Cheap Flights from Chicago to Boston, MA, United States - CHI to BOS
Popular flights from Chicago to Boston
If your flight days are flexible and you looking for a good deal, our charts on cheap flights provide some insight regarding affordable flight options for your next big adventure.
When Can I Buy the Cheapest Flight from Chicago to Boston (CHI to BOS)?
Airlines can adjust prices for plane 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 discovered that the best days to book flights are Tuesdays, Wednesdays, and Saturdays. Read our article to find more information about the best time to buy airline tickets.
How far in advance should you book flights from Chicago to Boston
The chart below shows up-to-date information regarding how far in advance a flight from Chicago to Boston should be booked.
|Advanced Purchase||Non Stop||One Stop|
|< 7 days||$248||$261|
Lowest Fares Chart By Month from Chicago to Boston
The chart below shows the lowest fare by month when flying from Chicago to Boston.
|Month||Origin||Destination||Carrier||Depart Date||Return Date||Stops||Price|
Cheapest Weekend Non-Stop Flights for the Next 30 Days from Chicago to Boston
If you're ready to take a trip in the next 30 days and want to fly on the weekend, you might be wondering which weekend is the cheapest to fly. The chart below shows up-to-date data regarding weekend flight prices from Chicago to Boston.
Next 30 Days
Non-Stop vs Connecting Flights from Chicago to Boston (CHI to BOS)
Your Chicago to Boston flight can be significantly cheaper by choosing 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 $163.
The average price for non-stop flights from Chicago to Boston is $119.
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|
Round Trip vs One Way Flights from Chicago to Boston (CHI to BOS)
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 $52.
The average price for round trip flights from Chicago to Boston is $119.
Chicago to Boston Flight Questions
Below are some common questions that asked about this flight route:
Airlines Flying from Chicago to Boston (CHI to BOS)
Below are the different airlines that fly from Chicago to Boston with the average price of their plane tickets. Just remember that different airlines offer different levels of comfort and service, so consider convenience when choosing your airline.
Below is the full flight schedule summary of the next 30 days for flights from Chicago to Boston.
Airports for Your Route
These pages contain information about the major airports in Chicago and Boston, so you can feel comfortable knowing how to get around whether you are about to take off or you just landed.
Farecompare Research Tools
Cheap Domestic Flights from Chicago - CHI
|Chicago to New York||American, JetBlue, Spirit, United||$78|
|Chicago to Providence||American, United||$173|
|Chicago to Manchester||American, United||$188|
|Chicago to Newark||American, JetBlue, United||$188|
|Chicago to Washington||American, JetBlue, Frontier, United||$79|
|Chicago to Orlando||American, JetBlue, Frontier, Spirit, United||$76|
|Chicago to Hartford||American, United||$270|
|Chicago to Las Vegas||American, Alaska, Frontier, Spirit, United, Virgin America||$127|
|Chicago to Los Angeles||American, Alaska, Frontier, Spirit, United, Virgin America||$94|
|Chicago to Philadelphia||American, Frontier, Spirit, United||$78|
|Chicago to Atlanta||American, Alaska, Spirit, United||$78|
|Chicago to Portland||American, JetBlue, United||$255|
Cheap Domestic Flights to Boston - BOS
|Indianapolis to Boston||American, JetBlue, United||$198|
|Milwaukee to Boston||American, Alaska, United||$199|
|Madison to Boston||American, Alaska, United||$290|
|Green Bay to Boston||American, United||$406|
|Moline to Boston||American, United||$312|
|Lansing to Boston||Alaska, United||$166|
|Appleton to Boston||United||$442|
|Grand Rapids to Boston||American, United||$172|
|Kalamazoo to Boston||American, United||$191|
|Peoria to Boston||American, United||$309|
|Bloomington - Normal to Boston||American||$312|
|South Bend to Boston||United||$312|
|Champaign to Boston||American, United||$311|
|Ft Wayne to Boston||American, United||$268|
|Dubuque to Boston||American||$440|
|Springfield to Boston||American, United||$322|
|Toledo to Boston||American||$321|