$140 Cheap flight deals from Chicago (CHI) to Tillamook (PDX)

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This Weekend's Flight Deals from Chicago to Tillamook

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, Sep 5 - Tue, Sep 8
ORD
O'Hare Intl.
PDX
Portland Intl.
$387 Roundtrip, just found
$387
Roundtrip
just found
Select Bargain Flight flight, departing Sat, Sep 5 from O'Hare Intl. to Portland Intl., returning Tue, Sep 8, priced at $387 just found
Sat, Sep 5 - Sun, Sep 6
MDW
Midway Intl.
PDX
Portland Intl.
$409 Roundtrip, found 5 days ago
$409
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Sat, Sep 5 from Midway Intl. to Portland Intl., returning Sun, Sep 6, priced at $409 found 5 days ago
Fri, Sep 4 - Mon, Sep 7
RFD
Greater Rockford
PDX
Portland Intl.
$835 Roundtrip, found 5 days ago
$835
Roundtrip
found 5 days ago
Select American Airlines flight, departing Fri, Sep 4 from Greater Rockford to Portland Intl., returning Mon, Sep 7, priced at $835 found 5 days ago

Airfares from $140 One Way, $267 Round Trip from Chicago to Tillamook

Prices starting at $267 for return flights and $140 for one-way flights to Tillamook were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Dec 5 - Sun, Dec 6
ORD
Chicago
PDX
Portland
$267 Roundtrip, found 2 days ago
$267
Roundtrip
found 2 days ago
Select Alaska Airlines flight, departing Sat, Dec 5 from Chicago to Portland, returning Sun, Dec 6, priced at $267 found 2 days ago
Tue, Oct 27 - Tue, Nov 10
ORD
Chicago
PDX
Portland
$278 Roundtrip, found 7 hours ago
$278
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Tue, Oct 27 from Chicago to Portland, returning Tue, Nov 10, priced at $278 found 7 hours ago
Fri, Oct 2 - Mon, Oct 5
ORD
Chicago
PDX
Portland
$287 Roundtrip, found 6 hours ago
$287
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Fri, Oct 2 from Chicago to Portland, returning Mon, Oct 5, priced at $287 found 6 hours ago
Tue, Sep 29 - Tue, Oct 6
MDW
Chicago
PDX
Portland
$344 Roundtrip, found 20 hours ago
$344
Roundtrip
found 20 hours ago
Select Southwest Airlines flight, departing Tue, Sep 29 from Chicago to Portland, returning Tue, Oct 6, priced at $344 found 20 hours ago
Fri, Oct 30 - Mon, Nov 9
ORD
Chicago
PDX
Portland
$351 Roundtrip, found 1 day ago
$351
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Fri, Oct 30 from Chicago to Portland, returning Mon, Nov 9, priced at $351 found 1 day ago

Tillamook economy flight packages

Price found within the past 48 hours. Click for updated prices.
Schooner Landing
3.0-star property

Schooner Landing

8.4/10 Very Good! (75 reviews)

Oct 8 - Oct 12

4 night stay

Chicago (CHI) to Portland (PDX)

Southwest Airlines • Coach

Portland (PDX) to Chicago (CHI)

Frontier Airlines • Coach
Price was $745, price is now $594 per person
$594
per person
found 1 day ago
Clean spacious rooms, fully equipped kitchen, unique floor plans.

Reviewed on Aug 19, 2026

Mark Spencer Hotel
3.0-star property

Mark Spencer Hotel

9.2/10 Wonderful! (2,382 reviews)

Oct 8 - Oct 12

4 night stay

Chicago (CHI) to Portland (PDX)

United • Roundtrip • Coach
Price was $774, price is now $600 per person
$600
per person
found 1 day ago
The room was clean and generally comfortable, but the first thing I noticed when I walked in was a strong, somewhat unusual smell. It gave me the impression that the room may have been used for partying before, and unfortunately, the smell was noticeable enough to affect my overall experience. One thing to keep in mind is the limited parking. If you’re planning to park at the hotel, I would definitely recommend reserving a parking spot in advance, as the underground parking has limited availability. Otherwise, you may have to park on the street or in an outdoor lot. Given the area, I personally didn’t feel very comfortable leaving a car outside, especially with the amount of reported car break-ins and broken windows around Portland. That said, the location is quite convenient, with plenty of restaurants, shops, and things to do nearby. And the staff were honestly one of the best parts of my stay. Everyone I interacted with was incredibly friendly, helpful, and welcoming. Overall, I think the hotel has a lot going for it, especially the staff and location. However, the smell in the room and the parking situation were significant enough for me to give it 3 stars.

Reviewed on Aug 28, 2026

The Pilot House by Avantstay Stunning Home Right On Arch Cape Beach!
3.5-star property

The Pilot House by Avantstay Stunning Home Right On Arch Cape Beach!

No reviews

Oct 19 - Oct 23

4 night stay

Chicago (ORD) to Portland (PDX)

United • Roundtrip • Coach
Price was $1,639, price is now $1,338 per person
$1,338
per person
found 10 hours ago

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More About Flying To Tillamook from Chicago

Route Information for Flights from Chicago to Tillamook

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

Chicago to Tillamook

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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.