CHI - RDM

$109 Find Cheap Flights from Chicago to Redmond

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Redmond departing on 4/30. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
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KAYAK searches hundreds of travel sites at once for deals on flights to Redmond

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Redmond, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Redmond, as well as popular online travel agencies
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Cheap Flight Deals from Chicago to Redmond (CHI-RDM)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Redmond that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Chicago to Redmond

KAYAK's recommended round-trip deals from the most popular airlines that fly from Chicago to Redmond.
Discover the best prices for you by selecting your travel dates on KAYAK.
Choose your dates
Hawaiian Airlines Logo
7:00 am - 12:22 pmORD-RDM
7h 22m1 stop
Hawaiian Airlines Logo
4:00 pm - 11:56 pmRDM-ORD
5h 56m1 stop
$248Hawaiian Airlines
Find Deal
Tue, Jun 3 - Sat, Jun 7
Delta Logo
1:40 pm - 10:56 pmORD-RDM
11h 16m2 stops
Delta Logo
12:30 pm - 9:40 pmRDM-ORD
7h 10m1 stop
$254Delta
Find Deal
Tue, Jun 3 - Sat, Jun 7
Delta Logo
1:40 pm - 10:56 pmORD-RDM
11h 16m2 stops
Delta Logo
7:00 am - 6:04 pmRDM-ORD
9h 04m2 stops
$259Delta
Find Deal
Tue, Jun 3 - Tue, Jun 10
Delta Logo
6:25 pm - 11:04 pmORD-RDM
6h 39m1 stop
Delta Logo
7:29 pm - 7:49 amRDM-ORD
10h 20m2 stops
$274Delta
Find Deal
Wed, Apr 23 - Thu, May 8
Alaska Airlines Logo
7:59 pm - 10:19 amORD-RDM
16h 20m1 stop
Alaska Airlines Logo
6:21 pm - 5:40 amRDM-ORD
9h 19m1 stop
$277Alaska Airlines
Find Deal
Sat, May 24 - Tue, May 27
Delta Logo
1:55 pm - 11:04 pmORD-RDM
11h 09m2 stops
Delta Logo
7:29 pm - 7:49 amRDM-ORD
10h 20m2 stops
$279Delta
Find Deal
Wed, Apr 23 - Thu, May 8
Alaska Airlines Logo
7:00 am - 12:22 pmORD-RDM
7h 22m1 stop
Alaska Airlines Logo
10:59 am - 11:56 pmRDM-ORD
10h 57m2 stops
$282Alaska Airlines
Find Deal
Tue, Jun 3 - Tue, Jun 10
Alaska Airlines Logo
9:00 am - 5:00 pmORD-RDM
10h 00m1 stop
Alaska Airlines Logo
8:24 am - 9:59 pmRDM-ORD
11h 35m1 stop
$286Alaska Airlines
Find Deal
Wed, Apr 23 - Thu, May 8
Alaska Airlines Logo
5:56 pm - 11:45 pmORD-RDM
7h 49m1 stop
Alaska Airlines Logo
8:24 am - 2:48 pmRDM-ORD
28h 24m1 stop
$296Alaska Airlines
Find Deal
Fri, May 2 - Mon, May 5
American Airlines Logo
6:00 am - 11:39 amORD-RDM
7h 39m1 stop
American Airlines Logo
3:17 pm - 12:37 amRDM-ORD
7h 20m1 stop
$299American Airlines
Find Deal
Thu, Aug 28 - Sun, Aug 31

KAYAK's insights & trends for Chicago to Redmond flights

Get data-powered insights and trends into flights from Chicago to Redmond to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Chicago to Redmond?

The average price of all round-trip flights from Chicago to Redmond clicked on KAYAK for each day over the last 12 months.
For Chicago to Redmond, Friday is the cheapest day to fly on average and Sunday is the most expensive. Flying from Redmond back to Chicago, the best deals are generally found on Thursday, with Monday being the most expensive.

What is the cheapest month to fly from Chicago to Redmond?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Redmond, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from Chicago to Redmond is January, where tickets cost $283 (return) on average. On the other hand, the most expensive months are December and March, where the average cost of round-trip tickets is $801 and $638 respectively.

How far in advance should I book a flight from Chicago to Redmond?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Redmond, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.
To get a below average price on the flight from Chicago to Redmond, you should book around 3 weeks before departure. For the absolute cheapest price, our data suggests you should book 4 weeks before departure.

Good to know

Low season

January

High season

December

Cheapest flight

$109
Best time to beat the crowds with an average 43% drop in price.
Most popular time to fly with an average 62% increase in price.
Flight from Chicago O'Hare Airport to Redmond

When to book flights from Chicago to Redmond

Are your dates flexible? Find out the best times to travel from Chicago to Redmond based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Chicago to Redmond

  • What is the cheapest flight from Chicago to Redmond?

    In the last 3 days, the lowest price for a flight from Chicago to Redmond was $109 for a one-way ticket and $248 for a round-trip.

  • Do I need a passport to fly between Chicago and Redmond?

    No

  • Which airports will I be using when flying from Chicago to Redmond?

    On your way to Redmond, you’ll fly out from one of these Chicago airports: Chicago Midway or Chicago O'Hare Intl. You’ll be landing at Bend/Redmond.

