$70 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.

Sat, Jul 5 - Sat, Jul 12
MDW
Midway Intl.
PDX
Portland Intl.
$228 Roundtrip, found 1 day ago
$228
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Jul 5 from Midway Intl. to Portland Intl., returning Sat, Jul 12, priced at $228 found 1 day ago
Sun, Jul 6 - Tue, Jul 8
ORD
O'Hare Intl.
PDX
Portland Intl.
$326 Roundtrip, found 12 hours ago
$326
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Sun, Jul 6 from O'Hare Intl. to Portland Intl., returning Tue, Jul 8, priced at $326 found 12 hours ago

Airfares from $70 One Way, $167 Round Trip from Chicago to Dundee

Prices starting at $167 for return flights and $70 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.

Tue, Aug 12 - Tue, Sep 23
ORD
Chicago
PDX
Portland
$167 Roundtrip, found 4 days ago
$167
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Tue, Aug 12 from Chicago to Portland, returning Tue, Sep 23, priced at $167 found 4 days ago
Thu, Sep 11 - Tue, Sep 23
ORD
Chicago
PDX
Portland
$175 Roundtrip, found 4 days ago
$175
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Thu, Sep 11 from Chicago to Portland, returning Tue, Sep 23, priced at $175 found 4 days ago
Tue, Jul 29 - Mon, Aug 4
ORD
Chicago
PDX
Portland
$177 Roundtrip, found 1 day ago
$177
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Jul 29 from Chicago to Portland, returning Mon, Aug 4, priced at $177 found 1 day ago
Thu, Jul 31 - Sat, Aug 2
MDW
Chicago
PDX
Portland
$188 Roundtrip, found 4 days ago
$188
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Thu, Jul 31 from Chicago to Portland, returning Sat, Aug 2, priced at $188 found 4 days ago
Fri, Oct 31 - Sat, Nov 8
ORD
Chicago
PDX
Portland
$202 Roundtrip, found 23 hours ago
$202
Roundtrip
found 23 hours ago
Select Alaska Airlines flight, departing Fri, Oct 31 from Chicago to Portland, returning Sat, Nov 8, priced at $202 found 23 hours ago

Dundee 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! (1,187 reviews)

Aug 11 - Aug 16

5 night stay

Chicago (CHI) to Portland (PDX)

Spirit Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
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

Hyatt Centric Downtown Portland
4.0-star property

Hyatt Centric Downtown Portland

9/10 Wonderful! (1,025 reviews)

Aug 11 - Aug 16

5 night stay

Chicago (CHI) to Portland (PDX)

Spirit Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Really cozy and comfortable hotel! Loved the friendly and helpful staff. This will be my go-to hotel whenever I am in Portland.

Reviewed on Dec 24, 2024

Mark Spencer Hotel
3.0-star property

Mark Spencer Hotel

9.2/10 Wonderful! (1,503 reviews)

Aug 11 - Aug 16

5 night stay

Chicago (CHI) to Portland (PDX)

Spirit Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Clean, comfortable, nicely decorated. Very helpful desk staff. My only (small) quibble is that they didn't tell us when we checked in about the complementary social hour. I only saw a sign about it 15 minutes after it had finished

Reviewed on Jun 10, 2025

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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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Discount Travel Planning Made Simple

You will have no problems finding budget flights from Chicago to Dundee on Orbitz.com. If your travel plans are flexible, you can search for fares three days before and after a specific date to find the best price.

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.