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

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
$389
Typical prices: $318-$358
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 $389 (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 24m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 50% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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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

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
$389Alaska 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
$394Delta
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
$399Delta
Fri, Aug 28 - Sat, Sep 5
United Airlines Logo
8:50 am - 2:55 pm
ORD
-
RDM
8h 05m
1 stop
United Airlines Logo
1:03 pm - 9:30 pm
RDM
-
ORD
6h 27m
1 stop
$409United Airlines
Tue, Oct 20 - Sat, Oct 24
Alaska Airlines Logo
2:21 pm - 8:23 pm
ORD
-
RDM
8h 02m
1 stop
Alaska Airlines Logo
1:32 pm - 11:59 pm
RDM
-
ORD
8h 27m
1 stop
$413Alaska Airlines
Fri, Aug 28 - Sat, Sep 5
Delta Logo
1:59 pm - 11:49 pm
ORD
-
RDM
11h 50m
2 stops
Delta Logo
1:52 pm - 11:29 pm
RDM
-
ORD
7h 37m
1 stop
$414Delta
Wed, Oct 7 - Tue, Oct 13
Delta Logo
6:00 pm - 10:46 pm
ORD
-
RDM
6h 46m
1 stop
Delta Logo
6:20 am - 9:53 pm
RDM
-
ORD
13h 33m
2 stops
$418Delta
Fri, Aug 28 - Sat, Sep 5
Delta Logo
5:57 pm - 11:49 pm
ORD
-
RDM
7h 52m
2 stops
Delta Logo
6:15 am - 9:30 pm
RDM
-
ORD
13h 15m
2 stops
$420Delta
Wed, Oct 7 - Tue, Oct 13
Delta Logo
1:55 pm - 10:46 pm
ORD
-
RDM
10h 51m
2 stops
Delta Logo
6:20 am - 5:57 pm
RDM
-
ORD
9h 37m
2 stops
$423Delta
Tue, Dec 8 - Tue, Jan 5
Alaska Airlines Logo
3:09 pm - 9:12 pm
ORD
-
RDM
8h 03m
1 stop
Alaska Airlines Logo
3:50 pm - 11:41 pm
RDM
-
ORD
5h 51m
1 stop
$425Alaska 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 5% 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 $389 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 $469 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 12572 reviews
8.5Crew
7.0Entertainment
8.1Boarding
7.0Food
7.8Comfort
Airline reviews

No screen to see where we were at and no tv.

10.0 ExcellentAnonymous, Jun 2026
EWR - PDX
Read more Alaska Airlines reviews

No screen to see where we were at and no tv.

Both flights were on time and without in-flight issues. Although we had to check our carry-on bags at the last minute (cabins were full, no more room), our bags were on the baggage carousel very quickly. (Happened both ways.) Staff was friendly. Boxed water tasted weird (a little like cardboard?) but not a huge deal. Overall good experience.

Someone rebooked my Alaska flight to a much later Delta flight. Now I am sitting at the Seattle airport after a long international flight and have to wait another 4 hours even though I would have been able to catch my initial flight

They lost my bag and 24 hours later have yet to find it

Long delay, no gate agent at deplaning waited 15 mins at the gate. Baggage claim was wrong carousel and over 20 mins after arrival

It was a very short flight so there really wasn’t any entertainment my. The little pretzels were good though and the cabin crew was awesome.

Flight delayed Didn’t send second leg of trip itemerary First class was fair, but not great.

Extremely professional crew there are very friendly and first class. Everything worked well on the plane. Food was to be expected. Drinks were very good. Shout out to Charlie in first class who was an excellent flight attendant.

Thanks for all you do to keep us safe and on time!

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.

Not really a “Delta” problem but worth mentioning: Boarding was a difficult process. TSA seemed understaffed and Pre-Check took longer than regular TSA. The supervisor was frazzled and yelled at travelers. Once through TSA, we had to put our carry-ons through another x-ray machine. Then queue up to board with both boarding pass and ID. Then, when we got to the stairs on the tarmac, we had to show our boarding pass again. Maybe this is just normal for Kona since the terminal is outdoors (but still a “secured” area).

flight was delayed 4+ hours. there was really no understanding of why? weather? the last hour of delay was post boarding. pilot seat was broken. was that the real reason? nonetheless, long day of inconveniences.

Love me some Delta. One of the few airlines to recognize and support veterans. Easy boarding, flight was on time and arrived early and the flight attendants were excellent on this flight.

I thought the service was very nice and pleasant. There were no hiccups and no issues so overall a good experience.

Very good flight. Crew was great. No issues and we even arrived early.

The flights are constantly late anymore, and they won't even give you a glass of water on the plane. For years, they were able to do a service on this flight from Atlanta to Knoxville and Knoxville Atlanta now they say it's too short of a flight. You can't even get a quick drink of water.

Flight got canceled 4 times, missed my connecting flight due to delays, have to wait to go home tomorrow

Third flight in two months where the crew was not there. Comfort seating does not guarantee overhead bin space. Passengers with children are allowed on the plane first - if you are flying to and from Orlando, this means half the plane has boarded before you get on. And somehow all the bin space is taken up. 3 out of 5 flights have had issues with equipment or procedure. Some of these instances caused the flight to be delayed because of a "nuisance" light. One time it was a bag that had been brought on board but did not belong to anyone so we had to return to the gate. Last night we were told the "AC" on the plane doesn't work well and we're 10th for take off- because the crew was late - and that it will get cool when we're in the air. Not sure if this is usual, but I didn't think flight crew could jump seat in first class. Movie and TV selection has not been refreshed for several months- flying one to two round trips each month easily exhausts the list of content.

Great experience nice pilot very soft and easy landing and take off

We sat on the runway for over an hour before departure. That was unwelcome.

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.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

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

Information on your arrival and departure airports