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Cheap Flight Deals from Chicago to Boston

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Round TripOne Way
CHI Chicago
BOS Boston
From $102.96
Jan 6, 2026 - Jan 12, 2026
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CHI Chicago
BOS Boston
From $149.99
Jan 30, 2026 - Feb 1, 2026
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CHI Chicago
PWM Portland
From $154.38
Apr 9, 2026 - Apr 16, 2026
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CHI Chicago
MHT Manchester
From $434.92
Jan 2, 2026 - Jan 7, 2026
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*All fares above were last found on:
Fares are one way/round trip. Fares incl. all fuel surcharges, taxes & fees and our service fees. Displayed fares are subject to change and cannot be guaranteed at the time of booking. See all booking terms and conditions.

When’s a good time to book a flight from Chicago to Boston?

What’s the cheapest day of the week to fly from Chicago to Boston?‡

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What is the cheapest month to fly from Chicago to Boston?‡

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‡This information is based on historical data from the last 365 days.

Finding Affordable Flights from Chicago to Boston
  • Plan Ahead - One of the keys to securing cheap flights from Chicago to Boston is to plan your trip well in advance. Airlines often offer lower prices for those who book tickets months ahead. Keep an eye on special promotions and sales events, which can yield significant savings.
  • Flexibility is Key - Being flexible with your travel dates can also lead to substantial cost savings. Consider flying during off-peak seasons or on weekdays when prices tend to be lower.
  • Set Price Alerts - To keep tabs on flight prices, consider setting up fare alerts. These alerts will notify you when fares from Chicago to Boston drop, giving you the opportunity to grab cheap deals.
  • Consider Nearby Airports - If Boston has multiple airports, check the prices at each one. Sometimes, flying into a nearby airport and then taking a short train or bus ride to your destination can be a much cheaper option.
  • Bundle and Save - Booking your flight and accommodation together as a package can often result in significant savings. CheapOair offers these bundled deals, so make sure to explore this option.

When is the Cheapest Time to Book Flights from Chicago to Boston?

‡

Got flexible travel dates? Use our flight data from the past year to discover ideal times to fly from Chicago to Boston. Find out which months and days typically offer lower fares and score our best savings.

CheapOair provides the predicted prices for one-way trips or round-trips with a duration of 7 days for domestic and 14 days for international trips based on historical data and available flight information. Graphs are estimates only. Prices are subject to change and can't be guaranteed until ticketed.
Estimated price for
Round-trip

‡Graphs are estimates only. Based on historical data and available flight information. Prices are subject to change and cannot be guaranteed until ticketed.

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Chicago to Boston Flight Route Information

Travel Distance:858 Miles
Airlines Flying This Route: American Airlines, Spirit Airlines, United Airlines
Weekly Flights:248
Avg. Flight Duration:02.17 Hours

Insights About Flying from Chicago to Boston

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

A. The month of August is considered the high season for flying from CHI to BOS. Traveling during the high season can affect ticket prices and availability, making this data crucial for trip planning.

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

A. There are a total of 994 direct flights from Chicago to Boston. For travelers seeking convenience and shorter travel times, this data is important when choosing flight options.

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

A. September, August, January, March, October is considered the low season for traveling from Chicago to Boston, Massachusetts. Travelers looking for cost-effective options and fewer crowds may consider traveling during this period.

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

A. There are as many as 33 daily flights available for travelers between CHI to BOS. This data offers flexibility in choosing departure times that best suit your schedule.

Q. At what time does the last flight depart to Boston?

A. The last flight to Boston typically departs between 9:00PM - 10:00PM. Travelers who prefer late-night departures will find this information valuable for planning their journey.

Q. What percentage of travelers spent an average of 1 days in Boston, Massachusetts?

A. Approximately 43.73% of travelers spent an average of 1 days exploring Boston. This information can assist in planning the duration of your stay in Boston

Q. What percentage of CHI to BOS flyers traveled with kids under 14?

A. About 6% of passengers on flights from Chicago to Boston were accompanied by children under the age of 14. This information is useful if you're planning a family trip and want to know how common it is to travel with young children on this route.

Q. What percentage of Chicago to Boston travelers were over 60 years old?

A. A notable 11% of travelers were aged 60 or older. This statistic provides insights for senior travelers or those seeking a mature travel demographic.

Q. What percentage of CHI to BOS travelers were millennials?

A. Millennials make up a significant portion of travelers on this route, accounting for 44% of all passengers. If you're a millennial looking to connect with like-minded travelers, this statistic might interest you.

Q. What percentage of Chicago to Boston travelers were female?

A. Almost half of the passengers, approximately 51% were female. Knowing the gender distribution can be useful for solo female travelers or those interested in gender-related travel insights.

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

A. 15% of travelers booked first or business class on this route.

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

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

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

A. Chicago to Boston Flight Prices usually vary between 0.01 - 288.

Q. Which is the most popular airport for connecting flights between Chicago to Boston?

A. Newark Liberty International Airport is the most popular airport for connecting flights between CHI to BOS.

Q. On which days one can have the most flight options in Boston?

A. Monday offer the most flight options in Boston.

§ 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.

Cheap Flights from Chicago to Boston

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

Currency: The US Dollar (USD) is used in Boston and all of USA.

Language: English is the primary language spoken in Boston. However, owing to its sizeable Latino populace, Spanish is also widely spoken here.

Local Transport: The city is served by the subways, trolleys, buses, taxis, and ride-sharing services. A ferry service connects Long Wharf with Boston Navy Yard.

Explore Boston

Capital of Massachusetts, Boston was founded in 1630. The city is among the oldest cities in the United States of America. Boston is famed for its significant role in the American Revolution. The city was the site of several historic events, namely, Battle of Bunker Hill, Boston Massacre, Boston Tea Party, and Siege of Boston. Today, the city is an international center of business, innovation, entrepreneurship, education, and medicine. Boston is lined with diverse neighborhoods, Downtown is home to city�s most popular attractions such as the Freedom Trail and the North End is the hub of Italian-American community. Do not forget to indulge in local food and spot some of the city�s oldest buildings while you explore these neighborhoods.

A culturally rich city, Boston hosts several annual events around the year. Few of the major festivals and events held in Boston are Boston Wine Expo (February), St. Patrick's Day (March), Boston Marathon (April), Boston Early Music Festival (June), Boston Pride Parade (June), Boston Harborfest (July), Salem Jazz and Soul Festival (August), Boston Arts Festival (September), Boston Book Festival (October), Halloween (October), and Festival of the Dead (October). Visitors can book Chicago to Boston flight tickets keeping in mind such prominent events.

Major attractions in Boston

  • Freedom Trail
  • Beacon Hill
  • Museum of Fine Arts Boston
  • Faneuil Hall Marketplace
  • John F. Kennedy Presidential Library and Museum
  • New England Aquarium
  • Boston Common
  • Skywalk Observatory
  • Boston Harborwalk
  • Boston Tea Party Ships & Museum

When to visit Boston

The best time to visit Boston is from May to October during late spring and early fall season when the weather is pleasant for sightseeing. Many travelers wish to visit Boston in October to celebrate Halloween in Salem. Airfares tend to peak in October, hence, it is advised to book flights in advance to score Chicago to Boston flight deals.

Share your Travel experience

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

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