RDM - CHI

$134 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 4/22. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$277
Typical prices: $330-$480
Alaska Airlines
Wed 4/29Sat 5/2
RDM - ORD • 1 stop
Cheapest one-way
$134
Typical prices: $222-$275
United Airlines
Wed 4/22
RDM - ORD • 1 stop
Top airlines
Alaska Airlines
Cheapest • from $277 (round-trip)
Alaska Airlines
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
December
Cheapest • 20% price drop
August
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
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

Wed, Apr 29 - Sat, May 2
Alaska Airlines Logo
9:28 am - 7:52 pm
RDM
-
ORD
8h 24m
1 stop
Alaska Airlines Logo
6:00 am - 12:58 pm
ORD
-
RDM
8h 58m
1 stop
$277Alaska Airlines
Mon, Apr 13 - Thu, Apr 16
Multiple Airlines Logo
12:10 pm - 6:47 am
RDM
-
ORD
16h 37m
1 stop
Multiple Airlines Logo
6:09 pm - 11:30 am
ORD
-
RDM
19h 21m
2 stops
$281Multiple Airlines
Wed, Apr 29 - Sat, May 2
Delta Logo
6:05 am - 4:39 pm
RDM
-
ORD
8h 34m
1 stop
Delta Logo
2:09 pm - 11:57 pm
ORD
-
RDM
11h 48m
2 stops
$282Delta
Tue, Apr 14 - Fri, Apr 17
United Airlines Logo
1:55 pm - 12:59 am
RDM
-
ORD
9h 04m
1 stop
United Airlines Logo
7:00 am - 12:38 pm
ORD
-
RDM
7h 38m
1 stop
$285United Airlines
Wed, Apr 29 - Sat, May 2
Delta Logo
11:35 am - 9:18 pm
RDM
-
ORD
7h 43m
2 stops
Delta Logo
2:09 pm - 11:57 pm
ORD
-
RDM
11h 48m
2 stops
$288Delta
Tue, Apr 14 - Fri, Apr 17
Delta Logo
6:05 am - 4:39 pm
RDM
-
ORD
8h 34m
1 stop
Delta Logo
1:36 pm - 11:57 pm
ORD
-
RDM
12h 21m
2 stops
$295Delta
Wed, Mar 11 - Sat, Mar 14
United Airlines Logo
1:54 pm - 11:38 pm
RDM
-
ORD
7h 44m
1 stop
United Airlines Logo
2:45 pm - 8:50 pm
ORD
-
RDM
8h 05m
1 stop
$298United Airlines
Mon, Mar 16 - Tue, Mar 17
United Airlines Logo
1:54 pm - 12:59 am
RDM
-
ORD
9h 05m
1 stop
United Airlines Logo
7:00 am - 12:58 pm
ORD
-
RDM
7h 58m
1 stop
$302United Airlines
Thu, Apr 9 - Mon, Apr 13
Delta Logo
12:35 pm - 9:34 pm
RDM
-
ORD
6h 59m
1 stop
Delta Logo
6:00 pm - 11:57 pm
ORD
-
RDM
7h 57m
1 stop
$303Delta
Mon, Apr 13 - Thu, Apr 16
Multiple Airlines Logo
12:10 pm - 6:47 am
RDM
-
ORD
16h 37m
1 stop
Multiple Airlines Logo
8:53 pm - 11:30 am
ORD
-
RDM
16h 37m
1 stop
$304Multiple Airlines
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 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 December, where tickets cost $324 (return) on average. On the other hand, the most expensive months are March and January, where the average cost of round-trip tickets is $603 and $456 respectively.

Good to know

Low seasonJanuary
Cheapest flight$134
Best time to beat the crowds but there is an average 12% 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 $134 for a one-way ticket and $277 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 $441 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 $300 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 11882 reviews
8.5Crew
7.0Entertainment
8.1Boarding
7.8Comfort
7.1Food
Airline reviews

Most of it was good. The flights were on time. The staff were helpful and friendly. I had a short time connecting flights and they let me deplane first and I made the connection. On the outbound from DTW to SEA I was seated in the middle of two very large people. I am petite and even with my arms crossed they were both hanging over into my seat touching me. The meal had way too much pepper and spice, my lips were burning. Other than those two issues, I was pleased with the service and the trip and will use Alaska Air again.

8.0 ExcellentAnonymous, Feb 2026
EUG - SEA
Read more Alaska Airlines reviews

Most of it was good. The flights were on time. The staff were helpful and friendly. I had a short time connecting flights and they let me deplane first and I made the connection. On the outbound from DTW to SEA I was seated in the middle of two very large people. I am petite and even with my arms crossed they were both hanging over into my seat touching me. The meal had way too much pepper and spice, my lips were burning. Other than those two issues, I was pleased with the service and the trip and will use Alaska Air again.

The seats were spacious and comfortable. Even in basic economy. However, the flight boarded 30 minutes late.

Alaska used to be a top notch airline. With it's growth it is now in line with the big airlines. Not bad, not great.

