CHI - RDM

$107 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 8/19. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 20% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flights Deals
Useful Info
Flights 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
Alaska Airlines Logo
6:00 am - 5:13 pmORD-RDM
13h 13m1 stop
Alaska Airlines Logo
1:44 pm - 11:59 pmRDM-ORD
8h 15m1 stop
$222Alaska Airlines
Find Deal
Thu, Oct 23 - Mon, Oct 27
Alaska Airlines Logo
8:00 am - 9:25 pmORD-RDM
15h 25m1 stop
Alaska Airlines Logo
8:28 am - 6:22 amRDM-ORD
19h 54m1 stop
$242Alaska Airlines
Find Deal
Tue, Jul 29 - Tue, Aug 5
 Logo
6:00 am - 12:44 pmORD-RDM
8h 44m1 stop
 Logo
1:38 pm - 10:30 pmRDM-ORD
6h 52m1 stop
Sat, Aug 30 - Sat, Sep 13
Hawaiian Airlines Logo
6:20 am - 12:37 pmORD-RDM
8h 17m1 stop
Hawaiian Airlines Logo
1:31 pm - 10:04 pmRDM-ORD
6h 33m1 stop
$244Hawaiian Airlines
Find Deal
Thu, Sep 4 - Mon, Sep 8
Alaska Airlines Logo
6:20 am - 12:37 pmORD-RDM
8h 17m1 stop
Alaska Airlines Logo
5:58 pm - 10:04 pmRDM-ORD
26h 06m1 stop
$246Alaska Airlines
Find Deal
Wed, Jul 30 - Wed, Aug 6
Hawaiian Airlines Logo
7:00 am - 12:18 pmORD-RDM
7h 18m1 stop
Hawaiian Airlines Logo
1:38 pm - 10:30 pmRDM-ORD
6h 52m1 stop
$247Hawaiian Airlines
Find Deal
Wed, Jul 30 - Wed, Aug 6
Delta Logo
2:15 pm - 10:54 pmORD-RDM
10h 39m2 stops
Delta Logo
12:35 pm - 10:08 pmRDM-ORD
7h 33m1 stop
$284Delta
Find Deal
Tue, Oct 7 - Sat, Oct 11
Delta Logo
2:00 pm - 10:44 pmMDW-RDM
10h 44m2 stops
Delta Logo
7:25 pm - 8:46 amRDM-MDW
11h 21m2 stops
$289Delta
Find Deal
Wed, Jul 16 - Mon, Jul 21
United Airlines Logo
4:50 pm - 10:45 pmORD-RDM
7h 55m1 stop
United Airlines Logo
7:32 pm - 5:18 amRDM-ORD
7h 46m1 stop
$409United Airlines
Find Deal
Wed, Jul 23 - Sun, Jul 27
United Airlines Logo
3:54 pm - 10:45 pmORD-RDM
8h 51m1 stop
United Airlines Logo
5:00 am - 12:30 amRDM-ORD
17h 30m1 stop
$472United Airlines
Find Deal
Useful Info

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 $590 respectively.

Good to know

Low seasonJanuary
High seasonDecember
Cheapest flight$107
Best time to beat the crowds with an average 38% drop in price.
Most popular time to fly with an average 76% 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 $107 for a one-way ticket and $222 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, Star Alliance, and SkyTeam 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 $456 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 $348 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.

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
8.5Crew
7.1Entertainment
8.1Boarding
7.1Food
7.8Comfort
Airline reviews

Great crew, smooth flight and landing. Wish they would offer Dr. Pepper and a choice of flavors of pretzels.

8.0 ExcellentCatlin, Jun 2025SJC - PDX
Read more Alaska Airlines reviews

Great crew, smooth flight and landing. Wish they would offer Dr. Pepper and a choice of flavors of pretzels.

Thank you still providing bags for vomit. My son had a migraine and needed a bag to vomit in and it was right there behind the seat in front of us. Thank you!

Flight was delayed 5 hours. Missed connecting flight. Very little apology or attempt to make anything better. Got a $150 credit for next flight. There won’t be another flight. First time on Alaska - last time. Keep your credit. Should have done something more

Well, the baggage porter on Maui told my mom that our carry on luggage was overweight and if she gave him a 50 dollar tip he would let it go through. She tipped him and he tells us that he needs my Alaska airlines cc to waive the extra baggage charge. Find out later that since my original reservation was not under my name using a Hawaiian airlines CC, I would have to pay for the luggage anyway. I told them I had to end up paying for my daughters ticket when you all said because she turned two using my Alaska Airlines cc, now they need to charge me for her seat/flight, but you guys didn't care and i ended up paying for the bags and my mom paid the porter 50 dollars extra for nothing .. It was a crappy experience. First it was a multi trip. PDX-HNL then HNL-OGG then OGG to PDX. All bought under one ticket. My daugher turned two during the flight from HNL-OGG, but when I bought the ticket and at the PDX airport they said since i bought the ticket before she was two, everything is fine. come to find out no, I had to pay her ticket HNL-OGG and again OGG to PDX. you guys scammed me. You should say it on your website and make sure people know that during flights if the child turns two they have to pay for their seat. If i knew that from the very beginning i would have bought her ticket and it would have been LESS than paying TWICE for her flight! and you scammed my mother with you porter who told her to pay him 50 dollars and he would take care of the extra luggage weight.

Flight was great. Boarding was crazy because another flight was boarding late next to ours so everyone was standing and in the way.

It was a quick flight, but coffee would have been great!

