CHI - RDM

$142 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 5/20. 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, 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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41.299.237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$267
Overall average: $527
Delta
Fri 3/6Tue 3/10
ORD - RDM • 1 stop
Cheapest one-way
$142
Typical prices: $154-$261
Alaska Airlines
Wed 5/20
ORD - RDM • 1 stop
Top airlines
Delta
Cheapest • from $267 (round-trip)
Alaska Airlines
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
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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, Mar 6 - Tue, Mar 10
Delta Logo
6:45 pm - 11:45 pm
ORD
-
RDM
7h 00m
1 stop
Delta Logo
6:20 am - 6:00 pm
RDM
-
ORD
9h 40m
2 stops
$267Delta
Sat, Apr 11 - Wed, Apr 15
Delta Logo
7:20 am - 11:52 am
ORD
-
RDM
6h 32m
1 stop
Delta Logo
6:05 am - 4:39 pm
RDM
-
ORD
8h 34m
1 stop
$277Delta
Tue, Mar 24 - Thu, Mar 26
Alaska Airlines Logo
6:00 am - 12:29 pm
ORD
-
RDM
8h 29m
1 stop
Alaska Airlines Logo
8:14 pm - 6:39 am
RDM
-
ORD
8h 25m
1 stop
$278Alaska Airlines
Sat, Apr 11 - Wed, Apr 15
Delta Logo
7:20 am - 11:52 am
ORD
-
RDM
6h 32m
1 stop
Delta Logo
11:35 am - 9:18 pm
RDM
-
ORD
7h 43m
2 stops
$282Delta
Sat, Apr 11 - Wed, Apr 15
Delta Logo
7:20 am - 11:52 am
ORD
-
RDM
6h 32m
1 stop
Delta Logo
11:35 am - 9:18 pm
RDM
-
ORD
7h 43m
2 stops
$283Delta
Fri, Mar 6 - Tue, Mar 10
United Airlines Logo
6:17 am - 12:11 pm
ORD
-
RDM
7h 54m
1 stop
United Airlines Logo
6:35 pm - 5:07 am
RDM
-
ORD
8h 32m
1 stop
$286United Airlines
Fri, May 8 - Sun, May 10
Alaska Airlines Logo
8:50 am - 9:38 pm
ORD
-
RDM
14h 48m
1 stop
Alaska Airlines Logo
1:52 pm - 11:59 pm
RDM
-
ORD
8h 07m
1 stop
$287Alaska Airlines
Sat, Apr 11 - Wed, Apr 15
Delta Logo
7:20 am - 11:52 am
ORD
-
RDM
6h 32m
1 stop
Delta Logo
6:05 am - 6:13 pm
RDM
-
ORD
10h 08m
2 stops
$292Delta
Sat, Apr 11 - Wed, Apr 15
Delta Logo
7:20 am - 11:52 am
ORD
-
RDM
6h 32m
1 stop
Delta Logo
11:35 am - 9:18 pm
RDM
-
ORD
7h 43m
2 stops
$293Delta
Fri, Mar 6 - Tue, Mar 10
Delta Logo
6:45 pm - 11:45 pm
ORD
-
RDM
7h 00m
1 stop
Delta Logo
11:24 am - 9:34 pm
RDM
-
ORD
8h 10m
2 stops
$295Delta
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.

Which airlines provide the cheapest flights from Chicago to Redmond?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Chicago to Redmond were found on Delta ($267) and United Airlines ($272).

Good to know

Low seasonJune
Cheapest flight$142
Best time to beat the crowds with an average 29% drop in price.
Most popular time to fly and prices are also 11% 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 $156 for a one-way ticket and $267 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 $438 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 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 11875 reviews
8.5Crew
8.1Boarding
7.1Food
7.8Comfort
7.0Entertainment
Airline reviews

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.

4.0 Okayjeff, Feb 2026
SFO - PDX
Read more Alaska Airlines reviews

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.

Flight attendants made this flight wonderful. They made sure everyone had what they needed and anticipated future needs. They made adjustments as needed. It was clear this was an experienced crew.

Very delayed for seemingly no reason. Made me miss an event

we bought Mediterranean boxes for lunch. The salami in mine had gone bad long ago, but my partner had good salami and could eat it. Could I buy assigned seats? I guess that I didn't spend enough, so sat at the back of the plane

the flight attendant was so great and the upgrade to first class was top notch

No WiFi. Terrible food. Very long walk to the gate and from the gate after landing. Gate changed without notice.

There was no food or entertainment, thus thus the neutral rating.

The Alaska Airlines app made it very difficult to find my boarding pass. It was very frustrating to use! The flight itself was flawless.

No communication with delayed and canceled flights. Completely in the dark for the whole experience.

You need categories to note when food and entertainment are not available. Alaska's system would not update flight info on the board for this flight, so there was some confusion after deplaning from the previous flight as to which gate and depart time were accurate for this flight.

Awesome! On time flight, early arrival, and a complimentary upgrade!

Paid for wifi that didn't work. No plug in seat to work. No entertainment.

We departed early and made up time in the air allowing us to arrive 30 minutes early. Capt was incredibly genuine and thanked every passenger for flying with Delta. Completely humble and professional!

Was forced to check in my small carry on, even though I informed the crew it has very fragile items inside

This was one of the worst flights I’ve been on in years. I upgraded to comfort and had such an uncomfortable experience. The person next to me was oversized - which I understand - however, they took up their space and mine. I could only use about 50% of my seat space to not be physically touching this person the entire flight and there was no spatial awareness. I also could not use the seat outlet because their body was obstructing it. It was very inconvenient. Their body kept touching me repeatedly during the flight and I felt very uncomfortable. To pay more for an upgraded space and then not even being able to use it was highly disappointing.

No wheel chair as requested at Atlanta arrival on first flight.

Only freetext wifi was available in flight; browsing WiFi required payment. Since the seats had no in flight entertainment, Delta should revisit this policy on this longer flight.

Only water, tea or coffee served midflight, even to comfort seating. Man next to me needed two seats and took up a portion of my seat and Delta did nothing.

The flight was great as well as the airline staff

First class and monitors weren’t working for mine & my husbands. Eventually fixed, but quite annoyed as we bought first class. Also, No foot rests.

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.

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. :/

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

I liked the snacks and the flight attendants were friendly.

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

Information on your arrival and departure airports