Cheap flights from Chicago to Eastern Massachusetts

View AU$107 flight on Tue, 9 Sep. 2025Opens in a new window

Popular airlines from Chicago to Eastern Massachusetts

  • Spirit Airlines

    Spirit Airlines

  • JetBlue Airways

    JetBlue Airways

  • Delta

    Delta

  • Southwest Airlines

    Southwest Airlines

  • American Airlines

    American Airlines

  • United

    United

  • Frontier Airlines

    Frontier Airlines

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Cheap Flights from Chicago (CHI) to Eastern Massachusetts (BOS)

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.

American Airlines
Thu, 4 Sep. - Sun, 7 Sep.
ORD
Chicago
BOS
Boston
AU$196 Return, found 2 days ago
AU$196
Return
found 2 days ago
Select American Airlines flight, departing Thu, 4 Sep. from Chicago to Boston, returning Sun, 7 Sep., priced at AU$196 found 2 days ago
American Airlines
Sun, 14 Sep. - Sun, 21 Sep.
ORD
Chicago
BOS
Boston
AU$211 Return, found 2 days ago
AU$211
Return
found 2 days ago
Select American Airlines flight, departing Sun, 14 Sep. from Chicago to Boston, returning Sun, 21 Sep., priced at AU$211 found 2 days ago
American Airlines
Wed, 19 Nov. - Sat, 22 Nov.
ORD
Chicago
BOS
Boston
AU$214 Return, found 21 hours ago
AU$214
Return
found 21 hours ago
Select American Airlines flight, departing Wed, 19 Nov. from Chicago to Boston, returning Sat, 22 Nov., priced at AU$214 found 21 hours ago
American Airlines
Thu, 4 Sep. - Sun, 7 Sep.
ORD
Chicago
BOS
Boston
AU$239 Return, found 2 days ago
AU$239
Return
found 2 days ago
Select American Airlines flight, departing Thu, 4 Sep. from Chicago to Boston, returning Sun, 7 Sep., priced at AU$239 found 2 days ago
Delta
Wed, 19 Nov. - Sat, 22 Nov.
ORD
Chicago
BOS
Boston
AU$268 Return, found 21 hours ago
AU$268
Return
found 21 hours ago
Select Delta flight, departing Wed, 19 Nov. from Chicago to Boston, returning Sat, 22 Nov., priced at AU$268 found 21 hours ago
United
Sun, 14 Sep. - Sun, 21 Sep.
ORD
Chicago
BOS
Boston
AU$293 Return, found 2 days ago
AU$293
Return
found 2 days ago
Select United flight, departing Sun, 14 Sep. from Chicago to Boston, returning Sun, 21 Sep., priced at AU$293 found 2 days ago

Find the cheapest month to fly from Chicago (CHI) to Boston (BOS)

October is typically the cheapest month to fly

From AU$86 - AU$264 per traveller.

Graph displaying average flight prices per month

*Available to Expedia members.