CHI - RDM

$179 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 4/29. 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, 0 bags

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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Everything you should know

Cheapest round-trip
$337
Typical prices: $533-$370
Alaska Airlines
Tue 4/28Sat 5/2
ORD - RDM • 1 stop
Cheapest one-way
$179
Typical prices: $201-$265
United Airlines
Wed 4/29
ORD - RDM • 1 stop
Top airlines
Cheapest • from $337 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Chicago and Redmond. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $288 (round-trip)
Shortest trip • 6h 28m (one-way)
Insights
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Redmond!
Flight Deals
Booking Insights
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, Apr 28 - Sat, May 2
Alaska Airlines Logo
6:00 am - 12:58 pm
ORD
-
RDM
8h 58m
1 stop
Alaska Airlines Logo
1:52 pm - 11:59 pm
RDM
-
ORD
8h 07m
1 stop
$337Alaska Airlines
Tue, May 12 - Sat, May 30
Alaska Airlines Logo
8:48 pm - 9:14 am
ORD
-
RDM
14h 26m
1 stop
Alaska Airlines Logo
7:00 am - 6:50 pm
RDM
-
ORD
9h 50m
1 stop
$357Alaska Airlines
Tue, Aug 18 - Wed, Aug 26
Alaska Airlines Logo
8:05 pm - 9:29 am
ORD
-
RDM
15h 24m
1 stop
Alaska Airlines Logo
1:33 pm - 11:57 pm
RDM
-
ORD
8h 24m
1 stop
$359Alaska Airlines
Tue, May 12 - Sat, May 30
Delta Logo
5:41 pm - 11:44 pm
ORD
-
RDM
8h 03m
2 stops
Delta Logo
6:10 am - 5:13 pm
RDM
-
ORD
9h 03m
1 stop
$362Delta
Wed, Jun 3 - Mon, Jun 8
Delta Logo
6:20 pm - 10:52 pm
ORD
-
RDM
6h 32m
1 stop
Delta Logo
7:25 pm - 8:05 am
RDM
-
ORD
10h 40m
2 stops
$363Delta
Tue, May 5 - Fri, May 8
Alaska Airlines Logo
2:13 pm - 10:29 pm
ORD
-
RDM
10h 16m
1 stop
Alaska Airlines Logo
7:33 pm - 6:40 am
RDM
-
ORD
9h 07m
1 stop
$368Alaska Airlines
Wed, Jun 3 - Mon, Jun 8
Delta Logo
1:22 pm - 10:52 pm
MDW
-
RDM
11h 30m
2 stops
Delta Logo
7:25 pm - 9:14 am
RDM
-
MDW
11h 49m
2 stops
$368Delta
Tue, Jun 9 - Wed, Jun 17
Delta Logo
1:16 pm - 10:58 pm
MDW
-
RDM
11h 42m
2 stops
Delta Logo
7:25 pm - 8:37 am
RDM
-
MDW
11h 12m
2 stops
$369Delta
Tue, Jun 9 - Wed, Jun 17
Delta Logo
5:57 pm - 11:52 pm
ORD
-
RDM
7h 55m
2 stops
Delta Logo
7:25 pm - 8:05 am
RDM
-
ORD
10h 40m
2 stops
$369Delta
Sat, May 23 - Tue, May 26
United Airlines Logo
3:47 pm - 10:35 pm
ORD
-
RDM
8h 48m
1 stop
United Airlines Logo
3:51 pm - 12:59 am
RDM
-
ORD
7h 08m
1 stop
$377United Airlines
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?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to Redmond departing in April.

Good to know

Low seasonFebruary
Cheapest flight$179
Best time to beat the crowds with an average 33% drop in price.
Most popular time to fly and prices are also 16% lower on average.
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 $179 for a one-way ticket and $337 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?

    Star Alliance, SkyTeam, and oneworld are the airline alliances operating flights between Chicago and Redmond, with Star Alliance 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 $433 and an overall rating of 7.9, Alaska Airlines is the most popular choice. Delta is also a great choice for the route, with an average price of $350 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.
7.9
Alaska AirlinesOverall score based on 12193 reviews
7.0Entertainment
8.1Boarding
8.5Crew
7.8Comfort
7.0Food
Airline reviews

