Flights from Chicago to Worcester

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, Sep 27 - Wed, Oct 1

ORD

O'Hare Intl.

BOS

Logan Intl.

$91 Roundtrip, found 5 days ago

$91

Roundtrip

found 5 days ago

Select JetBlue Airways flight, departing Sat, Sep 27 from O'Hare Intl. to Logan Intl., returning Wed, Oct 1, priced at $91 found 5 days ago

Fri, Sep 26 - Wed, Oct 1

ORD

O'Hare Intl.

BOS

Logan Intl.

$98 Roundtrip, found 5 days ago

$98

Roundtrip

found 5 days ago

Select JetBlue Airways flight, departing Fri, Sep 26 from O'Hare Intl. to Logan Intl., returning Wed, Oct 1, priced at $98 found 5 days ago

Fri, Sep 26 - Mon, Sep 29

ORD

O'Hare Intl.

BOS

Logan Intl.

$98 Roundtrip, found 5 days ago

$98

Roundtrip

found 5 days ago

Select United flight, departing Fri, Sep 26 from O'Hare Intl. to Logan Intl., returning Mon, Sep 29, priced at $98 found 5 days ago

Fri, Sep 26 - Sun, Oct 5

ORD

O'Hare Intl.

BOS

Logan Intl.

$105 Roundtrip, found 5 days ago

$105

Roundtrip

found 5 days ago

Select JetBlue Airways flight, departing Fri, Sep 26 from O'Hare Intl. to Logan Intl., returning Sun, Oct 5, priced at $105 found 5 days ago

Wed, Oct 1 - Wed, Oct 1

ORD

O'Hare Intl.

BOS

Logan Intl.

$108 Roundtrip, found 5 days ago

$108

Roundtrip

found 5 days ago

Select JetBlue Airways flight, departing Wed, Oct 1 from O'Hare Intl. to Logan Intl., returning Wed, Oct 1, priced at $108 found 5 days ago

Fri, Sep 26 - Mon, Sep 29

ORD

O'Hare Intl.

BOS

Logan Intl.

$116 Roundtrip, found 5 days ago

$116

Roundtrip

found 5 days ago

Select United flight, departing Fri, Sep 26 from O'Hare Intl. to Logan Intl., returning Mon, Sep 29, priced at $116 found 5 days ago

Fri, Sep 26 - Mon, Sep 29

ORD

O'Hare Intl.

BOS

Logan Intl.

$120 Roundtrip, found 5 days ago

$120

Roundtrip

found 5 days ago

Select United flight, departing Fri, Sep 26 from O'Hare Intl. to Logan Intl., returning Mon, Sep 29, priced at $120 found 5 days ago

Fri, Sep 26 - Mon, Oct 6

ORD

O'Hare Intl.

BOS

Logan Intl.

$121 Roundtrip, found 5 days ago

$121

Roundtrip

found 5 days ago

Select JetBlue Airways flight, departing Fri, Sep 26 from O'Hare Intl. to Logan Intl., returning Mon, Oct 6, priced at $121 found 5 days ago

Fri, Sep 26 - Mon, Sep 29

ORD

O'Hare Intl.

BOS

Logan Intl.

$126 Roundtrip, found 5 days ago

$126

Roundtrip

found 5 days ago

Select United flight, departing Fri, Sep 26 from O'Hare Intl. to Logan Intl., returning Mon, Sep 29, priced at $126 found 5 days ago

Fri, Sep 26 - Mon, Sep 29

ORD

O'Hare Intl.

BOS

Logan Intl.

$128 Roundtrip, found 5 days ago

$128

Roundtrip

found 5 days ago

Select United flight, departing Fri, Sep 26 from O'Hare Intl. to Logan Intl., returning Mon, Sep 29, priced at $128 found 5 days ago

Tue, Oct 21 - Tue, Oct 21

ORD

O'Hare Intl.

BOS

Logan Intl.

$131 Roundtrip, found 7 hours ago

$131

Roundtrip

found 7 hours ago

Select JetBlue Airways flight, departing Tue, Oct 21 from O'Hare Intl. to Logan Intl., returning Tue, Oct 21, priced at $131 found 7 hours ago

Fri, Sep 26 - Mon, Sep 29

ORD

O'Hare Intl.

BOS

Logan Intl.

$133 Roundtrip, found 5 days ago

$133

Roundtrip

found 5 days ago

Select United flight, departing Fri, Sep 26 from O'Hare Intl. to Logan Intl., returning Mon, Sep 29, priced at $133 found 5 days ago

Fri, Sep 26 - Mon, Sep 29

ORD

O'Hare Intl.

BOS

Logan Intl.

$135 Roundtrip, found 5 days ago

$135

Roundtrip

found 5 days ago

Select United flight, departing Fri, Sep 26 from O'Hare Intl. to Logan Intl., returning Mon, Sep 29, priced at $135 found 5 days ago

Wed, Oct 15 - Thu, Oct 30

ORD

O'Hare Intl.

BOS

Logan Intl.

$137 Roundtrip, found 7 hours ago

$137

Roundtrip

found 7 hours ago

Select JetBlue Airways flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Thu, Oct 30, priced at $137 found 7 hours ago

Wed, Oct 15 - Wed, Oct 29

ORD

O'Hare Intl.

BOS

Logan Intl.

$137 Roundtrip, found 7 hours ago

$137

Roundtrip

found 7 hours ago

Select Delta flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Wed, Oct 29, priced at $137 found 7 hours ago

Thu, Oct 16 - Tue, Oct 21

ORD

O'Hare Intl.

BOS

Logan Intl.

$137 Roundtrip, found 3 days ago

$137

Roundtrip

found 3 days ago

Select American Airlines flight, departing Thu, Oct 16 from O'Hare Intl. to Logan Intl., returning Tue, Oct 21, priced at $137 found 3 days ago

Wed, Oct 15 - Mon, Oct 20

ORD

O'Hare Intl.

BOS

Logan Intl.

$139 Roundtrip, found 1 day ago

$139

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Mon, Oct 20, priced at $139 found 1 day ago

Thu, Aug 7 - Wed, Aug 13

ORD

O'Hare Intl.

BOS

Logan Intl.

$142 Roundtrip, found 1 day ago

$142

Roundtrip

found 1 day ago

Select American Airlines flight, departing Thu, Aug 7 from O'Hare Intl. to Logan Intl., returning Wed, Aug 13, priced at $142 found 1 day ago

Tue, Oct 14 - Wed, Oct 29

ORD

O'Hare Intl.

BOS

Logan Intl.

$160 Roundtrip, found 7 hours ago

$160

Roundtrip

found 7 hours ago

Select Spirit Airlines flight, departing Tue, Oct 14 from O'Hare Intl. to Logan Intl., returning Wed, Oct 29, priced at $160 found 7 hours ago

Fri, Sep 26 - Mon, Sep 29

ORD

O'Hare Intl.

BOS

Logan Intl.

$281 Roundtrip, found 5 days ago

$281

Roundtrip

found 5 days ago

Select Frontier Airlines flight, departing Fri, Sep 26 from O'Hare Intl. to Logan Intl., returning Mon, Sep 29, priced at $281 found 5 days ago