Flights from Chicago to East 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.

Tue, Oct 7 - Tue, Oct 14

ORD

O'Hare Intl.

BOS

Logan Intl.

$117 Roundtrip, found 4 days ago

$117

Roundtrip

found 4 days ago

Select Delta flight, departing Tue, Oct 7 from O'Hare Intl. to Logan Intl., returning Tue, Oct 14, priced at $117 found 4 days ago

Wed, Oct 15 - Mon, Oct 20

ORD

O'Hare Intl.

BOS

Logan Intl.

$137 Roundtrip, found 3 hours ago

$137

Roundtrip

found 3 hours ago

Select United flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Mon, Oct 20, priced at $137 found 3 hours ago

Wed, Oct 15 - Tue, Oct 21

ORD

O'Hare Intl.

BOS

Logan Intl.

$137 Roundtrip, found 18 hours ago

$137

Roundtrip

found 18 hours ago

Select JetBlue Airways flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Tue, Oct 21, priced at $137 found 18 hours ago

Wed, Oct 15 - Mon, Oct 20

ORD

O'Hare Intl.

BOS

Logan Intl.

$139 Roundtrip, found 3 hours ago

$139

Roundtrip

found 3 hours ago

Select Spirit Airlines flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Mon, Oct 20, priced at $139 found 3 hours ago

Wed, Dec 17 - Thu, Dec 25

ORD

O'Hare Intl.

BOS

Logan Intl.

$145 Roundtrip, found 23 hours ago

$145

Roundtrip

found 23 hours ago

Select JetBlue Airways flight, departing Wed, Dec 17 from O'Hare Intl. to Logan Intl., returning Thu, Dec 25, priced at $145 found 23 hours ago

Tue, Sep 23 - Mon, Sep 29

ORD

O'Hare Intl.

BOS

Logan Intl.

$157 Roundtrip, found 1 day ago

$157

Roundtrip

found 1 day ago

Select JetBlue Airways flight, departing Tue, Sep 23 from O'Hare Intl. to Logan Intl., returning Mon, Sep 29, priced at $157 found 1 day ago

Tue, Oct 14 - Tue, Oct 21

ORD

O'Hare Intl.

BOS

Logan Intl.

$160 Roundtrip, found 18 hours ago

$160

Roundtrip

found 18 hours ago

Select Spirit Airlines flight, departing Tue, Oct 14 from O'Hare Intl. to Logan Intl., returning Tue, Oct 21, priced at $160 found 18 hours ago

Wed, Oct 15 - Mon, Oct 20

ORD

O'Hare Intl.

BOS

Logan Intl.

$166 Roundtrip, found 3 hours ago

$166

Roundtrip

found 3 hours ago

Select United flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Mon, Oct 20, priced at $166 found 3 hours ago

Sat, Dec 20 - Thu, Dec 25

ORD

O'Hare Intl.

BOS

Logan Intl.

$167 Roundtrip, found 23 hours ago

$167

Roundtrip

found 23 hours ago

Select United flight, departing Sat, Dec 20 from O'Hare Intl. to Logan Intl., returning Thu, Dec 25, priced at $167 found 23 hours ago

Fri, Sep 26 - Tue, Sep 30

ORD

O'Hare Intl.

BOS

Logan Intl.

$167 Roundtrip, found 1 day ago

$167

Roundtrip

found 1 day ago

Select American Airlines flight, departing Fri, Sep 26 from O'Hare Intl. to Logan Intl., returning Tue, Sep 30, priced at $167 found 1 day ago

Sun, Oct 5 - Wed, Oct 15

ORD

O'Hare Intl.

BOS

Logan Intl.

$169 Roundtrip, found 4 days ago

$169

Roundtrip

found 4 days ago

Select United flight, departing Sun, Oct 5 from O'Hare Intl. to Logan Intl., returning Wed, Oct 15, priced at $169 found 4 days ago

Wed, Oct 15 - Mon, Oct 20

ORD

O'Hare Intl.

BOS

Logan Intl.

$172 Roundtrip, found 3 hours ago

$172

Roundtrip

found 3 hours ago

Select American Airlines flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Mon, Oct 20, priced at $172 found 3 hours ago

Fri, Sep 26 - Mon, Sep 29

ORD

O'Hare Intl.

BOS

Logan Intl.

$177 Roundtrip, found 1 day ago

$177

Roundtrip

found 1 day ago

Select JetBlue Airways flight, departing Fri, Sep 26 from O'Hare Intl. to Logan Intl., returning Mon, Sep 29, priced at $177 found 1 day ago

Tue, Oct 14 - Mon, Oct 20

ORD

O'Hare Intl.

BOS

Logan Intl.

$180 Roundtrip, found 18 hours ago

$180

Roundtrip

found 18 hours ago

Select Spirit Airlines flight, departing Tue, Oct 14 from O'Hare Intl. to Logan Intl., returning Mon, Oct 20, priced at $180 found 18 hours ago

Fri, Sep 26 - Tue, Sep 30

ORD

O'Hare Intl.

BOS

Logan Intl.

$182 Roundtrip, found 1 day ago

$182

Roundtrip

found 1 day ago

Select United flight, departing Fri, Sep 26 from O'Hare Intl. to Logan Intl., returning Tue, Sep 30, priced at $182 found 1 day ago

Fri, Sep 26 - Tue, Sep 30

ORD

O'Hare Intl.

BOS

Logan Intl.

$184 Roundtrip, found 1 day ago

$184

Roundtrip

found 1 day ago

Select United flight, departing Fri, Sep 26 from O'Hare Intl. to Logan Intl., returning Tue, Sep 30, priced at $184 found 1 day ago

Fri, Sep 26 - Tue, Sep 30

ORD

O'Hare Intl.

BOS

Logan Intl.

$186 Roundtrip, found 1 day ago

$186

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Fri, Sep 26 from O'Hare Intl. to Logan Intl., returning Tue, Sep 30, priced at $186 found 1 day ago

Wed, Oct 15 - Mon, Oct 20

ORD

O'Hare Intl.

BOS

Logan Intl.

$187 Roundtrip, found 3 hours ago

$187

Roundtrip

found 3 hours ago

Select JetBlue Airways flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Mon, Oct 20, priced at $187 found 3 hours ago

Wed, Oct 15 - Mon, Oct 20

ORD

O'Hare Intl.

BOS

Logan Intl.

$189 Roundtrip, found 3 hours ago

$189

Roundtrip

found 3 hours ago

Select United flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Mon, Oct 20, priced at $189 found 3 hours ago

Tue, Oct 7 - Wed, Oct 15

MDW

Midway Intl.

BOS

Logan Intl.

$277 Roundtrip, found 4 days ago

$277

Roundtrip

found 4 days ago

Select Delta flight, departing Tue, Oct 7 from Midway Intl. to Logan Intl., returning Wed, Oct 15, priced at $277 found 4 days ago