My daughter has anxiety and became nauseous after boarding the plane and before take off. She went to the plane bathroom and ended up having to vomit, and your staff promptly removed us from the flight. We explained that it was due to my daughter’s anxiety, and that the condition would not continue in the air, but they removed us anyway. We have flown many many times before on many different airlines and my daughter’s anxiety has resulted in nausea and sickness before takeoff, and every airline has been accommodating and professional. This is was our first time flying with your airline, and also the first time we have ever been removed from a flight. This was the worst service we have ever experienced. This was a special surprise trip we gifted to my daughter for graduating college. I had also paid to upgrade the family to first class and sit all together which we had never done before and can’t afford on a normal basis. Our removal from the flight was not only extremely embarrassing, but devastating for my daughter. My daughter and I were removed from the plane and a call was made by your staff to medical personnel, a few questions were asked of my daughter, and then she was magically cleared. All of this took mere minutes. Why this could not have been performed while we were on the plane, or why this could not have been performed off the plane and then us allowed to reboard is beyond me. My wife and youngest daughter continued on the original flight alone and were very upset and crying due to the situation, yet the staff did nothing to console or assist them. My wife states that upon arrival in Portland and as they were exiting the plane, one of the stewardesses involved said “byyyyeeeee” to them sarcastically and laughed. Myself and my oldest daughter had to wait 4 hours for an alternate flight and were sat in regular seats because our first class seat purchase could not be honored. My wife wasn’t allowed to pick up our rental car and had to wait 4 hours with our luggage until I arrived. The delay prevented us from being able to carry out planned events and ruined the first day of our trip. Upon explaining all of this to your customer service, we received no sympathy, assistance, or compensation other than your staff submitting a request for a reimbursement of my and my daughters first class upgrade cost. When checking in early for our flight back home, the luggage cost for myself and my eldest daughter was no longer discounted as it was for my wife and youngest daughter. Customer service once again could not assist me over the phone and rectify what should have been a minor adjustment. Instead they stated I would have to wait until we physically checked bags in at the airport and then ask staff to adjust the luggage cost. With everything else we had experienced, I was not going to leave that to chance and instead paid full price for the luggage ahead of time. Or experience with Alaska Airlines was a complete disaster and I am baffled at the lack of empathy and assistance from your staff. I’m not sure of what else to say other than the fact that unless we are compensated by Alaska Airlines in some form to offset the horrendous service we received, we will be relaying our experience to family and friends and on social media, and doing all we can to urge everyone to avoid utilizing your services.

2.0 MediocreJerry, Apr 2026
ONT - PDX
Read more Alaska Airlines reviews

My daughter has anxiety and became nauseous after boarding the plane and before take off. She went to the plane bathroom and ended up having to vomit, and your staff promptly removed us from the flight. We explained that it was due to my daughter’s anxiety, and that the condition would not continue in the air, but they removed us anyway. We have flown many many times before on many different airlines and my daughter’s anxiety has resulted in nausea and sickness before takeoff, and every airline has been accommodating and professional. This is was our first time flying with your airline, and also the first time we have ever been removed from a flight. This was the worst service we have ever experienced. This was a special surprise trip we gifted to my daughter for graduating college. I had also paid to upgrade the family to first class and sit all together which we had never done before and can’t afford on a normal basis. Our removal from the flight was not only extremely embarrassing, but devastating for my daughter. My daughter and I were removed from the plane and a call was made by your staff to medical personnel, a few questions were asked of my daughter, and then she was magically cleared. All of this took mere minutes. Why this could not have been performed while we were on the plane, or why this could not have been performed off the plane and then us allowed to reboard is beyond me. My wife and youngest daughter continued on the original flight alone and were very upset and crying due to the situation, yet the staff did nothing to console or assist them. My wife states that upon arrival in Portland and as they were exiting the plane, one of the stewardesses involved said “byyyyeeeee” to them sarcastically and laughed. Myself and my oldest daughter had to wait 4 hours for an alternate flight and were sat in regular seats because our first class seat purchase could not be honored. My wife wasn’t allowed to pick up our rental car and had to wait 4 hours with our luggage until I arrived. The delay prevented us from being able to carry out planned events and ruined the first day of our trip. Upon explaining all of this to your customer service, we received no sympathy, assistance, or compensation other than your staff submitting a request for a reimbursement of my and my daughters first class upgrade cost. When checking in early for our flight back home, the luggage cost for myself and my eldest daughter was no longer discounted as it was for my wife and youngest daughter. Customer service once again could not assist me over the phone and rectify what should have been a minor adjustment. Instead they stated I would have to wait until we physically checked bags in at the airport and then ask staff to adjust the luggage cost. With everything else we had experienced, I was not going to leave that to chance and instead paid full price for the luggage ahead of time. Or experience with Alaska Airlines was a complete disaster and I am baffled at the lack of empathy and assistance from your staff. I’m not sure of what else to say other than the fact that unless we are compensated by Alaska Airlines in some form to offset the horrendous service we received, we will be relaying our experience to family and friends and on social media, and doing all we can to urge everyone to avoid utilizing your services.

I got an email 3 hours before the flight letting me know it got canceled

The internet was down, which made my work plans impossible while inflight.

With saver fares on Alaska, you are treated like a 2nd class citizen. Last to get a seat-most likely in the middle. Last to board. By then all overhead bins are taken. It’s sad to see Alaska treats its customer like India’s caste hierarchy. I’m in Portland Oregon. So I have to Alaska. Otherwise, I wouldn’t fly on them again.

Flight on time. Easy boarding. Changing my seat was very easy.

Flights were on time, which made making connections do much better. Well organized

Flight delays were really annoying, but otherwise the experience was fine

I paid almost $700 for super saver round trip…, You moved me to the back of plane… I’m old and have breathing and anxiety problems! You didn’t care! Moved me to the way back! Unacceptable!

