3 days in Illinois & Boston Itinerary

3 days in Illinois & Boston Itinerary

Created using Inspirock United States trip itinerary planner

Make it your trip
1
Chicago
— 1 night
Fly
2
Boston
— 1 night
Fly

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Chicago

— 1 night

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
On the 17th (Fri), take in panoramic vistas at Skydeck Chicago - Willis Tower, get up close and personal with brilliant marine life at Shedd Aquarium, then stroll around Millennium Park, and finally explore the world behind art at The Art Institute of Chicago. On the 18th (Sat), you'll have a packed day of sightseeing: engage your brain at Museum of Science and Industry, admire the striking features of 360 Chicago Observation Deck, and then get outside with Outdoor Activities.

Plan my Chicago trip by asking Inspirock to come up with tips and suggestions.

Use the Route module to find suitable travel options from your home destination to Chicago. In September, plan for daily highs up to 78°F, and evening lows to 61°F. Wrap up your sightseeing on the 18th (Sat) early enough to fly to Boston.

Things to do in Chicago

Museums · Parks · Childrens Museums · Tours

Boston

— 1 night

Beantown

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 19th (Sun): stroll around Boston Common, then walk around Boston Public Garden, then browse the different shops at Faneuil Hall Marketplace, and finally appreciate the extensive heritage of Freedom Trail.

For reviews, where to stay, more things to do, and more tourist information, refer to the Boston tour itinerary planner.

Getting from Chicago to Boston by flight takes about 4 hours. Other options: drive; or take a bus. The time zone difference when traveling from Chicago to Boston is 1 hour. September in Boston sees daily highs of 75°F and lows of 59°F at night. Wrap up your sightseeing on the 19th (Sun) early enough to fly back home.

Things to do in Boston

Parks · Historic Sites · Shopping

Illinois travel guide

4.4
Observation Decks · Parks · Art Museums
The Prairie State
The most populous state in the country's Midwest region, Illinois features a diverse landscape that includes both the enormous urban sprawl of Chicago and flat central plains, devoted almost entirely to farmland. With a great selection of things to do, Chicago is the state's centerpiece, featuring world-famous architecture and renowned museums. Farther away from this giant urban center, you can explore historical landmarks dedicated to local heroes Abraham Lincoln and Ernest Hemingway. The state also includes a prehistoric Native American site, one of only 20 World Heritage Sites in the United States, a unique feature well-worth adding to your itinerary.