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Search Cheap Flights from Chicago to Boston

Fly to Boston and Explore the Bay State

Check out these tricks to book cheap flights from CHI to BOS

Loyalty programs: Sign up for loyalty programs offered by airlines. Flyers can score points each time they travel and redeem these points to save on flights from Chicago to Boston.

Redeem Credit Card Reward Points: Most companies offer reward points when you spend via your credit card. Redeem these points while reserving your flights from CHI to BOS.

Budget Airlines: Flyers should search for no frills budget airlines which provide the lowest airfares. Low cost airlines end up being cheaper than the traditional ones.

Connecting Flights: Usually, direct flights end up being more expensive than connecting flights, flyers can look for a nice stopover instead, and get to explore two destinations at the price of one!

Google Alerts: Flyers can browse through airfares and set alerts on Google for their top choices. They will receive a notification if there a drop in the airfare, and they can book their Chicago to Boston flights for cheaper.

What to do in Boston?

Founded in 1630, Boston is the capital of Massachusetts. Among the oldest cities in the US, the city is known for its major role in the American Revolution. A haven for history buffs, Boston was the site of multiple historic events, namely, Boston Tea Party, Battle of Bunker Hill, Siege of Boston, and Boston Massacre. Presently, the city is a global hub of business, entrepreneurship, innovation, medicine, and education. Boston is home to distinct neighborhoods. The North End is the hub of Italian American community while Downtown has the city’s most famous attractions such as the Freedom Trail. Visitors must not forget to relish local foods and spot some of Boston’s oldest buildings while exploring these vibrant neighborhoods. Major attractions in Boston include Museum of Fine Arts Boston, Faneuil Hall Marketplace, John F. Kennedy Presidential Library and Museum, Skywalk Observatory, Boston Harborwalk, and Boston Tea Party Ships & Museum.

Popular Festivals and Events

Boston is a culturally rich city which hosts a number of annual festivals, concerts, and events around the year. Major festivals in Boston include are Boston Wine Expo (February), St. Patrick's Day (March), Boston Marathon (April), Patriots’ Day (April), Dragon Boat Festival (June), Boston Pride Parade (June), Fourth of July Celebrations (July), Boston Harborfest (July), Boston Salsa Festival (August), Salem Jazz and Soul Festival (August), Halloween (October), Boston Arts Festival (September), Festival of the Dead (October), and Boston Book Festival (October).

Best time to Visit Boston

The best time take flights from Chicago to Boston is during late spring (from May to October) when the weather is moderate. Many travelers fly to Boston to visit Salem in October to celebrate Halloween. Hence, it is advised to book flights in advance to secure Chicago to Boston flight deals.

Chicago to Boston Flight Route Facts

  • When does the earliest flight depart CHI?

    7:00AM - 8:00AM

  • When does the last flight depart BOS?

    9:00PM - 10:00PM

  • Which is the busiest month to travel from Chicago to Boston?


  • Which is the least-busy month to travel from CHI to BOS?

    September, August, January, March, October

  • What is the travel distance between Chicago and Boston?

    858 Miles

  • What are the top airlines offering flights from CHI to BOS?

    American Airlines, Spirit Airlines, United Airlines

  • How many weekly flights operate between CHI and BOS?

    There are 248 weekly flights between CHI and BOS.

  • How many daily flights fly between Chicago and Boston?

    There are 33 daily flights between CHI and BOS

  • Which is the busiest day in terms of passengers flying from CHI to BOS?


  • What percentage of Chicago to Boston travelers booked First or Business Class?

    15% of Boston travelers booked First or Business Class.

  • What percentage of Chicago to Boston travelers traveled with their kids under 14?

    6% traveled with their kids under 14.

  • What percentage of Chicago to Boston travelers were millennials?

    44% of Boston travelers were millenials.

  • What percentage of Chicago to Boston travelers were female?

    51% of Boston travelers were female.

  • What percentage of Chicago to Boston travelers were over the age of 60?

    11% of Boston travelers were over the age of 60.

  • What was the average flight duration of flights from Chicago to Boston?

    02.17 Hours

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