Flights from Chicago to Holliston

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 21 - Tue, Oct 21

ORD

O'Hare Intl.

BOS

Logan Intl.

$131 Roundtrip, found 5 days ago

$131

Roundtrip

found 5 days ago

Select JetBlue Airways flight, departing Tue, Oct 21 from O'Hare Intl. to Logan Intl., returning Tue, Oct 21, priced at $131 found 5 days ago

Mon, Sep 8 - Sat, Sep 13

ORD

O'Hare Intl.

BOS

Logan Intl.

$137 Roundtrip, found 1 hour ago

$137

Roundtrip

found 1 hour ago

Select JetBlue Airways flight, departing Mon, Sep 8 from O'Hare Intl. to Logan Intl., returning Sat, Sep 13, priced at $137 found 1 hour ago

Wed, Sep 10 - Sun, Sep 14

ORD

O'Hare Intl.

BOS

Logan Intl.

$137 Roundtrip, found 1 hour ago

$137

Roundtrip

found 1 hour ago

Select Delta flight, departing Wed, Sep 10 from O'Hare Intl. to Logan Intl., returning Sun, Sep 14, priced at $137 found 1 hour ago

Thu, Aug 7 - Wed, Aug 13

ORD

O'Hare Intl.

BOS

Logan Intl.

$142 Roundtrip, found 6 days ago

$142

Roundtrip

found 6 days ago

Select American Airlines flight, departing Thu, Aug 7 from O'Hare Intl. to Logan Intl., returning Wed, Aug 13, priced at $142 found 6 days ago

Thu, Aug 7 - Wed, Aug 13

ORD

O'Hare Intl.

BOS

Logan Intl.

$149 Roundtrip, found 6 days ago

$149

Roundtrip

found 6 days ago

Select United flight, departing Thu, Aug 7 from O'Hare Intl. to Logan Intl., returning Wed, Aug 13, priced at $149 found 6 days ago

Wed, Oct 15 - Mon, Oct 20

ORD

O'Hare Intl.

BOS

Logan Intl.

$155 Roundtrip, found 4 hours ago

$155

Roundtrip

found 4 hours ago

Select United flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Mon, Oct 20, priced at $155 found 4 hours ago

Tue, Oct 14 - Wed, Oct 29

ORD

O'Hare Intl.

BOS

Logan Intl.

$160 Roundtrip, found 5 days ago

$160

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Tue, Oct 14 from O'Hare Intl. to Logan Intl., returning Wed, Oct 29, priced at $160 found 5 days ago

Wed, Oct 15 - Mon, Oct 20

ORD

O'Hare Intl.

BOS

Logan Intl.

$165 Roundtrip, found 4 hours ago

$165

Roundtrip

found 4 hours ago

Select United flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Mon, Oct 20, priced at $165 found 4 hours ago

Wed, Oct 15 - Mon, Oct 20

ORD

O'Hare Intl.

BOS

Logan Intl.

$165 Roundtrip, found 4 hours ago

$165

Roundtrip

found 4 hours ago

Select American Airlines flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Mon, Oct 20, priced at $165 found 4 hours ago

Thu, Aug 7 - Wed, Aug 13

ORD

O'Hare Intl.

BOS

Logan Intl.

$167 Roundtrip, found 6 days ago

$167

Roundtrip

found 6 days ago

Select Spirit Airlines flight, departing Thu, Aug 7 from O'Hare Intl. to Logan Intl., returning Wed, Aug 13, priced at $167 found 6 days ago

Thu, Aug 7 - Wed, Aug 13

ORD

O'Hare Intl.

BOS

Logan Intl.

$170 Roundtrip, found 6 days ago

$170

Roundtrip

found 6 days ago

Select American Airlines flight, departing Thu, Aug 7 from O'Hare Intl. to Logan Intl., returning Wed, Aug 13, priced at $170 found 6 days ago

Wed, Oct 15 - Mon, Oct 20

ORD

O'Hare Intl.

BOS

Logan Intl.

$172 Roundtrip, found 4 hours ago

$172

Roundtrip

found 4 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 4 hours ago

Thu, Sep 11 - Fri, Sep 19

ORD

O'Hare Intl.

BOS

Logan Intl.

$173 Roundtrip, found 1 hour ago

$173

Roundtrip

found 1 hour ago

Select Delta flight, departing Thu, Sep 11 from O'Hare Intl. to Logan Intl., returning Fri, Sep 19, priced at $173 found 1 hour ago

Tue, Oct 7 - Fri, Oct 24

ORD

O'Hare Intl.

BOS

Logan Intl.

$175 Roundtrip, found 11 hours ago

$175

Roundtrip

found 11 hours ago

Select Spirit Airlines flight, departing Tue, Oct 7 from O'Hare Intl. to Logan Intl., returning Fri, Oct 24, priced at $175 found 11 hours ago

Thu, Aug 7 - Wed, Aug 13

ORD

O'Hare Intl.

BOS

Logan Intl.

$176 Roundtrip, found 6 days ago

$176

Roundtrip

found 6 days ago

Select United flight, departing Thu, Aug 7 from O'Hare Intl. to Logan Intl., returning Wed, Aug 13, priced at $176 found 6 days ago

Wed, Oct 15 - Mon, Oct 20

ORD

O'Hare Intl.

BOS

Logan Intl.

$177 Roundtrip, found 4 hours ago

$177

Roundtrip

found 4 hours ago

Select Spirit Airlines flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Mon, Oct 20, priced at $177 found 4 hours ago

Wed, Oct 15 - Mon, Oct 20

ORD

O'Hare Intl.

BOS

Logan Intl.

$191 Roundtrip, found 4 hours ago

$191

Roundtrip

found 4 hours ago

Select United flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Mon, Oct 20, priced at $191 found 4 hours ago

Thu, Sep 11 - Tue, Sep 16

ORD

O'Hare Intl.

PVD

T.F. Green

$217 Roundtrip, found 1 hour ago

$217

Roundtrip

found 1 hour ago

Select American Airlines flight, departing Thu, Sep 11 from O'Hare Intl. to T.F. Green, returning Tue, Sep 16, priced at $217 found 1 hour ago

Tue, Oct 14 - Tue, Oct 28

MDW

Midway Intl.

BOS

Logan Intl.

$277 Roundtrip, found 2 days ago

$277

Roundtrip

found 2 days ago

Select Delta flight, departing Tue, Oct 14 from Midway Intl. to Logan Intl., returning Tue, Oct 28, priced at $277 found 2 days ago

Sat, Jul 26 - Thu, Jul 31

ORD

O'Hare Intl.

BOS

Logan Intl.

$306 Roundtrip, found 3 days ago

$306

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Sat, Jul 26 from O'Hare Intl. to Logan Intl., returning Thu, Jul 31, priced at $306 found 3 days ago