Flights from Chicago to Wrentham

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, Aug 30 - Sun, Aug 31

ORD

O'Hare Intl.

PDX

Portland Intl.

$202 Roundtrip, found 4 days ago

$202

Roundtrip

found 4 days ago

Select Hawaiian Airlines flight, departing Sat, Aug 30 from O'Hare Intl. to Portland Intl., returning Sun, Aug 31, priced at $202 found 4 days ago

Sat, Aug 2 - Tue, Aug 12

ORD

O'Hare Intl.

PDX

Portland Intl.

$204 Roundtrip, found 5 days ago

$204

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Sat, Aug 2 from O'Hare Intl. to Portland Intl., returning Tue, Aug 12, priced at $204 found 5 days ago

Sun, Aug 24 - Wed, Sep 3

ORD

O'Hare Intl.

PDX

Portland Intl.

$206 Roundtrip, found 4 days ago

$206

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Sun, Aug 24 from O'Hare Intl. to Portland Intl., returning Wed, Sep 3, priced at $206 found 4 days ago

Tue, Aug 26 - Wed, Sep 3

ORD

O'Hare Intl.

PDX

Portland Intl.

$209 Roundtrip, found 4 days ago

$209

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Tue, Aug 26 from O'Hare Intl. to Portland Intl., returning Wed, Sep 3, priced at $209 found 4 days ago

Sun, Aug 24 - Sun, Aug 31

ORD

O'Hare Intl.

PDX

Portland Intl.

$213 Roundtrip, found 4 days ago

$213

Roundtrip

found 4 days ago

Select Hawaiian Airlines flight, departing Sun, Aug 24 from O'Hare Intl. to Portland Intl., returning Sun, Aug 31, priced at $213 found 4 days ago

Sun, Aug 24 - Fri, Aug 29

ORD

O'Hare Intl.

PDX

Portland Intl.

$216 Roundtrip, found 4 days ago

$216

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Sun, Aug 24 from O'Hare Intl. to Portland Intl., returning Fri, Aug 29, priced at $216 found 4 days ago

Tue, Aug 26 - Fri, Aug 29

ORD

O'Hare Intl.

PDX

Portland Intl.

$219 Roundtrip, found 4 days ago

$219

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Tue, Aug 26 from O'Hare Intl. to Portland Intl., returning Fri, Aug 29, priced at $219 found 4 days ago

Sat, Oct 25 - Wed, Oct 29

ORD

O'Hare Intl.

PDX

Portland Intl.

$219 Roundtrip, found 4 days ago

$219

Roundtrip

found 4 days ago

Select Alaska Airlines flight, departing Sat, Oct 25 from O'Hare Intl. to Portland Intl., returning Wed, Oct 29, priced at $219 found 4 days ago

Sat, Oct 25 - Wed, Oct 29

ORD

O'Hare Intl.

PDX

Portland Intl.

$220 Roundtrip, found 4 days ago

$220

Roundtrip

found 4 days ago

Select United flight, departing Sat, Oct 25 from O'Hare Intl. to Portland Intl., returning Wed, Oct 29, priced at $220 found 4 days ago

Tue, Aug 26 - Tue, Sep 2

ORD

O'Hare Intl.

PDX

Portland Intl.

$222 Roundtrip, found 4 days ago

$222

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Tue, Aug 26 from O'Hare Intl. to Portland Intl., returning Tue, Sep 2, priced at $222 found 4 days ago

Sat, Aug 2 - Tue, Aug 12

ORD

O'Hare Intl.

PDX

Portland Intl.

$223 Roundtrip, found 5 days ago

$223

Roundtrip

found 5 days ago

Select United flight, departing Sat, Aug 2 from O'Hare Intl. to Portland Intl., returning Tue, Aug 12, priced at $223 found 5 days ago

Sat, Aug 2 - Tue, Aug 12

ORD

O'Hare Intl.

PDX

Portland Intl.

$225 Roundtrip, found 5 days ago

$225

Roundtrip

found 5 days ago

Select American Airlines flight, departing Sat, Aug 2 from O'Hare Intl. to Portland Intl., returning Tue, Aug 12, priced at $225 found 5 days ago

Sat, Aug 30 - Sat, Aug 30

ORD

O'Hare Intl.

PDX

Portland Intl.

$225 Roundtrip, found 4 days ago

$225

Roundtrip

found 4 days ago

Select Hawaiian Airlines flight, departing Sat, Aug 30 from O'Hare Intl. to Portland Intl., returning Sat, Aug 30, priced at $225 found 4 days ago

Sat, Oct 25 - Wed, Oct 29

ORD

O'Hare Intl.

PDX

Portland Intl.

$225 Roundtrip, found 4 days ago

$225

Roundtrip

found 4 days ago

Select Alaska Airlines flight, departing Sat, Oct 25 from O'Hare Intl. to Portland Intl., returning Wed, Oct 29, priced at $225 found 4 days ago

Sat, Oct 25 - Wed, Oct 29

ORD

O'Hare Intl.

PDX

Portland Intl.

$225 Roundtrip, found 4 days ago

$225

Roundtrip

found 4 days ago

Select American Airlines flight, departing Sat, Oct 25 from O'Hare Intl. to Portland Intl., returning Wed, Oct 29, priced at $225 found 4 days ago

Sat, Aug 2 - Tue, Aug 12

ORD

O'Hare Intl.

PDX

Portland Intl.

$226 Roundtrip, found 5 days ago

$226

Roundtrip

found 5 days ago

Select American Airlines flight, departing Sat, Aug 2 from O'Hare Intl. to Portland Intl., returning Tue, Aug 12, priced at $226 found 5 days ago

Sat, Oct 25 - Wed, Oct 29

ORD

O'Hare Intl.

PDX

Portland Intl.

$227 Roundtrip, found 4 days ago

$227

Roundtrip

found 4 days ago

Select Delta flight, departing Sat, Oct 25 from O'Hare Intl. to Portland Intl., returning Wed, Oct 29, priced at $227 found 4 days ago

Wed, Aug 27 - Fri, Aug 29

ORD

O'Hare Intl.

PDX

Portland Intl.

$230 Roundtrip, found 4 days ago

$230

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Wed, Aug 27 from O'Hare Intl. to Portland Intl., returning Fri, Aug 29, priced at $230 found 4 days ago

Sat, Oct 25 - Wed, Oct 29

ORD

O'Hare Intl.

PDX

Portland Intl.

$230 Roundtrip, found 4 days ago

$230

Roundtrip

found 4 days ago

Select United flight, departing Sat, Oct 25 from O'Hare Intl. to Portland Intl., returning Wed, Oct 29, priced at $230 found 4 days ago

Sat, Oct 25 - Mon, Oct 27

ORD

O'Hare Intl.

PDX

Portland Intl.

$256 Roundtrip, found 18 hours ago

$256

Roundtrip

found 18 hours ago

Select Delta flight, departing Sat, Oct 25 from O'Hare Intl. to Portland Intl., returning Mon, Oct 27, priced at $256 found 18 hours ago