Boston to Chicago Flight Route Information
| Travel Distance: | 858 Miles |
|---|---|
| Airlines Flying This Route: | American Airlines, Spirit Airlines, United Airlines |
| Avg. Flight Duration: | 08.21 Hours |
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11/2/2026 Find Cheap Flights from Boston to Chicago (BOS to CHI)
BOS - Boston CHI - Chicago 
Find Cheap Flights from Boston to Chicago (BOS to CHI)
Fares Starting at $119
BOS - Boston CHI - Chicago 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 202610~Ref:kEiDhpsrtE2McgPBupmNQQ
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Cheap Flights from Boston to Chicago - Compare & Book Our Best Deals
With over 33 daily departures from Boston to Chicago, this route offers great flexibility for different travel plans. Browse one-way fares from $118.43, round-trip fares from $225.0, and other affordable options across different budgets. Compare flight choices, explore schedules, and book the best Boston to Chicago deals that fit your budget and travel preferences.
Top Airlines that fly from Boston to Chicago
Cheap Flight Deals from Boston to Chicago
BOS Boston Mon, Nov 2
CHI Chicago
from $119
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BOS Boston Tue, Nov 3
CHI Chicago
from $119
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BOS Boston Tue, Nov 10
CHI Chicago
from $119
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BOS Boston Wed, Nov 11
CHI Chicago
from $119
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BOS Boston Sat, Nov 14
CHI Chicago
from $119
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BOS Boston Tue, Nov 17
CHI Chicago
from $119
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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 . 202610~Ref:kEiDhpsrtE2McgPBupmNQQ
Insights about cheap flights from Boston to Chicago – 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 Boston to Chicago and enhance your travel experience!
Daily Flights
33
Cheapest Month
November, December, March, June, September
Avg. Flight Duration
08.21
Peak Season
August
Distance
858 miles
Direct Flights
990
When is the Cheapest Time to Book Flights from BOS to CHI?
Explore data-powered insights and trends for flights from Boston to Chicago. Discover average fares, cheap months to fly, when to book, and plan smarter.
What’s the cheapest day of the week to fly from Boston to Chicago?‡
What is the cheapest month to fly from Boston to Chicago?‡
‡This information is based on historical data from the last 365 days.
Finding Affordable Flights from Boston to Chicago
- Plan Ahead - One of the keys to securing cheap flights from Boston to Chicago 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 Boston to Chicago drop, giving you the opportunity to grab cheap deals.
- Consider Nearby Airports - If Chicago 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 BOS to CHI? ‡
‡Got flexible travel dates? Use our flight data from the past year to discover ideal time to fly from Boston to Chicago. 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.
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Insights About Flying from Boston to Chicago
Which is the high season to travel from Boston to Chicago?
The month of August is considered the high season for flying from BOS to CHI. 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 BOS to CHI?
There are a total of 990 direct flights from Boston to Chicago. For travelers seeking convenience and shorter travel times, this data is important when choosing flight options.
Which is the low season to travel from Boston to Chicago?
November, December, March, June, September is considered the low season for traveling from Boston to Chicago, Illinois. Travelers looking for cost-effective options and fewer crowds may consider traveling during this period.
How many daily flights are there between Boston to Chicago?
There are as many as 33 daily flights available for travelers between BOS to CHI. This data offers flexibility in choosing departure times that best suit your schedule.
At what time does the last flight depart to Chicago?
The last flight to Chicago 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 Chicago, Illinois?
Approximately 42.55% of travelers spent an average of 1 days exploring Chicago. This information can assist in planning the duration of your stay in Chicago
What percentage of BOS to CHI flyers traveled with kids under 14?
About 6% of passengers on flights from Boston to Chicago 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 Boston to Chicago 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 BOS to CHI travelers were millennials?
Millennials make up a significant portion of travelers on this route, accounting for 43% of all passengers. If you're a millennial looking to connect with like-minded travelers, this statistic might interest you.
What percentage of Boston to Chicago 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 Boston to Chicago travellers booked first or business class?
13% of travelers booked first or business class on this route.
At what time the earliest flight departs from Boston?
The earliest flight departs at 7:00AM - 8:00AM.
What is the price range of a Boston to Chicago flight?
Boston to Chicago Flight Prices usually vary between 10 - 69.76.
On which days one can have the most flight options in Chicago?
Monday offer the most flight options in 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.
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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.
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