports, don't miss a visit to Southernmost Point, then don't miss a visit to Duval Street, and finally stroll the grounds of Key West Cemetery.

To see ratings, traveler tips, and other tourist information, use the Key West travel planner.

Anaheim to Key West is an approximately 10-hour flight. You can also do a combination of train and flight; or drive. The time zone difference when traveling from Anaheim to Key West is 3 hours. Traveling from Anaheim in August, expect a bit warmer with lows of 81°F in Key West. Finish up your sightseeing early on the 16th (Fri) so you can travel to New York City.

Things to do in Key West

Outdoors Wildlife Tours
Find places to stay Aug 14 — 16:
Highlights from your plan
Parasailing & Paragliding
The Ernest Hemingway Home and Museum ©

28
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.
You'll find plenty of places to visit near New York City: Bronx Zoo (in Bronx) and Philadelphia (Independence Hall, Philadelphia Museum of Art, & more). There's still lots to do: take in the pleasant sights at Central Park, take in panoramic vistas at Top of the Rock, make a trip to Times Square, and admire the masterpieces at The Metropolitan Museum of Art.

Discover how to plan a New York City trip in just a few steps with Inspirock's itinerary builder.

Traveling by combination of flight and bus from Key West to New York City takes 6 hours. Alternatively, you can fly; or drive. Prepare for slightly colder weather when traveling from Key West in August: high temperatures in New York City hover around 84°F and lows are around 71°F. You'll have a few hours on the 14th (Sat) to wrap things up before traveling to Chicago.

Things to do in New York City

Museums Parks Historic Sites

Side Trips

Philadelphia, Brooklyn, Hoboken Waterfront Walkway, Bronx Zoo
Find places to stay Aug 17 — Sep 14:
Highlights from your plan
Central Park ©
Central Park
Empire State Building ©
Empire State Building
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art

22
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
You'll find plenty of places to visit near Chicago: Deep River County Park (in Hobart), Whiskey Acres Distilling Co. (in DeKalb) and Sandy Acres Clydesdales (in LaPorte). There's lots more to do: admire the masterpieces at The Art Institute of Chicago, take in the local highlights with Walking tours, take a leisurely stroll along Navy Pier, and get up close and personal with brilliant marine life at Shedd Aquarium.

To find other places to visit, photos, reviews, and more tourist information, read our Chicago trip planner .

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. Traveling from New York City in September, plan for a bit cooler nights in Chicago, with lows around 61°F. Finish your sightseeing early on the 6th (Sun) to allow enough time to travel back home.

Things to do in Chicago

Parks Museums Historic Sites

Side Trips

Oak Park, South Bend, Saint Joseph, Wheaton, Evanston
Find places to stay Sep 14 — Oct 6:
Highlights from your plan
Whiskey Acres Distilling Co. ©
Whiskey Acres Distilling Co.
The Art Institute of Chicago ©
The Art Institute of Chicago
Museum of Science and Industry ©
Museum of Science and Industry

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