CHI - RDM

$138 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 1/15. 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
$215
Overall average: $456
Delta
Sat 2/14Wed 2/18
ORD - RDM • 1 stop
Cheapest one-way
$138
Delta
Thu 1/15
MDW - RDM • 2 stops
Top airlines
Delta
Cheapest • from $215 (round-trip)
Alaska Airlines
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
January
Cheapest • 51% price drop
December
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

Sat, Feb 14 - Wed, Feb 18
Delta Logo
5:15 pm - 10:23 pmORD-RDM
7h 08m1 stop
Delta Logo
11:25 am - 11:52 pmRDM-ORD
10h 27m1 stop
$215Delta
Find Deal
Tue, Jan 27 - Sun, Feb 1
Alaska Airlines Logo
8:00 am - 11:52 pmORD-RDM
17h 52m1 stop
Alaska Airlines Logo
8:45 am - 2:38 pmRDM-ORD
27h 53m1 stop
$225Alaska Airlines
Find Deal
Tue, Jan 27 - Sun, Feb 1
Alaska Airlines Logo
8:00 am - 3:17 pmORD-RDM
9h 17m2 stops
Alaska Airlines Logo
8:45 am - 2:38 pmRDM-ORD
27h 53m1 stop
$230Alaska Airlines
Find Deal
Mon, Jan 26 - Sun, Feb 1
Alaska Airlines Logo
8:00 am - 9:15 pmORD-RDM
15h 15m1 stop
Alaska Airlines Logo
8:45 am - 2:38 pmRDM-ORD
27h 53m1 stop
$240Alaska Airlines
Find Deal
Mon, Jan 26 - Sun, Feb 1
Alaska Airlines Logo
6:06 pm - 12:30 pmORD-RDM
20h 24m2 stops
Alaska Airlines Logo
8:45 am - 2:38 pmRDM-ORD
27h 53m1 stop
$245Alaska Airlines
Find Deal
Sat, Feb 14 - Wed, Feb 18
Delta Logo
5:15 pm - 10:23 pmORD-RDM
7h 08m1 stop
Delta Logo
5:25 pm - 9:41 amRDM-ORD
14h 16m2 stops
$247Delta
Find Deal
Sat, Jan 17 - Wed, Jan 21
Hawaiian Airlines Logo
8:00 am - 12:54 pmORD-RDM
6h 54m1 stop
Hawaiian Airlines Logo
8:45 am - 5:10 pmRDM-ORD
6h 25m1 stop
$258Hawaiian Airlines
Find Deal
Wed, Jan 14 - Sun, Jan 18
Alaska Airlines Logo
3:35 pm - 9:15 pmORD-RDM
7h 40m1 stop
Alaska Airlines Logo
5:09 am - 1:10 pmRDM-ORD
6h 01m1 stop
$264Alaska Airlines
Find Deal
Wed, Jan 14 - Sun, Jan 18
Alaska Airlines Logo
3:35 pm - 12:30 pmORD-RDM
22h 55m2 stops
Alaska Airlines Logo
5:09 am - 1:10 pmRDM-ORD
6h 01m1 stop
$269Alaska Airlines
Find Deal
Mon, Jan 26 - Sun, Feb 1
Alaska Airlines Logo
6:06 pm - 12:30 pmORD-RDM
20h 24m2 stops
Alaska Airlines Logo
8:45 am - 1:10 pmRDM-ORD
26h 25m2 stops
$273Alaska Airlines
Find Deal
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.

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 $216 (return) on average. On the other hand, the most expensive months are December and March, where the average cost of round-trip tickets is $781 and $631 respectively.

Good to know

Low seasonNovember
Cheapest flight$138
Best time to beat the crowds but there is an average 12% increase in price.
Most popular time to fly with an average 77% increase in price.
Flight from Chicago Midway 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 $138 for a one-way ticket and $215 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, Star Alliance, and oneworld are the airline alliances operating flights between Chicago and Redmond, with SkyTeam 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 $442 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 $350 and an overall rating of 7.9.

  • 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 4 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 11390 reviews
8.1Boarding
7.0Entertainment
7.8Comfort
7.1Food
8.5Crew
Airline reviews

Food was bad. Just a drink for a 5 hour flight

8.0 ExcellentAnonymous, Nov 2025BOS - PDX
Read more Alaska Airlines reviews

Food was bad. Just a drink for a 5 hour flight

I liked that the crew was friendly, we left and arrived at near scheduled times, plenty of on-board crew to handle the cabin service for the flight and I found the price of my airline ticket to be excellent!

No accommodation or credit offered for cancelled layover flight to Eugene from portland

I've never flied them before but liked them. Weather was bad so a little scarey but they did a great job landing.

If they actually let me fly. I was rerouted to United and there was no Alaska airlines reps at all. Then the lady who worked the delta counter told me to go away and figure things out myself. Horrible experience.

Kayak I had marked one carry on, one checked bag. Yet when it completed the purchase marked it as no carry on. Fail on kayaks side! Then extended flight delayed due to computer issues. Crew of the plane did awesome but fail on both kayak and alaskan

Late. Too long a flight for a 737. 0.5 oz of pretzels for a 5+ hour flight at dinner time. One step above Ryan Air/ several below Delta.

Once again, Hawaiian Airlines upon checking in for our return flight, told us that we hadn’t paid for our extra comfort seats. This had happened on our incoming flight as well. Hawaiian Airlines had changed our flight and put us in standard seats. I sent them confirmation emails and receipts showing that I had paid for extra comfort seats and they ignored me and refused to accept my proof of payment. I ended up having to pay for our extra comfort seats again. On our return flight, once again, we were told we hadn’t paid for our extra comfort seats, which we had. I argued until a supervisor was summoned and researched further in their system and found that we had paid for them. If I hadn’t insisted, we would’ve been forced to buy our seats again or be assigned a standard seat. This kind of Customer Service is totally unacceptable. I would never use Hawaiian Airlines again if I have a choice.

