Flights from Chicago to Westwood

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.

Thu, Jun 12 - Mon, Jun 16

ORD

O'Hare Intl.

BOS

Logan Intl.

$137 Roundtrip, found 9 hours ago

$137

Roundtrip

found 9 hours ago

Select United flight, departing Thu, Jun 12 from O'Hare Intl. to Logan Intl., returning Mon, Jun 16, priced at $137 found 9 hours ago

Thu, Jun 12 - Mon, Jun 16

ORD

O'Hare Intl.

BOS

Logan Intl.

$137 Roundtrip, found 9 hours ago

$137

Roundtrip

found 9 hours ago

Select JetBlue Airways flight, departing Thu, Jun 12 from O'Hare Intl. to Logan Intl., returning Mon, Jun 16, priced at $137 found 9 hours ago

Tue, Jun 10 - Tue, Jun 17

ORD

O'Hare Intl.

BOS

Logan Intl.

$137 Roundtrip, found 9 hours ago

$137

Roundtrip

found 9 hours ago

Select Delta flight, departing Tue, Jun 10 from O'Hare Intl. to Logan Intl., returning Tue, Jun 17, priced at $137 found 9 hours ago

Wed, Oct 15 - Sun, Oct 19

ORD

O'Hare Intl.

BOS

Logan Intl.

$139 Roundtrip, found 16 hours ago

$139

Roundtrip

found 16 hours ago

Select Spirit Airlines flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Sun, Oct 19, priced at $139 found 16 hours ago

Tue, Sep 23 - Wed, Oct 1

ORD

O'Hare Intl.

BOS

Logan Intl.

$140 Roundtrip, found 1 day ago

$140

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Tue, Sep 23 from O'Hare Intl. to Logan Intl., returning Wed, Oct 1, priced at $140 found 1 day ago

Tue, Sep 23 - Wed, Oct 1

ORD

O'Hare Intl.

BOS

Logan Intl.

$143 Roundtrip, found 1 day ago

$143

Roundtrip

found 1 day ago

Select United flight, departing Tue, Sep 23 from O'Hare Intl. to Logan Intl., returning Wed, Oct 1, priced at $143 found 1 day ago

Wed, Oct 15 - Thu, Oct 16

ORD

O'Hare Intl.

BOS

Logan Intl.

$145 Roundtrip, found 3 days ago

$145

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Thu, Oct 16, priced at $145 found 3 days ago

Thu, Jun 12 - Mon, Jun 16

ORD

O'Hare Intl.

BOS

Logan Intl.

$150 Roundtrip, found 9 hours ago

$150

Roundtrip

found 9 hours ago

Select Spirit Airlines flight, departing Thu, Jun 12 from O'Hare Intl. to Logan Intl., returning Mon, Jun 16, priced at $150 found 9 hours ago

Wed, Aug 6 - Sun, Aug 10

ORD

O'Hare Intl.

BOS

Logan Intl.

$150 Roundtrip, found 20 hours ago

$150

Roundtrip

found 20 hours ago

Select United flight, departing Wed, Aug 6 from O'Hare Intl. to Logan Intl., returning Sun, Aug 10, priced at $150 found 20 hours ago

Thu, Jun 12 - Fri, Jun 13

ORD

O'Hare Intl.

BOS

Logan Intl.

$151 Roundtrip, found 10 hours ago

$151

Roundtrip

found 10 hours ago

Select United flight, departing Thu, Jun 12 from O'Hare Intl. to Logan Intl., returning Fri, Jun 13, priced at $151 found 10 hours ago

Wed, Oct 15 - Sun, Oct 19

ORD

O'Hare Intl.

BOS

Logan Intl.

$154 Roundtrip, found 16 hours ago

$154

Roundtrip

found 16 hours ago

Select United flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Sun, Oct 19, priced at $154 found 16 hours ago

Thu, Jun 12 - Mon, Jun 16

ORD

O'Hare Intl.

BOS

Logan Intl.

$155 Roundtrip, found 9 hours ago

$155

Roundtrip

found 9 hours ago

Select United flight, departing Thu, Jun 12 from O'Hare Intl. to Logan Intl., returning Mon, Jun 16, priced at $155 found 9 hours ago

Thu, Jun 12 - Fri, Jun 13

ORD

O'Hare Intl.

BOS

Logan Intl.

$155 Roundtrip, found 10 hours ago

$155

Roundtrip

found 10 hours ago

Select American Airlines flight, departing Thu, Jun 12 from O'Hare Intl. to Logan Intl., returning Fri, Jun 13, priced at $155 found 10 hours ago

Wed, Oct 8 - Wed, Oct 15

ORD

O'Hare Intl.

BOS

Logan Intl.

$160 Roundtrip, found 4 days ago

$160

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Wed, Oct 8 from O'Hare Intl. to Logan Intl., returning Wed, Oct 15, priced at $160 found 4 days ago

Thu, Jun 12 - Mon, Jun 16

ORD

O'Hare Intl.

BOS

Logan Intl.

$162 Roundtrip, found 9 hours ago

$162

Roundtrip

found 9 hours ago

Select Spirit Airlines flight, departing Thu, Jun 12 from O'Hare Intl. to Logan Intl., returning Mon, Jun 16, priced at $162 found 9 hours 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, Jun 12 - Mon, Jun 16

ORD

O'Hare Intl.

BOS

Logan Intl.

$167 Roundtrip, found 9 hours ago

$167

Roundtrip

found 9 hours ago

Select JetBlue Airways flight, departing Thu, Jun 12 from O'Hare Intl. to Logan Intl., returning Mon, Jun 16, priced at $167 found 9 hours ago

Mon, Aug 4 - Sat, Aug 9

ORD

O'Hare Intl.

BOS

Logan Intl.

$220 Roundtrip, found 5 days ago

$220

Roundtrip

found 5 days ago

Select Frontier Airlines flight, departing Mon, Aug 4 from O'Hare Intl. to Logan Intl., returning Sat, Aug 9, priced at $220 found 5 days ago

Sat, Aug 23 - Sun, Aug 24

MDW

Midway Intl.

BOS

Logan Intl.

$318 Roundtrip, found 3 days ago

$318

Roundtrip

found 3 days ago

Select Delta flight, departing Sat, Aug 23 from Midway Intl. to Logan Intl., returning Sun, Aug 24, priced at $318 found 3 days ago

Thu, Jun 12 - Mon, Jun 16

ORD

O'Hare Intl.

BOS

Logan Intl.

$1,112 Roundtrip, found 9 hours ago

$1,112

Roundtrip

found 9 hours ago

Select Alaska Airlines flight, departing Thu, Jun 12 from O'Hare Intl. to Logan Intl., returning Mon, Jun 16, priced at $1,112 found 9 hours ago