RDM - CHI

$133 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 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 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
$279
Typical prices: $320-$547
Alaska Airlines
Sat 1/24Tue 1/27
RDM - ORD • 1 stop
Cheapest one-way
$133
Typical prices: $149-$266
American Airlines
Thu 1/15
RDM - ORD • 1 stop
Top airlines
Alaska Airlines
Cheapest • from $279 (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 • 31% price drop
August
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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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

Sat, Jan 24 - Tue, Jan 27
Alaska Airlines Logo
1:34 pm - 11:50 pm
RDM
-
ORD
8h 16m1 stop
Alaska Airlines Logo
3:35 pm - 9:15 pm
ORD
-
RDM
7h 40m1 stop
$279Alaska Airlines
Sat, Jan 24 - Tue, Jan 27
Alaska Airlines Logo
1:34 pm - 11:50 pm
RDM
-
ORD
8h 16m1 stop
Alaska Airlines Logo
6:06 pm - 12:30 pm
ORD
-
RDM
20h 24m2 stops
$286Alaska Airlines
Fri, Feb 6 - Tue, Feb 10
Alaska Airlines Logo
8:45 am - 11:50 pm
RDM
-
ORD
13h 05m1 stop
Alaska Airlines Logo
3:35 pm - 9:15 pm
ORD
-
RDM
7h 40m1 stop
$291Alaska Airlines
Fri, Feb 6 - Tue, Feb 10
Alaska Airlines Logo
3:57 pm - 2:38 pm
RDM
-
ORD
20h 41m2 stops
Alaska Airlines Logo
6:06 pm - 11:52 pm
ORD
-
RDM
7h 46m1 stop
$296Alaska Airlines
Thu, Jan 29 - Mon, Feb 2
Alaska Airlines Logo
8:45 am - 5:10 pm
RDM
-
ORD
6h 25m1 stop
Alaska Airlines Logo
8:00 am - 11:52 pm
ORD
-
RDM
17h 52m1 stop
$304Alaska Airlines
Sat, Jan 24 - Tue, Jan 27
Alaska Airlines Logo
1:34 pm - 11:50 pm
RDM
-
ORD
8h 16m1 stop
Alaska Airlines Logo
3:35 pm - 10:46 pm
ORD
-
RDM
9h 11m2 stops
$306Alaska Airlines
Thu, Jan 29 - Mon, Feb 2
Delta Logo
5:50 am - 5:55 pm
RDM
-
MDW
10h 05m2 stops
Delta Logo
1:51 pm - 11:52 pm
MDW
-
RDM
12h 01m2 stops
$384Delta
Sun, Jan 4 - Tue, Jan 20
United Airlines Logo
7:15 pm - 5:27 am
RDM
-
ORD
8h 12m1 stop
United Airlines Logo
2:36 pm - 9:21 pm
ORD
-
RDM
8h 45m1 stop
$386United Airlines
Fri, Feb 6 - Tue, Feb 10
Delta Logo
7:00 am - 10:22 pm
RDM
-
MDW
13h 22m2 stops
Delta Logo
9:53 am - 4:31 pm
MDW
-
RDM
8h 38m2 stops
$476Delta
Sun, Jan 4 - Tue, Jan 20
Delta Logo
6:05 am - 5:19 pm
RDM
-
MDW
9h 14m2 stops
Delta Logo
1:49 pm - 10:47 pm
MDW
-
RDM
10h 58m2 stops
$1,009Delta
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.

How much is a round-trip flight from Redmond to Chicago?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Redmond to Chicago departing in January.

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 March and February, where the average cost of round-trip tickets is $609 and $570 respectively.

Good to know

Low seasonFebruary
Cheapest flight$133
Best time to beat the crowds but there is an average 39% increase in price.
Most popular time to fly and prices are also 2% 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 $133 for a one-way ticket and $279 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, Star Alliance, and oneworld are the airline alliances operating flights between Redmond and Chicago, with SkyTeam 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 $439 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 $318 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 11474 reviews
7.8Comfort
8.5Crew
8.1Boarding
7.1Food
7.0Entertainment
Airline reviews

I liked that I made it onto the flight rather than “missing” the connection. We left PDX early in the morning along with half of Portland arriving at about the same time as we did- 2 hours prior to our flight leaving. The layover was for less than an hour and we were concerned that we would not make the connection, but as it turns out, the flight leaving LAX was even more delayed in departure due to needing some maintenance repair for the a/c of the plane. As for the food- it seems not so very nice that you are not feeding people and offering complementary alcohol on the international flights any more.

8.0 Excellentjanelle, Dec 2025
PDX - LAX
Read more Alaska Airlines reviews

I liked that I made it onto the flight rather than “missing” the connection. We left PDX early in the morning along with half of Portland arriving at about the same time as we did- 2 hours prior to our flight leaving. The layover was for less than an hour and we were concerned that we would not make the connection, but as it turns out, the flight leaving LAX was even more delayed in departure due to needing some maintenance repair for the a/c of the plane. As for the food- it seems not so very nice that you are not feeding people and offering complementary alcohol on the international flights any more.

Flight was delayed but still made it to Phoenix on time. Boarding went quickly, the flight was smooth.

The food selections were not good, and entertainment was non existent.

Fine. But given how empty the flight was, I do not understand why my dog, in its carrier, could not be placed on the seat next to me (which was empty) rather than on the floor under seat. This seemed like overkill on the rule following by the flight staff.

A very good experience - all staff was friendly and helpful.

I would have liked if the flight existed. To be fair the federal government canceled it. But, since it WAS canceled, I would have liked it if Alaska Airlines had moved a finger to assist me rather then abandoning me with my luggage, unable to check it, for 14 hours in Portland. So federal regulations forbid them from storing my bag? Then at least help me find storage or SOMETHING.

It was all good, no delays which was a worry. All great

The staff was so kind and friendly! Boarding was efficient and communication was timely. I would seek out flying with Alaska Airlines in the future.

It was a pleasant experience. Considering we paid over $3000 for first class there really wasn’t anything special about first class. All the seats looked the same and everyone got the same great customer service. The only thing that was different between first class and couch was the drinks and the meal. We wouldn’t waste that much $ on first class on that plane again.

Check in online didn't accept my confirmation number so i could only check in with assistance at the airport and ended up with s creepy middle seat.

I noticed that the planes seem to be outdated. There was no entertainment per se. Also, the waiting area did not have any working electrical outlets

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

Lady Pilot was perfect in every way wheels up to wheels down communication, professionalism, excellent on time departure and on time arrival, excellent communication! Fantastic job with Superb attitude!!

The food is terrible. The staff is wonderful. Comfort is good.

Left on time, a bit delayed due to headwinds most of the trip.

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!

Flight scheduled to take off at 5.55pm but it did not take off until 7pm due to some food delivery delay.

Unfortunately, I was put into the middle seat in the first row of premium seating. Sounds nice right? No! that is the worst seat in the plane. I wish I was in economy rather than be in that seat! There is no seat back pocket, no tray table, no charger. Nothing! so unless you're row mates are willing to let you share their basic amenities any flyer should have, you are stuck. It was the worst experience ever! And the flight attendant forgot to take my drink order. I felt like the forgotten flyer.

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

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

Very bad! They kept delaying my flight and wouldn’t do anything about it

Door to door, the crew and staff were amazing. It was a stressful travel day with delays, but they were focused on customers and doing what they could to get us to our destinations.

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.

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.

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

Information on your arrival and departure airports