CHI - RDM

$150 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 4/26. 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
$283
Overall average: $370
Delta
Fri 5/8Sun 5/10
ORD - RDM • 1 stop
Cheapest one-way
$160
Typical prices: $230-$323
United Airlines
Sun 4/26
ORD - RDM • 1 stop
Top airlines
Delta
Cheapest • from $283 (round-trip)
Alaska Airlines
Best reviews • 8.0 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
San Francisco (SFO)
Cheapest • Avg $305 (round-trip)
Portland (PDX)
Shortest trip • 6h 28m (one-way)
Insights
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Insights
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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

Fri, May 8 - Sun, May 10
Delta Logo
7:12 am - 12:30 pm
ORD
-
RDM
7h 18m
1 stop
Delta Logo
6:10 am - 4:49 pm
RDM
-
ORD
8h 39m
1 stop
$283Delta
Wed, Apr 8 - Sat, Apr 18
Delta Logo
2:05 pm - 11:47 pm
MDW
-
RDM
11h 42m
2 stops
Delta Logo
6:05 am - 6:36 pm
RDM
-
MDW
10h 31m
2 stops
$288Delta
Sat, Apr 11 - Wed, Apr 15
American Airlines Logo
5:25 pm - 11:23 pm
ORD
-
RDM
7h 58m
1 stop
American Airlines Logo
2:50 pm - 12:32 am
RDM
-
ORD
7h 42m
1 stop
$297American Airlines
Sat, Apr 11 - Wed, Apr 15
Alaska Airlines Logo
6:00 am - 12:29 pm
ORD
-
RDM
8h 29m
1 stop
Alaska Airlines Logo
1:23 pm - 11:59 pm
RDM
-
ORD
8h 36m
1 stop
$298Alaska Airlines
Wed, Aug 5 - Tue, Aug 11
Alaska Airlines Logo
7:20 am - 11:39 am
ORD
-
RDM
6h 19m
1 stop
Alaska Airlines Logo
12:34 pm - 5:02 am
RDM
-
ORD
14h 28m
1 stop
$299Alaska Airlines
Sat, Apr 11 - Wed, Apr 15
American Airlines Logo
5:25 pm - 11:23 pm
ORD
-
RDM
7h 58m
1 stop
American Airlines Logo
2:50 pm - 12:32 am
RDM
-
ORD
7h 42m
1 stop
$300American Airlines
Wed, Jun 3 - Mon, Jun 8
Alaska Airlines Logo
2:10 pm - 9:37 pm
ORD
-
RDM
9h 27m
1 stop
Alaska Airlines Logo
7:27 pm - 6:20 am
RDM
-
ORD
8h 53m
1 stop
$309Alaska Airlines
Wed, Jun 3 - Mon, Jun 8
Delta Logo
6:20 pm - 10:52 pm
ORD
-
RDM
6h 32m
1 stop
Delta Logo
5:20 pm - 7:26 am
RDM
-
ORD
12h 06m
2 stops
$314Delta
Fri, May 8 - Sun, May 10
Alaska Airlines Logo
6:00 am - 12:58 pm
ORD
-
RDM
8h 58m
1 stop
Alaska Airlines Logo
5:20 am - 2:08 pm
RDM
-
ORD
6h 48m
1 stop
$319Alaska Airlines
Thu, Apr 9 - Sun, Apr 12
Alaska Airlines Logo
6:00 am - 12:29 pm
ORD
-
RDM
8h 29m
1 stop
Alaska Airlines Logo
5:50 am - 6:39 am
RDM
-
ORD
22h 49m
1 stop
$321Alaska 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 May.

Good to know

Low seasonJune
Cheapest flight$160
Best time to beat the crowds with an average 29% drop in price.
Most popular time to fly and prices are also 12% 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 $160 for a one-way ticket and $283 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?

