CHI - RDM

$179 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 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
$369
Typical prices: $560-$378
Alaska Airlines
火 7/14水 7/29
ORD - RDM • 1 stop
Cheapest one-way
$179
Typical prices: $194-$234
United Airlines
火 9/15
ORD - RDM • 1 stop
Top airlines
Cheapest • from $369 (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 • 47% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
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

火, 7月 14 - 水, 7月 29
Alaska Airlines Logo
6:20 am - 12:25 pm
ORD
-
RDM
8h 05m
1 stop
Alaska Airlines Logo
7:49 pm - 5:00 am
RDM
-
ORD
7h 11m
1 stop
$369Alaska Airlines
金, 10月 30 - 土, 10月 31
Alaska Airlines Logo
2:17 pm - 6:28 pm
ORD
-
RDM
6h 11m
1 stop
Alaska Airlines Logo
8:00 am - 6:20 pm
RDM
-
ORD
8h 20m
1 stop
$373Alaska Airlines
土, 7月 11 - 火, 7月 28
Delta Logo
5:55 pm - 10:57 pm
ORD
-
RDM
7h 02m
1 stop
Delta Logo
6:13 am - 6:57 pm
RDM
-
ORD
10h 44m
2 stops
$374Delta
水, 9月 23 - 月, 9月 28
Delta Logo
12:40 pm - 11:47 pm
ORD
-
RDM
13h 07m
2 stops
Delta Logo
1:33 pm - 11:47 pm
RDM
-
ORD
8h 14m
1 stop
$378Delta
木, 8月 6 - 火, 8月 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
土, 8月 22 - 火, 9月 1
Delta Logo
7:45 am - 6:45 pm
ORD
-
RDM
13h 00m
2 stops
Delta Logo
6:20 am - 6:19 pm
RDM
-
ORD
9h 59m
2 stops
$380Delta
水, 9月 23 - 月, 9月 28
Delta Logo
1:47 pm - 11:08 pm
MDW
-
RDM
11h 21m
2 stops
Delta Logo
7:24 pm - 8:50 am
RDM
-
MDW
11h 26m
2 stops
$384Delta
水, 9月 23 - 月, 9月 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
水, 9月 23 - 月, 9月 28
Delta Logo
1:14 pm - 11:47 pm
MDW
-
RDM
12h 33m
2 stops
Delta Logo
7:24 pm - 8:50 am
RDM
-
MDW
11h 26m
2 stops
$389Delta
金, 7月 17 - 月, 8月 3
Alaska Airlines Logo
2:20 pm - 10:09 pm
ORD
-
RDM
9h 49m
1 stop
Alaska Airlines Logo
7:28 am - 6:57 pm
RDM
-
ORD
9h 29m
1 stop
$389Alaska 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 July.

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 July, 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$179
Best time to beat the crowds with an average 36% drop in price.
Most popular time to fly and prices are also 9% 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 5 days, the lowest price for a flight from Chicago to Redmond was $179 for a one-way ticket and $369 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 $466 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 12468 reviews
8.1Boarding
8.5Crew
7.0Entertainment
7.1Food
7.8Comfort
Airline reviews

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.

8.0 ExcellentDane, May 2026
BOS - PDX
Read more Alaska Airlines reviews

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.

They called me 2 hours before my original flight from SFO was to depart to let me know it was delayed and that I would miss my connection. They then rebooked on a different flight leaving a half hour earlier to a different connecting airport, so that I would not miss my connection. It all worked out and I arrived at my destination without a problem and 15 minutes earlier than the original flight would have. Nice!

Couldn’t order food for the family because all the good food was unavailable. We opted for bringing something on with us. I also didn’t like that I had to have T-mobile for online movies. Stupid.

Alaska is by far the best airline to fly with 😍

They were flexible and able to get me home a day earlier due to a family members illness. Flight was on time and great friendly crew.

The flight crew home was so, so friendly and HILARIOUS. I’ll keep flying Alaska like I have for the last 30+ years!

Deboarding the plane was chaos. The passengers in the back of the plane started deplaning before the passengers in the middle of the plane could even retrieve their overhead bags. The staff of the plane did nothing to help.

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.

Connection flights should be spaced out farther because too close I missed my connection.

Definitely a southern flavor. Cordiality was evident even though no drinks or snacks were served.

On time! There were plenty of airport employees who were able to keep us moving in the right direction. The crew on the plane were professional.

Left /arrived on time. Decent seat space. Like the wifi/plugs and entertainment. Windows and tray table were kinda gross. Attendants didn't start snack service til 40mins before landing. Two rows before us, captain came on to say there's turbulence and recalled staff to seats. So, no drink/snack. Later, attendants didn't stop to see if we had trash nor even look our way. Felt invisible! Almost all pilot announcements were not only unintelligible, but so quiet. We had no idea what she said.

Average seat comfort, a drink and chips were provided, early boarding because we checked a carryon at the gate was nice. Ticket pricing shenanigans, including fees to pick a seat, check a bag, and get food onboard - evidence the industry is reinvigorating last century’s strategies- destroys the experience before one ever arrives at the airport. It’s difficult to recognize any value or sustain loyalty in the end-to-end process making air travel more drudgery than pleasure.

Gate agent was unhelpful for handicapped boarding. Flight attendant seemed untrained.

No service flight that took 5 hrs and a stop at an unscheduled airport. Crew and pilots did their jobs

Clean planes and not take my comfort class seat away.

Weather caused a long delay, but the efficiency and updates from the pilot were helpful. We were able to make our connection fortunately.

Planes were clean, no water or snacks on either flight.

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.

No meal service to the back of the plane as it started late or was too slow to get it out before it was time to land.

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

Information on your arrival and departure airports