RDM - CHI

$132 Find Cheap Flights from Redmond to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Redmond to Chicago departing on 11/11. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Redmond to Chicago, 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 Redmond to Chicago, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$273
Overall average: $612
Delta
Tue 11/11Fri 11/14
RDM - ORD • 1 stop
Cheapest one-way
$132
Typical prices: $165-$218
Delta
Tue 11/11
RDM - ORD • 1 stop
Top airlines
Delta
Cheapest • from $273 (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 • 37% price drop
August
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 Chicago!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Redmond to Chicago (RDM-CHI)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Redmond to Chicago 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 Redmond to Chicago

Tue, Nov 11 - Fri, Nov 14
Delta Logo
7:00 am - 5:18 pmRDM-ORD
8h 18m1 stop
Delta Logo
2:12 pm - 6:54 pmORD-RDM
6h 42m1 stop
$273Delta
Find Deal
Tue, Nov 11 - Fri, Nov 14
Delta Logo
7:34 pm - 10:01 amRDM-ORD
12h 27m2 stops
Delta Logo
2:12 pm - 6:54 pmORD-RDM
6h 42m1 stop
$278Delta
Find Deal
Tue, Nov 11 - Fri, Nov 14
Delta Logo
7:34 pm - 10:01 amRDM-ORD
12h 27m2 stops
Delta Logo
7:20 am - 6:54 pmORD-RDM
13h 34m2 stops
$284Delta
Find Deal
Tue, Nov 11 - Fri, Nov 14
Delta Logo
7:34 pm - 9:01 amRDM-MDW
11h 27m2 stops
Delta Logo
1:15 pm - 10:53 pmMDW-RDM
11h 38m2 stops
$284Delta
Find Deal
Mon, Nov 17 - Wed, Nov 19
Alaska Airlines Logo
4:00 pm - 6:22 amRDM-ORD
12h 22m2 stops
Alaska Airlines Logo
8:00 am - 8:58 pmORD-RDM
14h 58m1 stop
$288Alaska Airlines
Find Deal
Sun, Nov 16 - Wed, Nov 19
Alaska Airlines Logo
5:57 pm - 6:22 amRDM-ORD
10h 25m1 stop
Alaska Airlines Logo
8:00 am - 3:20 pmORD-RDM
9h 20m2 stops
$298Alaska Airlines
Find Deal
Sun, Nov 16 - Wed, Nov 19
Delta Logo
7:00 am - 5:18 pmRDM-ORD
8h 18m1 stop
Delta Logo
2:12 pm - 6:54 pmORD-RDM
6h 42m1 stop
$302Delta
Find Deal
Thu, Mar 12 - Mon, Mar 16
United Airlines Logo
6:35 pm - 5:03 amRDM-ORD
8h 28m1 stop
United Airlines Logo
2:09 pm - 9:26 pmORD-RDM
9h 17m1 stop
$319United Airlines
Find Deal
Wed, Nov 26 - Sun, Nov 30
United Airlines Logo
1:17 pm - 11:59 pmRDM-ORD
8h 42m1 stop
United Airlines Logo
12:15 am - 9:07 pmORD-RDM
22h 52m1 stop
$1,218United Airlines
Find Deal
Tue, Nov 25 - Sun, Nov 30
Multiple Airlines Logo
7:15 am - 10:29 pmRDM-ORD
13h 14m2 stops
Multiple Airlines Logo
7:00 am - 3:16 pmORD-RDM
10h 16m1 stop
$1,225Multiple Airlines
Find Deal
Booking Insights

KAYAK's insights & trends for Redmond to Chicago flights

Get data-powered insights and trends into flights from Redmond to Chicago 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 Redmond to Chicago?

The average price of all round-trip flights from Redmond to Chicago clicked on KAYAK for each day over the last 12 months.

