Flights from Boston to Chicago, United States Last modified: Sep 25, 2016 12:50 AM
Boston to Chicago Last modified: Sep 25, 2016 12:50 AM
We've scanned 23,629,223,180 round trip itineraries and found the cheapest flights from Boston to Chicago. American & JetBlue frequently offer the best deals on Boston 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 thinking 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?
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||$117||$255|
Cheapest Day To Fly from Boston to Chicago
We've examined 23,636,053,052 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 Monday. See the chart below to compare prices for other days of the week.
Compare Flight Prices from Boston to Chicago 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 Boston to Chicago flights.
|Month||Origin||Destination||Carrier||Depart Date||Return Date||Stops||Price|
Cheap Last Minute Flights from Boston to Chicago
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
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 $194.
The average price for direct flights from Boston to Chicago is $89.
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|
One Way Flights vs Round Trip Flights from Boston to Chicago
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 $139.
The average price for round trip flights from Boston to Chicago is $89.
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 25, 2016 12:50 AMNumber of routes searched: 304Number of itineraries searched: 1,397,175
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.
More Cheap Flights
|Flights from New York to Chicago||American, Alaska, JetBlue, Delta, Spirit, United||$107|
|Flights from Newark to Chicago||American, JetBlue, Delta, United||$117|
|Flights from Hartford to Chicago||American, Delta, United||$177|
|Flights from Providence to Chicago||American||$187|
|Flights from Westchester County to Chicago||American, Delta, United||$177|
|Flights from Albany to Chicago||American, Delta, United||$277|
|Flights from Burlington to Chicago||JetBlue, Delta, United||$241|
|Flights from Manchester to Chicago||Delta, United||$187|
|Flights from Portland to Chicago||JetBlue, Delta, United||$202|
|Flights from Long Island MacArthur to Chicago||American||$220|
|Flights from Newburgh to Chicago||Check Dates|
|Flights from Bangor to Chicago||Delta, United||$498|
|Flights from New Haven to Chicago||American||$189|
|Flights from Nantucket to Chicago||JetBlue||Check Dates|
|Flights from New York to Atlanta||American, JetBlue, Delta, Frontier, Spirit, United||$109|
|Flights from New York to Los Angeles||American, Alaska, JetBlue, Delta, Spirit, Sun Country, United, Virgin America||$248|
|Flights from New York to Toronto||American, Air Canada, Delta, United, WestJet||$174|
|Flights from New York to Detroit||American, JetBlue, Delta, Spirit||$141|
|Flights from New York to London||American, Air Berlin, Air Canada, Air France, Royal Air Maroc, Finnair, Alitalia, British Airways, Delta, Norwegian Shuttle, Aer Lingus, Icelandair, Iberia, KLM, Kuwait, Lufthansa, Swiss, El Al, China Eastern, Austrian, Qatar, Brussels, Tap Portugal, United, Air Europa, Virgin Atlantic, WestJet||$384|
|Flights from New York to Milwaukee||Delta||$226|
|Flights from New York to Dallas - Ft Worth||American, Alaska, JetBlue, Delta, Spirit, United, Virgin America||$93|
|Flights from New York to Orlando||American, JetBlue, Delta, Spirit, United||$137|
|Flights from New York to Minneapolis - St Paul||American, Delta, Spirit, Sun Country||$232|
|Flights from New York to Miami||American, Delta, Frontier||$137|
|Flights from New York to Indianapolis||American, Delta||$143|
|Flights from New York to Las Vegas||American, JetBlue, Delta, Spirit, Sun Country, United, Virgin America||$192|
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|Flights from New York to Charlotte||American, JetBlue, Delta||$127|
|Flights from New York to San Francisco||American, Alaska, JetBlue, Delta, Sun Country, United, Virgin America||$267|
|Flights from Boston to New York||JetBlue, Delta||$97|