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 09 Jun 15
 Return 16 Jun 15

Flying with Spirit Airlines

Price subject to availability

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Boston (BOS) to Chicago (CHI)
 Depart 10 Jun 15
 Return 17 Jun 15

Price subject to availability

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Boston (BOS) to Chicago (CHI)
 Depart 15 Jun 15
 Return 17 Jun 15

Price subject to availability

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  • Price
  • Dep date
  1 more OneTravel.com flights available on this route
$234   Dep 14 Jun 15 - Rtn 30 Jun 15
Boston to Chicago
BOS to ORD OneTravel.com
Boston (BOS) to Chicago (CHI)
 Depart 09 Jun 15
 Return 16 Jun 15

Price subject to availability

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  • Price
  • Dep date
  15 more CheapOair.com flights available on this route
$194   Dep 12 Oct 15 - Rtn 14 Oct 15
Boston to Chicago
BOS to CHI CheapOair.com
$199   Dep 10 Jun 15 - Rtn 13 Jun 15
Boston to Chicago
BOS to CHI CheapOair.com
$201   Dep 17 Jun 15 - Rtn 24 Jun 15
Boston to Chicago
BOS to ORD CheapOair.com
$204   Dep 09 Jun 15 - Rtn 10 Jun 15
Boston to Chicago
BOS to ORD CheapOair.com
$204   Dep 08 Sep 15 - Rtn 10 Sep 15
Boston to Chicago
BOS to ORD CheapOair.com
$204   Dep 09 Sep 15 - Rtn 15 Sep 15
Boston to Chicago
BOS to ORD CheapOair.com
$204   Dep 11 Sep 15 - Rtn 12 Sep 15
Boston to Chicago
BOS to ORD CheapOair.com
$204   Dep 10 Oct 15 - Rtn 14 Oct 15
Boston to Chicago
BOS to ORD CheapOair.com
$204   Dep 12 Oct 15 - Rtn 16 Oct 15
Boston to Chicago
BOS to ORD CheapOair.com
$206   Dep 13 Jun 15 - Rtn 17 Jun 15
Boston to Chicago
BOS to ORD CheapOair.com
$209   Dep 09 Jun 15 - Rtn 13 Jun 15
Boston to Chicago
BOS to ORD CheapOair.com
$214   Dep 02 Jun 15 - Rtn 09 Jun 15
Boston to Chicago
BOS to CHI CheapOair.com
$214   Dep 09 Sep 15 - Rtn 13 Sep 15
Boston to Chicago
BOS to CHI CheapOair.com
$218   Dep 15 Jun 15 - Rtn 17 Jun 15
Boston to Chicago
BOS to CHI CheapOair.com
$221   Dep 24 Jun 15 - Rtn 30 Jun 15
Boston to Chicago
BOS to ORD CheapOair.com
Boston (BOS) to Chicago (ORD)
 Depart 19 Aug 15
 Return 26 Aug 15

Flying with Spirit Airlines

Price subject to availability

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  • Price
  • Dep date
  15 more momondo.com flights available on this route
$176   Dep 26 Aug 15 - Rtn 02 Sep 15
Boston to Chicago
BOS to ORD momondo.com
$186   Dep 22 Jul 15 - Rtn 29 Jul 15
Boston to Chicago
BOS to ORD momondo.com
$186   Dep 05 Aug 15 - Rtn 12 Aug 15
Boston to Chicago
BOS to ORD momondo.com
$186   Dep 12 Aug 15 - Rtn 19 Aug 15
Boston to Chicago
BOS to ORD momondo.com
$196   Dep 29 Jul 15 - Rtn 05 Aug 15
Boston to Chicago
BOS to ORD momondo.com
$210   Dep 26 Aug 15 - Rtn 02 Sep 15
Boston to Chicago
BOS to ORD momondo.com
$220   Dep 22 Jul 15 - Rtn 29 Jul 15
Boston to Chicago
BOS to ORD momondo.com
$230   Dep 05 Aug 15 - Rtn 12 Aug 15
Boston to Chicago
BOS to ORD momondo.com
$230   Dep 26 Aug 15 - Rtn 02 Sep 15
Boston to Chicago
BOS to ORD momondo.com
$234   Dep 19 Aug 15 - Rtn 26 Aug 15
Boston to Chicago
BOS to ORD momondo.com
$260   Dep 12 Aug 15 - Rtn 19 Aug 15
Boston to Chicago
BOS to ORD momondo.com
$353   Dep 05 Aug 15 - Rtn 12 Aug 15
Boston to Chicago
BOS to ORD momondo.com
$360   Dep 29 Jul 15 - Rtn 05 Aug 15
Boston to Chicago
BOS to ORD momondo.com
$364   Dep 29 Jul 15 - Rtn 05 Aug 15
Boston to Chicago
BOS to ORD momondo.com
$386   Dep 05 Aug 15 - Rtn 12 Aug 15
Boston to Chicago
BOS to ORD momondo.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 Chicago212
      Cheapest flight forBoston to Chicago$166
      Average flight deal forBoston to Chicago$277
      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 is 6% more expensive than Chicago
      Boston Chicago
      Imported beer (0.33 liter bottle)$2.50$1.80
      1 hour taxi waiting fee$28.00$30.00
      Large bottle of water$1.80$1.86
      1 mile taxi journey$2.80$1.91
      source

        Facts and figures about flying from Boston to Chicago

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