CHI - RDM

$207 Find Cheap Flights from Chicago to Redmond - Compare and Save

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 9/15. 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

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Everything you should know

Cheapest round-trip
$413
Typical prices: $348-$368
Alaska Airlines
Wed 9/2Sat 9/5
ORD - RDM • 1 stop
Cheapest one-way
$207
Typical prices: $189-$269
Alaska Airlines
Tue 9/15
ORD - RDM • 1 stop
Top airlines
Cheapest • from $413 (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
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Insights
Top layover airports
Cheapest • Avg $288 (round-trip)
Shortest trip • 6h 24m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 48% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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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

Wed, Sep 2 - Sat, Sep 5
Alaska Airlines Logo
2:18 pm - 9:38 pm
ORD
-
RDM
9h 20m
1 stop
Alaska Airlines Logo
7:07 am - 7:21 pm
RDM
-
ORD
10h 14m
1 stop
$413Alaska Airlines
Wed, Sep 2 - Sat, Sep 5
Delta Logo
12:54 pm - 6:45 pm
ORD
-
RDM
7h 51m
1 stop
Delta Logo
6:15 am - 8:30 pm
RDM
-
ORD
12h 15m
2 stops
$418Delta
Wed, Sep 9 - Sun, Sep 13
Alaska Airlines Logo
2:18 pm - 9:38 pm
ORD
-
RDM
9h 20m
1 stop
Alaska Airlines Logo
7:07 am - 7:21 pm
RDM
-
ORD
10h 14m
1 stop
$419Alaska Airlines
Tue, Sep 22 - Wed, Sep 30
Delta Logo
2:00 pm - 11:58 pm
MDW
-
RDM
11h 58m
2 stops
Delta Logo
7:24 pm - 8:48 am
RDM
-
MDW
11h 24m
2 stops
$423Delta
Wed, Sep 2 - Sat, Sep 5
Delta Logo
2:00 pm - 10:58 pm
ORD
-
RDM
10h 58m
2 stops
Delta Logo
6:15 am - 8:30 pm
RDM
-
ORD
12h 15m
2 stops
$423Delta
Wed, Sep 9 - Sun, Sep 13
Delta Logo
12:50 pm - 6:44 pm
ORD
-
RDM
7h 54m
1 stop
Delta Logo
7:24 pm - 8:30 am
RDM
-
ORD
11h 06m
2 stops
$424Delta
Tue, Aug 11 - Sat, Aug 15
Delta Logo
7:44 pm - 11:49 pm
ORD
-
RDM
6h 05m
1 stop
Delta Logo
1:52 pm - 11:29 pm
RDM
-
ORD
7h 37m
1 stop
$425Delta
Tue, Sep 22 - Mon, Sep 28
Delta Logo
1:19 pm - 11:58 pm
MDW
-
RDM
12h 39m
2 stops
Delta Logo
7:24 pm - 9:07 am
RDM
-
MDW
11h 43m
2 stops
$429Delta
Wed, Sep 23 - Thu, Oct 1
Alaska Airlines Logo
7:20 am - 6:07 pm
ORD
-
RDM
12h 47m
2 stops
Alaska Airlines Logo
1:37 pm - 11:59 pm
RDM
-
ORD
8h 22m
1 stop
$433Alaska Airlines
Thu, Jul 23 - Mon, Jul 27
Multiple Airlines Logo
7:15 am - 11:35 am
ORD
-
RDM
30h 20m
1 stop
Multiple Airlines Logo
12:15 pm - 12:49 am
RDM
-
ORD
34h 34m
2 stops
$434Multiple 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 September.

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 December, where tickets cost $139 (return) on average. On the other hand, the most expensive months are June and May, where the average cost of round-trip tickets is $356 and $347 respectively.

Good to know

Low seasonFebruary
Cheapest flight$207
Best time to beat the crowds with an average 39% drop in price.
Most popular time to fly with an average 4% 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 5 days, the lowest price for a flight from Chicago to Redmond was $207 for a one-way ticket and $413 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 $473 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 $400 and an overall rating of 7.8.

