CHI - RDM

$139 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 9/20. 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.
1 adult
1 adult, Economy

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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Flight Deals

Cheap Flights 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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Redmond

Tue, Oct 7 - Sat, Oct 11
Hawaiian Airlines Logo
3:50 pm - 10:26 pmORD-RDM
8h 36m1 stop
Hawaiian Airlines Logo
1:38 pm - 11:59 pmRDM-ORD
8h 21m1 stop
$278Hawaiian Airlines
Find Deal
Sat, Nov 1 - Tue, Nov 4
Alaska Airlines Logo
7:00 am - 12:03 pmORD-RDM
7h 03m1 stop
Alaska Airlines Logo
1:00 pm - 11:59 pmRDM-ORD
8h 59m1 stop
$279Alaska Airlines
Find Deal
Sat, Nov 1 - Tue, Nov 4
Delta Logo
7:50 am - 11:46 amORD-RDM
5h 56m1 stop
Delta Logo
7:00 am - 9:43 pmRDM-ORD
12h 43m2 stops
$284Delta
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Mon, Sep 15 - Wed, Sep 17
Hawaiian Airlines Logo
6:20 am - 12:37 pmORD-RDM
8h 17m1 stop
Hawaiian Airlines Logo
3:41 pm - 12:03 amRDM-ORD
6h 22m1 stop
$288Hawaiian Airlines
Find Deal
Sat, Oct 25 - Wed, Oct 29
Delta Logo
3:00 pm - 10:15 pmMDW-RDM
9h 15m2 stops
Delta Logo
7:26 pm - 8:55 amRDM-MDW
11h 29m2 stops
$289Delta
Find Deal
Sat, Oct 25 - Wed, Oct 29
Delta Logo
1:25 pm - 10:35 pmORD-RDM
11h 10m2 stops
Delta Logo
11:25 am - 9:43 pmRDM-ORD
8h 18m2 stops
$289Delta
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Wed, Oct 1 - Mon, Oct 6
 Logo
2:04 pm - 2:25 pmORD-RDM
26h 21m3 stops
 Logo
3:15 pm - 5:35 amRDM-ORD
12h 20m2 stops
Wed, Oct 1 - Mon, Oct 6
 Logo
2:04 pm - 2:25 pmORD-RDM
26h 21m3 stops
 Logo
3:15 pm - 5:35 amRDM-ORD
12h 20m2 stops
Mon, Sep 8 - Thu, Sep 11
United Airlines Logo
3:47 pm - 10:47 pmORD-RDM
9h 00m1 stop
United Airlines Logo
1:55 pm - 11:12 pmRDM-ORD
7h 17m1 stop
$1,155United Airlines
Find Deal
Mon, Sep 8 - Thu, Sep 11
United Airlines Logo
12:53 pm - 6:25 pmORD-RDM
7h 32m1 stop
United Airlines Logo
6:00 am - 12:29 amRDM-ORD
16h 29m2 stops
$1,285United Airlines
Find Deal
Booking Insights

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.

How much is a round-trip flight from Chicago to Redmond?

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 $600 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 4 weeks before departure, which saves you about 53% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 20 weeks before departure.

Good to know

Low seasonNovember
Cheapest flight$139
Best time to beat the crowds but there is an average 10% increase in price.
Most popular time to fly with an average 80% 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 $139 for a one-way ticket and $278 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 $450 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 $333 and an overall rating of 7.9.

  • 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.

Reviews of the top 4 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 10000 reviews
7.1Food
8.5Crew
7.8Comfort
8.1Boarding
7.0Entertainment
Airline reviews

Planes were on time. Pilot kept everyone updated. Crew was friendly and helpful

10.0 ExcellentAnonymous, Aug 2025BIL - PDX
Read more Alaska Airlines reviews

Planes were on time. Pilot kept everyone updated. Crew was friendly and helpful

Flight was switched to a different airline. Caused scheduling issues. Flight delayed an hour, but arrived only 20 minutes late thanks to tail winds.

Would have been nice if my flight was on time and I didn't miss my connection and had to spend the night in Seattle, losing one night at the VRBO I paid for in Sitka. And, my connecting flight was still at the gate when my flight was taxiing to it's gate. But, it took off. Too bad for me. I really can't believe you even want me to review or comment on my experience.

You no longer give receipts for baggage at the counter. And it is next to impossible to get it on your webpage. Spent 20 min trying and gave up... I need receipt to submit for reimbursement and don't have time to waste on your poor webpage Disappointing .....

The flight attendants were unkempt and show no customer service skills. They avoided eye contact. There were no smiles and they were dismissive and snarky.

