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.

Sat, Sep 6 - Tue, Sep 16

ORD

O'Hare Intl.

SEA

Seattle - Tacoma Intl.

$127 Roundtrip, found 6 hours ago

$127

Roundtrip

found 6 hours ago

Select Hawaiian Airlines flight, departing Sat, Sep 6 from O'Hare Intl. to Seattle - Tacoma Intl., returning Tue, Sep 16, priced at $127 found 6 hours ago

Tue, Sep 9 - Tue, Sep 16

ORD

O'Hare Intl.

SEA

Seattle - Tacoma Intl.

$127 Roundtrip, found 6 hours ago

$127

Roundtrip

found 6 hours ago

Select Alaska Airlines flight, departing Tue, Sep 9 from O'Hare Intl. to Seattle - Tacoma Intl., returning Tue, Sep 16, priced at $127 found 6 hours ago

Sat, Sep 6 - Thu, Sep 18

ORD

O'Hare Intl.

SEA

Seattle - Tacoma Intl.

$134 Roundtrip, found 6 hours ago

$134

Roundtrip

found 6 hours ago

Select Hawaiian Airlines flight, departing Sat, Sep 6 from O'Hare Intl. to Seattle - Tacoma Intl., returning Thu, Sep 18, priced at $134 found 6 hours ago

Wed, Jul 16 - Tue, Jul 22

ORD

O'Hare Intl.

SEA

Seattle - Tacoma Intl.

$137 Roundtrip, found 15 hours ago

$137

Roundtrip

found 15 hours ago

Select Delta flight, departing Wed, Jul 16 from O'Hare Intl. to Seattle - Tacoma Intl., returning Tue, Jul 22, priced at $137 found 15 hours ago

Fri, Sep 5 - Tue, Sep 16

ORD

O'Hare Intl.

SEA

Seattle - Tacoma Intl.

$141 Roundtrip, found 6 hours ago

$141

Roundtrip

found 6 hours ago

Select Hawaiian Airlines flight, departing Fri, Sep 5 from O'Hare Intl. to Seattle - Tacoma Intl., returning Tue, Sep 16, priced at $141 found 6 hours ago

Tue, Jul 8 - Tue, Jul 15

ORD

O'Hare Intl.

SEA

Seattle - Tacoma Intl.

$147 Roundtrip, found 1 day ago

$147

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Jul 8 from O'Hare Intl. to Seattle - Tacoma Intl., returning Tue, Jul 15, priced at $147 found 1 day ago

Fri, Sep 5 - Thu, Sep 18

ORD

O'Hare Intl.

SEA

Seattle - Tacoma Intl.

$148 Roundtrip, found 6 hours ago

$148

Roundtrip

found 6 hours ago

Select Hawaiian Airlines flight, departing Fri, Sep 5 from O'Hare Intl. to Seattle - Tacoma Intl., returning Thu, Sep 18, priced at $148 found 6 hours ago

Thu, Jul 17 - Tue, Jul 22

ORD

O'Hare Intl.

SEA

Seattle - Tacoma Intl.

$151 Roundtrip, found 15 hours ago

$151

Roundtrip

found 15 hours ago

Select Delta flight, departing Thu, Jul 17 from O'Hare Intl. to Seattle - Tacoma Intl., returning Tue, Jul 22, priced at $151 found 15 hours ago

Fri, Sep 5 - Fri, Sep 19

ORD

O'Hare Intl.

SEA

Seattle - Tacoma Intl.

$155 Roundtrip, found 6 hours ago

$155

Roundtrip

found 6 hours ago

Select Hawaiian Airlines flight, departing Fri, Sep 5 from O'Hare Intl. to Seattle - Tacoma Intl., returning Fri, Sep 19, priced at $155 found 6 hours ago

Wed, Jul 16 - Mon, Jul 21

ORD

O'Hare Intl.

SEA

Seattle - Tacoma Intl.

