For Unpublished Cheap Flight Deals,
Call Us at 1-888-437-4930
  • Great
    Based on 2,012 reviews
  • Safe & Secure Booking
  • Low Fare Promise
  • Buy with Confidence
  • 10 Million+ Customers
    Per Year
  • Compare & Book Over
    650 Airlines Instantly!
  • Fast, Safe &
  • Live 24/7
    Customer Support
Download Our App

Find the deals you want & manage your trips ... all while on the go.

Apply for Our Credit Card

Earn rewards points & other travel perks when you spend.

Apply Now
Check out our Blog

Get inspired, learn expert tips & add to your travel bucket list.

Read it Now
Check Your Flight Status

Get there on time,
every time!

Check Status

Search Cheap Flights from Chicago to Boston

Boston is the capital city of the Commonwealth of Massachusetts in the United States. A hotbed of Colonial and Revolutionary War history, the city is the go-to point for all history enthusiasts and nationalists alike. Boston’s star attraction is the Freedom Trail, which is a 2.5-mile-long road that runs through or passes close to some of the most historic attractions in the city. Boston is situated on the other side of the Charles River and thus flanks the city of Cambridge. This city is home to two of America's most prestigious universities - the Harvard and the Massachusetts Institute of Technology.

Things to do in Boston

Freedom Trail

The nearly three-mile-long Freedom Trail is a road that runs through or passes close to 16 of the city's principal historic monuments and sites. One can start by picking up brochures at the Visitor Center and then starting one’s tour through attractions like State House, Old Granary Burying Ground, King's Chapel Burying Ground, Old South Meeting House, and the Old State House.

Faneuil Hall

Known as the ‘Cradle of Liberty,’ Faneuil Hall is a mid-18th century market hall in Boston where America’s Founding Fathers used to give their patriotic speeches against the Colonial Britain. The hall’s ground floor features market stalls. Going upwards one finds an 18th and 19th century council chamber, and further upwards is located the Ancient and Honorable Artillery Museum.

Boston Museum of Fine Arts

Boston Museum of Fine Arts is one of the leading art museums in the US. It is home to many remarkable collections of impressionist paintings, ancient Egyptian treasures, Asian and Persian fine arts, and works from ancient Greece and the Middle East. Some major highlights here include a 900-year-old lacquered-wood sculpture of a Buddhist Bodhisattva and the ivory and gold statue of the Minoan Snake Goddess dating back to 1500 BC.

Best Time to Visit Boston

Summer season, the months from June to October are the best to book flights from Chicago to Boston. It is the season when tourists can have a great time enjoying baseball games, outdoor concerts and festivals. Tourists can book flights from CHI to BOS during summers to enjoy famous cultural events like Boston Pops Fireworks Spectacular, Boston Comic Con, Boston Film Festival and Phantom Gourmet Food Festival.

    Chicago to Boston Flight Route Facts

  • What is the cheapest return flight price from CHI to BOS?$123
  • What is the fare range for flights between CHI to BOS? $123 - $370
  • When does the earliest flight depart CHI? 5:35AM JetBlue Airways Flight #854
  • When does the latest flight depart BOS? 10:05PM American Airlines Flight #2387
  • Which is the busiest month to travel from Chicago to Boston?November
  • Which is the least busy month to travel from CHI to BOS?December
  • What is the travel distance between Chicago to Boston?849 miles
  • How many weekly flights are there are between CHI to BOS? There are 16 weekly flights between CHI and BOS.
  • How many daily flights fly between Chicago to Boston? There are 2 daily flights between CHI and BOS
  • Which is the busiest day in terms of passengers flying from CHI to BOS?Monday
  • In last 30 days, what is the %age of BOS visitors who spent less than 3 days in the city?50.00 %
  • Name the airport nearby BOS? Logan International Airport
  • Name the airports nearby CHI? Midway International Airport