Flights from Boston (BOS) to Chicago (CHI)

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We compare hundreds of flights from Boston to Chicago from a range of airlines and travel agents to get you the best deals. Find cheap flights along this route.
Boston (BOS) to Chicago (ORD)
 Depart 29 Aug 16
 Return 05 Sep 16

Discount subject to availability

Boston (BOS) to Chicago (ORD)
 Depart 14 Sep 16
 Return 20 Sep 16

Flying with United Airlines

Price subject to availability

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  • Dep date
  1 more CheapOair.com flights available on this route
$76   Dep 18 Oct 16 - Rtn 22 Oct 16
Boston to Chicago
BOS to CHI CheapOair.com
Boston (BOS) to Chicago (CHI)
 Depart 01 Nov 16
 Return 08 Nov 16

Flying with American Airlines

Price subject to availability

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  • Price
  • Dep date
  2 more OneTravel.com flights available on this route
$136   Dep 14 Sep 16 - Rtn 29 Sep 16
Boston to Chicago
BOS to ORD OneTravel.com
$233   Dep 27 Oct 16 - Rtn 31 Oct 16
Boston to Chicago
BOS to MDW OneTravel.com
Boston (BOS) to Chicago (CHI)
 Depart 14 Sep 16
 Return 21 Sep 16

Price subject to availability

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Boston (BOS) to Chicago (ORD)
 Depart 01 Oct 16
 Return 04 Oct 16

Price subject to availability

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      Travel information for Boston to Chicago

      Photo of Chicago   Chicago
      Partners with flight deals forBoston to Chicago5
      Deals on offer forBoston to Chicago434
      Cheapest flight forBoston to Chicago$66
      Average flight deal forBoston to Chicago$518
      Average flight time forBoston to Chicago2 hrs 40 mins
      Distance from Boston to Chicago852 miles

       How much do things cost in Chicago and Boston?

      Boston Chicago
      Local draught beer (0.5 liter)$5.50$5.00
      Large bottle of water$1.89$1.77
      3 course meal for 2$60.00$65.00
      Bottle of local beer (0.5 liter)$1.56$1.33
      Imported beer (0.33 liter)$7.00$6.00
      source

        Facts and figures about flying from Boston to Chicago

      • The standard cancellation rate when flying from Boston to Chicago is 4.6 percent
      • Every week American Airlines Inc. has 214 flights from Boston to Chicago
      • Flights from Boston to Chicago are not usually diverted
      • Flights from Boston to Chicago typically have a delay of 1 hr 12 mins
      • The Boeing 757 Mixed is the largest aircraft operating flights between Boston and Chicago
      • The Embraer EMB 170/EMB 190 is the smallest airplane available for flights between Boston and Chicago
      • There are on average 2337 seats available each day on flights from Boston to Chicago
      • The most popular aircraft flying between Boston and Chicago is a Boeing 737-800 (winglets)