Flights from Chicago to Westport

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 5 - Wed, Aug 13

ORD

O'Hare Intl.

BOS

Logan Intl.

$117 Roundtrip, found 3 hours ago

$117

Roundtrip

found 3 hours ago

Select Delta flight, departing Tue, Aug 5 from O'Hare Intl. to Logan Intl., returning Wed, Aug 13, priced at $117 found 3 hours ago

Thu, Oct 16 - Thu, Oct 23

ORD

O'Hare Intl.

BOS

Logan Intl.

$129 Roundtrip, found 2 days ago

$129

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Thu, Oct 16 from O'Hare Intl. to Logan Intl., returning Thu, Oct 23, priced at $129 found 2 days ago

Tue, Sep 2 - Sat, Sep 6

ORD

O'Hare Intl.

BOS

Logan Intl.

$137 Roundtrip, found 5 days ago

$137

Roundtrip

found 5 days ago

Select United flight, departing Tue, Sep 2 from O'Hare Intl. to Logan Intl., returning Sat, Sep 6, priced at $137 found 5 days ago

Tue, Jun 17 - Wed, Jun 25

ORD

O'Hare Intl.

BOS

Logan Intl.

$137 Roundtrip, found 1 hour ago

$137

Roundtrip

found 1 hour ago

Select JetBlue Airways flight, departing Tue, Jun 17 from O'Hare Intl. to Logan Intl., returning Wed, Jun 25, priced at $137 found 1 hour ago

Wed, Oct 15 - Mon, Oct 20

ORD

O'Hare Intl.

BOS

Logan Intl.

$137 Roundtrip, found 1 day ago

$137

Roundtrip

found 1 day ago

Select American Airlines flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Mon, Oct 20, priced at $137 found 1 day 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

Tue, Aug 5 - Thu, Aug 14

ORD

O'Hare Intl.

BOS

Logan Intl.

$145 Roundtrip, found 3 hours ago

$145

Roundtrip

found 3 hours ago

Select Delta flight, departing Tue, Aug 5 from O'Hare Intl. to Logan Intl., returning Thu, Aug 14, priced at $145 found 3 hours ago

Thu, Aug 7 - Mon, Aug 11

ORD

O'Hare Intl.

BOS

Logan Intl.

$147 Roundtrip, found 1 hour ago

$147

Roundtrip

found 1 hour ago

Select Delta flight, departing Thu, Aug 7 from O'Hare Intl. to Logan Intl., returning Mon, Aug 11, priced at $147 found 1 hour ago

Thu, Aug 7 - Mon, Aug 11

ORD

O'Hare Intl.

BOS

Logan Intl.

$149 Roundtrip, found 1 hour ago

$149

Roundtrip

found 1 hour ago

Select United flight, departing Thu, Aug 7 from O'Hare Intl. to Logan Intl., returning Mon, Aug 11, priced at $149 found 1 hour ago

Wed, Jun 18 - Wed, Jun 25

ORD

O'Hare Intl.

BOS

Logan Intl.

$155 Roundtrip, found 1 hour ago

$155

Roundtrip

found 1 hour ago

Select Delta flight, departing Wed, Jun 18 from O'Hare Intl. to Logan Intl., returning Wed, Jun 25, priced at $155 found 1 hour ago

Thu, Aug 7 - Mon, Aug 11

ORD

O'Hare Intl.

BOS

Logan Intl.

$157 Roundtrip, found 1 hour ago

$157

Roundtrip

found 1 hour ago

Select JetBlue Airways flight, departing Thu, Aug 7 from O'Hare Intl. to Logan Intl., returning Mon, Aug 11, priced at $157 found 1 hour ago

Thu, Aug 7 - Mon, Aug 11

ORD

O'Hare Intl.

BOS

Logan Intl.

$160 Roundtrip, found 1 hour ago

$160

Roundtrip

found 1 hour ago

Select United flight, departing Thu, Aug 7 from O'Hare Intl. to Logan Intl., returning Mon, Aug 11, priced at $160 found 1 hour ago

Thu, Aug 7 - Mon, Aug 11

ORD

O'Hare Intl.

BOS

Logan Intl.

$161 Roundtrip, found 1 hour ago

$161

Roundtrip

found 1 hour ago

Select United flight, departing Thu, Aug 7 from O'Hare Intl. to Logan Intl., returning Mon, Aug 11, priced at $161 found 1 hour ago

Sat, Aug 23 - Sun, Aug 24

ORD

O'Hare Intl.

BOS

Logan Intl.

$165 Roundtrip, found 3 days ago

$165

Roundtrip

found 3 days ago

Select United flight, departing Sat, Aug 23 from O'Hare Intl. to Logan Intl., returning Sun, Aug 24, priced at $165 found 3 days ago

Thu, Oct 16 - Sat, Oct 18

ORD

O'Hare Intl.

BOS

Logan Intl.

$172 Roundtrip, found 2 days ago

$172

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Thu, Oct 16 from O'Hare Intl. to Logan Intl., returning Sat, Oct 18, priced at $172 found 2 days ago

Wed, Oct 15 - Mon, Oct 20

ORD

O'Hare Intl.

BOS

Logan Intl.

$172 Roundtrip, found 1 day ago

$172

Roundtrip

found 1 day ago

Select United flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Mon, Oct 20, priced at $172 found 1 day ago

Sat, Jul 12 - Sat, Jul 19

ORD

O'Hare Intl.

BOS

Logan Intl.

$210 Roundtrip, found 3 days ago

$210

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Sat, Jul 12 from O'Hare Intl. to Logan Intl., returning Sat, Jul 19, priced at $210 found 3 days ago

Thu, Jun 19 - Fri, Jun 20

MDW

Midway Intl.

BOS

Logan Intl.

$250 Roundtrip, found 1 day ago

$250

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Thu, Jun 19 from Midway Intl. to Logan Intl., returning Fri, Jun 20, priced at $250 found 1 day ago

Mon, Jun 30 - Fri, Jul 4

MDW

Midway Intl.

PVD

T.F. Green

$281 Roundtrip, found 1 hour ago

$281

Roundtrip

found 1 hour ago

Select Delta flight, departing Mon, Jun 30 from Midway Intl. to T.F. Green, returning Fri, Jul 4, priced at $281 found 1 hour ago

Wed, Jul 9 - Tue, Jul 15

ORD

O'Hare Intl.

PVD

T.F. Green

$303 Roundtrip, found 2 days ago

$303

Roundtrip

found 2 days ago

Select JetBlue Airways flight, departing Wed, Jul 9 from O'Hare Intl. to T.F. Green, returning Tue, Jul 15, priced at $303 found 2 days ago