  • 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 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.
7.9
Alaska AirlinesOverall score based on 12607 reviews
8.1Boarding
7.8Comfort
7.0Entertainment
8.5Crew
7.1Food
Airline reviews

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.

2.0 MediocreAnonymous, Feb 2026
SFO - RDM
Read more Alaska Airlines reviews

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.

The flight attendants were nice, but the cabin and seats were uncomfortable.

There was no food or entertainment so quit asking about that! Everything else was fine.

Terrible. My flight was pushed out three times finally the fourth time it was canceled completely. They sent me to a hotel that would not accept the voucher. And I had to pay for my cab and Uber . I arrived at the airport at five and didn’t get into my hotel until 1145.

5 hours delay, while seated moved passengers around on the plane. We were out on the runway, had to return to the gate. Changed tires.

Flight was switched to a different airline. Caused scheduling issues. Flight delayed an hour, but arrived only 20 minutes late thanks to tail winds.

Plane was delayed and got me in past bedtime. But more importantly, my tsa precheck number wasn’t on my ticket so had to deal with the general line. Oh well, guess the delay helped that situation.

Could have had more of a beverage selection than water and apple juice.

The plane boarded on time. Takeoff and landing were smooth despite the wind. The flight was too short for any food, drinks, or entertainment.

Took off and landed at the correct airports so they did pretty good.

The crew was very inconsiderate and rude. My flight was scheduled to depart at 6:00am. I received a call from the crew at 5:40am, asking if I was going to make the flight because I was the only one that hasn't boarded yet and boarding ends at 5:50am. I let them know that I will be at the gate in a few minutes, before the 5:50am cutoff. When I arrived at the gate at 5:45am the gate was closed. Departing early on last minute notice without having all passengers on board is inconsiderate and unprofessional.

Very easy to use and convenient, you can perform any action within the same portal

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

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.

Everything could have benn better. Short fly, no food, no entertainment and no wifi.

Stop changing gates. Stop cancelling flights Stop moving my seat.

The staff was frielndly. The plane was terrible, it was too small and should be decommissioned. There were no back seat screens at all. The only beverages we had a choice from was coffee, tea or water. The only bathroom in the back was behind the flight attendant's jump seat and wasn't working. And I literally felt like I was sitting on top of the guy next to me. It was terribly hot in the plane and we had to sit on the tarmac in Chicago for 1/2 hour due to congestion in Mpls. Wouldn't they have know that before they even boarded us so that we could have sat in comfort in the terminal?

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.

The Pilot was one of the best I've had, very informative about turbulence and got us to our destination early

It was very cold because the air conditioner was on high power, and my son got sick.

The flight was delayed by a hour and I wish they had communicated it sooner. No issues on the plane, it did take a while for food to come.

Know that the movies that you are going to be offered are the oldest be rated movies they could possibly get. They may have one or two new movies that they keep advertising but when you’re flying 15 hours, there is nothing to see past the first new movie.

Great experience. Boarding was fast, staff were very nice and funny, everything at the seat worked well.

Horrible! Several delays and then was cancelled! I spent over 24 hours in the airport and was unable to get a hotel or food voucher.

Boarded early; and arrived home 40 mins early. After a long flight, it’s nice to be back home early. These flights have no amenities; no snacks. So need to bring your own

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

I will never book a flight through Cheap fare. They booked me from Portland Main . And would not give me a refund, so I bought 2 tickets one for 299. From Portland Main to ORD. Then I had to buy a ticket from Oregon PDX to ORD that was another 440. So Just so you know they even told me it was there fault but no refund. Bad bussniess. I did inform United but they said they couldn't help me due to the fact I booked through Cheap Tickets. Never again. And I'm spreding the word. I let everyone know at my 50th class reunion

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

Information on your arrival and departure airports