$161 Roundtrip, found 15 hours ago

$161

Roundtrip

found 15 hours ago

Select Delta flight, departing Wed, Jul 16 from O'Hare Intl. to Seattle - Tacoma Intl., returning Mon, Jul 21, priced at $161 found 15 hours ago

Sat, Sep 6 - Sun, Sep 21

ORD

O'Hare Intl.

SEA

Seattle - Tacoma Intl.

$165 Roundtrip, found 6 hours ago

$165

Roundtrip

found 6 hours ago

Select Hawaiian Airlines flight, departing Sat, Sep 6 from O'Hare Intl. to Seattle - Tacoma Intl., returning Sun, Sep 21, priced at $165 found 6 hours ago

Mon, Jul 7 - Tue, Jul 15

ORD

O'Hare Intl.

SEA

Seattle - Tacoma Intl.

$165 Roundtrip, found 1 day ago

$165

Roundtrip

found 1 day ago

Select United flight, departing Mon, Jul 7 from O'Hare Intl. to Seattle - Tacoma Intl., returning Tue, Jul 15, priced at $165 found 1 day ago

Tue, Jun 10 - Tue, Jun 17

ORD

O'Hare Intl.

SEA

Seattle - Tacoma Intl.

$169 Roundtrip, found 2 days ago

$169

Roundtrip

found 2 days ago

Select Hawaiian Airlines flight, departing Tue, Jun 10 from O'Hare Intl. to Seattle - Tacoma Intl., returning Tue, Jun 17, priced at $169 found 2 days ago

Wed, Sep 3 - Tue, Sep 9

ORD

O'Hare Intl.

SEA

Seattle - Tacoma Intl.

$169 Roundtrip, found 3 days ago

$169

Roundtrip

found 3 days ago

Select American Airlines flight, departing Wed, Sep 3 from O'Hare Intl. to Seattle - Tacoma Intl., returning Tue, Sep 9, priced at $169 found 3 days ago

Sun, Sep 7 - Thu, Sep 18

ORD

O'Hare Intl.

SEA

Seattle - Tacoma Intl.

$172 Roundtrip, found 6 hours ago

$172

Roundtrip

found 6 hours ago

Select Hawaiian Airlines flight, departing Sun, Sep 7 from O'Hare Intl. to Seattle - Tacoma Intl., returning Thu, Sep 18, priced at $172 found 6 hours ago

Thu, May 29 - Sat, May 31

ORD

O'Hare Intl.

SEA

Seattle - Tacoma Intl.

$174 Roundtrip, found 2 days ago

$174

Roundtrip

found 2 days ago

Select Hawaiian Airlines flight, departing Thu, May 29 from O'Hare Intl. to Seattle - Tacoma Intl., returning Sat, May 31, priced at $174 found 2 days ago

Sun, Jun 1 - Thu, Jun 5

ORD

O'Hare Intl.

SEA

Seattle - Tacoma Intl.

$226 Roundtrip, found 2 days ago

$226

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Sun, Jun 1 from O'Hare Intl. to Seattle - Tacoma Intl., returning Thu, Jun 5, priced at $226 found 2 days ago

Fri, May 30 - Sun, Jun 1

ORD

O'Hare Intl.

SEA

Seattle - Tacoma Intl.

$227 Roundtrip, found 2 days ago

$227

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Fri, May 30 from O'Hare Intl. to Seattle - Tacoma Intl., returning Sun, Jun 1, priced at $227 found 2 days ago

Fri, May 30 - Sun, Jun 1

MDW

Midway Intl.

SEA

Seattle - Tacoma Intl.

$271 Roundtrip, found 2 days ago

$271

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Fri, May 30 from Midway Intl. to Seattle - Tacoma Intl., returning Sun, Jun 1, priced at $271 found 2 days ago

Wed, Sep 10 - Sat, Sep 13

ORD

O'Hare Intl.

SEA

Seattle - Tacoma Intl.

$549 Roundtrip, found 5 days ago

$549

Roundtrip

found 5 days ago

Select JetBlue Airways flight, departing Wed, Sep 10 from O'Hare Intl. to Seattle - Tacoma Intl., returning Sat, Sep 13, priced at $549 found 5 days ago