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 (MDW)
 Depart 01 Sep 15
 Return 08 Sep 15

Price subject to availability

 
 
Boston (BOS) to Chicago (CHI)
 Depart 14 Sep 15
 Return 16 Sep 15

Price subject to availability

 
 
Boston (BOS) to Chicago (CHI)
 Depart 14 Sep 15
 Return 16 Sep 15

Price subject to availability

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  • Price
  • Dep date
  15 more CheapOair.com flights available on this route
$98   Dep 17 Sep 15 - Rtn 22 Sep 15
Boston to Chicago
BOS to CHI CheapOair.com
$98   Dep 14 Oct 15 - Rtn 19 Oct 15
Boston to Chicago
BOS to CHI CheapOair.com
$105   Dep 29 Aug 15 - Rtn 31 Aug 15
Boston to Chicago
BOS to ORD CheapOair.com
$110   Dep 20 Feb 16 - Rtn 24 Feb 16
Boston to Chicago
BOS to ORD CheapOair.com
$116   Dep 19 Sep 15 - Rtn 28 Sep 15
Boston to Chicago
BOS to CHI CheapOair.com
$123   Dep 30 Aug 15 - Rtn 01 Sep 15
Boston to Chicago
BOS to ORD CheapOair.com
$123   Dep 05 Sep 15 - Rtn 08 Sep 15
Boston to Chicago
BOS to ORD CheapOair.com
$134   Dep 13 Sep 15 - Rtn 14 Sep 15
Boston to Chicago
BOS to CHI CheapOair.com
$158   Dep 18 Feb 16 - Rtn 24 Feb 16
Boston to Chicago
BOS to ORD CheapOair.com
$181   Dep 16 Feb 16 - Rtn 23 Feb 16
Boston to Chicago
BOS to ORD CheapOair.com
$185   Dep 11 Aug 15 - Rtn 13 Aug 15
Boston to Chicago
BOS to ORD CheapOair.com
$200   Dep 28 Aug 15 - Rtn 30 Aug 15
Boston to Chicago
BOS to ORD CheapOair.com
$206   Dep 17 Feb 16 - Rtn 18 Feb 16
Boston to Chicago
BOS to ORD CheapOair.com
$231   Dep 15 Aug 15 - Rtn 18 Aug 15
Boston to Chicago
BOS to ORD CheapOair.com
$250   Dep 09 Aug 15 - Rtn 12 Aug 15
Boston to Chicago
BOS to ORD CheapOair.com
Boston (BOS) to Chicago (ORD)
 Depart 28 Oct 15
 Return 04 Nov 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
$80   Dep 04 Nov 15 - Rtn 11 Nov 15
Boston to Chicago
BOS to ORD momondo.com
$80   Dep 04 Nov 15 - Rtn 11 Nov 15
Boston to Chicago
BOS to ORD momondo.com
$96   Dep 21 Oct 15 - Rtn 28 Oct 15
Boston to Chicago
BOS to ORD momondo.com
$146   Dep 30 Sep 15 - Rtn 07 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
$146   Dep 07 Oct 15 - Rtn 14 Oct 15
Boston to Chicago
BOS to ORD momondo.com
$146   Dep 14 Oct 15 - Rtn 21 Oct 15
Boston to Chicago
BOS to ORD momondo.com
$146   Dep 14 Oct 15 - Rtn 21 Oct 15
Boston to Chicago
BOS to ORD momondo.com
$159   Dep 21 Oct 15 - Rtn 28 Oct 15
Boston to Chicago
BOS to ORD momondo.com
$173   Dep 28 Oct 15 - Rtn 04 Nov 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
$225   Dep 21 Oct 15 - Rtn 28 Oct 15
Boston to Chicago
BOS to ORD momondo.com
$314   Dep 21 Oct 15 - Rtn 28 Oct 15
Boston to Chicago
BOS to ORD momondo.com
Boston (BOS) to Chicago (CHI)
 Depart 26 Aug 15
 Return 31 Aug 15

Flying with Spirit Airlines

Price subject to availability

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Boston (BOS) to Chicago (CHI)
 Depart 02 Sep 15
 Return 09 Sep 15

Price subject to availability

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      Travel information for Boston to Chicago

      Photo of Chicago   Chicago
      Partners with flight deals forBoston to Chicago7
      Deals on offer forBoston to Chicago166
      Cheapest flight forBoston to Chicago$79
      Average flight deal forBoston to Chicago$157
      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
      Taxi - fixed fee$2.65$3.25
      Cappuccino$3.80$3.60
      Local draught beer (0.5 liter)$5.00$4.00
      Cheap meal$15.00$12.00
      source

        Facts and figures about flying from Boston to Chicago

      • Flights from Boston to Chicago typically have a delay of 1 hr 12 mins
      • The Embraer EMB 170/EMB 190 is the smallest airplane available for flights between Boston and Chicago
      • The Boeing 757 Mixed is the largest aircraft operating flights between Boston and 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
      • Every week American Airlines Inc. has 214 flights from Boston to Chicago
      • Flights from Boston to Chicago are not usually diverted
      • The standard cancellation rate when flying from Boston to Chicago is 4.6 percent