RDM - CHI

$109 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 5/24. 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.
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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 Flight Deals 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.

Recent round-trip flight deals from Redmond to Chicago

KAYAK's recommended round-trip deals from the most popular airlines that fly from Redmond to Chicago.
Discover the best prices for you by selecting your travel dates on KAYAK.
Hawaiian Airlines Logo
1:25 pm - 10:23 pmRDM-ORD
6h 58m1 stop
Hawaiian Airlines Logo
6:00 am - 11:01 amORD-RDM
7h 01m1 stop
$211Hawaiian Airlines
Find Deal
Sat, May 24 - Sat, May 31
United Airlines Logo
1:55 pm - 12:59 amRDM-ORD
9h 04m1 stop
United Airlines Logo
6:48 am - 12:11 pmORD-RDM
7h 23m1 stop
$219United Airlines
Find Deal
Sat, May 24 - Sun, May 25
Delta Logo
6:00 am - 2:10 pmRDM-ORD
6h 10m1 stop
Delta Logo
4:30 pm - 10:12 pmORD-RDM
7h 42m1 stop
$220Delta
Find Deal
Sat, May 24 - Sat, May 31
Delta Logo
11:20 am - 9:40 pmRDM-ORD
8h 20m2 stops
Delta Logo
4:30 pm - 10:12 pmORD-RDM
7h 42m1 stop
$225Delta
Find Deal
Sat, May 24 - Sat, May 31
Delta Logo
7:10 am - 9:40 pmRDM-ORD
12h 30m2 stops
Delta Logo
7:30 am - 6:49 pmORD-RDM
13h 19m2 stops
$230Delta
Find Deal
Sat, May 24 - Sat, May 31
Delta Logo
7:29 pm - 8:36 amRDM-MDW
11h 07m2 stops
Delta Logo
9:20 am - 6:49 pmMDW-RDM
11h 29m2 stops
$230Delta
Find Deal
Sat, May 24 - Sat, May 31
Alaska Airlines Logo
8:00 am - 11:56 pmRDM-ORD
13h 56m2 stops
Alaska Airlines Logo
7:00 am - 12:32 pmORD-RDM
7h 32m1 stop
$274Alaska Airlines
Find Deal
Sat, May 24 - Sun, May 25
Hawaiian Airlines Logo
1:38 pm - 11:59 pmRDM-ORD
8h 21m1 stop
Hawaiian Airlines Logo
6:00 am - 12:44 pmORD-RDM
8h 44m1 stop
$280Hawaiian Airlines
Find Deal
Mon, Jun 30 - Wed, Jul 2
Delta Logo
7:00 am - 5:20 pmRDM-ORD
8h 20m1 stop
Delta Logo
7:40 am - 6:50 pmORD-RDM
13h 10m2 stops
$284Delta
Find Deal
Wed, Jul 16 - Sat, Jul 19
Alaska Airlines Logo
6:21 pm - 6:55 pmRDM-ORD
22h 34m1 stop
Alaska Airlines Logo
6:00 am - 11:01 amORD-RDM
7h 01m1 stop
$296Alaska Airlines
Find Deal
Fri, Jun 6 - Mon, Jun 9
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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 $346 (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$109
Best time to beat the crowds but there is an average 42% increase in price.
Most popular time to fly and prices are also 7% 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 $109 for a one-way ticket and $211 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 $572 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 $397 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.

Top 3 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 9972 reviews
8.5Crew
7.9Comfort
7.1Food
7.1Entertainment
8.1Boarding
Airline reviews

OUr pilot was very good and also a good landing in a very gusting Phoenix. Most important.

8.0 ExcellentAnonymous, Apr 2025PDX - PHX
Read more Alaska Airlines reviews

OUr pilot was very good and also a good landing in a very gusting Phoenix. Most important.

Boarding was quick and easy as always the crew is on their game as always I always have an enjoyable flight so I’m good.

It was alright other than the changes in the Alaska Lounge. That and the migraine I had were disappointing. Other then that everything went well.

It was a short flight so no refreshments or entertainment which was fine.

Flying in both directions across country the gate designated on my boarding pass was wrong. From w to e across the country the passenger next to me coughed the entire way.

Although both planes (flights) had mechanical issue delaying both of my flights, the crew members handled everything with ease. Both flights had the smoothest take off and landing. I opted to upgrade my seat to first class and really lucked out getting the seat at the very front of the plane. Awesome treat to myself. I really enjoyed my flight.

The staff from check-in counter to the flight crew were great. Flight was right on schedule. 10/10

Changed flight from San Fran to Seattle Then with a Delayed takeoff barely made my connection Waited over an hour for luggage 😜

It was good. There was a mistake made in Seattle. Somehow we were bumped out of our seats as if we weren't on the flight anymore. The woman at the gate caught it and announced our name to come up and she fixed it.

I wouldn’t fly with Alaska again if you paid me.

Flight was delayed due to weather. Crew did a nice job of making us comfortable. No complain complaints.

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

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

The crew were very nice. I would have appreciated a pillow for comfort. I had a special meal that was sloppy, but the salad was great. Thanks

The plane was in Moline all night. Consequently, we assumed an on time departure at 8:15am. Unfortunately, and as is the normal case with United in Moline, we departed 2.5 hours late. When the crew came, it was discovered that there was very little heat in the plane. Seems this should have been checked hours before the crew arrived. Then when we boarded and the plane was to be de-iced, the United de-icing truck was not working! We awaited the American Airlines truck. All of this caused us to miss our connection in Chicago. My suggestion is never take United Airlines flight from Moline. We have been disappointed 80% of the time and have vowed to not take United again from Moline.

Flight was delayed two hours. No snacks and no tv screens. My bag got stuck in Chicago

The aircrew was solid, the flight was chill, I had no issues. The gate agent was not the best. I was trying to use a military bag upgrade to move my bag from under the seat to the overhead bins and he told me there’s no overhead bins on the plane, argued with me why booking put a military member in basic economy (I don’t really understand this) and made it an issue to even try to help me stating I’d have to call reservations to get a bag upgrade. When every other agent with United can add it at the gate, this man couldn’t be bothered.

They canceled our flight and left us stranded to figure it out

Everything was very good. Was able to change a make run flight leaving on direct earlier in the app -seamless!!! Well done

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

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