$101 Cheap flight deals from Portland (PDX) to Niles (RFD)

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This Weekend's Flight Deals from Portland to Niles

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, Jan 3 - Sun, Jan 4
PDX
Portland Intl.
ORD
O'Hare Intl.
$379 Roundtrip, found 1 day ago
$379
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Sat, Jan 3 from Portland Intl. to O'Hare Intl., returning Sun, Jan 4, priced at $379 found 1 day ago
Sun, Jan 4 - Sat, Jan 10
PDX
Portland Intl.
RFD
Greater Rockford
$490 Roundtrip, found 5 days ago
$490
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sun, Jan 4 from Portland Intl. to Greater Rockford, returning Sat, Jan 10, priced at $490 found 5 days ago
Fri, Jan 2 - Tue, Jan 6
PDX
Portland Intl.
MDW
Midway Intl.
$582 Roundtrip, found 4 days ago
$582
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Fri, Jan 2 from Portland Intl. to Midway Intl., returning Tue, Jan 6, priced at $582 found 4 days ago

Airfares from $101 One Way, $203 Round Trip from Portland to Niles

Prices starting at $203 for return flights and $101 for one-way flights to Niles were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, Feb 25 - Sat, Feb 28
PDX
Portland
MDW
Chicago
$203 Roundtrip, found 2 days ago
$203
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Wed, Feb 25 from Portland to Chicago, returning Sat, Feb 28, priced at $203 found 2 days ago
Thu, Jan 15 - Tue, Jan 20
PDX
Portland
ORD
Chicago
$204 Roundtrip, found 5 days ago
$204
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Thu, Jan 15 from Portland to Chicago, returning Tue, Jan 20, priced at $204 found 5 days ago
Wed, Feb 25 - Sat, Feb 28
PDX
Portland
MDW
Chicago
$213 Roundtrip, found 2 days ago
$213
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Wed, Feb 25 from Portland to Chicago, returning Sat, Feb 28, priced at $213 found 2 days ago
Sat, Apr 25 - Tue, Apr 28
PDX
Portland
ORD
Chicago
$215 Roundtrip, found 3 days ago
$215
Roundtrip
found 3 days ago
Select Bargain Flight flight, departing Sat, Apr 25 from Portland to Chicago, returning Tue, Apr 28, priced at $215 found 3 days ago
Tue, Feb 3 - Tue, Feb 10
PDX
Portland
ORD
Chicago
$217 Roundtrip, found 1 day ago
$217
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Feb 3 from Portland to Chicago, returning Tue, Feb 10, priced at $217 found 1 day ago

Niles economy flight packages

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

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (2,790 reviews)

Feb 26 - Mar 1

3 night stay

Portland (PDX) to Chicago (ORD)

American Airlines • Roundtrip • Coach
Price was $570, price is now $422 per person
$422
per person
found 1 day ago
Staff is TOP NOTCH! I am in a wheelchair right now, recovering from a knee surgery, and staff could not have been more solicitous and helpful. Also, when we checked in, upon learning of my daughter‘s birthday on Christmas, the front desk representative gave us a complementary room upgrade and sent up chocolates! The room was very clean and the shower was fantastic. Not enough good words about the buffet, as long as you’re clear that it is a “breakfast“ buffet and not a “brunch“ buffet :-). I think I was expecting a sliced roast beef and an omelette bar, but it is in fact a very extensive selection of breakfast foods. The restaurant recommendation was spot on. We had a delicious dinner of fine Mediterranean/Sardinian foodat Nora’s next door and enjoyed it immensely. I have now joined the capital RIU club and plan on spending much more time at their other properties, particularly in Costa Rica, where I am moving next month. Kudos to all, and thank you for our wonderful stay!

Reviewed on Dec 28, 2025

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.4/10 Exceptional! (1,773 reviews)

Feb 11 - Feb 14

3 night stay

Portland (PDX) to Chicago (ORD)

United • Roundtrip • Coach
Save 100% on your flight
Price was $1,080, price is now $760 per person
$760
per person
found 1 day ago
Food was amazing and the staff was amazing. Room was incredible! Felt like we were royalty on our visit!

Reviewed on Oct 13, 2025

Fairmont Chicago at Millennium Park
4.5-star property

Fairmont Chicago at Millennium Park

8.6/10 Excellent! (2,008 reviews)

Feb 26 - Mar 1

3 night stay

Portland (PDX) to Chicago (ORD)

American Airlines • Roundtrip • Coach
Price was $685, price is now $509 per person
$509
per person
found 1 day ago
Solid place to stay

Reviewed on Nov 5, 2025

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More About Flying To Niles from Portland

Route Information for Flights from Portland to Niles

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

Portland to Niles

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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.