$89 Cheap flight deals from Portland (PDX) to Evanston (CHI)

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This Weekend's Flight Deals from Portland to Evanston

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.

Sun, Apr 19 - Tue, Apr 28
PDX
Portland Intl.
ORD
O'Hare Intl.
$546 Roundtrip, found 5 hours ago
$546
Roundtrip
found 5 hours ago
Select Alaska Airlines flight, departing Sun, Apr 19 from Portland Intl. to O'Hare Intl., returning Tue, Apr 28, priced at $546 found 5 hours ago

Airfares from $89 One Way, $225 Round Trip from Portland to Evanston

Prices starting at $225 for return flights and $89 for one-way flights to Evanston 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, May 23 - Thu, Jun 11
PDX
Portland
ORD
Chicago
$225 Roundtrip, found 2 days ago
$225
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, May 23 from Portland to Chicago, returning Thu, Jun 11, priced at $225 found 2 days ago
Thu, Apr 30 - Tue, May 5
PDX
Portland
ORD
Chicago
$231 Roundtrip, found 5 days ago
$231
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Thu, Apr 30 from Portland to Chicago, returning Tue, May 5, priced at $231 found 5 days ago
Sat, May 9 - Tue, May 12
PDX
Portland
ORD
Chicago
$256 Roundtrip, found 1 day ago
$256
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, May 9 from Portland to Chicago, returning Tue, May 12, priced at $256 found 1 day ago
Sat, May 9 - Tue, May 12
PDX
Portland
ORD
Chicago
$256 Roundtrip, found 1 day ago
$256
Roundtrip
found 1 day ago
Select United flight, departing Sat, May 9 from Portland to Chicago, returning Tue, May 12, priced at $256 found 1 day ago
Tue, May 12 - Sat, May 16
PDX
Portland
ORD
Chicago
$276 Roundtrip, found 1 day ago
$276
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, May 12 from Portland to Chicago, returning Sat, May 16, priced at $276 found 1 day ago

Evanston economy flight packages

Price found within the past 48 hours. Click for updated prices.
Eurostars Magnificent Mile
4.0-star property

Eurostars Magnificent Mile

9/10 Wonderful! (3,357 reviews)

Jun 6 - Jun 9

3 night stay

Portland (PDX) to Chicago (ORD)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,229, price is now $848 per person
$848
per person
found 1 day ago
In convenient area either by walking or uber

Reviewed on Oct 18, 2025

Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (3,688 reviews)

Jun 6 - Jun 9

3 night stay

Portland (PDX) to Chicago (ORD)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,360, price is now $936 per person
$936
per person
found 1 day ago
I recommend 100% Everything was good, the staff, room and the food. Also, it is located in a good area.

Reviewed on Jan 14, 2026

Hotel Felix River North/Magnificent Mile
4.0-star property

Hotel Felix River North/Magnificent Mile

8.2/10 Very Good! (2,604 reviews)

Jun 6 - Jun 9

3 night stay

Portland (PDX) to Chicago (ORD)

American Airlines • Roundtrip • Coach
Price was $1,196, price is now $893 per person
$893
per person
found 1 day ago
The rooms were clean and smelled fresh.

Reviewed on Jan 8, 2026

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More About Flying To Evanston from Portland

Route Information for Flights from Portland to Evanston

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

Portland to Evanston

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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.