$65 Cheap flight deals from Chicago (CHI) to Otter Rock (PDX)

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

This Weekend's Flight Deals from Chicago to Otter Rock

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Jun 7 - Sun, Jun 8
MDW
Midway Intl.
PDX
Portland Intl.
$298 Roundtrip, found 19 hours ago
$298
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Sat, Jun 7 from Midway Intl. to Portland Intl., returning Sun, Jun 8, priced at $298 found 19 hours ago
Sat, Jun 7 - Thu, Jul 3
ORD
O'Hare Intl.
PDX
Portland Intl.
$461 Roundtrip, found 7 hours ago
$461
Roundtrip
found 7 hours ago
Select Alaska Airlines flight, departing Sat, Jun 7 from O'Hare Intl. to Portland Intl., returning Thu, Jul 3, priced at $461 found 7 hours ago

Airfares from $65 One Way, $159 Round Trip from Chicago to Otter Rock

Prices starting at $159 for return flights and $65 for one-way flights to Otter Rock were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, Aug 6 - Thu, Aug 14
MDW
Chicago
PDX
Portland
$159 Roundtrip, found 6 hours ago
$159
Roundtrip
found 6 hours ago
Select Southwest Airlines flight, departing Wed, Aug 6 from Chicago to Portland, returning Thu, Aug 14, priced at $159 found 6 hours ago
Wed, Aug 6 - Wed, Aug 13
ORD
Chicago
PDX
Portland
$165 Roundtrip, found 5 hours ago
$165
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Wed, Aug 6 from Chicago to Portland, returning Wed, Aug 13, priced at $165 found 5 hours ago
Sat, Aug 16 - Mon, Aug 18
ORD
Chicago
PDX
Portland
$177 Roundtrip, found 1 day ago
$177
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Aug 16 from Chicago to Portland, returning Mon, Aug 18, priced at $177 found 1 day ago
Tue, Sep 9 - Sat, Sep 13
ORD
Chicago
PDX
Portland
$179 Roundtrip, found 1 day ago
$179
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Sep 9 from Chicago to Portland, returning Sat, Sep 13, priced at $179 found 1 day ago
Tue, Aug 26 - Sun, Aug 31
ORD
Chicago
PDX
Portland
$180 Roundtrip, found 9 hours ago
$180
Roundtrip
found 9 hours ago
Select Alaska Airlines flight, departing Tue, Aug 26 from Chicago to Portland, returning Sun, Aug 31, priced at $180 found 9 hours ago

Otter Rock economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel Lucia
4.0-star property

Hotel Lucia

9.2/10 Wonderful! (1,184 reviews)

Jul 19 - Jul 23

4 night stay

Chicago (CHI) to Portland (PDX)

Spirit Airlines • Non-stop roundtrip • Coach
per person
found 1 day ago
The staff were excellent and the common areas were fresh and fun. We intentionally ordered the least expensive room for a quick trip, and while the anticipated small size wasn't a problem, per se, the fan blew directly onto the bed as a result, and was too strong even on low. Staff immediately brought us a stand up fan, and offered to look for a room in a different configuration. The bed and pillows were comfortable but the queen was a full. Again, quick trip, low price, no complaints. The soaps and lotions were lovely, and it was nice to have hot coffee downstairs every morning. We never made it to the craft beer hour but next time! Will return and go up a class or two in the room.

Reviewed on May 25, 2025

The Independence
3.0-star property

The Independence

9.6/10 Exceptional! (774 reviews)

Jul 17 - Jul 21

4 night stay

Chicago (CHI) to Portland (PDX)

Alaska Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
per person
found 14 hours ago
The breakfast was out of most items, including coffee by 8:00 a.m. there were only a few scraps of cold scrambled eggs, and cold potatoes. It took 25 minutes to refill hot foods, fruit and coffee while guests waited around in a line. When I expressed to the the front desk person that the hotel needs to improve planning, this was met with an unwillingness to take ownership on behalf of the hotel, a "not my job" response. Upon my check out, the same person was at the buffet getting food with other employees and returned to the front desk chewing food and was fairly dismissive in processing my room check out. Overall, the rooms are nice, but the service today did not match the 9.4 rating I saw while making the reservation.

Reviewed on Sep 18, 2023

Capitol Hill Motel
2.5-star property

Capitol Hill Motel

9.2/10 Wonderful! (798 reviews)

Jul 19 - Jul 25

6 night stay

Chicago (ORD) to Portland (PDX)

Spirit Airlines • Non-stop • Coach

Portland (PDX) to Chicago (ORD)

Alaska Airlines • Non-stop • Coach
per person
found 1 day ago
This is a great little motel - very clean and well-maintained, with free parking. Although it's on a busy road it is well-lit and felt safe. It was convenient to have a fridge and microwave since I stayed for a few days. No frills but excellent value!

Reviewed on Oct 19, 2023

Don't see what you're looking for?
See all available trips from Chicago to Otter Rock
View all trips

More About Flying To Otter Rock from Chicago

Route Information for Flights from Chicago to Otter Rock

Origin Airport IATA Code
CHI
Destination Airport IATA Code
PDX
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to Otter Rock

Orbitz On-the-Go is your one-stop shop for discount vacation air travel. Our cutting-edge mobile tools leave you time to pack for the trip. Shop our sales on domestic flights from Chicago to Otter Rock.

Best Bargains Anywhere

Cheap vacations start at Orbitz On-the-Go. Find the best deals on international flights from Chicago to Otter Rock.

Complete Travel Planning

Your phone becomes a full-service vacation travel agency with Orbitz mobile phone apps. From reservations to arrivals, every detail is in the palm of your hand. Book budget flights from Chicago to Otter Rock; add a car and hotel, share your itinerary and keep up with changes. Orbitz apps cover all the bases for you.

Totally Stress-Free

Free Alerts from Orbitz On-the-Go keep your vacation free from worry. Free Alerts updates you the moment any changes occur. You’ll always have the most current flight, gate and baggage claim details. So sit back and enjoy your low fare on Chicago to Otter Rock flights.

More Miles Faster = Maximum Value

Orbitz On-the-Go securely stores your frequent flier and loyalty program information. Watch your miles add up when you book discount Chicago to Otter Rock flights with Orbitz. Make your vacation mileage-friendly with low cost air tickets on Chicago to Otter Rock flights. Orbitz is your destination for vacation value.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.