$129 Cheap flight deals from Chicago (CHI) to Prineville (RDM)

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This Weekend's Flight Deals from Chicago to Prineville

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, Jun 29 - Fri, Jul 4
ORD
O'Hare Intl.
RDM
Robert's Field
$396 Roundtrip, found 1 day ago
$396
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Sun, Jun 29 from O'Hare Intl. to Robert's Field, returning Fri, Jul 4, priced at $396 found 1 day ago

Airfares from $129 One Way, $263 Round Trip from Chicago to Prineville

Prices starting at $263 for return flights and $129 for one-way flights to Prineville 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, Jul 29 - Mon, Aug 4
ORD
Chicago
RDM
Redmond
$263 Roundtrip, found 5 days ago
$263
Roundtrip
found 5 days ago
Select Alaska Airlines flight, departing Tue, Jul 29 from Chicago to Redmond, returning Mon, Aug 4, priced at $263 found 5 days ago
Sat, Aug 9 - Sat, Aug 16
ORD
Chicago
RDM
Redmond
$263 Roundtrip, found 6 days ago
$263
Roundtrip
found 6 days ago
Select Alaska Airlines flight, departing Sat, Aug 9 from Chicago to Redmond, returning Sat, Aug 16, priced at $263 found 6 days ago
Tue, Sep 9 - Sat, Sep 13
ORD
Chicago
RDM
Redmond
$275 Roundtrip, found 4 days ago
$275
Roundtrip
found 4 days ago
Select Bargain Flight flight, departing Tue, Sep 9 from Chicago to Redmond, returning Sat, Sep 13, priced at $275 found 4 days ago
Sat, Aug 23 - Tue, Aug 26
ORD
Chicago
RDM
Redmond
$279 Roundtrip, found 16 hours ago
$279
Roundtrip
found 16 hours ago
Select Alaska Airlines flight, departing Sat, Aug 23 from Chicago to Redmond, returning Tue, Aug 26, priced at $279 found 16 hours ago
Tue, Sep 9 - Sat, Sep 13
ORD
Chicago
RDM
Redmond
$283 Roundtrip, found 4 days ago
$283
Roundtrip
found 4 days ago
Select American Airlines flight, departing Tue, Sep 9 from Chicago to Redmond, returning Sat, Sep 13, priced at $283 found 4 days ago

Prineville economy flight packages

Price found within the past 48 hours. Click for updated prices.
Sugarloaf Mt Motel
2.0-star property

Sugarloaf Mt Motel

8.2/10 Very Good! (1,003 reviews)

Aug 15 - Aug 18

3 night stay

Chicago (ORD) to Redmond (RDM)

Alaska Airlines • Coach

Redmond (RDM) to Chicago (ORD)

Spirit Airlines • Coach
per person
found 21 hours ago
Friendly and efficient. Clean and up to date rooms.

Reviewed on May 24, 2025

Best Western Newberry Station
2.5-star property

Best Western Newberry Station

8.8/10 Excellent! (1,002 reviews)

Aug 19 - Aug 23

4 night stay

Chicago (ORD) to Redmond (RDM)

Alaska Airlines • Non-stop • Coach

Redmond (RDM) to Chicago (ORD)

United • Non-stop • Coach
per person
found 10 hours ago
We have stayed here multiple times on our way through to the coast and it is one of our favorite hotels to stay at. The hotel is beautifully furnished, very clean and the staff incredibly helpful, friendly and accommodating.

Reviewed on Dec 29, 2024

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More About Flying To Prineville from Chicago

Route Information for Flights from Chicago to Prineville

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

Chicago to Prineville

Chicago to Prineville flights are offered at fantastic discount by Orbitz. Book air tickets now and cut those extra costs out of your travel budget to ensure a rewarding travel experience. With guaranteed low prices like these, can you afford to miss this discount?

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Get a great package with your Chicago to Prineville flights

With frequent updates on your flight status, including delays and changes in bookings, traveling becomes more hassle-free than ever. Not only do we offer huge discounted deals on flights from Chicago to Prineville, we also have fantastic savings on vacation packages, hotel room, cruises, activities, and car rentals so you can pick and choose and create the best travel package for you.

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.