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 12 Oct 16
 Return 19 Oct 16

Flying with Spirit Airlines

Price subject to availability

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  1 more CheapOair.com flights available on this route
$80   Dep 26 Oct 16 - Rtn 02 Nov 16
Boston to Chicago
BOS to ORD CheapOair.com
Boston (BOS) to Chicago (ORD)
 Depart 02 Oct 16
 Return 09 Oct 16

Discount subject to availability

Boston (BOS) to Chicago (ORD)
 Depart 18 Oct 16
 Return 25 Oct 16

Flying with Spirit Airlines

Price subject to availability

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  • Dep date
  1 more OneTravel.com flights available on this route
$80   Dep 02 Nov 16 - Rtn 09 Nov 16
Boston to Chicago
BOS to CHI OneTravel.com
Boston (BOS) to Chicago (ORD)
 Depart 02 Nov 16
 Return 09 Nov 16

Price subject to availability

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  15 more Smartfares.com flights available on this route
$96   Dep 03 Dec 16 - Rtn 06 Dec 16
Boston to Chicago
BOS to ORD Smartfares.com
$118   Dep 13 Oct 16 - Rtn 18 Oct 16
Boston to Chicago
BOS to ORD Smartfares.com
$151   Dep 27 Oct 16 - Rtn 30 Oct 16
Boston to Chicago
BOS to ORD Smartfares.com
$151   Dep 04 Nov 16 - Rtn 07 Nov 16
Boston to Chicago
BOS to ORD Smartfares.com
$171   Dep 17 Feb 17 - Rtn 20 Feb 17
Boston to Chicago
BOS to ORD Smartfares.com
$181   Dep 20 Oct 16 - Rtn 23 Oct 16
Boston to Chicago
BOS to ORD Smartfares.com
$201   Dep 14 Oct 16 - Rtn 17 Oct 16
Boston to Chicago
BOS to ORD Smartfares.com
$206   Dep 21 Oct 16 - Rtn 23 Oct 16
Boston to Chicago
BOS to ORD Smartfares.com
$212   Dep 04 Apr 17 - Rtn 11 Apr 17
Boston to Chicago
BOS to ORD Smartfares.com
$226   Dep 06 Oct 16 - Rtn 12 Oct 16
Boston to Chicago
BOS to ORD Smartfares.com
$251   Dep 03 Nov 16 - Rtn 06 Nov 16
Boston to Chicago
BOS to ORD Smartfares.com
$286   Dep 04 Nov 16 - Rtn 06 Nov 16
Boston to Chicago
BOS to ORD Smartfares.com
$311   Dep 18 Nov 16 - Rtn 20 Nov 16
Boston to Chicago
BOS to ORD Smartfares.com
$316   Dep 07 Oct 16 - Rtn 12 Oct 16
Boston to Chicago
BOS to ORD Smartfares.com
$316   Dep 14 Oct 16 - Rtn 16 Oct 16
Boston to Chicago
BOS to ORD Smartfares.com
Boston (BOS) to Chicago (CHI)
 Depart 12 Oct 16
 Return 19 Oct 16

Price subject to availability

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  • Dep date
  13 more CheapAir.com flights available on this route
$80   Dep 19 Oct 16 - Rtn 26 Oct 16
Boston to Chicago
BOS to CHI CheapAir.com
$80   Dep 26 Oct 16 - Rtn 02 Nov 16
Boston to Chicago
BOS to CHI CheapAir.com
$80   Dep 02 Nov 16 - Rtn 09 Nov 16
Boston to Chicago
BOS to CHI CheapAir.com
$86   Dep 29 Oct 16 - Rtn 05 Nov 16
Boston to Chicago
BOS to CHI CheapAir.com
$96   Dep 15 Oct 16 - Rtn 22 Oct 16
Boston to Chicago
BOS to CHI CheapAir.com
$96   Dep 22 Oct 16 - Rtn 29 Oct 16
Boston to Chicago
BOS to CHI CheapAir.com
$116   Dep 31 Oct 16 - Rtn 07 Nov 16
Boston to Chicago
BOS to CHI CheapAir.com
$126   Dep 28 Oct 16 - Rtn 04 Nov 16
Boston to Chicago
BOS to CHI CheapAir.com
$146   Dep 21 Oct 16 - Rtn 28 Oct 16
Boston to Chicago
BOS to CHI CheapAir.com
$146   Dep 24 Oct 16 - Rtn 31 Oct 16
Boston to Chicago
BOS to CHI CheapAir.com
$151   Dep 17 Oct 16 - Rtn 24 Oct 16
Boston to Chicago
BOS to CHI CheapAir.com
$191   Dep 04 Nov 16 - Rtn 11 Nov 16
Boston to Chicago
BOS to CHI CheapAir.com
$196   Dep 14 Oct 16 - Rtn 21 Oct 16
Boston to Chicago
BOS to CHI CheapAir.com
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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 Chicago521
      Cheapest flight forBoston to Chicago$79
      Average flight deal forBoston to Chicago$715
      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
      Imported beer (0.33 liter)$7.00$6.00
      1 mile taxi journey$2.80$1.80
      Bottle of local beer (0.5 liter)$1.56$1.33
      Large bottle of water$1.89$1.77
      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
      • There are on average 2337 seats available each day on flights from Boston to Chicago
      • The standard cancellation rate when flying from Boston to Chicago is 4.6 percent
      • The most popular aircraft flying between Boston and Chicago is a Boeing 737-800 (winglets)
      • 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
      • Flights from Boston to Chicago are not usually diverted