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 11 May 15
 Return 20 May 15

Flying with Spirit Airlines

Price subject to availability

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  • Price
  • Dep date
  5 more CheapOair.com flights available on this route
$174   Dep 10 Oct 15 - Rtn 12 Oct 15
Boston to Chicago
BOS to CHI CheapOair.com
$185   Dep 23 Jun 15 - Rtn 30 Jun 15
Boston to Chicago
BOS to ORD CheapOair.com
$188   Dep 23 Jun 15 - Rtn 01 Jul 15
Boston to Chicago
BOS to ORD CheapOair.com
$194   Dep 29 Apr 15 - Rtn 06 May 15
Boston to Chicago
BOS to CHI CheapOair.com
$341   Dep 23 Apr 15 - Rtn 29 Apr 15
Boston to Chicago
BOS to ORD CheapOair.com
Boston (BOS) to Chicago (CHI)
 Depart 13 May 15
 Return 20 May 15

Price subject to availability

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Boston (BOS) to Chicago (ORD)
 Depart 01 Jul 15
 Return 08 Jul 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
$186   Dep 08 Jul 15 - Rtn 15 Jul 15
Boston to Chicago
BOS to ORD momondo.com
$186   Dep 15 Jul 15 - Rtn 22 Jul 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
$200   Dep 08 Jul 15 - Rtn 15 Jul 15
Boston to Chicago
BOS to ORD momondo.com
$206   Dep 24 Jun 15 - Rtn 01 Jul 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
$235   Dep 15 Jul 15 - Rtn 22 Jul 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
$276   Dep 01 Jul 15 - Rtn 08 Jul 15
Boston to Chicago
BOS to ORD momondo.com
$317   Dep 08 Jul 15 - Rtn 15 Jul 15
Boston to Chicago
BOS to ORD momondo.com
$330   Dep 08 Jul 15 - Rtn 15 Jul 15
Boston to Chicago
BOS to ORD momondo.com
$352   Dep 22 Jul 15 - Rtn 29 Jul 15
Boston to Chicago
BOS to ORD momondo.com
$356   Dep 08 Jul 15 - Rtn 15 Jul 15
Boston to Chicago
BOS to ORD momondo.com
$357   Dep 22 Jul 15 - Rtn 29 Jul 15
Boston to Chicago
BOS to ORD momondo.com
$368   Dep 15 Jul 15 - Rtn 22 Jul 15
Boston to Chicago
BOS to ORD momondo.com
Boston (BOS) to Chicago (CHI)
 Depart 12 May 15
 Return 20 May 15

Flying with Spirit Airlines

Price subject to availability

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Boston (BOS) to Chicago (MDW)
 Depart 12 May 15
 Return 10 Jun 15

Flying with MN Airlines

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 Chicago177
      Cheapest flight forBoston to Chicago$135
      Average flight deal forBoston to Chicago$262
      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
      Cheap meal$13.00$11.00
      Large bottle of water$1.80$1.86
      Local draught beer (0.5 liter)$5.00$4.00
      Taxi - fixed fee$2.70$3.25
      source

        Facts and figures about flying from Boston to Chicago

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