When flying from Redmond to Chicago, you should consider leaving on a Thursday and avoid Mondays if you are looking for the best rates. For your return to Redmond, you’ll find the best rates on Fridays and the most expensive ones on Sundays.

What is the cheapest month to fly from Redmond to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Redmond to Chicago, 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 Redmond to Chicago is January, where tickets cost $280 (return) on average. On the other hand, the most expensive months are February and March, where the average cost of round-trip tickets is $749 and $609 respectively.

Good to know

Low seasonFebruary
Cheapest flight$132
Best time to beat the crowds but there is an average 67% increase in price.
Most popular time to fly and prices are also 10% lower on average.
Flight from Redmond to Chicago O'Hare Airport

When to book flights from Redmond to Chicago

Are your dates flexible? Find out the best times to travel from Redmond to Chicago 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 Redmond to Chicago

  • What is the cheapest flight from Redmond to Chicago?

    In the last 3 days, the lowest price for a flight from Redmond to Chicago was $132 for a one-way ticket and $273 for a round-trip.

  • Do I need a passport to fly between Redmond and Chicago?

    No, a passport isn't needed to fly from Redmond to Chicago. However, local authorities might ask for an official ID.

  • Which aircraft models fly most regularly from Redmond to Chicago?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Redmond to Chicago?

    Star Alliance, SkyTeam, and oneworld are the airline alliances operating flights between Redmond and Chicago, with Star Alliance being the most commonly used for this route.

  • Which is the best airline for flights from Redmond to Chicago, Alaska Airlines or Delta?

    The two airlines most popular with KAYAK users for flights from Redmond to Chicago are Alaska Airlines and Delta. With an average price for the route of $464 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 $368 and an overall rating of 7.9.

  • How does KAYAK find such low prices on flights from Redmond to Chicago?

    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 Redmond to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Redmond to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Redmond 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 Redmond to Chicago?

    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 Chicago with an airline and back to Redmond with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Redmond to Chicago?

    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 Chicago from Redmond 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 Redmond to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Redmond to Chicago. 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 Redmond to Chicago? 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 11095 reviews
7.0Entertainment
8.1Boarding
7.8Comfort
8.5Crew
7.1Food
Airline reviews

Process of checking bag, boarding, etc. was all very quick, easy, and streamlined. Only problem I had was the seating: very cramped and uncomfortable, but I suppose that’s the perils of coach. Thankfully it wasn’t a super long flight so it didn’t ruin the experience overall.

6.0 GoodAnonymous, Oct 2025PDX - MCI
Read more Alaska Airlines reviews

Process of checking bag, boarding, etc. was all very quick, easy, and streamlined. Only problem I had was the seating: very cramped and uncomfortable, but I suppose that’s the perils of coach. Thankfully it wasn’t a super long flight so it didn’t ruin the experience overall.

The boarding was confusing because the PA system at PDX was so quiet you couldn’t hear anything being said . The seats were uncomfortable. The food was pretty bad and I normally don’t mind airplane food. The flight attendants were not friendly. I learned upon check in that Hawaiian airlines had reassigned our seats of the second leg of the trip. I had confirmed and paid for special seats but they put me and my companion on standard seats in different rows. Hawaiian also did the same on my return flight after the flight times had changed. I happened to go online to check my reservation and saw the flight had changed. I gad received no notice. I saw that my confirmed seats that I had paid extra were gone. After much back and forth with the airlines they refused to correct their error. I showed them confirmation documents of my seat reservation and receipt of payment but they refused to correct the seat change or reimburse me. I had to pay $200 again to reserve the original seats. Shameful and manipulative. They basically held me hostage. If I wanted to be in that flight I had to pay up.

