Call for deals too good to be published.
Download Our App

Get CheapOair deals on the GO!

Download
Apply for Our Credit Card

Earn rewards fast. Go where you want!

Learn More
Check Your Flight Status

Get there on time, every time!

Check Status

Facts About Flying from Boston to Chicago

Q. What percent of Boston to Chicago travellers booked first or business class?

A. 13% of travelers booked first or business class on this route.

Q. What percent of BOS to CHI flyers travelled with their kids under 14?

A. 6% of flyers travelled with their kids under 14.

Q. What percent of BOS to CHI travellers were millennials?

A. 43% of travelers were millenials.

Q. What percent of Boston to Chicago travellers were female?

A. 51% of travelers were female.

Q. What percent of Boston to Chicago travellers were over 60 years?

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

Q. At what time the earliest flight departs from Boston ?

A. The earliest flight departs at 7:00AM - 8:00AM.

Q. At what time the last flight departs to Chicago?

A. The last flight departs at 9:00PM - 10:00PM.

Q. . Which is the high season to travel from Boston to Chicago?

A. The month of August is considered to be the high season to travel from BOS to CHI.

Q. Which is the low season to travel from Boston to Chicago?

A. November, December, March, June, September is considered to be the low season for traveling from Boston to Chicago, Illinois.

Q. What is the price range of a Boston to Chicago flight?

A. Boston to Chicago Flight Prices usually vary between 10 - 69.76.

Q. How many daily flights are there between Boston to Chicago?

A. There are as many as 33 daily flights between BOS to CHI.

Q. What percent of travelers spent an average of 1 days in Chicago, Illinois?

A. 42.55% of travelers spent an average of 1 days in Chicago

Q. How many direct flights are available from BOS to CHI?

A. There are 990 direct flights from Boston to Chicago.

§ All flight facts are based on last 3 months' data except the highest and lowest booking months that are based on last 3 months' data.

Book Cheap Flights from Boston to Chicago

Fly to the Windy City for less

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

A guide to Chicago

Chicago is an international center of technology, industry, and finance. The metropolitan city is a cultural hub with a 24*7 nightlife, extensive shopping venues, and a thriving culinary scene. Chicago is home to many state-of-the-art museums, live performance venues, and theater companies. The city is home to a diverse local populace with multiple ethnic neighborhoods, namely, Little Italy, Little Seoul, Puerto Rican Paseo Boricua, Chinatown, and Little Vietnam. Food lovers must not forget to grab a bite as they explore these vibrant neighborhoods and get a taste of the world, in cosmopolitan Chicago.

Chicago hosts several annual festivals around the year. Few of the major festivals held in Chicago are Chicago Wine Fest (April), 57th Street Art Fair (June), Chicago Blues Festival (June), Taste of Chicago (July), Chicago Food Truck Festival (July), Chicago Craft Beer Festival (July), Lollapalooza Chicago (August), Chicago Hot Dog Fest (August), Illinois State Fair (August), Chicago Jazz Festival (September), Chicago World Music Festival (September), and Windy City Wine Festival (September). Visitors can book Boston to Chicago flight tickets keeping in mind such prominent events.

Major attractions in Chicago

  • The Art Institute of Chicago
  • Millennium Park
  • Navy Pier
  • 360 Chicago
  • Chicago Riverwalk and Lakefront Trail
  • Willis Tower SkyDeck
  • Lincoln Park
  • Museum of Science and History
  • Michigan Avenue and the Magnificent Mile
  • Field Museum of Natural History

When to Visit Chicago

Weather-wise, the best time to visit Chicago is between September and October and from April through May. However, summer is the peak tourist season when the city is flooded with tourists. It is advisable to book your flights from Boston to Chicago in advance.

Share your Travel experience:

Once you’re done sharing photos from your trip to Chicago, do not forget to share your Chicago 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.