I can honestly say in the 54 years of my life this was the worst flying experience I have ever had. I was delayed on the tarmac going into Dallas for an hour and 2 hours on the tarmac leaving Dallas. a 4 hour flight turned into a 6 hour flight due to Alaska incompetence. To be honest I will never take another Alaska flight.

So much better coming back to Seattle than my trip TO Chicago. This crew actually communicated with the passengers!! Rebecca, one of the crew, stopped and visited with me about sign language. She should get a bonus of some kind!! She's a very neat gal!! It was still warm inside the plane, but it was packed! I still think you could do better than those teeny tiny pretzels! These were spicy and tasted terrible! All in all, still a better ride coming home. Go Seahawks!!

Arrival delay waiting for another flight to be towed and deboarded

I am mobility challenged and ground crew were accommodating to my needs. One must walk up a ramp to board Alaska planes. Terminal to tarmac to ramp to plane.

The flight was scheduled for 2:30 PM. Early in the morning we got a text message saying the flight was delayed and rescheduled for 3:00 PM. We got to the airport with that in mind. Then we got a message during check-in at the flight was rescheduled again for 2:30 PM. We almost missed our flight. In fact, our bags Were told that they would not make it. At the end, everything worked out. But it is very stressful.

Most aspects were good however if they assign boarding zones they ought to enforce them or why bother? My luggage from SAN-JFK-MAD was lost in NY so I without my main bag for two days upon arrival in Spain. They were helpful in tracking it and eventually delivered it to my hotel. The flub was because of a delay upon arrival in NYC. I had booked 2 1/2 hours between flights but we had to hold on the taxiway for an hour after landing while waiting for a clear gate which likely caused the baggage error.

Excellent check-in. Crew was good. Excellent communication from flight deck.

Great overall. There was a bit of turbulence so they could only serve water because too much turbulence for the carts. Was glad they prioritized safety though

Excellent flight, the planes were newer, they did a nice job with boarding, great service overall.

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane

My flight was 6 pm 6/6. Every hour they delayed it again - air condition issues then no pilot then the crew had worked too many hours and cancelled the flight at 11 pm. Sent customers to NJ a 45 minutes uber ride to a hotel. Had to be back by 5 am for a 7 am flight and again no pilot etc with another three hours of delays.

Both flights were late 2+ hours with ZERO communication from the airlines or their staff. No offers for compensation. WiFi didn’t work for streaming and they said to only use browsing but that didn’t work either. Waste of $$. No drinks only boxed water or apple juice. No snack. One of the worst flight experiences I’ve ever had.

The ticket and bag check in was chaotic at SEATAC. No clear communication or signage for bag drop off.

This was actually an Alaska flight. I was not able to check in online using the Kayak app or the web for Hawaiian or Alaska airlines. So I contacted Hawaiian and they advised that I had to go to the counter when I arrive at the airport. So I waited in line at the Hawaiian counter for 45 minutes. When I got to the ticket agent she advised that I needed to go to the Alaskan Airlines ticket counter. So I went to that counter which thankfully was not busy. I received my boarding pass and then went to security. I arrived at the gate as boarding was beginning. The frustration is that Hawaiian or Kayak should have directed me to the correct ticket counter. When it is “operated by” a average person doesn't know what that means. Kayak app was silent on what action to take when I was unable to check in online and Hawaiian just stated my ticket number and confirmation numbers were invalid. Communication is key and this process could be cleaned up. Thank goodness I am savvy and speak English, I can’t imagine this process for someone who may not be.

If I knew I would be on Alaska Airlines flying back, I never would have bought the ticket. My flight kept getting delayed and Alaska always seems to be late which is why I don’t fly on them.

Good. They changed our gate very late and then when we landed, we had to wait 20 minutes to get off the airplane because another plane was in a slot.

Very nice experience. The boarding however seemed somewhat mixed up, and we were delayed taking off.

Flight was canceled with no voucher of any kind and next available flight was two days later.

Boarding was chaotic. Microphone not working properly and second agent was distracted from task with baggage and late arrivals.

I DID NOT GO TO HAWAII ON HAWAIIAN AIRLINES. YOU DID NOT INFORM ME THAT BY CHOOSING BASIC ECONOMY, I MIGHT BE REQUIRED TO FLY STANDBY. I AM ELDERLY AS WAS MY COMPANION WHO IS ALSO SEVERELY DISABLED AND THERE WOULD BE NO WAY WE COULD TRAVEL ON STANDBY. THEY TOLD ME THAT ALL OF THE BASIC ECONOMY SEATS HAD BEEN SELECTED BY OTHER PASSENGERS AND WE HAD TO PAY AN ADDITIONAL $942 TO GET A SECURED SEAT ON THE PLAN AND, IN SPITE OF THE ADDITIONAL COST, WE WERE NOT ALLOW US TO AMEND OUR TRAVEL PLANS TO EXTEND OUR VACATION. ULTIMATELY, THE FLIGHT WAS DELAYED. WE WERE OFFERED A REFUND IF WE CANCELED OUR TRIP ALTOGETHER WHICH WE DID. IT IS YOUR DUTY TO INFORM YOUR CUSTOMERS OF THE POTENTIAL PROBLEMS THEY MAY FACE, AND YOU DID NOT DO SO. I WILL NOT UTILIZE YOUR SERVICES EVER AGAIN.

It was very pleasant. The staff and crew are very polite.

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.

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,

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

Information on your arrival and departure airports

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.