When I bought my tickets I up great my seats for extra $104 each seats 8A and 8B in the way back from Portland to Palm Springs they gave me the seats 15. I thought it was for round trip same seats . So I was very disappointed ☹️

One disappointment. There was a gate change from B8 to B10, they had announced it maybe 20 minutes before the boarding time, possibly less. I didn’t hear the announcement as I was listening to music on my head phones at B8. At the boarding time, I got up and asked the gal at the B8 boarding desk, why the destination sign had not changed and if the flight was delayed as there was no plane behind her through the window, she said that perhaps the flight was delayed and the screen will probably update in -5 minutes ( she apparently didn’t know the boarding gate was changed ( 2 down from our location) I put my headphones on and went back to sit down . Just before the B10 door closed, I got a phone call asking me if I was still taking the flight, I said. “Yes” but I was at the gate stated on my ticket B8, then I was informed of the gate change, I got up and ran to the gate, and down the hallway to the jet ramp. I was the last to board!! Very frustrating . I was shocked that I got no emails or text messages from Alaska informing me of a last minute change!!

The crew was the best I’ve ever had HOWEVER when we arrived in Salt Lake City there were no Alaskan Airline employees to be found so we weren’t able to leave the plane until ANOTHER airline took pity on us. How could that possible happen?

The pilot performed the smoothest landing I’ve ever experienced. What a light touch. And I’m an avid traveler!

They closed boarding too early. They made me pay extra to continue flying with them. Their customer service is non-responsive. I used to love Alaska Airlines, but they've definitely regressed.

The vibe and energy of the Alaska staff on ground in Redmond is some of the best we’ve seen!

Didn't buy food and did not use entertainment as these were not the purpose of my flight.

Website could be better with faster access to specific flight information and boarding pass once reservation is made. Not a fan of no seat selection on line. I had to consult gate agent each time to change seats on flights with lots of open seats. This cannot possibly be cost effective for airline. On plus side, Alaska seat legroom seemed larger than American. ns

Delayed flight (1hour) plus a long layover after an overnight flight with no backup plane available.

We were delayed, which I think had to do with air traffic control. Otherwise, everything was great.

The boarding process needs to be refined. Sometimes the gate crew calls out the zones and then flip to showing the.zones boarding on the gate monitor display. So, unless you are huddled around the gate lanes watching the monitor, you could miss your boarding zone. Suggest the zones be announced each time a new zone is allowed to board.

The boarding process needs to be refined. Sometimes the gate crew call out the boarding zone, and then flip to the monitor to show which zones are boarding. So unless everyone is gathered around to see the monitor there is usually confusion as wi which zones are boarding.

On time flight. Seat comfort could be better in the Comfort section.

My issue was with TSA agents for delta airlines. My luggage got flagged. The agent was going thru another persons first. He took 20 min to go thru hers. I asked them to bring mine closer so I could sit down . They said you can go sit it will be fine. I said I am supposed to keep my eyes on my bags at all times. The agent was meticulously unwrapping 2 gifts that the lady had and then tried to re warp it. He was trying to be kind i get it but 20 min for me to stand watching him do that was ridiculous. It was 6 am and there were a ton of travelers. Mine was flagged for some air packed tea that I bought in Turkey. My previous delta flight and 2 others before didn’t flag it. Consistency would be nice. Also on the flight the window shades were down for take off and landing - I thought that was very odd I thought they had to remain open for take off and landing.

The flight was an hour and a half late departing which was inconvenient

Delay in SLC jammed us up in Chicago. Got caught up in rush hour traffic

The crew took good care of us. The flight from ATL to SFO is a longer one, and there were multiple beverage offerings. I like the 757's that Delta uses. Good airplane that is comfortable. I do wish Delta would separate Priority boarding from the better seats. I would gladly take a smaller seat in an open row than be jammed into Comfort just to get priority boarding, just to make sure I don't have to check a bag.

The flight was great. The gate location was way to far away!!!

The food options were limited and very specific. Some type of entertainment option for a 4.5 hour flight would have been nice.