My only complaint was how far it was from plane to baggage claim

had to be rerouted due to a medical emergency onboard. Alaska crew treated the patient with utmost respect and continued to keep the passengers updated the entire way through, which I appreciate. But it took 4 hours from landing until we were able to be airborne again, causing us to not get into SFO until ~2 am. I understand it was a tough situation for everyone, but that was an indecent wait.

Okay considering we had weather delays which the Pilot notified us of immediately!

Generally on time departures and arrivals, clean planes, sky miles membership provides great benefits (complimentary upgrades, etc).

Flight from Fort Wayne to Atlanta was the smallest in terms of cabin space that I've ever seen. A carry on I've used for 20 years BARELY fit in overhead compartment. I'm 5'10" and felt very cramped. Not the best experience.

I am writing to express my dissatisfaction with the poor service and unprofessional staff we encountered when traveling with an infant. Our flight was delayed, and the gate staff failed to manage the boarding process appropriately. Due to incorrect, unavailable, or missing 'pink tag' stroller and car seat check-in procedures at the gate, we were forced to board last. Furthermore, the gate staff was rude and dismissive, causing significant distress to our infant. To make matters worse, one of our checked items—an infant sleeper/lounger—was returned to us broken. Given the unsafe handling of essential equipment and unprofessional treatment, I expect a prompt resolution regarding compensation for the damaged items.

We departed and landed early which was a nice surprise. The boarding process was slow.

N Everything was perfect from boarding to assistance to baggage in Tampa

Subpar. The seating on the plane is almost unbearable. We are literally touching and/or sitting on each other which is totally unacceptable and shameful. Pilots and crew was very accommodating and friendly.

The boarding was organized and informative but the plane was tight meaning that you were sitting on one another and extremely uncomfortable. It’s disappointing that can’t have common seating comfort on the plane.

Loved the crew! Sucks that we went from 1 hour and 8 minute layover to a 3 hour layover. But weather sucks like that.

I was told that they needed to check my bag at the gate and to pick it up at the gate in Richmond. No big deal. I know they can't control the weather, but we flew around RIC for 45 minutes to avoid the storm and were 25 minutes late leaving as well. Once we landed, we were told to go to baggage claim to pick up our luggage. I went to bathroom, paid for parking, and went to the assigned baggage claim location. United flight people came down with us as well. They got their luggage immediately. Next, South West people came down about 10 minutes later. They got their luggage next. We finally got our luggage around 30 minutes in waiting. Was not a wonderful experience. No reflection on Delta, but the ground crew was lousy at best.

The checking was disaster, the crew wasn't behave well. It took us two hours to check in, after that thr line at the TSA was long, we barely make the flight. Bad airline

Fabulous if you have a portable wheelchair. They can store it in the galley and you can just walk out with it. Really nice and the flat seats are just incredible, very nice. iPads for movies, also pretty nice,

The crew were exceptionally nice and accommodating. My wife was tired after the flight from Haneda, Tokyo. They let her sleep and served her dinner later after she woke up, before we landed in PDX.

No charging outlets worked. Other than collecting trash attendants didn’t come around. No one could hear flight attendants announcements during the flight. Seat pads were horrible. Sitting on a board for 5 hours. What happened to Hawaiian airlines comfort, hospitality, and extras? Our pilots did an excellent job trying to minimize turbulence and incredible job in landing in windy conditions.

I like that if they asked you to checked in a bag at the gate they give you priority to board

Horrible food and crew. Crew were laughing and talking loud while people were trying to sleep

Yall need to integrate your system with Alaska more efficiently. They booted me off the first flight because of a discrepancy on your end.

The crew at Hawaiian Airlines was fantastic. Kind and hard working. The pilots were great with giving us all the updates to make sure we were informed.

Very good. Nice plane and we sat in economy plus - bigger seats, more room. They served a meal and snacks, and the meal was an apple stuffed pancake that was very good! The snack for us was a hummus sandwich - also very good. The flight attendants were helpful and nice. They have plenty of movies and shows to watch. My only negative -- they changed our flights around and did not adjust the layovers, so we ended up with a very long and unnecessary layover in Honolulu.

I liked the Starlink WiFi but didn't like how they said they were the only airline to offer a free meal and it turns out to be just a standalone sandwich and then charge for snacks to go with it. Rather have the free snacks like Southwest, but have the option to purchase a decent meal for a 5+ hour flight.

No meal service to the back of the plane as it started late or was too slow to get it out before it was time to land.

Terrible, if possible won't be flying again anytime soon!

Efficient boarding and early departure. Very smooth flight. Early arrival in ATL. Great flight.

Smooth and easy boarding, comfortable for the entire 5 hour flight, and the seat back entertainment was great! I appreciated all the features, from location info and maps, movies, the ability to connect with Bluetooth headphones, and good selection of movies. Food was good, normal airline snacks (I didn’t purchase anything)

Awful. No counter attendants. No dinner offered due to delays.

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

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

Information on your arrival and departure airports