$131 Cheap flight deals from Chicago (CHI) to Dundee (PDX)

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This Weekend's Flight Deals from Chicago to Dundee

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 24 - Sun, Jul 26
ORD
O'Hare Intl.
PDX
Portland Intl.
$396 Roundtrip, found 5 hours ago
$396
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Fri, Jul 24 from O'Hare Intl. to Portland Intl., returning Sun, Jul 26, priced at $396 found 5 hours ago
Sat, Jul 25 - Sat, Aug 1
MDW
Midway Intl.
PDX
Portland Intl.
$407 Roundtrip, found 6 days ago
$407
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Sat, Jul 25 from Midway Intl. to Portland Intl., returning Sat, Aug 1, priced at $407 found 6 days ago

Airfares from $131 One Way, $258 Round Trip from Chicago to Dundee

Prices starting at $258 for return flights and $131 for one-way flights to Dundee 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 24 - Thu, Oct 1
ORD
Chicago
PDX
Portland
$258 Roundtrip, found 7 hours ago
$258
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Thu, Sep 24 from Chicago to Portland, returning Thu, Oct 1, priced at $258 found 7 hours ago
Tue, Aug 11 - Wed, Aug 12
ORD
Chicago
PDX
Portland
$293 Roundtrip, found 13 hours ago
$293
Roundtrip
found 13 hours ago
Select Alaska Airlines flight, departing Tue, Aug 11 from Chicago to Portland, returning Wed, Aug 12, priced at $293 found 13 hours ago
Sat, Nov 7 - Sat, Nov 14
ORD
Chicago
PDX
Portland
$293 Roundtrip, found 17 hours ago
$293
Roundtrip
found 17 hours ago
Select Bargain Flight flight, departing Sat, Nov 7 from Chicago to Portland, returning Sat, Nov 14, priced at $293 found 17 hours ago
Sat, Nov 7 - Sat, Nov 14
ORD
Chicago
PDX
Portland
$297 Roundtrip, found 17 hours ago
$297
Roundtrip
found 17 hours ago
Select United flight, departing Sat, Nov 7 from Chicago to Portland, returning Sat, Nov 14, priced at $297 found 17 hours ago
Sat, Nov 7 - Sat, Nov 14
ORD
Chicago
PDX
Portland
$297 Roundtrip, found 17 hours ago
$297
Roundtrip
found 17 hours ago
Select American Airlines flight, departing Sat, Nov 7 from Chicago to Portland, returning Sat, Nov 14, priced at $297 found 17 hours ago

Dundee economy flight packages

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

Rockaway Shores

9/10 Wonderful! (42 reviews)

Sep 11 - Sep 14

3 night stay

Chicago (CHI) to Portland (PDX)

Frontier Airlines • Non-stop roundtrip • Coach
Price was $951, price is now $733 per person
$733
per person
found 1 day ago

City Centre Motel by OYO
2.0-star property

City Centre Motel by OYO

7/10 Good! (1,003 reviews)

Aug 27 - Aug 31

4 night stay

Chicago (CHI) to Portland (PDX)

American Airlines • Non-stop • Coach

Portland (PDX) to Chicago (CHI)

Frontier Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,137, price is now $837 per person
$837
per person
found 15 hours ago

Coast River Inn by OYO Seaside
2.0-star property

Coast River Inn by OYO Seaside

8.4/10 Very Good! (1,055 reviews)

Aug 27 - Aug 31

4 night stay

Chicago (CHI) to Portland (PDX)

American Airlines • Non-stop • Coach

Portland (PDX) to Chicago (CHI)

Frontier Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,309, price is now $970 per person
$970
per person
found 15 hours ago
We got tied up in some road construction and was running late. I called and finally spoke to an onsite representative who assured me they were open until 10:00 p.m. At 9:46 p.m. we finally made it and the front desk had already taken steps to ensure we’d be checked in even if the office was closed! Superb customer service for some very frazzled travelers.

Reviewed on Jul 21, 2026

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Dundee first class flight packages

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

Hotel deLuxe

8.6/10 Excellent! (1,053 reviews)

Aug 28 - Sep 2

5 night stay

Chicago (CHI) to Portland (PDX)

American Airlines • Roundtrip • FirstClass
Price was $1,373, price is now $1,142 per person
$1,142
per person
found 1 day ago
This is an old building (historic Portland architecture) tgat has been upgraded as Hotel Deluxe. Though the bones of the building are a bit worn through the decades, we found the room and hotel to be clean, comfortable, and very much enjoyed our stay. There is no mini-fridge in the room so we weren’t able to keep our leftovers from dining out, but aside from that we loved our romantic getaway here and would stay again. We found the cocktails and service at the hotel bar/lounge, The Driftwood Room, top notch. Would recommend.

Reviewed on Jul 21, 2026

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

The Nines, a Luxury Collection Hotel, Portland

9.2/10 Wonderful! (1,007 reviews)

Aug 28 - Sep 2

5 night stay

Chicago (CHI) to Portland (PDX)

American Airlines • Roundtrip • FirstClass
Price was $1,515, price is now $1,223 per person
$1,223
per person
found 1 day ago
This hotel was beautiful the beds were so comfortable the staff was friendly and very helpful it's located in a central location easy to walk to all other areas the TriMet was right at the corner to hop on so you can visit anything all over Portland

Reviewed on Jul 20, 2026

Skamania Lodge
3.5-star property

Skamania Lodge

9.2/10 Wonderful! (1,016 reviews)

Aug 28 - Sep 2

5 night stay

Chicago (CHI) to Portland (PDX)

American Airlines • Roundtrip • FirstClass
Price was $1,532, price is now $1,266 per person
$1,266
per person
found 1 day ago
Dog rooms are only on first floor. Two doubles (not queens) was tight for 3 people and a dog. Note that they charge you a $75 dog fee plus daily parking and resort fees separate from what you pay Expedia. They said that you could eat on patio with dog but the restaurant with patio is not open for breakfast. We got food to go. They said it would be 30 minutes but was 90 minutes. Then they forgot the syrup, fruit and potatoes! The food was good at least. Restaurant staff not helpful or knowledgeable. They should just say we are busy and it will take 90 minutes. We would have gone into town. In the summer be prepared for weddings and conferences. It is a popular spot. The room was clean and if you get a room with a view, it is beautiful. Grounds are nice and well cared for.

Reviewed on Jul 20, 2026

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More About Flying To Dundee from Chicago

Route Information for Flights from Chicago to Dundee

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

Chicago to Dundee

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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.