Flights from Boston to Chicago, United States
Boston to Chicago Last modified: Sep 22, 2017 3:21 -04:00Prices shown were found by travelers like you over the past 30 days
We've scanned 2,601,477,176 round trip itineraries and found the cheapest flights to Chicago. American & United frequently offer the best deals to Chicago flights, or select your preferred carrier below to see the cheapest days to fly.
Where To Buy Cheap Flights from Boston to Chicago?
The best way to find a great deal on airfare is to search multiple sites. When you run a search on FareCompare, we search multiple sites and fare sources all at once so you don't have to - which is why we think FareCompare is the best place to find cheap tickets. Airlines can adjust prices for tickets from Boston to Chicago based on the day and time that you decide to book your flight. We have collected data from all airlines, and have found that Tuesdays, Wednesdays, and Saturdays are often the best days to book flights. If you'd like to learn more, read our article about the best time to buy airline tickets.
How far in advance should I book tickets from Boston to Chicago? Prices shown were found by travelers like you over the past 30 days
The chart below shows up-to-date information regarding how far in advance to book your flight from Boston to Chicago.
|Advanced Purchase||Non Stop||Connecting|
|< 7 days||$112||$233|
Cheapest Day To Fly from Boston to Chicago Prices shown were found by travelers like you over the past 30 days
We've examined 2,602,074,297 itinerary searches that we've seen for departures in the next 90 days and found that the cheapest day to fly from Boston to Chicago is Sunday. See the chart below to compare prices for other days of the week.
Compare Flight Prices from Boston to Chicago by Month Prices shown were found by travelers like you over the past 30 days
Low priced flights are most commonly available by purchasing between one and three months in advance. International or holiday flights may need to be purchased even further in advance. The chart below shows the cheapest flight prices by month for Boston to Chicago flights.
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Cheap Last Minute Flights from Boston to Chicago Prices shown were found by travelers like you over the past 30 days
Looking for cheap last minute flights or a weekend getaway? We've got you covered with weekend flight deals from Boston to Chicago. The chart below shows the best last minute deals and cheap flights this weekend we could find.
Next 30 Days
Connecting Flights vs Direct Flights from Boston to Chicago Prices shown were found by travelers like you over the past 30 days
Flights between some cities may be significantly cheaper if you choose a multi-stop airline ticket. Although these connecting flights sacrifice some convenience, on average, travelers save 20%-60% when they choose to fly multi-stop versus a direct flight.
The average price for connecting flights from Boston to Chicago is $224.
The average price for direct flights from Boston to Chicago is $150.
The chart below shows up to date information regarding non-stop flights from Boston to Chicago.
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One Way Flights vs Round Trip Flights from Boston to Chicago Prices shown were found by travelers like you over the past 30 days
We have found that there is often no price difference between buying a round trip flight versus a one way flight. Increased flexibility is the main benefit when it comes to buying a one way flight from Boston to Chicago. However, booking a round trip flight can be a simpler process. You can compare round trip and one way flights by using our flight comparison.
The average price for one way flights from Boston to Chicago is $63.
The average price for round trip flights from Boston to Chicago is $147.
Boston to Chicago Flight Questions
Below are some common questions that asked about this flight route:
Airlines in Boston flying to Chicago Last modified: Sep 22, 2017 3:21 -04:00Number of routes searched: 269Number of itineraries searched: 1,322,076
Wondering which airlines fly out of Boston to Chicago? We've gathered the average price of Boston airlines with flights to Chicago. Different airlines offer different levels of comfort and service, so consider convenience when choosing your airline.
Below is the full flight schedule summary showing which days of the week individual carriers offer flights for the next 30 days.
Boston to Chicago Airports
These are the major commercial airports we're currently monitoring in Boston and Chicago. If your route includes a city with multiple airports, you may be able to find substantial savings by choosing an alternate airport.
Farecompare Research Tools
FareCompare's Flight Schedule Search Tool helps you find information about airline schedule filings, including flight numbers, depart times, and travel distance.