Wheelchair assistant was on the spot, and very helpful. Gate agent was kind, and made sure I boarded the plane without having to try to hurry with my painful hip. My seat was so comfortable, 20A. I am tall, 5'9 and I need to stretch out my legs due to chronic nerve pain in my back that runs down my right leg, in addition to the bursitis in my right hip. Alaska air has the best economy seating in the market. So much room for legs, elbows, etc. When I arrived in SEA, the next Wheelchair was waiting to take me to the next gate. Great communication.

Great. I did have a little issue getting into the Lounge, which is likely more an American Airlines issue. I did not carry my physical AAdvantage Executive credit card with me on this trip, which Admirals Club membership is a part of the benefits of having this card. The instructions on the AA website and the Citi cards website make it seem like you don't need the physical card, as both sites state you can enter with your boarding pass and driver's license. But both lounges said you were required to present the physical card (and not the digital version, via Apple Pay), as only the physical card says "Admirals Club" on the back.I also do not have a physical Admirals Club membership card, so while both lounges eventually let me in, both denied me entrance initially for this reason.

Everything from the time I booked my flight through to the end when I got home was smooth and wonderful. Service was great, the flight attendants were attentive and there were no outstanding delays.

Worst first/business class I have ever flown after 75 years on planes. Barely acceptable seats, terrible food, uninterested attendants, unavailable WiFi. I’ll never fly this airline again.

Delayed and no entertainment? I also forgot my headphones and immediately reported it and have not heard back yet.

Very delayed for seemingly no reason. Made me miss an event

The crew was very friendly. Boarding was quick and efficient.

Totally worth the miles to upgrade to Delta Comfort. Plenty of legroom.

This was my first time flying Delta ever and I had a great experience!

Smallest leg room I've ever had on a plane.

They took all carry-on luggage from Groups 6 -9 - I was group 5 and waiting in line to board - they made me check my luggage too. That then went to baggage claim and delayed departure from the airport. There was overhead room in my seating area - Delta over reacted. Also, had a gentleman next to me that took up 1/2 my seat.

Flight delay was frustrating, also you cannot checkin online without delta app, web browser check-in throw errors

The gate agent was most helpful in getting me on to fly standby. I greatly appreciate it.

bulkhead seat had very little legroom - even in bsiness class.

The plane was an older model, so it wasn’t as comfortable as others. The flight attendants were not helpful during onboarding. It was a full flight so there was chaos finding space for baggage.

Sorry I didn't realize I was writing a review for each leg. Please see my previous review - it applies to the entire flight, not just a single leg.

This is the first time I've been disappointed with Delta. I was called by Delta to see if I would volunteer to change flights since my original flight home was overbooked. I accepted. The modified booking only provided me a 35 minute layover - when you subtract the fact that boarding closes for a flight 15 minutes early, that gave me 20 minutes to run for one end of the airport to the other. I barely made it. On the 2.5 hour flight to Tampa, the crew repeatedly let us know over the intercom that they cannot serve drinks or snacks due to safety/turbulence. I would have accepted this reason if they did not CONTINUALLY SERVE DRINKS AND COOKED FOOD to First class. If safety is the excuse then the entire plane should be strapped in for safety. On top of this the air conditioning vents were not working correctly and the plane was uncomfortably warm. I love Delta and am a loyal Delta traveler, and I have never had an experience like this. I don't know if there's a disconnect between availability among third-party sites like KAYAK and the airlines or what, but when overbooking causes issues like this for travelers it should be reviewed and changes to the booking process should be made. I blame BOTH KAYAK and Delta for this terrible experience.

No charging outlets worked. Other than collecting trash attendants didn’t come around. No one could hear flight attendants announcements during the flight. Seat pads were horrible. Sitting on a board for 5 hours. What happened to Hawaiian airlines comfort, hospitality, and extras? Our pilots did an excellent job trying to minimize turbulence and incredible job in landing in windy conditions.

I like that if they asked you to checked in a bag at the gate they give you priority to board

Horrible food and crew. Crew were laughing and talking loud while people were trying to sleep

Yall need to integrate your system with Alaska more efficiently. They booted me off the first flight because of a discrepancy on your end.

The crew at Hawaiian Airlines was fantastic. Kind and hard working. The pilots were great with giving us all the updates to make sure we were informed.

Very good. Nice plane and we sat in economy plus - bigger seats, more room. They served a meal and snacks, and the meal was an apple stuffed pancake that was very good! The snack for us was a hummus sandwich - also very good. The flight attendants were helpful and nice. They have plenty of movies and shows to watch. My only negative -- they changed our flights around and did not adjust the layovers, so we ended up with a very long and unnecessary layover in Honolulu.

I liked the Starlink WiFi but didn't like how they said they were the only airline to offer a free meal and it turns out to be just a standalone sandwich and then charge for snacks to go with it. Rather have the free snacks like Southwest, but have the option to purchase a decent meal for a 5+ hour flight.

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!

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

They did the one thing that really matters - got to Chicago early.

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

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

Information on your arrival and departure airports