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 |
Call usPhone-Only Deals! Call XXXX-XXX-XXXXPhone-Only Deals! Call XXXX-XXX-XXXX
Grab better fares
More flight options
Call live travel experts
Earn 2X ClubMiles points
USD
10/13/2026 Find Cheap Flights from Chicago to Boston (CHI to BOS)
CHI - Chicago BOS - Boston 
Find Cheap Flights from Chicago to Boston (CHI to BOS)
Fares Starting from $109
CHI - Chicago BOS - Boston Great deal! This is the lowest price we've seen for this one way route in the last 12 hours. Prices may change and aren't guaranteed for all flights or dates. Click on the price to continue your search and check the latest available fare. Ref. id 202609~Ref:iuKc7QsUwUOJYGl89EJa9g
Save now - use
Cheap Flights from Chicago to Boston - Compare & Book Our Best Deals
With over 33 daily departures from Chicago to Boston, this route offers great flexibility for different travel plans. Browse one-way fares from $108.23, round-trip fares from $208.84, and other affordable options across different budgets. Compare flight choices, explore schedules, and book the best Chicago to Boston deals that fit your budget and travel preferences.
Top Airlines that fly from Chicago to Boston
Cheap Flight Deals from Chicago to Boston
CHI Chicago Tue, Oct 13
BOS Boston
from $109
Book Now
CHI Chicago Wed, Oct 14
BOS Boston
from $122
Book Now
CHI Chicago Tue, Oct 20
BOS Boston
from $122
Book Now
CHI Chicago Tue, Oct 27
BOS Boston
from $122
Book Now
CHI Chicago Tue, Nov 3
BOS Boston
from $122
Book Now
CHI Chicago Wed, Nov 4
BOS Boston
from $122
Book Now
CHI Chicago Tue, Nov 10
BOS Boston
from $122
Book Now
CHI Chicago Wed, Nov 11
BOS Boston
from $122
Book Now
Show more
*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. 202609~Ref:iuKc7QsUwUOJYGl89EJa9g
Insights about cheap flights from Chicago to Boston – Direct Flights, Duration & Best Travel Time
When it comes to booking cheap flights, having the right information at your fingertips can make all the difference. Dive into the insights for cheap flights from Chicago to Boston and enhance your travel experience!
Daily Flights
33
Cheapest Month
September, August, January, March, October
Avg. Flight Duration
02.17
Peak Season
August
Distance
858 miles
Direct Flights
994
When is the Cheapest Time to Book Flights from CHI to BOS?
Explore data-powered insights and trends for flights from Chicago to Boston. Discover average fares, cheap months to fly, when to book, and plan smarter.
What’s the cheapest day of the week to fly from Chicago to Boston?‡
What is the cheapest month to fly from Chicago to Boston?‡
‡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 should I book flights from CHI to BOS? ‡
‡Got flexible travel dates? Use our flight data from the past year to discover ideal time to fly from Chicago to Boston. Find out which months and days typically offer lower fares and let CheapOair search for the best options.
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.
Book with Confidence. Trusted by 40M+ Travelers
Price Match Promise
ⓘ
Found a better deal? We'll match it!
24/7 Customer Support
Speak to our travel experts anytime, anywhere.
ClubMiles Rewards
Stack points & airline miles to save.
Easy Cancellations
Convenient options online and 24/7 global concierge.
Insights About Flying from Chicago to Boston
Which is the high season to travel from Chicago to Boston?
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.
How many direct flights are available from CHI to BOS?
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.
Which is the low season to travel from Chicago to Boston?
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.
How many daily flights are there between Chicago to Boston?
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.
At what time does the last flight depart to Boston?
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.
What percentage of travelers spent an average of 1 days in Boston, Massachusetts?
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
What percentage of CHI to BOS flyers traveled with kids under 14?
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.
What percentage of Chicago to Boston travelers were over 60 years old?
A notable 11% of travelers were aged 60 or older. This statistic provides insights for senior travelers or those seeking a mature travel demographic.
What percentage of CHI to BOS travelers were millennials?
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.
What percentage of Chicago to Boston travelers were female?
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.
What percent of Chicago to Boston travellers booked first or business class?
15% of travelers booked first or business class on this route.
At what time the earliest flight departs from Chicago?
The earliest flight departs at 7:00AM - 8:00AM.
What is the price range of a Chicago to Boston flight?
Chicago to Boston Flight Prices usually vary between 0.01 - 288.
Which is the most popular airport for connecting flights between Chicago to Boston?
Newark Liberty International Airport is the most popular airport for connecting flights between CHI to BOS.
On which days one can have the most flight options in Boston?
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.
Start saving today. Never miss a promotion.
Cheap Flights from Chicago to Boston
Grab cheap flights from Chicago to Boston
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.
Check your flight status
Get there on time, every time!
Recent posts View all posts
Find Your Perfect Island Match on National Cheap Flight Day
Read moreDream Bucket-List Destinations to Book on National Cheap Flight Day
Read moreThe Best Long-Weekend Destinations for National Cheap Flight Day
Read moreGreat International Cities to Discover on National Cheap Flight Day!
Read more5 Fall City Escapes to Consider on National Cheap Flight Day
Read moreWhat our customers say about our service?
-
Helpful Assistance When my itinerary changed and the original flights no longer worked, the support representative quickly helped me find better alternatives. They were professional, courteous, and went above and beyond to resolve the issue. I'm grateful for the excellent assistance and smooth experience.
Read more
-
Excellent Service I recently needed help with a flight schedule change and had a great experience with customer service. Laura was professional, friendly, and very helpful throughout the process. She quickly found a solution and kept me informed of the next steps. I truly appreciate her excellent service.
Read more
-
Highly Recommended When my flight was unexpectedly canceled, I needed help rearranging my travel plans. The customer service representative was calm, professional, and extremely helpful throughout the process. They quickly found alternative flight options and assisted with the necessary follow-up. I truly appreciate the excellent support and dedication to resolving my issue.
Read more
-
Great Prices offered CheapOair has always offered great prices, and my booking experience has been smooth and hassle-free every time.
Read more
Save up to $100 off our fees
First time app users get up to $100 off our fees on flights.
- Earn up to 6X points
- 24/7 priority support
- In-App calls at no cost
- Manage your bookings on the go
Scan QR and install