Complete flight rebooked and 6 hours delayed. Zero accountability from the airline or Kayak for the issues and I’m injured which is why I opted to pay more to fly than drive because it’s painful to sit or stand too long. What was supposed to be a 3ish hour travel day turned into a 9 hour excruciatingly painful experience that has left me in worse pain than when I initially started.

It was a good flight, short so there was no food or water service

Checking in very confusing compared to Hawaiian Airlines - much simpler! Front checking in at airport can improve. Hawaiian service always gives the extra mile, with a smile. Alaska can use and spread the Aloha Spirit. Mahalo nui loa Thank you 🤙

Very nice as always. Not that it’s anyone’s fault really but for some reason the seat (16C) was really hard…. Not typical for your planes… dunno what or why… maybe it was just me ?, The flight was great otherwise

Plane was delayed getting boarded and then again delayed in take-off order. Alaska Airlines must have very little clout at JFK so they don't get priority treatment. All the delays meant we missed the last flight from Portland to Eugene. Alaska did give us hotel voucher for the night...but sent us to a downtown Portland hotel rather than to a nearby airport motel which made for a longer ride at night and then again in the morning. Just made an already long, late night even longer. Hotel was an old outdated Hilton in a slightly seedy part of town. Alaska gave us Lyft vouchers for getting to the hotel, but the return voucher for getting back to the airport in the morning didn't work.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

Mechanic delay in addition to a 2 hour change in takeoff time was frustrating.

Delayed due to thunderstorms and no in-flight service due to rough weather — both of which are out of Delta’s control. Flight was good overall.

The flight attendants in SLC were rude. I arrived 40 minutes early to gate. Ticket said I needed check in for seat assignments and tried check in and attendants said they weren’t doing it. And proceeded to never call me to give me a ticket so when time to board I received the very last seat. Please relay to employees to do their job better..,

On this flight I felt the food offering was not as complete as on previous flights. The tomato salad was a bit off and there was nothing additional such a bread or butter. The breakfast was only one option, so you either ate what they had or ate nothing. The crew was efficient, but most seemed frustrated throughout the flight. The flight arrived early and was obstacle-free, so I’m overall quite happy, but the shine in the rest of the experience just wasn’t there.

The seats got pretty uncomfortable pretty fast. The armrests are bigger than on other planes, so I had less room in the actual seat. My butt hurt by the end of the flight. :/ comfort was the primary issue. The crew were fantastic!

I believe that a four-hour trip should have a meal. Delta had none.

Great flight with Delta! Boarding was quick and easy, the amenities were solid, and the plane was in great shape. The flight attendants had a fun, lively energy while staying professional. All in all, a smooth trip — even managed to catch up on some rest. Thanks, Delta!

I was uncomfortably cold on the plane. Other than that it was uneventful and therefore as enjoyable as a plane ride can be.

Attendants seemed un-engaged and indifferent when asked for assistance.

Overall it was a good flight. The thing I most appreciated was that you eliminated plastic cups and water bottles and stir sticks and had paper cups, wood stir sticks and cans. Plus, I saw that the airline staff were actually keeping the used paper cups separate and unfolding the used cardboard meal boxes and keeping those items separate from the trash. Good for them! This makes me want to support Alaska Airlines and fly Alaska again. Thank for taking this step in working to reduce single use plastics! Kudos!

It was pretty good except there was no food, which was understandable because it was a short flight but I would have liked to at least have a snack; otherwise it was great. Staff/crew, great. Thank you

I was on Alaska and its backup airline. I was scheduled for wheelchair service but ON ONE SHOWED UP. When I asked, desk attendant said they didn’t have any.

As noted above, getting on to the plane was rushed and upsetting since no boarding passes were available to me prior to boarding. Others were in line waiting as well. The flight and experience itself was fine. Very large plane. Two seats near windows; 4 seats in the middle aisles. Good leg room though and comfortable seats.

The trip was fine, however once we reached Seattle, our next flight only had an hour turn-around time and we had to cross the entire Seattle airport, taking three shuttles. Once there, Alaska/Hawaiian Air had still not issued my boarding passes to us and we had to wait at the counter for them. Boarding was already started and at the second to last seating level when we finally got our boarding passes. This was a bit nuts.

I am disappointed with Alaska. They are just like the cheapo airlines, nickle and dimeing us for everything. We now have to pay extra to pick our seats? Really?

I could not use my Hawaiian airlines confirmation number to check in. I figured out on my own that I had to use Alaska airlines confirmation number to check in on the Alaska airlines site. I called Hawaiian airlines and they told me that they could not help me.

Alaska Airlines crew had the empty two people seats but they lied to us and said they can adjust us , so we have to seat apart

Ok but why they need to sell the ear buds?

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

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

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