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Recent Boston Posts

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

  • What is the cheapest return flight price from CHI to BOS?


  • What is the fare range for flights from CHI to BOS?

    $89 - $339

  • When does the earliest flight depart CHI?

    5:05AM JetBlue Airways Flight #566

  • When does the latest flight depart BOS?

    10:40PM United Airlines Flight #875

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


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


  • What is the travel distance between Chicago and Boston?

    849 miles

  • How many weekly flights operate between CHI and BOS?

    There are 12 weekly flights between CHI and BOS.

  • How many daily flights fly between Chicago and Boston?

    There are 1 daily flights between CHI and BOS

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


  • In last 30 days, what is the %age of BOS visitors who spent less than 3 days in the city?

    80.00 %

  • Which airport is located close to BOS?

    Logan International Airport

  • Which airport is located close to CHI?

    Midway International Airport

Boston Reviews

Professional and helpful

Your customer service agent Mr.Mateus was extremely helpful and I truly appreciate his professionalism and patience.

- Belinda  Oct 14, 2019
Excellent service

This is the best service received from any agent. Excellent service.

- Morris  Oct 13, 2019