RDM - CHI

$139 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 10/1. 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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Flights 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

Sat, Aug 16 - Sat, Aug 23
Hawaiian Airlines Logo
12:58 pm - 11:39 pmRDM-ORD
8h 41m1 stop
Hawaiian Airlines Logo
6:20 am - 11:19 amORD-RDM
6h 59m1 stop
$252Hawaiian Airlines
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Tue, Aug 5 - Wed, Aug 13
Hawaiian Airlines Logo
12:58 pm - 11:39 pmRDM-ORD
8h 41m1 stop
Hawaiian Airlines Logo
6:00 am - 12:44 pmORD-RDM
8h 44m1 stop
$278Hawaiian Airlines
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Wed, Aug 6 - Tue, Aug 12
Alaska Airlines Logo
3:51 pm - 11:39 pmRDM-ORD
5h 48m1 stop
Alaska Airlines Logo
6:00 am - 12:44 pmORD-RDM
8h 44m1 stop
$279Alaska Airlines
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Wed, Oct 29 - Sat, Nov 1
Delta Logo
6:20 am - 8:58 pmRDM-ORD
12h 38m2 stops
Delta Logo
5:00 pm - 10:20 pmORD-RDM
7h 20m1 stop
$284Delta
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Wed, Sep 17 - Sun, Sep 21
Hawaiian Airlines Logo
11:08 am - 10:07 pmRDM-ORD
8h 59m1 stop
Hawaiian Airlines Logo
6:20 am - 11:19 amORD-RDM
6h 59m1 stop
$288Hawaiian Airlines
Find Deal
Wed, Aug 6 - Thu, Aug 14
Alaska Airlines Logo
1:38 pm - 11:59 pmRDM-ORD
8h 21m1 stop
Alaska Airlines Logo
6:00 am - 12:44 pmORD-RDM
8h 44m1 stop
$289Alaska Airlines
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Wed, Oct 29 - Sat, Nov 1
Delta Logo
7:25 pm - 8:45 amRDM-MDW
11h 20m2 stops
Delta Logo
1:00 pm - 10:44 pmMDW-RDM
11h 44m2 stops
$289Delta
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Thu, Aug 7 - Mon, Aug 11
American Airlines Logo
1:55 pm - 10:43 pmRDM-ORD
6h 48m1 stop
American Airlines Logo
2:30 pm - 7:48 pmORD-RDM
7h 18m1 stop
$299American Airlines
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Tue, Aug 5 - Wed, Aug 13
American Airlines Logo
1:35 pm - 12:52 amRDM-ORD
9h 17m1 stop
American Airlines Logo
6:00 am - 11:42 amORD-RDM
7h 42m1 stop
$326American Airlines
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Tue, Dec 23 - Tue, Dec 30
United Airlines Logo
7:40 pm - 5:10 amRDM-ORD
7h 30m1 stop
United Airlines Logo
6:15 am - 3:07 pmORD-RDM
10h 52m1 stop
$463United Airlines
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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 May, where tickets cost $337 (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
High seasonNovember
Cheapest flight$139
Best time to beat the crowds but there is an average 54% increase in price.
Most popular time to fly and prices are also 0% 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 $139 for a one-way ticket and $252 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?

    SkyTeam, oneworld, and Star Alliance are the airline alliances operating flights between Redmond and Chicago, with oneworld 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 $523 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 $391 and an overall rating of 8.0.

  • 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 10000 reviews
7.1Entertainment
8.1Boarding
7.8Comfort
8.5Crew
7.1Food
Airline reviews

Friendly staff, everything went smoothly. Gluten free snacks would would be the cherry on top!

10.0 ExcellentAnonymous, Jul 2025RDM - PDX
Read more Alaska Airlines reviews

Friendly staff, everything went smoothly. Gluten free snacks would would be the cherry on top!

We have always flown with Alaska when we can. As they have great customer service. This trip we had to transfer to Air LINGUS in Denver to go to Dublin. That’s where things went bad! Our checked luggage didn’t arrive. The process to make a claim was way more complicated than it should be. It took 5 days to recover our luggage. The whole time we couldn’t talk to a real person who could tell us anything. The whole time Alaska blamed Air lingus and vis a versa. No one seemed want to help us. That was the worst part.

I'm a platinum member with American Airlines, however, my ticket did not display status and thus I did not board with an early group. I traveled with my two daughters and we were given a row of seats that did not recline. Not the treatment I would have expected for a platinum customer. The flight was also a bit late leaving Portland. Also on my flight to Portland we were not given premium seats. In fact, we were in the last row of the aircraft.

It was fine. 2 hour delay due to mechanical issue. I understand issues will occur, just wish instead of Capt repeatedly telling us we will be getting off the ground “momentarily” they would just be honest and either say they have no idea-or it’s going to be a few hours! All in all FAs are usually pretty nice :)

I was at risk of not getting on the flight, as when I presented my boarding pass at the gate, it showed me as not having checked in. I was sent to the desk as the last of the other passengers boarded. The agent there said he could see that I had done all of my part and allowed times recommended, but it showed me as not checked in and he couldn't figure out how to correct it. He actually asked them to hold the flight as he struggled with it. He called for support, someone corrected it, and he printed boarding passes for both flights to reduce further issues. I did get on, and needed to ask someone to exit my seat.

We had a birthday one day off and almost missed the plane Our fault

5 hour delay from Portland to Newark. Boarded and then were told we had to get off and wait five hours for flight. No food vouchers or any other compensation because they said it was an air traffic control issue. Plane is bare minimum like a discount airline. They have free entertainment but you have to get to it on your own device no screens in the seats

Alaska app and website had numerous problems so couldn’t get boarding passes or check seats

Very good. Gate personnel were excellent flight attendants were also able to change my seat at the last minute everyone, courteous, polite, and.

