Flights from Chicago to Watertown

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, Aug 26 - Wed, Aug 27

ORD

O'Hare Intl.

BOS

Logan Intl.

$93 Roundtrip, found 22 hours ago

$93

Roundtrip

found 22 hours ago

Select JetBlue Airways flight, departing Tue, Aug 26 from O'Hare Intl. to Logan Intl., returning Wed, Aug 27, priced at $93 found 22 hours ago

Tue, Aug 26 - Thu, Aug 28

ORD

O'Hare Intl.

BOS

Logan Intl.

$105 Roundtrip, found 22 hours ago

$105

Roundtrip

found 22 hours ago

Select JetBlue Airways flight, departing Tue, Aug 26 from O'Hare Intl. to Logan Intl., returning Thu, Aug 28, priced at $105 found 22 hours ago

Tue, Aug 26 - Sun, Aug 31

ORD

O'Hare Intl.

BOS

Logan Intl.

$115 Roundtrip, found 22 hours ago

$115

Roundtrip

found 22 hours ago

Select JetBlue Airways flight, departing Tue, Aug 26 from O'Hare Intl. to Logan Intl., returning Sun, Aug 31, priced at $115 found 22 hours ago

Tue, Aug 26 - Tue, Aug 26

ORD

O'Hare Intl.

BOS

Logan Intl.

$117 Roundtrip, found 22 hours ago

$117

Roundtrip

found 22 hours ago

Select Delta flight, departing Tue, Aug 26 from O'Hare Intl. to Logan Intl., returning Tue, Aug 26, priced at $117 found 22 hours ago

Tue, Sep 2 - Wed, Sep 17

ORD

O'Hare Intl.

BOS

Logan Intl.

$126 Roundtrip, found 3 days ago

$126

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Tue, Sep 2 from O'Hare Intl. to Logan Intl., returning Wed, Sep 17, priced at $126 found 3 days ago

Tue, Sep 2 - Wed, Sep 17

ORD

O'Hare Intl.

BOS

Logan Intl.

$127 Roundtrip, found 3 days ago

$127

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Tue, Sep 2 from O'Hare Intl. to Logan Intl., returning Wed, Sep 17, priced at $127 found 3 days ago

Thu, Sep 4 - Sat, Sep 13

ORD

O'Hare Intl.

BOS

Logan Intl.

$127 Roundtrip, found 1 day ago

$127

Roundtrip

found 1 day ago

Select United flight, departing Thu, Sep 4 from O'Hare Intl. to Logan Intl., returning Sat, Sep 13, priced at $127 found 1 day ago

Tue, Oct 21 - Tue, Oct 21

ORD

O'Hare Intl.

BOS

Logan Intl.

$132 Roundtrip, found 1 day ago

$132

Roundtrip

found 1 day ago

Select JetBlue Airways flight, departing Tue, Oct 21 from O'Hare Intl. to Logan Intl., returning Tue, Oct 21, priced at $132 found 1 day ago

Tue, Oct 21 - Wed, Oct 29

MDW

Midway Intl.

BOS

Logan Intl.

$137 Roundtrip, found 3 hours ago

$137

Roundtrip

found 3 hours ago

Select Delta flight, departing Tue, Oct 21 from Midway Intl. to Logan Intl., returning Wed, Oct 29, priced at $137 found 3 hours ago

Wed, Aug 20 - Fri, Aug 22

ORD

O'Hare Intl.

BOS

Logan Intl.

$137 Roundtrip, found 22 hours ago

$137

Roundtrip

found 22 hours ago

Select Delta flight, departing Wed, Aug 20 from O'Hare Intl. to Logan Intl., returning Fri, Aug 22, priced at $137 found 22 hours ago

Thu, Sep 4 - Sat, Sep 13

ORD

O'Hare Intl.

BOS

Logan Intl.

$144 Roundtrip, found 1 day ago

$144

Roundtrip

found 1 day ago

Select United flight, departing Thu, Sep 4 from O'Hare Intl. to Logan Intl., returning Sat, Sep 13, priced at $144 found 1 day ago

Sat, Oct 18 - Sat, Oct 18

ORD

O'Hare Intl.

BOS

Logan Intl.

$147 Roundtrip, found 4 days ago

$147

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 $147 found 4 days ago

Sat, Oct 18 - Thu, Oct 23

ORD

O'Hare Intl.

BOS

Logan Intl.

$149 Roundtrip, found 1 day ago

$149

Roundtrip

found 1 day ago

Select United flight, departing Sat, Oct 18 from O'Hare Intl. to Logan Intl., returning Thu, Oct 23, priced at $149 found 1 day ago

Sat, Oct 11 - Mon, Oct 27

ORD

O'Hare Intl.

BOS

Logan Intl.

$155 Roundtrip, found 6 days ago

$155

Roundtrip

found 6 days ago

Select Delta flight, departing Sat, Oct 11 from O'Hare Intl. to Logan Intl., returning Mon, Oct 27, priced at $155 found 6 days ago

Thu, Sep 4 - Sat, Sep 13

ORD

O'Hare Intl.

BOS

Logan Intl.

$157 Roundtrip, found 1 day ago

$157

Roundtrip

found 1 day ago

Select United flight, departing Thu, Sep 4 from O'Hare Intl. to Logan Intl., returning Sat, Sep 13, priced at $157 found 1 day ago

Sun, Aug 31 - Tue, Sep 16

ORD

O'Hare Intl.

BOS

Logan Intl.

$158 Roundtrip, found 3 days ago

$158

Roundtrip

found 3 days ago

Select Delta flight, departing Sun, Aug 31 from O'Hare Intl. to Logan Intl., returning Tue, Sep 16, priced at $158 found 3 days ago

Tue, Sep 2 - Wed, Sep 10

ORD

O'Hare Intl.

BOS

Logan Intl.

$160 Roundtrip, found 1 day ago

$160

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Tue, Sep 2 from O'Hare Intl. to Logan Intl., returning Wed, Sep 10, priced at $160 found 1 day ago

Thu, Sep 4 - Sat, Sep 13

ORD

O'Hare Intl.

BOS

Logan Intl.

$162 Roundtrip, found 1 day ago

$162

Roundtrip

found 1 day ago

Select United flight, departing Thu, Sep 4 from O'Hare Intl. to Logan Intl., returning Sat, Sep 13, priced at $162 found 1 day ago

Sat, Aug 23 - Sun, Aug 24

ORD

O'Hare Intl.

BOS

Logan Intl.

$167 Roundtrip, found 22 hours ago

$167

Roundtrip

found 22 hours ago

Select American Airlines flight, departing Sat, Aug 23 from O'Hare Intl. to Logan Intl., returning Sun, Aug 24, priced at $167 found 22 hours ago

Sat, Aug 30 - Sat, Sep 6

ORD

O'Hare Intl.

BOS

Logan Intl.

$208 Roundtrip, found 1 day ago

$208

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Sat, Aug 30 from O'Hare Intl. to Logan Intl., returning Sat, Sep 6, priced at $208 found 1 day ago