Flight delay caused me to miss my connecting flight home, but I was put up at a nearby motel, and it was great

My seat. The reprentative on the phone was bad. The passengers screamed at each other and no one stopped them. The directions boarding the plane were unclear. There was a medical incident and the ICU nurse present said the women was having a cardic incident. Cooler heads determined it was a UTI. I had a allergy attack and a guy got a mask from the flight attendent and told me to wear it. He "had kidney failure". Why didnt they tell him to wear the mask, why was he even on the plane? It was embarrassing, he said hurtful things. By the way, I have a degree in Medical Micrbiology from Northwestern Medical school. MT(ASCP). Look it up. I Know the difference between allergies and an infection. But we had to listen to the unstable screaming man.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

Good seats in Main cabin, excellent service and excellent landing

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

Very smooth, on-time, and pleasantly uneventful flight. The team at the gate and on board were professional and genuinely courteous. The pilot kept us well updated throughout, and both takeoff and landing were steady and enjoyable without any drama. Just a good, solid flight. Thank you! 💗

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

No lunch on a x-country flight scheduled for 10:50 am departure, arrived 5+ hrs later. That requires a black box label before you pay for the tickets. Worst, when I checked in online, it's specifically said that lunch was served on his flight for economy Plus passengers.

We had a lot of really rough weather but that was not Delta's fault. Pilot was amazing.

First, Delta needs more flights to/from Miami. Second, a 1000pm leaving at 1230pm is unacceptable from their biggest airport world hub. Another aircraft could have been used such as the aircraft scheduled to be used in the morning for that exact same route. Yes, I did get me there but the lack of sleep the next day didn't help me enjoy my entire trip since I was busy with activities during the weekend. This can be and is expected from Spirit (going bankrupt) and Frontier (despite they're nickel and dimers). But from Delta's World Hub? That's totally unacceptable!

This flight was straightforward and without difficulty. Service was OK, but I continue to be underwhelmed by level of attention given to Sky Priority passengers.

It would’ve been nice for all that money to have a more substantial snack for free. I remember once upon a time getting a very nice turkey sandwich with Swiss cheese on whole wheat bread for no charge along with a drink. I guess those days are gone. it’s a little insulting being given a cookie or a bag of baked chips Going forward I’ll just bring my own.

Alaska was fine as usual. My frustration came with accessing boarding passes. On the first trip, I could only get one to print ans took a picture of the second one. On our return trip, the system was down? Friends who booked directly with Alaska had theirs process. I even tried the 800 number and had others try it too. It said something in Spanish and hung up. The agent at the airport succeeded.

Delayed and cancelled flights were hard and very stressful, both ways!

The crew was quite good, they came by often with drinks or to collect trash. But what wasn't nice was the flight was over weigh and several people had to be rebooked. I was questioned whether I should have a seat when I was getting to it. The in-flight entertainment kept buffering and interrupting. And the route took the airplane through high winds which caused us a longer flight

Wasn’t on the flight due to Alaska cancellation…also after all the rerouting, I was going to be on a later flight that left SFO at 7:47pm, which meant an almost 6 hour layover. That same Hawaiian flight was delayed for another 2hours.

I had to cancel the flight because with a 3 hour delay for 'unexpected maintenance' in getting to LAX, I couldn't connect to an overseas flight that I had booked on Scandinavian Air.

The flight was CANCELED!!! Can’t get much more “poor” than that. I had to switch to American Airlines, add another layover and got home in Honolulu 4 hours later than I was supposed to be home. One bright spot was Josh with Alaska Airlines at SFO. He got me on a United Flight that got me home a few hours before I would have. Without him I would have gotten home almost 7 hours after my originally scheduled flight.

Canceled my flight within 24 hours, causing me arriving home midnight. Will never book Hawaiian airlines anymore

I like Hawaiian, it was great that they had good internet connection across the Pacific Ocean, thanks to Star Link satellites. The seating was comfortable, ( I was in economy ). Maybe I missed it, but I only got offered a beverage once. It was a nonstop flight KOA to SMF. I would take it again next time I go that way.

I always love flying Hawaii and I have nothing to add

Previously flown Hawaiian Airlines on similar routes, I found Alaska Airlines to be noticeably more comfortable. The seats on Alaska Airlines provided better support and cushioning, which made a significant difference on the long flight to the islands. When you’re spending 5-6 hours in the air, seat comfort really matters, and Alaska Airlines delivered where it counts. After comparing both carriers, I’ve decided to book with Alaska Airlines for all my future Hawaii trips. The superior seat comfort alone makes it worth choosing Alaska over Hawaiian Airlines. If you’re planning a trip to Hawaii and prioritizing comfort, I’d recommend giving Alaska Airlines a try. You won’t be disappointed. Highly recommended for Hawaii travel!

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

Always wish for more healthy, gluten free options. We have to bring our own.

Having a long layover, I was very appreciative of the ability to stand by for an earlier flight. Other airlines like Delta have refused this to me in the past, just to be mean (because my ticket class wasn't high enough). United went out of their way to help me get to my destination early, which I really appreciated given that it was the third leg of a 24+ hour journey for me.

Other than a way way too cold cabinets for the entire flight, all was great

One bag is incorrect and not acceptable for an international flight. The food was not just good. I won't fly with them again.

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

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

Crew and customer service were excellent. This flight also had plenty of leg room and seat mounted screens for entertainment. A very pleasant flight all around!

It would have been better if the crew has supported my husband's reasons for needing to keep the space clear around his feet, rather than insisting that he put his knapsack in that space.

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

Information on your arrival and departure airports