Find Cheap Flights from Chicago (CHI) to Boston (BOS)

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Things to know before you book your flights from Chicago to Boston

Currency: The US Dollar (USD) is used in Boston and all of USA.

Language: English is the primary language spoken in Boston. However, owing to its sizeable Latino populace, Spanish is also widely spoken here.

Local Transport: The city is served by the subways, trolleys, buses, taxis, and ride-sharing services. A ferry service connects Long Wharf with Boston Navy Yard.

Explore Boston

Capital of Massachusetts, Boston was founded in 1630. The city is among the oldest cities in the United States of America. Boston is famed for its significant role in the American Revolution. The city was the site of several historic events, namely, Battle of Bunker Hill, Boston Massacre, Boston Tea Party, and Siege of Boston. Today, the city is an international center of business, innovation, entrepreneurship, education, and medicine. Boston is lined with diverse neighborhoods, Downtown is home to city’s most popular attractions such as the Freedom Trail and the North End is the hub of Italian-American community. Do not forget to indulge in local food and spot some of the city’s oldest buildings while you explore these neighborhoods.

A culturally rich city, Boston hosts several annual events around the year. Few of the major festivals and events held in Boston are Boston Wine Expo (February), St. Patrick's Day (March), Boston Marathon (April), Boston Early Music Festival (June), Boston Pride Parade (June), Boston Harborfest (July), Salem Jazz and Soul Festival (August), Boston Arts Festival (September), Boston Book Festival (October), Halloween (October), and Festival of the Dead (October). Visitors can book Chicago to Boston flight tickets keeping in mind such prominent events.

Major attractions in Boston

  • Freedom Trail
  • Beacon Hill
  • Museum of Fine Arts Boston
  • Faneuil Hall Marketplace
  • John F. Kennedy Presidential Library and Museum
  • New England Aquarium
  • Boston Common
  • Skywalk Observatory
  • Boston Harborwalk
  • Boston Tea Party Ships & Museum

When to visit Boston

The best time to visit Boston is from May to October during late spring and early fall season when the weather is pleasant for sightseeing. Many travelers wish to visit Boston in October to celebrate Halloween in Salem. Airfares tend to peak in October, hence, it is advised to book flights in advance to score Chicago to Boston flight deals.

Share your Travel experience

Once you’re done sharing photos from your trip to Boston, do not forget to share your Boston experience with us through the CheapOair review section. Help and inspire other travelers by sharing your valuable opinion. Remember, your reviews can help us make our service better.

Boston Travelers' Reviews

Nice and easy flights!

All was easy from departures both ways to arrivals. Nice for a change! - Anonymous  Aug 17, 2019

Boston ??

Great city with so much to offer! - Pamela  Aug 15, 2019

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