
Popular airlines from Boston to Historic Route 66
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Cheap Flights from Boston (BOS) to Historic Route 66 (CHI)
Prices were available within the past 7 days for one-way flights and round trip tickets for the period specified. Prices and availability are subject to change. Additional terms apply.

Thu, 4 Sep. - Wed, 10 Sep.
BOS
Boston
ORD
Chicago
AU$183 Return, found 1 day ago
AU$183
Return
found 1 day ago

Fri, 31 Oct. - Mon, 3 Nov.
BOS
Boston
ORD
Chicago
AU$209 Return, found 2 hours ago
AU$209
Return
found 2 hours ago

Thu, 4 Sep. - Wed, 10 Sep.
BOS
Boston
ORD
Chicago
AU$211 Return, found 1 day ago
AU$211
Return
found 1 day ago

Thu, 28 Aug. - Wed, 3 Sep.
BOS
Boston
ORD
Chicago
AU$213 Return, found 3 days ago
AU$213
Return
found 3 days ago

Thu, 4 Sep. - Wed, 10 Sep.
BOS
Boston
ORD
Chicago
AU$257 Return, found 1 day ago
AU$257
Return
found 1 day ago

Thu, 25 Dec. - Fri, 2 Jan.
BOS
Boston
ORD
Chicago
AU$305 Return, found 6 days ago
AU$305
Return
found 6 days ago
Find the cheapest month to fly from Boston (BOS) to Chicago (ORD)
September is typically the cheapest month to fly
From AU$74 - AU$174 per traveller.
Graph displaying average flight prices per month
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