Flights from Chicago to Detroit

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, Jun 28 - Sun, Jun 29

ORD

O'Hare Intl.

PDX

Portland Intl.

$184 Roundtrip, found 5 days ago

$184

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Sat, Jun 28 from O'Hare Intl. to Portland Intl., returning Sun, Jun 29, priced at $184 found 5 days ago

Tue, Jul 8 - Tue, Jul 15

ORD

O'Hare Intl.

PDX

Portland Intl.

$188 Roundtrip, found 4 days ago

$188

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Tue, Jul 8 from O'Hare Intl. to Portland Intl., returning Tue, Jul 15, priced at $188 found 4 days ago

Sat, Jun 28 - Sat, Jul 5

ORD

O'Hare Intl.

PDX

Portland Intl.

$203 Roundtrip, found 5 days ago

$203

Roundtrip

found 5 days ago

Select United flight, departing Sat, Jun 28 from O'Hare Intl. to Portland Intl., returning Sat, Jul 5, priced at $203 found 5 days ago

Tue, Jul 8 - Tue, Jul 15

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, Jul 8 from O'Hare Intl. to Portland Intl., returning Tue, Jul 15, priced at $209 found 4 days ago

Sat, Jun 28 - Sun, Jun 29

ORD

O'Hare Intl.

PDX

Portland Intl.

$214 Roundtrip, found 5 days ago

$214

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Sat, Jun 28 from O'Hare Intl. to Portland Intl., returning Sun, Jun 29, priced at $214 found 5 days ago

Sat, Jun 28 - Sat, Jul 5

ORD

O'Hare Intl.

PDX

Portland Intl.

$216 Roundtrip, found 5 days ago

$216

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Sat, Jun 28 from O'Hare Intl. to Portland Intl., returning Sat, Jul 5, priced at $216 found 5 days ago

Wed, Jun 25 - Wed, Jul 2

ORD

O'Hare Intl.

PDX

Portland Intl.

$223 Roundtrip, found 5 days ago

$223

Roundtrip

found 5 days ago

Select Delta flight, departing Wed, Jun 25 from O'Hare Intl. to Portland Intl., returning Wed, Jul 2, priced at $223 found 5 days ago

Fri, Jun 27 - Sat, Jun 28

ORD

O'Hare Intl.

PDX

Portland Intl.

$225 Roundtrip, found 5 days ago

$225

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Fri, Jun 27 from O'Hare Intl. to Portland Intl., returning Sat, Jun 28, priced at $225 found 5 days ago

Wed, Jul 9 - Mon, Jul 14

ORD

O'Hare Intl.

PDX

Portland Intl.

$226 Roundtrip, found 5 hours ago

$226

Roundtrip

found 5 hours ago

Select Spirit Airlines flight, departing Wed, Jul 9 from O'Hare Intl. to Portland Intl., returning Mon, Jul 14, priced at $226 found 5 hours ago

Tue, Jul 8 - Tue, Jul 15

ORD

O'Hare Intl.

PDX

Portland Intl.

$227 Roundtrip, found 4 days ago

$227

Roundtrip

found 4 days ago

Select American Airlines flight, departing Tue, Jul 8 from O'Hare Intl. to Portland Intl., returning Tue, Jul 15, priced at $227 found 4 days ago

Sat, Jul 5 - Sat, Jul 12

ORD

O'Hare Intl.

PDX

Portland Intl.

$227 Roundtrip, found 5 hours ago

$227

Roundtrip

found 5 hours ago

Select Hawaiian Airlines flight, departing Sat, Jul 5 from O'Hare Intl. to Portland Intl., returning Sat, Jul 12, priced at $227 found 5 hours ago

Sat, Jun 28 - Sat, Jul 5

ORD

O'Hare Intl.

PDX

Portland Intl.

$227 Roundtrip, found 5 days ago

$227

Roundtrip

found 5 days ago

Select United flight, departing Sat, Jun 28 from O'Hare Intl. to Portland Intl., returning Sat, Jul 5, priced at $227 found 5 days ago

Wed, Jun 25 - Mon, Jul 7

ORD

O'Hare Intl.

PDX

Portland Intl.

$230 Roundtrip, found 5 days ago

$230

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Wed, Jun 25 from O'Hare Intl. to Portland Intl., returning Mon, Jul 7, priced at $230 found 5 days ago

Tue, Jul 8 - Tue, Jul 15

ORD

O'Hare Intl.

PDX

Portland Intl.

$231 Roundtrip, found 4 days ago

$231

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Tue, Jul 8 from O'Hare Intl. to Portland Intl., returning Tue, Jul 15, priced at $231 found 4 days ago

Thu, Oct 30 - Mon, Nov 3

ORD

O'Hare Intl.

PDX

Portland Intl.

$233 Roundtrip, found 3 days ago

$233

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Thu, Oct 30 from O'Hare Intl. to Portland Intl., returning Mon, Nov 3, priced at $233 found 3 days ago

Sat, Jun 28 - Sun, Jun 29

ORD

O'Hare Intl.

PDX

Portland Intl.

$233 Roundtrip, found 5 days ago

$233

Roundtrip

found 5 days ago

Select Frontier Airlines flight, departing Sat, Jun 28 from O'Hare Intl. to Portland Intl., returning Sun, Jun 29, priced at $233 found 5 days ago

Tue, Jul 8 - Tue, Jul 15

ORD

O'Hare Intl.

PDX

Portland Intl.

$237 Roundtrip, found 4 days ago

$237

Roundtrip

found 4 days ago

Select United flight, departing Tue, Jul 8 from O'Hare Intl. to Portland Intl., returning Tue, Jul 15, priced at $237 found 4 days ago

Sat, Jul 5 - Mon, Jul 14

ORD

O'Hare Intl.

PDX

Portland Intl.

$238 Roundtrip, found 5 hours ago

$238

Roundtrip

found 5 hours ago

Select Hawaiian Airlines flight, departing Sat, Jul 5 from O'Hare Intl. to Portland Intl., returning Mon, Jul 14, priced at $238 found 5 hours ago

Tue, Jul 8 - Tue, Jul 15

ORD

O'Hare Intl.

PDX

Portland Intl.

$247 Roundtrip, found 4 days ago

$247

Roundtrip

found 4 days ago

Select Alaska Airlines flight, departing Tue, Jul 8 from O'Hare Intl. to Portland Intl., returning Tue, Jul 15, priced at $247 found 4 days ago

Sat, Jun 28 - Sat, Jul 5

MDW

Midway Intl.

PDX

Portland Intl.

$248 Roundtrip, found 1 day ago

$248

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Sat, Jun 28 from Midway Intl. to Portland Intl., returning Sat, Jul 5, priced at $248 found 1 day ago