CHI - RDM

$95 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 3/12. 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.
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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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Cheap Flight Deals 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.

Recent round-trip flight deals from Chicago to Redmond

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Chicago to Redmond.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
7:40 am - 9:15 pmORD-RDM
15h 35m1 stop
5:59 pm - 5:40 amRDM-ORD
9h 41m1 stop
$262Alaska Airlines
Find Deal
Tue, Apr 8 - Tue, Apr 15
1:45 pm - 10:45 pmORD-RDM
11h 00m2 stops
6:20 am - 5:30 pmRDM-ORD
9h 10m1 stop
$268Delta
Find Deal
Tue, Apr 8 - Tue, Apr 15
6:25 pm - 11:03 pmORD-RDM
6h 38m1 stop
6:20 am - 5:30 pmRDM-ORD
9h 10m1 stop
$273Delta
Find Deal
Fri, Apr 25 - Tue, Apr 29
1:45 pm - 10:45 pmORD-RDM
11h 00m2 stops
5:36 pm - 7:55 amRDM-ORD
12h 19m2 stops
$274Delta
Find Deal
Tue, Apr 8 - Tue, Apr 15
6:25 pm - 11:03 pmORD-RDM
6h 38m1 stop
5:36 pm - 7:55 amRDM-ORD
12h 19m2 stops
$278Delta
Find Deal
Fri, Apr 25 - Tue, Apr 29
6:30 am - 12:11 pmORD-RDM
7h 41m1 stop
7:30 pm - 5:39 amRDM-ORD
8h 09m1 stop
$279United Airlines
Find Deal
Sat, Jul 5 - Sat, Jul 12
6:30 am - 12:11 pmORD-RDM
7h 41m1 stop
6:55 pm - 6:00 amRDM-ORD
9h 05m1 stop
$289United Airlines
Find Deal
Fri, Aug 15 - Tue, Aug 19
2:05 pm - 9:15 pmORD-RDM
9h 10m1 stop
1:03 pm - 1:05 pmRDM-ORD
22h 02m1 stop
$320Alaska Airlines
Find Deal
Thu, Apr 3 - Mon, Apr 7
6:00 am - 12:30 pmORD-RDM
8h 30m1 stop
4:00 pm - 11:56 pmRDM-ORD
5h 56m1 stop
$524Hawaiian Airlines
Find Deal
Thu, May 22 - Mon, May 26
6:00 am - 1:07 pmORD-RDM
9h 07m1 stop
3:00 pm - 12:44 amRDM-ORD
7h 44m1 stop
$636American Airlines
Find Deal
Wed, Mar 12 - Wed, Mar 12

Flights from Chicago to Redmond - Travel Insights & Trends

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 $625 respectively.

Good to know

Low season

April

High season

December

Cheapest flight

$95
Best time to beat the crowds but there is an average 1% increase in price.
Most popular time to fly with an average 57% 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 $95 for a one-way ticket and $262 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, oneworld, 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 $499 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 $425 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.

See more FAQs

Top 3 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 9691 reviews
7.1Food
8.2Boarding
7.1Entertainment
7.9Comfort
8.5Crew
Airline reviews

It was a really smooth flight. I hate heights. All made it feel smooth. Thankyou

10.0 ExcellentAnonymous, Feb 2025BOI - PDX
Read more Alaska Airlines reviews

It was a really smooth flight. I hate heights. All made it feel smooth. Thankyou

I’m still waiting on my luggage. They canceled my flight on valentines day and my girlfriend broke up with me. Alaska airlines literally ruined my life.

Quick boarding, efficient and pleasant crew. Wish they worked the mic better in the terminal to be understood more clearly.

They left my luggage behind in Seattle. However, they delivered it to my home the next morning.

Overall good , very dependable Airline and all its staff, etc but what could have been improved was allowing more than 40 minutes during layover in Portland as ultimately that brief layover was reduced to about 10 minutes with delays and causes us to panic as we rushed thru the Airport to our connecting flight. The Plane arrives at the Portland Airport very far from one Gate to another but thankfully the staff waited for us at the last minute to Board and were very caring and compassionate and assisted us in every regard . Thank you

Flight crew had the courtesy to ask passengers from my first flight to allow those of us disembarking to go first so that we could make it onto our connecting flights. Worked like a charm. Both crew and fellow passengers working together for a better outcome for all.

We missed our connection to Portland and ended up having to drive.

I had to miss that flight as my first flight was cancelled in Idaho Falls. Bad day all around . Couldn’t be rebooked!

My Alaska Airlines trip from bend, Oregon to Portland, Oregon was good. Everything was well organized boarding was easy and the flight was quick. The only reason I rated the food and entertainment as mediocre is because the flight was too quick to have any food or entertainment.

We had TSA pre check and paid to get it! They told us we would not have to do many of the things such as take your shoes off which I had to do! I’m 78 years old with NO criminal record and. they also patted my ankles down, Why? We boarded the plane in an orderly fashion only to sit there while they perform repairs to the lavatory. Why didn’t they do that before we boarded? I also paid extra to have more room because of my age but that was not what I had hoped for. I know you can’t control who sit in what seat but the guy next to me was bigger than average and took up part of my space.

Boarding is, as it always is… horrible. Gate lice. Slow moving zones. Too many people with carry ons

I loved having a most black flight crew during Black History Month; rather by design or accident I appreciated the representation. ❤️

This was the second flight this week with flight attendant Marcus I’m not sure if his last name is Lane or Lang but this guy is awesome. He funny, attentive and his service is 5 stars. Marcus makes business travel more enjoyable !

Although the flight left late, we arrived early. It was one of the quickest boarding and off boarding experiences I’ve had. It was kind of annoying the only drinks they had were water, coffee, and tea. The flight was very smooth, temperature was just right, and flight attendants were friendly.

Lower number on this flight so spaced out passengers. Able to enjoy more room to relax during flight. It was lovely.

Kind staff. Snacks are small but that’s the new normal.

The young man who was our flight attendant in first class was lazy and did not do his job well at all. Never offered drinks upon boarding - actually I take that back... said "are you okay with water" as if I do not want to get you anything else, only passed the snacks around once, got my drink order wrong and then never offered a second round of drinks. He was the worst I have ever seen on Delta and we fly a lot.

Great service. Great staff. Boarding was a little slow, but I think there was a service dog slowing things down.

Flight left early and arrived early. the whole trip was excellent.

Seats were really tight and the seat belts did not give enough slack.

Our seats were all the way in back of the plane,

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

The seats on this flight were almost roomy enough to be the basic amount needed for human existence.

The flight attendants in First Class were mediocre at best. They did not take our tray away until we were about to land and only did so when I press the call button. The United person at the United Club was asked to get us our boarding pass since we missed the flight due in Chicago. She argued that we did not have seats on the flight given to us in Moline. Furthermore, she was adamant that we did not have a First Class ticket. After I spent much time with her trying to show we were correct, she reluctantly agreed. She was probably the most incompetent ticketing person I have ever met and I have traveled 3 million miles on United plus many additional miles with other carriers. United has definitely deteriorated in more than on way.

Short flight - no food understandable. Flight was delayed for over an hour. Overall, it was good.

We arrived early and finally made it to our gate almost an hour after.

Was a pain having to leave the plane and reboard but glad the plane was fixed

Plane was was better than th YVR to ORD flight but was a fraction of the distance. Fly your better planes on longer distance flights.

Nothing wrong with the flight itself. But due to 2+ hrs waiting in immigration and the additional security checkup in O’hare, I nearly missed the flight.

They need to improve their boarding process. Group 1 and/or paying first class passengers shouldn't be in the middle of boarding process

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

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