  • Which aircraft models fly most regularly from Chicago to Redmond?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Chicago to Redmond?

    oneworld, SkyTeam, and Star Alliance are the airline alliances operating flights between Chicago and Redmond, with oneworld being the most commonly used for this route.

  • Which is the best airline for flights from Chicago to Redmond, Alaska Airlines or Delta?

    The two airlines most popular with KAYAK users for flights from Chicago to Redmond are Alaska Airlines and Delta. With an average price for the route of $499 and an overall rating of 8.0, Alaska Airlines is the most popular choice. Delta is also a great choice for the route, with an average price of $412 and an overall rating of 8.0.

  • How does KAYAK find such low prices on flights from Chicago to Redmond?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Redmond.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Redmond?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Redmond from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Redmond?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Redmond with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Redmond?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Redmond from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top 3 airlines serving from Chicago to Redmond

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Redmond. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Redmond? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
Alaska AirlinesOverall score based on 9823 reviews
7.1Food
7.1Entertainment
8.2Boarding
7.9Comfort
8.5Crew
Airline reviews

They were all very kind, but misinformed. We came from Idaho to Spokane, Washington and were told that my husband and I could get passes to sit with William until his flight took off. (William has special needs.) When we got to the airport we were told only one of us could sit with William, so my husband and I were separated for 2 hours as I sat with William. What is WORSE . . . is I asked for a meet and assist in Portland and they NEVER showed up. NOR did they call me to tell me they hadn't met him. William's grandmother in Portland is disabled and can't walk into find him. Fortunately, some kind citizens helped him to find the meeting point with me on the phone in terror. I have a heart condition, complete with prior heart attack, this type of customer service is UNACCEPTABLE.

6.0 GoodAnonymous, Mar 2025GEG - PDX
Read more Alaska Airlines reviews

They were all very kind, but misinformed. We came from Idaho to Spokane, Washington and were told that my husband and I could get passes to sit with William until his flight took off. (William has special needs.) When we got to the airport we were told only one of us could sit with William, so my husband and I were separated for 2 hours as I sat with William. What is WORSE . . . is I asked for a meet and assist in Portland and they NEVER showed up. NOR did they call me to tell me they hadn't met him. William's grandmother in Portland is disabled and can't walk into find him. Fortunately, some kind citizens helped him to find the meeting point with me on the phone in terror. I have a heart condition, complete with prior heart attack, this type of customer service is UNACCEPTABLE.

Could have had more of a beverage selection than water and apple juice.

Ted. F/A in fist class did a great job! Very nice

Crew was overly aggressive with rules enforcement and not friendly in general.

Loved the crew and everything went without a hitch! We took our dog for the first time and I was a little nervous but the crew was fantastic!

Behind schedule. Lots of time on tarmac. Perhaps unavoidable. Better than crashing!!

It was fine. Very friendly crew. Smooth flight. Landing was a little rough though.

It was a very smooth fast flight, crew was prompt and comforting. Alaska airlines are the best.

It was a really smooth flight. I hate heights. All made it feel smooth. Thankyou

I’m still waiting on my luggage. They canceled my flight on valentines day and my girlfriend broke up with me. Alaska airlines literally ruined my life.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

The plane was old with small storage areas that had problems closing/latching and not enough storage for everyone, and worn, damaged seats. Service was great but feel a little unsafe on such well used planes.

Terrible and im avoiding them in the future. My initial flight was delayed causing me to rebook my flight and when speaking with the representative to rebook I explained this is the second time my flights were delayed and they did nothing to help me. I wasn't booked to comfort plus or given a voucher or anything. I was almost late for my meeting that I needed to attend on Monday because of the games delta played delaying my flights even more and putting me in the very back of the plane next to an extremely intoxicated passenger

Flights on time. .Ride was as comfortable as can be expected in steerage. Luggage arrived at destination. Attendants were fairly friendly.

Great staff. Wifi is terrible. Signing up for skylines is a painstaking process. Had to call customer service just to get my flight itinerary and confirmation sent to me. Consistent delays. A well staffed company that is run so poorly. Upper management needs to be renewed.

The WiFi didn't seem as fast as it normally is

Thank you for not flipping the plane on the run way. You guys get a 5 star rating for the flight!!!

The crew was wonderful and attentive. The seats near exit row were restrictive. Offer healthy snacks please

Delta is a premier airline so my expectations are most always met.

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

Our seats were all the way in back of the plane,

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

The seats on this flight were almost roomy enough to be the basic amount needed for human existence.

The flight attendants in First Class were mediocre at best. They did not take our tray away until we were about to land and only did so when I press the call button. The United person at the United Club was asked to get us our boarding pass since we missed the flight due in Chicago. She argued that we did not have seats on the flight given to us in Moline. Furthermore, she was adamant that we did not have a First Class ticket. After I spent much time with her trying to show we were correct, she reluctantly agreed. She was probably the most incompetent ticketing person I have ever met and I have traveled 3 million miles on United plus many additional miles with other carriers. United has definitely deteriorated in more than on way.

Short flight - no food understandable. Flight was delayed for over an hour. Overall, it was good.

We arrived early and finally made it to our gate almost an hour after.

Was a pain having to leave the plane and reboard but glad the plane was fixed

Everything you need to know for your flight from Chicago to Redmond

Information on your arrival and departure airports

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