CHI - RDM

$185 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
$367
Typical prices: $318-$358
Alaska Airlines
Wed 9/2Sat 9/5
ORD - RDM • 1 stop
Cheapest one-way
$185
Typical prices: $189-$269
Alaska Airlines
Tue 9/15
ORD - RDM • 1 stop
Top airlines
Cheapest • from $367 (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
$367Alaska 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
$369Alaska Airlines
Tue, Aug 18 - Tue, Aug 25
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
$374Delta
Sat, Jul 4 - Thu, Jul 9
Alaska Airlines Logo
7:17 pm - 11:59 pm
ORD
-
RDM
6h 42m
1 stop
Alaska Airlines Logo
4:00 pm - 5:00 am
RDM
-
ORD
11h 00m
1 stop
$377Alaska Airlines
Thu, Aug 6 - Tue, Aug 11
Alaska Airlines Logo
8:20 pm - 9:04 am
ORD
-
RDM
14h 44m
1 stop
Alaska Airlines Logo
7:28 am - 6:57 pm
RDM
-
ORD
9h 29m
1 stop
$379Alaska Airlines
Tue, Aug 18 - Tue, Aug 25
Delta Logo
2:00 pm - 10:58 pm
ORD
-
RDM
10h 58m
2 stops
Delta Logo
7:36 pm - 8:30 am
RDM
-
ORD
10h 54m
2 stops
$380Delta
Wed, Sep 23 - Mon, Sep 28
Delta Logo
5:59 pm - 11:08 pm
ORD
-
RDM
7h 09m
1 stop
Delta Logo
7:24 pm - 8:30 am
RDM
-
ORD
11h 06m
2 stops
$384Delta
Wed, Sep 23 - Mon, Sep 28
Delta Logo
1:00 pm - 11:47 pm
MDW
-
RDM
12h 47m
2 stops
Delta Logo
7:24 pm - 8:50 am
RDM
-
MDW
11h 26m
2 stops
$389Delta
Wed, Sep 23 - Mon, Sep 28
Delta Logo
2:05 pm - 11:08 pm
ORD
-
RDM
11h 03m
2 stops
Delta Logo
7:24 pm - 8:30 am
RDM
-
ORD
11h 06m
2 stops
$389Delta
Fri, Aug 28 - Mon, Aug 31
Delta Logo
12:54 pm - 6:45 pm
ORD
-
RDM
7h 51m
1 stop
Delta Logo
6:15 am - 6:19 pm
RDM
-
ORD
10h 04m
2 stops
$394Delta
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$185
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 $185 for a one-way ticket and $367 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 $408 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 12550 reviews
7.0Food
8.5Crew
8.1Boarding
7.8Comfort
7.0Entertainment
Airline reviews

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

2.0 MediocreAnonymous, Jun 2026
RDM - PDX
Read more Alaska Airlines reviews

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.

Short trip, was nice to have a drink on the short flight still.

Nice to get moved from a middle seat to an aisle seat upon request, but why wasn’t I put in an aisle seat to begin with? The flight was not full.

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.

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

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.

Horrible. Faucet in sink not working, wifi not working. Didn’t bring food or snacks

Flight was delayed before take off and at landing. Baggage took 20 minutes. Flight crew would not serve full soft drink and had to ask multiple times before receiving water.

From checking to boarding, it was a seamless experience. The service agents were so helpful. The flight crew was so pleasant.

Gate agent showed up 20 minutes before boarding and was not at all friendly. Had to take this flight due to the one on the day before being cancelled and any later options were already full with long standby lists. Despite having paid for Delta Comfort seats, Delta did not allow me (or anyone) to choose their seat. The agent assigned them for everyone just prior to boarding. Self seat selection was allowed on the original flight. Flight staff was great - very friendly.

Flight attendants were great. Cheerful, upbeat and friendly. Jet, in particular, was fantastic.

I have Precheck. Flew HPN to DEN and return this past weekend. Delta didn't attach my Precheck number to this trip. So it was waiting in general line especially in Denver. Unavailable.

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.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

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

Information on your arrival and departure airports