Popular airlines from Chicago to Cambridge
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Today's featured flight deals from Chicago to Cambridge
Nonstop
Carry-on included
Lower price than typical
- Chicago (MDW) to Boston (BOS).Southwest Airlines, nonstop.Departing on Wed, Jul 9 at 7:30pm from Chicago, arriving at 10:45pm in Boston.Returning on Fri, Jul 18 at 5:50am from Boston, arriving at 1:05pm in Chicago.Select Southwest Airlines flight departing on Wed, Jul 9 at 7:30pm from Chicago, returning on Fri, Jul 18 at 5:50am from Boston priced at $14770% less than typical$147
- Chicago (ORD) to Boston (BOS).American Airlines, nonstop.Departing on Wed, Jul 9 at 7:17am from Chicago, arriving at 10:40am in Boston.Returning on Sun, Jul 13 at 5:00am from Boston, arriving at 12:45pm in Chicago.Select American Airlines flight departing on Wed, Jul 9 at 7:17am from Chicago, returning on Sun, Jul 13 at 5:00am from Boston priced at $15465% less than typical$154
- Chicago (ORD) to Boston (BOS).Delta, nonstop.Departing on Wed, Jul 9 at 7:00am from Chicago, arriving at 10:31am in Boston.Returning on Sun, Jul 13 at 5:00am from Boston, arriving at 12:45pm in Chicago.Select Delta flight departing on Wed, Jul 9 at 7:00am from Chicago, returning on Sun, Jul 13 at 5:00am from Boston priced at $15465% less than typical$154
- Chicago (ORD) to Boston (BOS).American Airlines, nonstop.Departing on Wed, Jul 9 at 9:55am from Chicago, arriving at 1:18pm in Boston.Returning on Sun, Jul 13 at 5:00am from Boston, arriving at 12:45pm in Chicago.Select American Airlines flight departing on Wed, Jul 9 at 9:55am from Chicago, returning on Sun, Jul 13 at 5:00am from Boston priced at $15465% less than typical$154
- Chicago (MDW) to Boston (BOS).Southwest Airlines, nonstop.Departing on Mon, Jul 28 at 6:00am from Chicago, arriving at 9:15am in Boston.Returning on Fri, Aug 1 at 5:00am from Boston, arriving at 4:25pm in Chicago.Select Southwest Airlines flight departing on Mon, Jul 28 at 6:00am from Chicago, returning on Fri, Aug 1 at 5:00am from Boston priced at $14765% less than typical$147
- Chicago (MDW) to Boston (BOS).Southwest Airlines, nonstop.Departing on Mon, Jul 28 at 8:30pm from Chicago, arriving at 11:45pm in Boston.Returning on Fri, Aug 1 at 5:00am from Boston, arriving at 4:25pm in Chicago.Select Southwest Airlines flight departing on Mon, Jul 28 at 8:30pm from Chicago, returning on Fri, Aug 1 at 5:00am from Boston priced at $14765% less than typical$147
- Chicago (MDW) to Boston (BOS).Southwest Airlines, nonstop.Departing on Thu, Jul 10 at 6:00am from Chicago, arriving at 9:15am in Boston.Returning on Tue, Jul 15 at 5:25am from Boston, arriving at 7:00am in Chicago.Select Southwest Airlines flight departing on Thu, Jul 10 at 6:00am from Chicago, returning on Tue, Jul 15 at 5:25am from Boston priced at $13765% less than typical$137
- Chicago (MDW) to Boston (BOS).Southwest Airlines, nonstop.Departing on Sat, Aug 9 at 12:45pm from Chicago, arriving at 4:10pm in Boston.Returning on Sat, Aug 16 at 5:20am from Boston, arriving at 8:40am in Chicago.Select Southwest Airlines flight departing on Sat, Aug 9 at 12:45pm from Chicago, returning on Sat, Aug 16 at 5:20am from Boston priced at $14765% less than typical$147
- Chicago (MDW) to Boston (BOS).Southwest Airlines, nonstop.Departing on Wed, Jul 9 at 7:30pm from Chicago, arriving at 10:45pm in Boston.Returning on Mon, Jul 14 at 7:00am from Boston, arriving at 8:40am in Chicago.Select Southwest Airlines flight departing on Wed, Jul 9 at 7:30pm from Chicago, returning on Mon, Jul 14 at 7:00am from Boston priced at $20755% less than typical$207
Cheap Flights from Chicago to Cambridge (CHI-BOS)
Prices were available within the past 7 days and start at $69 for one-way flights and $127 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Wed, Jul 9 - Wed, Jul 23
ORD
Chicago
BOS
Boston
$127 Roundtrip, just found
$127
Roundtrip
just found
Tue, Jul 29 - Tue, Aug 5
ORD
Chicago
BOS
Boston
$129 Roundtrip, found 1 hour ago
$129
Roundtrip
found 1 hour ago
Fri, Jul 18 - Mon, Jul 21
ORD
Chicago
BOS
Boston
$137 Roundtrip, just found
$137
Roundtrip
just found
Wed, Jul 16 - Wed, Jul 23
ORD
Chicago
BOS
Boston
$137 Roundtrip, just found
$137
Roundtrip
just found
Thu, Oct 30 - Mon, Nov 3
ORD
Chicago
BOS
Boston
$137 Roundtrip, just found
$137
Roundtrip
just found
Wed, Jul 16 - Wed, Jul 23
MDW
Chicago
BOS
Boston
$137 Roundtrip, just found
$137
Roundtrip
just found
Find the cheapest month to fly from Chicago (CHI) to Boston (BOS)
August is typically the cheapest month to fly
From $48 - $147 per traveler.
Graph displaying average flight prices per month
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