Chicago to Boston Last modified: May 20, 2022 2:29 -04:00
We've scanned 40,788 round trip itineraries and found the cheapest flights to Boston. JetBlue & !! frequently offer the best deals to Boston flights, or select your preferred carrier below to see the cheapest days to fly.
Where To Buy Cheap Flights from Chicago to Boston?
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 Chicago to Boston 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 Chicago to Boston?
The chart below shows up-to-date information regarding how far in advance to book your flight from Chicago to Boston.
|Advanced Purchase||Non Stop||Connecting|
|< 7 days||$345||$394|
Cheapest Day To Fly from Chicago to Boston
We've examined 81,576 itinerary searches that we've seen for departures in the next 90 days and found that the cheapest day to fly from Chicago to Boston is Monday. See the chart below to compare prices for other days of the week.
Compare Flight Prices from Chicago to Boston by Month
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 Chicago to Boston flights.
|Month||Origin||Destination||Carrier||Depart Date||Return Date||Stops||Price|
Cheap Last Minute Flights from Chicago to Boston
Looking for cheap last minute flights or a weekend getaway? We've got you covered with weekend flight deals from Chicago to Boston. 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 Chicago to Boston
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 Chicago to Boston is $290.
The average price for direct flights from Chicago to Boston is $348.
The chart below shows up to date information regarding non-stop flights from Chicago to Boston.
|Carrier||Mon||Tue||Wed||Thu||Fri||Sat||Sun||Earliest Flight||Latest Flight|
One Way Flights vs Round Trip Flights from Chicago to Boston
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 Chicago to Boston. 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 Chicago to Boston is $99.
The average price for round trip flights from Chicago to Boston is $287.
Chicago to Boston Flight Questions
Below are some common questions that asked about this flight route:
Chicago to Boston Airports
These are the major commercial airports we're currently monitoring in Chicago and Boston. 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.