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 29 Apr 15
 Return 06 May 15

Price subject to availability

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Boston (BOS) to Chicago (CHI)
 Depart 28 Apr 15
 Return 05 May 15

Flying with Spirit Airlines

Price subject to availability

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Boston (BOS) to Chicago (ORD)
 Depart 29 Apr 15
 Return 06 May 15

Flying with Spirit Airlines

Price subject to availability

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  • Price
  • Dep date
  7 more CheapOair.com flights available on this route
$154   Dep 12 May 15 - Rtn 13 May 15
Boston to Chicago
BOS to ORD CheapOair.com
$154   Dep 13 May 15 - Rtn 19 May 15
Boston to Chicago
BOS to ORD CheapOair.com
$184   Dep 29 Aug 15 - Rtn 01 Sep 15
Boston to Chicago
BOS to ORD CheapOair.com
$184   Dep 09 Oct 15 - Rtn 15 Oct 15
Boston to Chicago
BOS to ORD CheapOair.com
$189   Dep 11 Aug 15 - Rtn 19 Aug 15
Boston to Chicago
BOS to ORD CheapOair.com
$201   Dep 23 Aug 15 - Rtn 27 Aug 15
Boston to Chicago
BOS to ORD CheapOair.com
$225   Dep 09 Apr 15 - Rtn 13 Apr 15
Boston to Chicago
BOS to ORD CheapOair.com
Boston (BOS) to Chicago (ORD)
 Depart 27 May 15
 Return 03 Jun 15

Flying with Spirit Airlines

Price subject to availability

   View more dates
 
  • Price
  • Dep date
  15 more momondo.com flights available on this route
$161   Dep 10 Jun 15 - Rtn 17 Jun 15
Boston to Chicago
BOS to ORD momondo.com
$180   Dep 27 May 15 - Rtn 03 Jun 15
Boston to Chicago
BOS to ORD momondo.com
$186   Dep 17 Jun 15 - Rtn 24 Jun 15
Boston to Chicago
BOS to ORD momondo.com
$186   Dep 24 Jun 15 - Rtn 01 Jul 15
Boston to Chicago
BOS to ORD momondo.com
$186   Dep 01 Jul 15 - Rtn 08 Jul 15
Boston to Chicago
BOS to ORD momondo.com
$199   Dep 10 Jun 15 - Rtn 17 Jun 15
Boston to Chicago
BOS to ORD momondo.com
$219   Dep 17 Jun 15 - Rtn 24 Jun 15
Boston to Chicago
BOS to ORD momondo.com
$245   Dep 24 Jun 15 - Rtn 01 Jul 15
Boston to Chicago
BOS to ORD momondo.com
$280   Dep 01 Jul 15 - Rtn 08 Jul 15
Boston to Chicago
BOS to ORD momondo.com
$287   Dep 27 May 15 - Rtn 03 Jun 15
Boston to Chicago
BOS to ORD momondo.com
$294   Dep 27 May 15 - Rtn 03 Jun 15
Boston to Chicago
BOS to ORD momondo.com
$301   Dep 03 Jun 15 - Rtn 10 Jun 15
Boston to Chicago
BOS to ORD momondo.com
$310   Dep 03 Jun 15 - Rtn 10 Jun 15
Boston to Chicago
BOS to ORD momondo.com
$317   Dep 03 Jun 15 - Rtn 10 Jun 15
Boston to Chicago
BOS to ORD momondo.com
$335   Dep 03 Jun 15 - Rtn 10 Jun 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 Chicago4
      Deals on offer forBoston to Chicago182
      Cheapest flight forBoston to Chicago$125
      Average flight deal forBoston to Chicago$286
      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 8% more expensive than Chicago
      Boston Chicago
      Cheap meal$13.00$11.00
      Cappuccino$3.91$3.79
      Large bottle of water$1.70$1.86
      1 mile taxi journey$2.80$2.00
      source

        Facts and figures about flying from Boston to Chicago

      • Every week American Airlines Inc. has 214 flights from Boston to Chicago
      • Flights from Boston to Chicago typically have a delay of 1 hr 12 mins
      • Flights from Boston to Chicago are not usually diverted
      • 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
      • The standard cancellation rate when flying from Boston to Chicago is 4.6 percent
      • 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