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Cheap flight tickets from Chicago to Boston

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      American Airlines
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      Compare Chicago to Boston flight deals

      Find the cheapest month or even day of the year to fly to Boston

      Book the best Boston fare with no extra fees

      Flight deals from Chicago to Boston

      Looking for a cheap last-minute deal or the best return flight from Chicago to Boston? If you want to travel next month, return fares start from RM849. Find the lowest prices on one-way and return tickets right here.
      Boston.RM399 per passenger.Departing Sat, 19 Sep.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Sat, 19 Sep, arriving in Boston Logan International.Price includes taxes and charges.From RM399, select.
      Boston.RM424 per passenger.Departing Sat, 3 Oct.One-way flight with jetBlue.Outbound direct flight with jetBlue departs from Chicago O'Hare International on Sat, 3 Oct, arriving in Boston Logan International.Price includes taxes and charges.From RM424, select.
      Boston.RM434 per passenger.Departing Tue, 17 Nov.One-way flight with Delta.Outbound direct flight with Delta departs from Chicago O'Hare International on Tue, 17 Nov, arriving in Boston Logan International.Price includes taxes and charges.From RM434, select.
      Boston.RM434 per passenger.Departing Wed, 17 Feb.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 17 Feb, arriving in Boston Logan International.Price includes taxes and charges.From RM434, select.
      Boston.RM434 per passenger.Departing Wed, 16 Sep.One-way flight with American Airlines.Outbound direct flight with American Airlines departs from Chicago O'Hare International on Wed, 16 Sep, arriving in Boston Logan International.Price includes taxes and charges.From RM434, select.
      Boston.RM434 per passenger.Departing Mon, 11 Jan.One-way flight with Delta.Outbound direct flight with Delta departs from Chicago O'Hare International on Mon, 11 Jan, arriving in Boston Logan International.Price includes taxes and charges.From RM434, select.
      Boston.RM434 per passenger.Departing Sat, 5 Dec.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 5 Dec, arriving in Boston Logan International.Price includes taxes and charges.From RM434, select.
      Boston.RM510 per passenger.Departing Mon, 17 May.One-way flight with Delta.Outbound direct flight with Delta departs from Chicago O'Hare International on Mon, 17 May, arriving in Boston Logan International.Price includes taxes and charges.From RM510, select.
      Boston.RM510 per passenger.Departing Tue, 16 Mar.One-way flight with Delta.Outbound direct flight with Delta departs from Chicago O'Hare International on Tue, 16 Mar, arriving in Boston Logan International.Price includes taxes and charges.From RM510, select.
      Boston.RM510 per passenger.Departing Tue, 6 Apr.One-way flight with Delta.Outbound direct flight with Delta departs from Chicago O'Hare International on Tue, 6 Apr, arriving in Boston Logan International.Price includes taxes and charges.From RM510, select.
      Boston.RM551 per passenger.Departing Fri, 9 Jul.One-way flight with Delta.Outbound direct flight with Delta departs from Chicago O'Hare International on Fri, 9 Jul, arriving in Boston Logan International.Price includes taxes and charges.From RM551, select.
      Boston.RM552 per passenger.Departing Wed, 2 Jun.One-way flight with Delta.Outbound direct flight with Delta departs from Chicago O'Hare International on Wed, 2 Jun, arriving in Boston Logan International.Price includes taxes and charges.From RM552, select.

      Find the cheapest month to fly from Chicago to Boston

      We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago to Boston flights are currently cheapest in September.
      Sep
      from RM399
      Oct
      from RM424
      Nov
      from RM434
      Dec
      from RM434
      Jan
      from RM434
      Feb
      from RM434
      Mar
      from RM510
      Apr
      from RM510
      May
      from RM510
      Jun
      from RM552
      Jul
      from RM551
      Aug
      Find prices

      Direct flights from Chicago to Boston

      Air France
      Air New Zealand
      American Airlines
      ANA (All Nippon Airways)
      Avianca
      British Airways
      Cathay Pacific
      Delta
      EL AL Israel Airlines
      Emirates
      Etihad Airways
      Finnair
      Iberia
      Icelandair
      ITA Airways
      Japan Airlines
      jetBlue
      KLM
      Korean Air
      Qatar Airways
      Royal Jordanian
      Scandinavian Airlines
      Southwest Airlines
      TAP Air Portugal
      United
      Virgin Atlantic
      WestJet

      Alternative Chicago to Boston routes

      Looking for the cheapest, fastest or easiest route from Chicago to Boston? You could fly into the following airports instead.

