Flights from Chicago (CHI) to Boston (BOS)

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We compare hundreds of flights from Chicago to Boston from a range of airlines and travel agents to get you the best deals. Find cheap flights along this route.
Chicago (ORD) to Boston (BOS)
 Depart 24 Aug 15
 Return 23 Sep 15

Flying with United Airlines

Price subject to availability

 
 
Chicago (ORD) to Boston (BOS)
 Depart 03 Sep 15
 Return 10 Sep 15

Flying with Spirit Airlines

Price subject to availability

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  • Price
  • Dep date
  6 more Flightnetwork flights available on this route
$150   Dep 03 Sep 15 - Rtn 10 Sep 15
Chicago to Boston
ORD to BOS Flightnetwork
$184   Dep 03 Sep 15 - Rtn 10 Sep 15
Chicago to Boston
MDW to BOS Flightnetwork
$189   Dep 03 Sep 15 - Rtn 10 Sep 15
Chicago to Boston
ORD to BOS Flightnetwork
$201   Dep 03 Sep 15 - Rtn 10 Sep 15
Chicago to Boston
ORD to BOS Flightnetwork
$238   Dep 03 Sep 15 - Rtn 10 Sep 15
Chicago to Boston
ORD to BOS Flightnetwork
$259   Dep 03 Sep 15 - Rtn 10 Sep 15
Chicago to Boston
MDW to BOS Flightnetwork
Chicago (CHI) to Boston (BOS)
 Depart 16 Sep 15
 Return 23 Sep 15

Price subject to availability

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  • Price
  • Dep date
  10 more CheapOair.com flights available on this route
$98   Dep 25 Sep 15 - Rtn 29 Sep 15
Chicago to Boston
CHI to BOS CheapOair.com
$105   Dep 22 Sep 15 - Rtn 29 Sep 15
Chicago to Boston
ORD to BOS CheapOair.com
$110   Dep 23 Sep 15 - Rtn 24 Sep 15
Chicago to Boston
ORD to BOS CheapOair.com
$116   Dep 01 Oct 15 - Rtn 05 Oct 15
Chicago to Boston
CHI to BOS CheapOair.com
$131   Dep 02 Dec 15 - Rtn 11 Dec 15
Chicago to Boston
CHI to BOS CheapOair.com
$144   Dep 08 Aug 15 - Rtn 12 Aug 15
Chicago to Boston
CHI to BOS CheapOair.com
$173   Dep 17 Aug 15 - Rtn 20 Aug 15
Chicago to Boston
CHI to BOS CheapOair.com
$213   Dep 20 Sep 15 - Rtn 27 Sep 15
Chicago to Boston
ORD to BOS CheapOair.com
$254   Dep 13 Aug 15 - Rtn 16 Aug 15
Chicago to Boston
CHI to BOS CheapOair.com
$255   Dep 10 Aug 15 - Rtn 17 Aug 15
Chicago to Boston
CHI to BOS CheapOair.com
Chicago (ORD) to Boston (BOS)
 Depart 21 Oct 15
 Return 28 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
$80   Dep 04 Nov 15 - Rtn 11 Nov 15
Chicago to Boston
ORD to BOS momondo.com
$96   Dep 21 Oct 15 - Rtn 28 Oct 15
Chicago to Boston
ORD to BOS momondo.com
$98   Dep 28 Oct 15 - Rtn 04 Nov 15
Chicago to Boston
ORD to BOS momondo.com
$146   Dep 30 Sep 15 - Rtn 07 Oct 15
Chicago to Boston
ORD to BOS momondo.com
$146   Dep 07 Oct 15 - Rtn 14 Oct 15
Chicago to Boston
ORD to BOS momondo.com
$146   Dep 07 Oct 15 - Rtn 14 Oct 15
Chicago to Boston
ORD to BOS momondo.com
$146   Dep 14 Oct 15 - Rtn 21 Oct 15
Chicago to Boston
ORD to BOS momondo.com
$146   Dep 14 Oct 15 - Rtn 21 Oct 15
Chicago to Boston
ORD to BOS momondo.com
$154   Dep 28 Oct 15 - Rtn 04 Nov 15
Chicago to Boston
ORD to BOS momondo.com
$159   Dep 30 Sep 15 - Rtn 07 Oct 15
Chicago to Boston
ORD to BOS momondo.com
$165   Dep 04 Nov 15 - Rtn 11 Nov 15
Chicago to Boston
ORD to BOS momondo.com
$176   Dep 23 Sep 15 - Rtn 30 Sep 15
Chicago to Boston
ORD to BOS momondo.com
$176   Dep 23 Sep 15 - Rtn 30 Sep 15
Chicago to Boston
ORD to BOS momondo.com
$224   Dep 21 Oct 15 - Rtn 28 Oct 15
Chicago to Boston
ORD to BOS momondo.com
$312   Dep 21 Oct 15 - Rtn 28 Oct 15
Chicago to Boston
ORD to BOS momondo.com
Chicago (CHI) to Boston (BOS)
 Depart 02 Sep 15
 Return 09 Sep 15

Price subject to availability

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Chicago (ORD) to Boston (BOS)
 Depart 25 Aug 15
 Return 27 Aug 15

Flying with Spirit Airlines

Price subject to availability

   View more dates
 
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      Travel information for Chicago to Boston

      Photo of Boston   Boston
      Partners with offers for flights fromChicago to Boston6
      Flights available forChicago to Boston259
      Lowest ticket price forChicago to Boston$80
      Average deal price forChicago to Boston$131
      Flight duration forChicago to Boston2 hrs 16 mins
      Chicago to Bostononly 852 miles

       How much do things cost in Boston and Chicago?

      • Chicago is 6% cheaper than Boston
      Chicago Boston
      3 course meal for 2$60.00$55.00
      Imported beer (0.33 liter bottle)$1.98$2.40
      1 mile taxi journey$1.81$2.90
      Cheap meal$12.00$15.00
      source

        Facts and figures about flying from Chicago to Boston

      • Flights from Chicago to Boston are not usually diverted
      • The smallest aircraft for flights between Chicago and Boston is an Embraer EMB 170/EMB 190
      • Flights from Chicago to Boston are cancelled 4.8 percent of the time
      • American Airlines Inc. operates 206 flights a week from Chicago to Boston
      • Flights between Chicago and Boston typically provide 2388 seats for passengers on a daily basis
      • From Chicago to Boston, the most frequently used aircraft is a Boeing 737-800 (winglets)
      • Flights from Chicago to Boston are typically delayed by 1 hr
      • The Boeing 757 Mixed is the largest aircraft operating flights between Chicago and Boston