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Search Cheap Flights from Boston to Chicago

Take flights from BOS to CHI for less

5 ways to book cheap flights from Boston to Chicago

Roundtrip tickets: As per trends, round trip tickets are cheaper than one-way tickets. Book round trip flights from Boston to Chicago to save on plane tickets.

Loyalty Programs: Many airlines and online travel portals offer loyalty programs wherein passengers score points each time they travel. Redeem these points to save on plane tickets.

Mailing lists: Travel agencies and online travel portals send updates regarding upcoming discounts and sales. Subscribe to mailing lists to save on flights from BOS to CHI.

Multi-city flights: Book a multicity flight to save on tickets. It is often the case that direct flights are more expensive. You may look for a cheap stopover alternative and get to explore two destinations at the price of one.

Set Google Alerts: When looking for Boston to Chicago flights, browse through airfares and set alerts on Google for your top choices. You will receive a notification in case the airfare changes. As soon as the fare drops, you can book your cheap flight tickets.

Getting to know Chicago

Also known as the Windy City, Chicago is the third most populous city in the US. Located along the banks of the Lake Michigan, Chicago is famed for its vibrant art scene, thriving culinary scene, and spectacular architecture. The culturally rich city has a plethora of museums, performing art venues, art galleries, leafy parks, and much more. Chicago’s diversity is reflected in its many ethnic neighborhoods, namely, Puerto Rican Paseo Boricua, Little Vietnam, Little Italy, Little Seoul, and Chinatown. Food lovers must not forget to try the ethnic cuisines while strolling through these colorful neighborhoods. Music and theater enthusiasts can catch live performances at top venues such as Symphony Center, Lincoln Hall, Chicago Shakespeare Theater, and Jazz Showcase. Other major attractions in Chicago are Millennium Park, Navy Pier, Chicago Riverwalk and Lakefront Trail, Lincoln Park, 360 Chicago, and Michigan Avenue and the Magnificent Mile.

Popular Festivals and Events

Chicago hosts a number of annual festivals around the year. Few of the major festivals are Chicago Wine Fest (April), Chicago Blues Festival (June), 57th Street Art Fair (June), Chicago Food Truck Festival (July), Taste of Chicago (July), Chicago Craft Beer Festival (July), Lollapalooza Chicago (August), Bristol Renaissance Faire (August), Illinois State Fair (August), Chicago Hot Dog Fest (August), Chicago World Music Festival (September), Chicago Jazz Festival (September), and NYE Fireworks (December).

Best Time to Visit Chicago

Chicago is flooded with tourists during summer season due to amiable weather and a flurry of events. The best time to take flights from Boston to Chicago is from April to May and from September to October.

Boston to Chicago Flight Route Facts

  • When does the earliest flight depart BOS?

    7:00AM - 8:00AM

  • When does the last flight depart CHI?

    9:00PM - 10:00PM

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


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

    November, December, March, June, September

  • What is the travel distance between Boston and Chicago?

    858 Miles

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

    American Airlines, Spirit Airlines, United Airlines

  • How many daily flights fly between Boston and Chicago?

    There are 33 daily flights between BOS and CHI

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


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

    13% of Chicago travelers booked First or Business Class.

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

    6% traveled with their kids under 14.

  • What percentage of Boston to Chicago travelers were millennials?

    43% of Chicago travelers were millenials.

  • What percentage of Boston to Chicago travelers were female?

    51% of Chicago travelers were female.

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

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

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

    08.21 Hours

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