$127 Cheap flight deals from Chicago (CHI) to Oceanside (PDX)

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This Weekend's Flight Deals from Chicago to Oceanside

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.

Fri, Jul 10 - Mon, Jul 13
ORD
O'Hare Intl.
PDX
Portland Intl.
$352 Roundtrip, found 14 hours ago
$352
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Fri, Jul 10 from O'Hare Intl. to Portland Intl., returning Mon, Jul 13, priced at $352 found 14 hours ago
Fri, Jul 10 - Fri, Jul 17
RFD
Greater Rockford
PDX
Portland Intl.
$463 Roundtrip, found 3 days ago
$463
Roundtrip
found 3 days ago
Select American Airlines flight, departing Fri, Jul 10 from Greater Rockford to Portland Intl., returning Fri, Jul 17, priced at $463 found 3 days ago
Fri, Jul 10 - Fri, Jul 17
MDW
Midway Intl.
PDX
Portland Intl.
$470 Roundtrip, found 3 days ago
$470
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Fri, Jul 10 from Midway Intl. to Portland Intl., returning Fri, Jul 17, priced at $470 found 3 days ago

Airfares from $127 One Way, $250 Round Trip from Chicago to Oceanside

Prices starting at $250 for return flights and $127 for one-way flights to Oceanside were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Thu, Sep 10 - Mon, Sep 14
ORD
Chicago
PDX
Portland
$250 Roundtrip, found 10 hours ago
$250
Roundtrip
found 10 hours ago
Select Frontier Airlines flight, departing Thu, Sep 10 from Chicago to Portland, returning Mon, Sep 14, priced at $250 found 10 hours ago
Sat, Sep 26 - Fri, Oct 2
ORD
Chicago
PDX
Portland
$255 Roundtrip, found 9 hours ago
$255
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Sat, Sep 26 from Chicago to Portland, returning Fri, Oct 2, priced at $255 found 9 hours ago
Sat, Dec 5 - Mon, Dec 7
ORD
Chicago
PDX
Portland
$344 Roundtrip, found 1 day ago
$344
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Sat, Dec 5 from Chicago to Portland, returning Mon, Dec 7, priced at $344 found 1 day ago
Wed, Sep 23 - Mon, Sep 28
MDW
Chicago
PDX
Portland
$349 Roundtrip, found 1 day ago
$349
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Sep 23 from Chicago to Portland, returning Mon, Sep 28, priced at $349 found 1 day ago
Wed, Sep 23 - Thu, Oct 1
ORD
Chicago
PDX
Portland
$349 Roundtrip, found 6 hours ago
$349
Roundtrip
found 6 hours ago
Select United flight, departing Wed, Sep 23 from Chicago to Portland, returning Thu, Oct 1, priced at $349 found 6 hours ago

Oceanside economy flight packages

Price found within the past 48 hours. Click for updated prices.
Kimpton Riverplace Hotel by IHG
4.5-star property

Kimpton Riverplace Hotel by IHG

9.2/10 Wonderful! (1,003 reviews)

Aug 10 - Aug 13

3 night stay

Chicago (ORD) to Portland (PDX)

Alaska Airlines • Coach

Portland (PDX) to Chicago (ORD)

Frontier Airlines • Coach
Price was $781, price is now $664 per person
$664
per person
found 1 day ago
Great place to stay either pets. There was plenty of green space to let the dogs get out their wiggles.

Reviewed on Jun 28, 2026

The Nines, a Luxury Collection Hotel, Portland
5.0-star property

The Nines, a Luxury Collection Hotel, Portland

9.2/10 Wonderful! (1,003 reviews)

Aug 7 - Aug 11

4 night stay

Chicago (CHI) to Portland (PDX)

American Airlines • Non-stop roundtrip • Coach
Price was $913, price is now $704 per person
$704
per person
found 1 day ago
It's a nice hotel but nowhere near luxury class and was overpriced. Paid almost 30 for a tiny piece of fish. Was told it came with peas when we asked what it came with. There were literally 12 peas. So I guess technically it came with peas. After eating the 4 bites of fish, we went out for dinner after dinner. Luxury prices but not a luxury experience.

Reviewed on Jun 27, 2026

Red Lion Inn & Suites McMinnville
2.5-star property

Red Lion Inn & Suites McMinnville

8.2/10 Very Good! (1,002 reviews)

Aug 5 - Aug 12

7 night stay

Chicago (ORD) to Portland (PDX)

Alaska Airlines • Roundtrip • Coach
Price was $1,046, price is now $868 per person
$868
per person
found 1 day ago
Disappointed overall - the manager did partially refund our stay, which I appreciated, but I expected more from a major hotel brand. Amenities were largely old and not well maintained - the hotel washer and drier didn't work well, our bathtub didn't drain, the pullout bed had crumbs on the mattress (which was stained), couch was stained, elevator was very dirty...just a long list of little things that add up to an unpleasant stay overall. The room layout was nice, the beds were comfy, bedding was clean, etc. Not a disaster, but not sure I'll stay at a Red Lion again.

Reviewed on Jul 2, 2026

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More About Flying To Oceanside from Chicago

Route Information for Flights from Chicago to Oceanside

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

Chicago to Oceanside

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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.