Flights from Chicago to West Falmouth

Cheapest flights from Chicago

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Oct 18 - Thu, Oct 23

ORD

O'Hare Intl.

BOS

Logan Intl.

$137 Roundtrip, found 9 hours ago

$137

Roundtrip

found 9 hours ago

Select American Airlines flight, departing Sat, Oct 18 from O'Hare Intl. to Logan Intl., returning Thu, Oct 23, priced at $137 found 9 hours ago

Sat, Oct 18 - Thu, Oct 23

ORD

O'Hare Intl.

BOS

Logan Intl.

$137 Roundtrip, found 9 hours ago

$137

Roundtrip

found 9 hours ago

Select Delta flight, departing Sat, Oct 18 from O'Hare Intl. to Logan Intl., returning Thu, Oct 23, priced at $137 found 9 hours ago

Sat, Oct 18 - Thu, Oct 23

ORD

O'Hare Intl.

BOS

Logan Intl.

$137 Roundtrip, found 9 hours ago

$137

Roundtrip

found 9 hours ago

Select United flight, departing Sat, Oct 18 from O'Hare Intl. to Logan Intl., returning Thu, Oct 23, priced at $137 found 9 hours ago

Sat, Oct 18 - Thu, Oct 23

ORD

O'Hare Intl.

BOS

Logan Intl.

$137 Roundtrip, found 9 hours ago

$137

Roundtrip

found 9 hours ago

Select JetBlue Airways flight, departing Sat, Oct 18 from O'Hare Intl. to Logan Intl., returning Thu, Oct 23, priced at $137 found 9 hours ago

Wed, Oct 15 - Mon, Oct 20

ORD

O'Hare Intl.

BOS

Logan Intl.

$139 Roundtrip, found 2 days ago

$139

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Mon, Oct 20, priced at $139 found 2 days ago

Sat, Oct 18 - Sat, Oct 18

ORD

O'Hare Intl.

BOS

Logan Intl.

$145 Roundtrip, found 4 days ago

$145

Roundtrip

found 4 days ago

Select Delta flight, departing Sat, Oct 18 from O'Hare Intl. to Logan Intl., returning Sat, Oct 18, priced at $145 found 4 days ago

Tue, Aug 5 - Fri, Aug 8

ORD

O'Hare Intl.

BOS

Logan Intl.

$155 Roundtrip, found 19 hours ago

$155

Roundtrip

found 19 hours ago

Select Spirit Airlines flight, departing Tue, Aug 5 from O'Hare Intl. to Logan Intl., returning Fri, Aug 8, priced at $155 found 19 hours ago

Tue, Aug 5 - Tue, Aug 12

ORD

O'Hare Intl.

BOS

Logan Intl.

$155 Roundtrip, found 19 hours ago

$155

Roundtrip

found 19 hours ago

Select Delta flight, departing Tue, Aug 5 from O'Hare Intl. to Logan Intl., returning Tue, Aug 12, priced at $155 found 19 hours ago

Tue, Jul 22 - Mon, Jul 28

ORD

O'Hare Intl.

BOS

Logan Intl.

$165 Roundtrip, found 4 days ago

$165

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Tue, Jul 22 from O'Hare Intl. to Logan Intl., returning Mon, Jul 28, priced at $165 found 4 days ago

Sat, Oct 18 - Thu, Oct 23

ORD

O'Hare Intl.

BOS

Logan Intl.

$165 Roundtrip, found 9 hours ago

$165

Roundtrip

found 9 hours ago

Select United flight, departing Sat, Oct 18 from O'Hare Intl. to Logan Intl., returning Thu, Oct 23, priced at $165 found 9 hours ago

Wed, Oct 15 - Mon, Oct 20

ORD

O'Hare Intl.

BOS

Logan Intl.

$167 Roundtrip, found 2 days ago

$167

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Mon, Oct 20, priced at $167 found 2 days ago

Sat, Oct 18 - Thu, Oct 23

ORD

O'Hare Intl.

BOS

Logan Intl.

$172 Roundtrip, found 9 hours ago

$172

Roundtrip

found 9 hours ago

Select American Airlines flight, departing Sat, Oct 18 from O'Hare Intl. to Logan Intl., returning Thu, Oct 23, priced at $172 found 9 hours ago

Sat, Aug 9 - Tue, Aug 12

ORD

O'Hare Intl.

BOS

Logan Intl.

$173 Roundtrip, found 19 hours ago

$173

Roundtrip

found 19 hours ago

Select Delta flight, departing Sat, Aug 9 from O'Hare Intl. to Logan Intl., returning Tue, Aug 12, priced at $173 found 19 hours ago

Thu, Aug 7 - Wed, Aug 13

ORD

O'Hare Intl.

BOS

Logan Intl.

$175 Roundtrip, found 19 hours ago

$175

Roundtrip

found 19 hours ago

Select Delta flight, departing Thu, Aug 7 from O'Hare Intl. to Logan Intl., returning Wed, Aug 13, priced at $175 found 19 hours ago

Thu, Aug 7 - Sun, Aug 10

ORD

O'Hare Intl.

BOS

Logan Intl.

$176 Roundtrip, found 19 hours ago

$176

Roundtrip

found 19 hours ago

Select JetBlue Airways flight, departing Thu, Aug 7 from O'Hare Intl. to Logan Intl., returning Sun, Aug 10, priced at $176 found 19 hours ago

Sat, Aug 9 - Mon, Aug 11

ORD

O'Hare Intl.

BOS

Logan Intl.

$177 Roundtrip, found 19 hours ago

$177

Roundtrip

found 19 hours ago

Select JetBlue Airways flight, departing Sat, Aug 9 from O'Hare Intl. to Logan Intl., returning Mon, Aug 11, priced at $177 found 19 hours ago

Sat, Sep 6 - Sat, Oct 4

ORD

O'Hare Intl.

BOS

Logan Intl.

$179 Roundtrip, found 3 days ago

$179

Roundtrip

found 3 days ago

Select United flight, departing Sat, Sep 6 from O'Hare Intl. to Logan Intl., returning Sat, Oct 4, priced at $179 found 3 days ago

Wed, Aug 6 - Sun, Aug 10

ORD

O'Hare Intl.

BOS

Logan Intl.

$182 Roundtrip, found 19 hours ago

$182

Roundtrip

found 19 hours ago

Select JetBlue Airways flight, departing Wed, Aug 6 from O'Hare Intl. to Logan Intl., returning Sun, Aug 10, priced at $182 found 19 hours ago

Thu, Jul 10 - Sat, Jul 19

MDW

Midway Intl.

BOS

Logan Intl.

$284 Roundtrip, found 6 hours ago

$284

Roundtrip

found 6 hours ago

Select Frontier Airlines flight, departing Thu, Jul 10 from Midway Intl. to Logan Intl., returning Sat, Jul 19, priced at $284 found 6 hours ago

Sat, Jul 5 - Wed, Jul 9

ORD

O'Hare Intl.

HYA

Barnstable Municipal

$333 Roundtrip, found 6 days ago

$333

Roundtrip

found 6 days ago

Select American Airlines flight, departing Sat, Jul 5 from O'Hare Intl. to Barnstable Municipal, returning Wed, Jul 9, priced at $333 found 6 days ago