Flight was smooth and comfortable. We were able to check a bag at counter due to full flight and boarded with an earlier group. We were there very early and didn’t hear the gate change just noticed our flight was no longer displayed st the gate. There were two other flights with gate shuffles - may be unavoidable but not desirable. First time I had to print my own luggage tag and attach at arrival. Not a fan of that process.

The crew was EXTREMELY helpful And sweet and the flight was smooth!

I received an email from Kayak with confirmation number for Hawaiian and another for Alaska. I received emails from Kayak for both my outbound and return flight to say "time to check in." Despite trying each number (Hawaiian and Alaska), I could not check in for outbound or return. It was then confusing at the airport - I hda "no place to go" to figure out how to check in. All the kiosks are marked "scan bag,etc." I wandered around with no agent to talk to. That was a bit stressful. Either Kayak, or airline, needed better communication on what to expect and to do.

Everything was great and smooth. Given the short flight there was no entertainment but the rating does not give this option. My first flight with Hawaiian was a success all around.

When I purchased my ticket, it said i was flying with Hawaii airlines. Which is now operated by Alaska. Naturally I went to check in with Hawaii airlines once at the airport. However, there was no one at the desk until 7 am and their kiosk couldn’t find my tickets. I went over to Alaska and they said they couldn’t help me and to wait for Hawaii. My flight left at 7:15 so I didn’t have time to wait. They even told me to ask United which was next to the Hawaii desk what time Hawaii opened. I called the Hawaii airlines number and the operator told me to ask Alaska for help since my flight was operated by Alaska. So I went back and almost got brushed off again and sent to Hawaii. The Alaska desk attendant told me to check in at their kiosk but it didn’t work. I ran over to an older lady who was helping check bags and asked for help printing my boarding passes. Thankful she was able to do it right away! This whole debacle took a little over an hour. I wish there was better communication and knowledge between the two airlines because it could have been easily handled if everyone between the two airlines was on the same page. Once I ran through the airport to get to my gate, we were greeted with a smile and they seemed glad we made our flight! We were the last to board and barely made it. After the headache our flight was great! No complaints there.

Biggest issue: awfully narrow seats, + not a lot of leg room. Other than that, everything was good. Cabin crew seemed like very nice people.

The Kayak confirmation number did not work for checking in the day before. I checked in at 8.30 using my ticket number. When I arrived at the airport, I was informed that the flight was overbooked, and since I had checked in late, I did not have a seat. The Next flight was not until ten PM. I called my wife, who had been taking care of our kids all weekend, and she was upset, calling me a liar and telling me to stay in SD. It turned my weekend getaway into a nightmare! I blame the Kayak website and will not book flights using your app in the future.

comfortable but the food is horrible. I have flown Hawaiian several times now and no matter what they say the food is its the same squashed bread with melted goop inside. Tastes fake and isnt what they represent, its quite nasty. What happend to real food? And there is NO entertainment!! so not sure why they are asking for a review on that.

Good and friendly staff. Nicely enjoyed the complimentary drink and snack.

Better WiFi. I cannot understand that in 2025, United is so behind on a technology that is now a necessity and still painfully unreliable, slow and keeps disconnecting.

Trip was great. A wild landing in Ottawa with the wind and rain, but the pilot did a great job. Always love flying United.👍

Excellent experience. Starting with the agent at the Premier bag drop who noticed I was very early for my scheduled flight and offered to rebook me on an earlier flight with my seat preference. She would not let me leave the counter until she knew that all of the changes and new boarding pass showed up on my United app. At the gate, the flight boarded quickly such that we departed early and the flight was smooth. We arrived 20 minutes early at ORD and I was able to be home in time for dinner. One of the best flights I've had.

Salina to travers city was great! But the sept 24 Tranverse city was not! Traverse city to chichago was cancelled, i went to Denver & got to Salina 6 hours later!

See previous note about the passenger in Denver who threw my husband's bag out of the overhead bin in order to maker room for his own. And the flight attendant back up the new passenger.

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

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

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