      Boston Logan International

      5km from central Boston
      ClosestCheapest
      from RM399
      Search flights

      Worcester

      68km from central Boston
      from RM532
      Search flights

      Manchester

      72km from central Boston
      from RM635
      Search flights

      Fall River

      76km from central Boston
      from RM2,678
      Search flights

      Provincetown

      76km from central Boston
      Search flights

      Providence

      76km from central Boston
      from RM514
      Search flights

      Portsmouth

      82km from central Boston
      from RM2,869
      Search flights

      Chicago to Boston: Flight information

      The things to know before you go.
      Cheapest flight foundRM399
      Cheapest month to flySeptember
      Average flight time2 hrs, 26 mins
      Most popular airlineAmerican Airlines
      Average flights per week715

      Finding cheap flights from Chicago to Boston: Frequently asked questions

      There are 7 airports in Boston: Boston Logan International, Worcester, Manchester, Fall River, Provincetown, Providence, and Portsmouth.
      The best price we found for a return flight from Chicago to Boston is RM715. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
      2 hours and 26 minutes is the average flight time from Chicago to Boston.
      American Airlines, United and Southwest Airlines fly direct from Chicago to Boston.
      As of September 2026, there are 715 flights per week flying from Chicago to Boston.
      The cheapest month to fly from Chicago to Boston is usually September.
      If you're flying from Chicago, the cheapest airport near Boston is Boston Logan International – which is 4.5 km away from the centre of Boston. We've found flights into this airport from RM715.
      After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Boston on Saturday, 19 September 2026.
      Yes – the average flight time is 2 hours and 26 minutes.
      We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Boston but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

      We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Boston is around 40 days in advance, so don’t leave your flight to the last minute.

      In September, the average temperature is usually around 19°C. July is typically the warmest month in Boston, when it usually averages around 27°C. You can expect the least rain in November. The coldest month is January, with temperatures averaging -3°C. The rainiest month is January.
      The cheapest airline that flies to Boston is Frontier Airlines. And the cheapest airline that flies to Worcester Airport is Delta.

      How to find cheap flights from Chicago to Boston

      Looking for cheap flight tickets from Chicago to Boston? Whether you are aiming to find one-way or return flights, here are a few tips on how to secure the best ticket price and make your journey as smooth as possible.

      • Simply hit 'search'. We've compared tickets from all major online travel agents and airlines flying from Chicago-Boston to find the cheapest flights. And with us there are no hidden extras - what you see is what you pay.

      • Flex your dates to find the flight price for your Chicago-Boston flight. If your travel dates are flexible, use Skyscanner's 'Whole month' tool to find the cheapest month, and even day to fly to Boston from Chicago.

      • Set up a Price Alert. You can easily track the price of your flight from Chicago to Boston by creating an alert. Whenever prices go down or up, you'll get a push notification or e-mail to help you get the best flight deal.

      • Look for non-stop flights. Only interested in direct flights between Chicago and Boston ? Make sure to tick 'Direct flights only' when performing a search. If there are flights without stops available, these will appear in the results.

      • Include nearby airports in your search. Widen your search for Chicago to Boston flight deals by selecting the "add nearby airports" option. This will allow you to see flight prices for all the nearest airports at your departure point and your destination and could help you save on your next trip.

      • Find the cheapest Business class flights from Chicago to Boston. Check the difference in price of your Chicago-Boston air ticket when travelling in Economy, Premium economy, Business or First class. Note that not all cabin classes are available on every route or airline.

      • Search for cheap flights when out and about. To get the best flight booking experience regardless of where you are, download our app and search for flight tickets from Chicago to Boston on the go.

      Book flight tickets from Chicago to Boston with peace of mind

      • Find flexible flights. Your airline might be offering flexible tickets from Chicago to Boston , which means you won't lose out if your flight has to be changed or cancelled.

      • Add travel cost protection. Avoid travel pitfalls and choose travel cost protection - it's available at the checkout as you book your Chicago-Boston flight with us.

      • Reduce your carbon footprint by selecting a greener flight option. To check whether there are any lower emissions flights available on the route Chicago-Boston , simply check the “only show flights with lower CO₂ emissions” box later on in your search.

      Combine your flight to Boston with hotels and car hire

      Once you've secured your flight booking from Chicago to Boston, we will help you discover the best prices and exclusive rates for cheap hotels in Boston or nearby. And if you're looking for car hire, we've got you covered too. We allow you to compare hundreds of car hire companies in one search and find the best price on car rental in Boston.

      Compare Chicago-Boston tickets with other routes

      Not entirely set on flying from Chicago to Boston yet? You can easily browse other destinations by searching flights to 'Everywhere' - this will allow you to find the cheapest place to travel from your chosen departure point in Malaysia or abroad.


      Plan the rest of your trip from Chicago to Boston

      Prices shown on this page are estimated lowest prices only. Found in the last 12 days.