Cheap Flights from Boston to Chicago, IL, United States - BOS to CHI
Popular flights from Boston to Chicago
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.
|Departure Date||Return Date||Lowest Price|
|Feb 29, 2016||Mar 4, 2016||$103|
|Departure Date||Return Date||Lowest Price|
|May 5, 2016||May 6, 2016||$113|
When Can I Buy the Cheapest Flight from Boston to Chicago (BOS to CHI)?
Airlines can adjust prices for plane 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 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 Boston to Chicago
The chart below shows up-to-date information regarding how far in advance a flight from Boston to Chicago should be booked.
|Advanced Purchase||Non Stop||One Stop|
|< 7 days||$248||$255|
Lowest Fares Chart By Month from Boston to Chicago
The chart below shows the lowest fare by month when flying from Boston to Chicago.
|Month||Origin||Destination||Carrier||Depart Date||Return Date||Stops||Price|
Cheapest Weekend Non-Stop Flights for the Next 30 Days from Boston to Chicago
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 Boston to Chicago.
Next 30 Days
Non-Stop vs Connecting Flights from Boston to Chicago (BOS to CHI)
Your Boston to Chicago 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 Boston to Chicago is $141.
The average price for non-stop flights from Boston to Chicago is $113.
The chart below shows up to date information regarding non-stop flights from Boston to Chicago.
|Carrier||Mon||Tue||Wed||Thu||Fri||Sat||Sun||Earliest Flight||Latest Flight|
Round Trip vs One Way Flights from Boston to Chicago (BOS to CHI)
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 $60.
The average price for round trip flights from Boston to Chicago is $113.
More Cheap Flights
|New York to Chicago||American, Alaska, JetBlue, Spirit, United||$74|
|Newark to Chicago||American, Alaska, JetBlue, Spirit, United||$137|
|Hartford to Chicago||American, United||$264|
|Providence to Chicago||American, United||$170|
|Westchester County to Chicago||American, United||$315|
|Albany to Chicago||American, United||$326|
|Burlington to Chicago||American, JetBlue, United||$282|
|Manchester to Chicago||American, United||$173|
|Portland to Chicago||American, JetBlue, United||$294|
|Long Island MacArthur to Chicago||American, United||$275|
|Newburgh to Chicago||Silver, American, United||Check Dates|
|Bangor to Chicago||American, United||$214|
|New Haven to Chicago||American||$285|
|Nantucket to Chicago||American, JetBlue, United||Check Dates|
|New York to Atlanta||American, Alaska, Frontier, Spirit, United||$124|
|New York to Los Angeles||American, Alaska, JetBlue, Spirit, Sun Country, United, Virgin America||$239|
|New York to Toronto||American, Air Canada, Alaska, JetBlue, Porter, United, WestJet||$183|
|New York to Detroit||American, JetBlue, Spirit, United||$87|
|New York to London||American, Air Berlin, Air France, Finnair, Alitalia, JetBlue, British Airways, airBaltic, Condor, OpenSkies, Aer Lingus, Iberia, Meridiana, KLM, Kuwait, Lufthansa, LOT, Thomas Cook, Czech, Austrian, TAROM, SATA, SAS, Brussels, Tap Portugal, United, Air Europa, Virgin Atlantic||$647|
|New York to Milwaukee||American, United||$145|
|New York to Dallas - Ft Worth||American, JetBlue, Spirit, Sun Country, United, Virgin America||$86|
|New York to Orlando||American, JetBlue, Spirit, United||$127|
|New York to Minneapolis - St Paul||American, Sun Country, United||$255|
|New York to Miami||American, Frontier, United||$95|
|New York to Indianapolis||American, Alaska, United||$138|
|New York to Las Vegas||American, Alaska, JetBlue, Spirit, United, Virgin America||$223|
|Boston to Atlanta||American, Spirit, United||$151|
|New York to Charlotte||American, JetBlue, United||$127|
|New York to San Francisco||American, Alaska, JetBlue, Sun Country, United, Virgin America||$236|
|Boston to New York||American, JetBlue||$97|
Airlines Flying from Boston to Chicago (BOS to CHI)
Below are the different airlines that fly from Boston to Chicago 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 Boston to Chicago.
Airports for Your Route
These pages contain information about the major airports in Boston and Chicago, so you can feel comfortable knowing how to get around whether you are about to take off or you just landed.
Boston to Chicago Flight Questions
Below are some common questions that asked about this flight route: