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 06 Aug 15
 Return 13 Aug 15

Flying with Spirit Airlines

Price subject to availability

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  • Price
  • Dep date
  1 more Flightnetwork flights available on this route
$278   Dep 06 Aug 15 - Rtn 13 Aug 15
Boston to Chicago
BOS to MDW Flightnetwork
Boston (BOS) to Chicago (ORD)
 Depart 07 Nov 15
 Return 11 Nov 15

Flying with United Airlines

Price subject to availability

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  • Price
  • Dep date
  15 more CheapOair.com flights available on this route
$179   Dep 11 Aug 15 - Rtn 18 Aug 15
Boston to Chicago
BOS to CHI CheapOair.com
$179   Dep 25 Aug 15 - Rtn 27 Aug 15
Boston to Chicago
BOS to CHI CheapOair.com
$179   Dep 13 Oct 15 - Rtn 15 Oct 15
Boston to Chicago
BOS to CHI CheapOair.com
$180   Dep 04 Aug 15 - Rtn 13 Aug 15
Boston to Chicago
BOS to ORD CheapOair.com
$196   Dep 25 Jul 15 - Rtn 28 Jul 15
Boston to Chicago
BOS to ORD CheapOair.com
$203   Dep 06 Nov 15 - Rtn 12 Nov 15
Boston to Chicago
BOS to CHI CheapOair.com
$203   Dep 03 Aug 15 - Rtn 11 Aug 15
Boston to Chicago
BOS to ORD CheapOair.com
$206   Dep 21 Aug 15 - Rtn 25 Aug 15
Boston to Chicago
BOS to ORD CheapOair.com
$211   Dep 04 Aug 15 - Rtn 05 Aug 15
Boston to Chicago
BOS to ORD CheapOair.com
$211   Dep 05 Aug 15 - Rtn 07 Aug 15
Boston to Chicago
BOS to ORD CheapOair.com
$218   Dep 20 Aug 15 - Rtn 24 Aug 15
Boston to Chicago
BOS to ORD CheapOair.com
$221   Dep 14 Jul 15 - Rtn 21 Jul 15
Boston to Chicago
BOS to ORD CheapOair.com
$223   Dep 19 Aug 15 - Rtn 23 Aug 15
Boston to Chicago
BOS to ORD CheapOair.com
$234   Dep 03 Aug 15 - Rtn 10 Aug 15
Boston to Chicago
BOS to CHI CheapOair.com
$239   Dep 02 Aug 15 - Rtn 05 Aug 15
Boston to Chicago
BOS to CHI CheapOair.com
Boston (BOS) to Chicago (CHI)
 Depart 29 Jul 15
 Return 05 Aug 15

Price subject to availability

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Boston (BOS) to Chicago (ORD)
 Depart 30 Sep 15
 Return 07 Oct 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
$146   Dep 07 Oct 15 - Rtn 14 Oct 15
Boston to Chicago
BOS to ORD momondo.com
$146   Dep 07 Oct 15 - Rtn 14 Oct 15
Boston to Chicago
BOS to ORD momondo.com
$176   Dep 09 Sep 15 - Rtn 16 Sep 15
Boston to Chicago
BOS to ORD momondo.com
$176   Dep 16 Sep 15 - Rtn 23 Sep 15
Boston to Chicago
BOS to ORD momondo.com
$176   Dep 23 Sep 15 - Rtn 30 Sep 15
Boston to Chicago
BOS to ORD momondo.com
$176   Dep 23 Sep 15 - Rtn 30 Sep 15
Boston to Chicago
BOS to ORD momondo.com
$176   Dep 30 Sep 15 - Rtn 07 Oct 15
Boston to Chicago
BOS to ORD momondo.com
$182   Dep 16 Sep 15 - Rtn 23 Sep 15
Boston to Chicago
BOS to ORD momondo.com
$212   Dep 09 Sep 15 - Rtn 16 Sep 15
Boston to Chicago
BOS to ORD momondo.com
$363   Dep 16 Sep 15 - Rtn 23 Sep 15
Boston to Chicago
BOS to ORD momondo.com
$363   Dep 16 Sep 15 - Rtn 23 Sep 15
Boston to Chicago
BOS to ORD momondo.com
$366   Dep 09 Sep 15 - Rtn 16 Sep 15
Boston to Chicago
BOS to ORD momondo.com
$375   Dep 09 Sep 15 - Rtn 16 Sep 15
Boston to Chicago
BOS to ORD momondo.com
$378   Dep 23 Sep 15 - Rtn 30 Sep 15
Boston to Chicago
BOS to ORD momondo.com
$378   Dep 30 Sep 15 - Rtn 07 Oct 15
Boston to Chicago
BOS to ORD momondo.com
Boston (BOS) to Chicago (CHI)
 Depart 19 Aug 15
 Return 25 Aug 15

Flying with Spirit Airlines

Price subject to availability

   View more dates
 
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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 Chicago175
      Cheapest flight forBoston to Chicago$145
      Average flight deal forBoston to Chicago$226
      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
      1 mile taxi journey$3.00$1.81
      Cappuccino$3.84$3.51
      One-way ticket (local transport)$2.50$2.38
      Bottle of local beer (0.5 liter)$1.92$1.75
      source

        Facts and figures about flying from Boston to Chicago

      • Every week American Airlines Inc. has 214 flights from Boston to Chicago
      • 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
      • Flights from Boston to Chicago typically have a delay of 1 hr 12 mins
      • Flights from Boston to Chicago are not usually diverted
      • 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
      • The Embraer EMB 170/EMB 190 is the smallest airplane available for flights between Boston and Chicago