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 (CHI)
 Depart 27 Feb 16
 Return 05 Mar 16

Price subject to availability

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Boston (BOS) to Chicago (ORD)
 Depart 26 Apr 16
 Return 02 May 16

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Boston (BOS) to Chicago (ORD)
 Depart 28 Feb 16
 Return 06 Mar 16

Flying with Iberia

Price subject to availability

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Boston (BOS) to Chicago (ORD)
 Depart 05 Jun 16
 Return 13 Jun 16

Flying with American Airlines

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  • Price
  • Dep date
  1 more OneTravel.com flights available on this route
$112   Dep 05 May 16 - Rtn 08 May 16
Boston to Chicago
BOS to CHI OneTravel.com
Boston (BOS) to Chicago (ORD)
 Depart 21 Apr 16
 Return 28 Apr 16

Flying with JetBlue Airways

Price subject to availability

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  • Price
  • Dep date
  15 more momondo.com flights available on this route
$162   Dep 13 Apr 16 - Rtn 20 Apr 16
Boston to Chicago
BOS to ORD momondo.com
$162   Dep 26 Apr 16 - Rtn 03 May 16
Boston to Chicago
BOS to ORD momondo.com
$169   Dep 11 Apr 16 - Rtn 18 Apr 16
Boston to Chicago
BOS to ORD momondo.com
$182   Dep 23 Apr 16 - Rtn 30 Apr 16
Boston to Chicago
BOS to ORD momondo.com
$192   Dep 01 May 16 - Rtn 08 May 16
Boston to Chicago
BOS to ORD momondo.com
$194   Dep 03 May 16 - Rtn 10 May 16
Boston to Chicago
BOS to ORD momondo.com
$241   Dep 28 Apr 16 - Rtn 05 May 16
Boston to Chicago
BOS to ORD momondo.com
$269   Dep 06 May 16 - Rtn 13 May 16
Boston to Chicago
BOS to ORD momondo.com
$276   Dep 18 Apr 16 - Rtn 25 Apr 16
Boston to Chicago
BOS to ORD momondo.com
$276   Dep 21 Apr 16 - Rtn 28 Apr 16
Boston to Chicago
BOS to ORD momondo.com
$276   Dep 23 Apr 16 - Rtn 30 Apr 16
Boston to Chicago
BOS to ORD momondo.com
$276   Dep 01 May 16 - Rtn 08 May 16
Boston to Chicago
BOS to ORD momondo.com
$276   Dep 13 May 16 - Rtn 20 May 16
Boston to Chicago
BOS to ORD momondo.com
$281   Dep 13 May 16 - Rtn 20 May 16
Boston to Chicago
BOS to ORD momondo.com
$296   Dep 08 May 16 - Rtn 15 May 16
Boston to Chicago
BOS to ORD momondo.com
Boston (BOS) to Chicago (ORD)
 Depart 27 Feb 16
 Return 01 Mar 16

Flying with JetBlue Airways

Price subject to availability

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  • Price
  • Dep date
  1 more CheapOair.com flights available on this route
$108   Dep 27 Feb 16 - Rtn 02 Mar 16
Boston to Chicago
BOS to CHI CheapOair.com
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      Travel information for Boston to Chicago

      Photo of Chicago   Chicago
      Partners with flight deals forBoston to Chicago6
      Deals on offer forBoston to Chicago296
      Cheapest flight forBoston to Chicago$95
      Average flight deal forBoston to Chicago$447
      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
      Large bottle of water$1.89$1.77
      3 bedroom apartment in the suburbs$2619.50$1834.15
      Gasoline$2.75$3.34
      3 course meal for 2$60.00$65.00
      Cappuccino$3.70$3.82
      source

        Facts and figures about flying from Boston to Chicago

      • Every week American Airlines Inc. has 214 flights from Boston to Chicago
      • The Embraer EMB 170/EMB 190 is the smallest airplane available for flights between Boston and Chicago
      • The most popular aircraft flying between Boston and Chicago is a Boeing 737-800 (winglets)
      • The standard cancellation rate when flying from Boston to Chicago is 4.6 percent
      • There are on average 2337 seats available each day on 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