    SkyTeam, Star Alliance, and oneworld are the airline alliances operating flights between Chicago and Redmond, with SkyTeam 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 $431 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 $349 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 11982 reviews
7.1Food
7.8Comfort
8.1Boarding
7.0Entertainment
8.5Crew
Airline reviews

It was fine. I upgraded to premium economy & lived the extra legroom. Unfortunately, I was seated next to a man who sniffled A LOT during the flight and had his earphones on so loud that I could hear the music sitting next to him!

10.0 ExcellentMillie, Mar 2026
PHX - PDX
Read more Alaska Airlines reviews

It was fine. I upgraded to premium economy & lived the extra legroom. Unfortunately, I was seated next to a man who sniffled A LOT during the flight and had his earphones on so loud that I could hear the music sitting next to him!

I enjoyed the feet space in comparison to other airlines. The snacks were also better, great service and the pilot greeted and said hi which made me feel safer.

Well the seats were very tight but the plane was very clean, the attendance great and good entertainment. Maybe they had it, but I wanted a map on the app. Thanks

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.

I like flying Alaska Airlines. I think the staff are happy, the plane is comfortable, the entertainment reasonable, the food acceptable.

The tray wasn’t cleaned, it had crumbs from the last flight Other than that it was very comfortable by

SBP to PDX 2/17/2026. One person ahead of us at the counter. One ahead of is at TSA. First to board. First row, first class. First to be served. Food and service very good. First off the aircraft. Flight was nice other than some moderately hard bumps on climb out (please find a way to control that!). Air Force landing (none of that Navy slam you to the deck stuff). Wheel chair at the bottom of the ramp waiting for my wife. Luggage out quickly, walked right up to the parking shuttle bus. First stop on the bus. I like the EMB 175 aircraft. This was as close to a perfect flight as I will ever see. Bravo!

Everything was fine. The snacks are a little on the tiny side.

Santa Rosa Airport is the best! Glad to have experienced it.

Delay for switching planes. Then delay after delay (mechanical) after boarding so that we were almost 3 hrs late, getting in at 230am. Crew was good.

The whole experience was excellent. As it most often is with Delta

Cabin was not pressurized properly. Several passengers had respiratory difficulties.

I was happy that I was able to get a last minute flight but unfortunately my seat was a middle seat. Even with Delta Comfort I wasn't comfortable

There’s not much to say about a one hour flight. This is a connection from LA to RNO that I missed the previous night due to a mechanical check delay on my originating flight from JFK to LAX. The short flight itself was fine. Instructions from the pilot and crew were per usual. The coffee was barely lukewarm, which possibly was purposeful so we would down it quickly. Bags were already on carousel upon reaching baggage claim, which was excellent.

Flight was warm for first few hours and quite rough

Seat was extremely hard which made even a short 1 hour 20 minute flight fairly uncomfortable.

Everything was good except wifi and a leaking drink chiller. The floor was all wet and my bag was soaked. Did not notice until debarking. Have not heard back from Delta. Even though this was leg one of an international flight in first class, they denied access to their Sky Club - very disappointing!

The staff was fine. The plane was extremely tight, and I paid for the wifi and it did not work at all. I was actually going to ask for a refund.

two hour delay and the Delta representative on the PA system was unable to understand

An awesome flight crew. FC seat cushion just doesn’t cut it for a 3+ hour flight.

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.

Flight scheduled to take off at 5.55pm but it did not take off until 7pm due to some food delivery delay.

Unfortunately, I was put into the middle seat in the first row of premium seating. Sounds nice right? No! that is the worst seat in the plane. I wish I was in economy rather than be in that seat! There is no seat back pocket, no tray table, no charger. Nothing! so unless you're row mates are willing to let you share their basic amenities any flyer should have, you are stuck. It was the worst experience ever! And the flight attendant forgot to take my drink order. I felt like the forgotten flyer.

Alaska was fine as usual. My frustration came with accessing boarding passes. On the first trip, I could only get one to print ans took a picture of the second one. On our return trip, the system was down? Friends who booked directly with Alaska had theirs process. I even tried the 800 number and had others try it too. It said something in Spanish and hung up. The agent at the airport succeeded.

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.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

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

Information on your arrival and departure airports