It was horrible. Last minute gate change, delays, more delays and then we had to wait for a stweardess to onboard. No explanation for the wait. No apologies. We got to RDM way past schedule @ 1:30 am!!!! Stressful and exhausting. We'd avoid flying Alaska ever again.

Everything was good until we were boarding our connection flight in Atlanta, we were told to gate check our carry-on, but when we got inside the plane, there was plenty of room in the overhead.

Did not know my son and I had different seating arrangements. He was fine, but it was disappointing.

Flight was canceled, and no effort was made to help with rebooking, no hotel vouchers, no car transportation and minimal food voucher and most places for food were closed by the time the voucher was given. Waited for 3 hours for bags. Simply the worst travel experience I have ever had

Food was surprisingly good but the WiFi was not great

this crew didn't care much. bumping carts into seats more times than i care to remember

Very late arrival at PWM. Late jet getting to ATL. Equipment problem with aircraft - could not get enough water onto plane., Another delay getting FAA approval for flight with bottled H2O. Not the crew’s problem.

Everything was fine except the entertainment was not working for half of the flight.

Easy boarding with an extremely kind attendant. Seats were spacious and we had 3 seats for 2 people so we could stretch out. Comfortable air flow and very attentive and hospital attendants. Bathrooms and food were the only negative. Bathrooms were so small you could hardly get in and close the door. I don’t think an obese person would fit or a person with a movement disability. Food was the trending food for flights, nonexistent. We spent $40 getting sandwich and snack at airport for our 6 hour flught.

At first, we were on the runway for about an hour, literally. The Captain did explain that the Control Tower just had a change shift (sounds like an unrealistic excuse) and then that we had to change a runway. A regular economy seat is made for 12 yo twiggy. I understand Delta wants to push for an upgrade, but after sitting in a Comfort seat and in First class. I would say First class is not worthy of my money. The landing was delayed because of the weather in NYC, I don't hold that against Delta, of course. The Captain did alert us to that upon takeoff in Vegas and again as we reached NY.

No one fussed at me about my pap machine as a 3rd pice on the plane. Boarding was pleasant and smooth. The boarding agent in Anchorage was a fun character- he could be in a movie. :~) The on-board crew were downright pleasant. No militant attitudes on Delta. Like all planes these days the seats are too narrow for standard Americans and at 5’2” there is barely enough leg room. I don’t know how tall people fold themselves into the seats. But that’s nothing specific to Delta

I was put in seat 6B with no warning. Had no seat in front of me just sticks out in the aisle so I had to hold what I could and put the rest in a bin way further down.

I was traveling with my two young children and brooked this flight as it was the best option. There were no screens for movies etc. which normally would be fine, however, when you list free in flight entertainment that should be mentioned. We don't rely on them but count on it as a worst case scenario backup for the kids to keep the peace if needed. The main issue though was the food selection. I have dietary restrictions so I was excited to preorder meals. Nothing that was offered on board or for preorder was ok for me to eat, not even the snack boxes. It was very frustrating for a 5+ hour flight. Otherwise the flight was good and went smoothly.

Usually we have a pleasant trip on HA. Not this time! All stewards were unpleasant, rude, rushed, condescending. First step onto the plane, WE greeted the crew with an “Hello!”. They greeted us with a terse smile then ignored us. Not a good start. Even over the PA announcements, they were rushed and unpleasant. One Stewart even berated a passenger in front of us when all they asked is if the purchase cart had vodka to purchase. The steward said “LIKE WE SAID OVER THE PA, THIS ONLY HAS FOOD OR BEVERAGE!” Vodka is a beverage! It was a legitimate question. Not sure why she treated the passenger this way. Taking trash was even unpleasant, No “Thank you” or at least a smile. I work in CS. I know good CS can make or break your trip. There was absolutely no “aloha” on this trip. All clearly did not want to be on this plane and felt strongly that they did not want to provide a premium service to their clients. This might be our last HA and cancellation of my HA-MC if we are treated the same way going home. We are typically treated with kindness and warmth in the past with HA. This trip was unacceptable.

Plenty of overhead compartment room. The seat choice option is horrendous as best.

Really disappointed with in flight entertainment, 6 hr flight with no built in screens

I was put in a middle seat with the people on either side of me kept passing their grandchild over me and talking back and forth while I was trying to rest or watch a movie. So inconsiderate and totally disturbing. I asked if they would sit next to each other to alleviate the constant impeding my comfort but they refused.

The flight crew were great. Very helpful and friendly. Seats comfy. Thanks

Overall it was a good flight, but the food should be looked at. No options. The seat was also uncomfortable and very tight.

Late boarding, full flight. Absolutely no food and barely a bag of pretzels. No video screens and slim pickings of movies. No live tv and poor selection of shows.

It’s great, I’ve always fly & ride with Hawaiian Airlines going Inter island or to the mainland.

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.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The first flight was better in terms of the aircraft.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

There's just no way to sit fully upright and comfortably in these seats. There needs to be 2 more inches of room, and that's not something that only one person on the flight needs - the whole flight needs 2 more inches of room. If that means you sell 6 less seats, so be it. It's too close for anyone. Forcing people to pay for "premium" economy just to get "barely enough space to breathe" isn't really an answer to that.

The crew were very nice. The Chocolate is good and v there’s no entertainment. Thanks

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