11 days in Boston, Chicago & Florida Itinerary

11 days in Boston, Chicago & Florida Itinerary

Created using Inspirock United States journey builder

Plan created by another user. Make it yours
1
Boston
— 1 night
2
Chicago
— 3 nights
3
Miami Beach
— 1 day
4
Orlando
— 3 nights

1
night
Boston

Boston ©
Rich in museums, restaurants, shops, and historical sites, Boston attracts over 16 million visitors each year. New England's largest and most influential city, Boston ranks among the world's major centers of education and culture.
Kick off your visit on the 22nd (Mon): catch a live event at Fenway Park, stop by Brookline Booksmith, and then explore the world behind art at Museum of Fine Arts. Get ready for a full day of sightseeing on the 23rd (Tue): get advice or help at Boston Public Library, then admire the natural beauty at Boston Public Garden, then browse the different shops at Faneuil Hall Marketplace, and finally get to know the fascinating history of Freedom Trail.

To see reviews, more things to do, traveler tips, and tourist information, read Boston trip itinerary maker tool.

Chennai, India to Boston is an approximately 23.5-hour flight. The time zone changes from India Standard Time (IST) to Eastern Standard Time (EST), which is usually a -10.5 hour difference. Plan for much colder temperatures traveling from Chennai in October, with highs in Boston at 20°C and lows at 11°C. Wrap up your sightseeing on the 23rd (Tue) to allow time to travel to Chicago.

Things to do in Boston

Museums · Historic Sites · Shopping

Side Trip

Brookline Booksmith
Find places to stay Oct 22 — 23:
Highlights from your plan
Museum of Fine Arts ©
Museum of Fine Arts
Fenway Park ©
Fenway Park
Freedom Trail ©
Freedom Trail

3
nights
Chicago

Chicago
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Take a break from Chicago with a short trip to Bengtson's Pumpkin Fest in Homer Glen, about 42 minutes away. There's much more to do: admire the masterpieces at The Art Institute of Chicago, learn about wildlife with up-close encounters at Lincoln Park Zoo, tour the pleasant surroundings at Millennium Park, and catch a live event at Wrigley Field.

To see ratings, other places to visit, traveler tips, and more tourist information, you can read our Chicago trip planner.

Fly from Boston to Chicago in 4.5 hours. Alternatively, you can drive; or take a bus. Traveling from Boston to Chicago, you'll gain 1 hour due to the time zone difference. In October, daily temperatures in Chicago can reach 21°C, while at night they dip to 11°C. Finish up your sightseeing early on the 26th (Fri) so you can travel to Miami Beach.

Things to do in Chicago

Parks · Museums · Zoos & Aquariums

Side Trip

Bengtson's Pumpkin Fest
Find places to stay Oct 23 — 26:
Highlights from your plan
Millennium Park
Millennium Park
The Art Institute of Chicago ©
The Art Institute of Chicago
Bengtson's Pumpkin Fest ©
Bengtson's Pumpkin Fest

1
day
Miami Beach

Miami Beach ©
Separated by water from the neighboring city of Miami, Miami Beach sits on a barrier island between Biscayne Bay and the Atlantic Ocean.
On the 27th (Sat), get a taste of the local shopping with Lincoln Road, then have fun at Lock & Load Miami, then get to know the fascinating history of Art Deco Historic District, and finally enjoy the sand and surf at South Beach.

To see ratings and other tourist information, read our Miami Beach online holiday planner.

Fly from Chicago to Miami Beach in 6 hours. Alternatively, you can drive; or do a combination of bus and subway. The time zone difference moving from Central Standard Time to Eastern Standard Time is 1 hour. Expect warmer temperatures when traveling from Chicago in October; daily highs in Miami Beach reach 36°C and lows reach 27°C. Finish your sightseeing early on the 27th (Sat) so you can travel to Orlando.

Things to do in Miami Beach

Parks · Neighborhoods · Historic Sites

Side Trip

Lock & Load Miami
Find places to stay Oct 26 — 27:
Highlights from your plan
Lock & Load Miami ©
Lock & Load Miami
South Beach ©
South Beach
Lincoln Road ©
Lincoln Road

3
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.
On the 28th (Sun), discover the magic at Walt Disney World Resort. Here are some ideas for day two: find something for the whole family at Universal's Islands of Adventure.

To find maps, reviews, more things to do, and more tourist information, read our Orlando trip itinerary planner.

Traveling by flight from Miami Beach to Orlando takes 4 hours. Alternatively, you can drive; or take a bus. Expect a bit cooler evenings in Orlando when traveling from Miami Beach in October, with lows around 24°C. On the 30th (Tue), you'll have the morning to explore before heading back home.

Things to do in Orlando

Theme Parks · Nightlife
Find places to stay Oct 27 — 30:
Highlights from your plan
Walt Disney World Resort ©
Walt Disney World Resort
Universal's Islands of Adventure ©
Universal's Islands of Adventure
Happily Ever After Fireworks ©
Happily Ever After Fireworks

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