RDM - CHI

$150 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 6/6. 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

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Everything you should know

Cheapest round-trip
$270
Overall average: $414
Delta
Fri 4/17Wed 4/22
RDM - ORD • 2 stops
Cheapest one-way
$150
Typical prices: $230-$335
Delta
Sat 6/6
RDM - ORD • 1 stop
Top airlines
Delta
Cheapest • from $270 (round-trip)
Alaska Airlines
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Redmond and Chicago. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Phoenix (PHX)
Cheapest • Avg $288 (round-trip)
Portland (PDX)
Shortest trip • 5h 48m (one-way)
Insights
Insights
Insights
Insights
When to travel
December
Cheapest • 24% 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

Fri, Apr 17 - Wed, Apr 22
Delta Logo
6:05 am - 9:18 pm
RDM
-
ORD
13h 13m
2 stops
Delta Logo
6:00 pm - 11:06 pm
ORD
-
RDM
7h 06m
1 stop
$270Delta
Wed, Apr 15 - Sat, Apr 18
United Airlines Logo
1:55 pm - 12:59 am
RDM
-
ORD
9h 04m
1 stop
United Airlines Logo
6:25 am - 11:55 am
ORD
-
RDM
7h 30m
1 stop
$272United Airlines
Fri, Apr 17 - Wed, Apr 22
Delta Logo
6:05 am - 9:18 pm
RDM
-
ORD
13h 13m
2 stops
Delta Logo
7:35 am - 5:01 pm
ORD
-
RDM
11h 26m
2 stops
$275Delta
Wed, Apr 15 - Sat, Apr 18
Delta Logo
11:35 am - 9:18 pm
RDM
-
ORD
7h 43m
2 stops
Delta Logo
7:35 am - 11:53 am
ORD
-
RDM
6h 18m
1 stop
$282Delta
Fri, Apr 17 - Wed, Apr 22
United Airlines Logo
1:55 pm - 12:59 am
RDM
-
ORD
9h 04m
1 stop
United Airlines Logo
6:25 am - 11:55 am
ORD
-
RDM
7h 30m
1 stop
$285United Airlines
Thu, May 7 - Tue, May 12
United Airlines Logo
12:55 pm - 10:58 pm
RDM
-
ORD
8h 03m
1 stop
United Airlines Logo
2:20 pm - 8:58 pm
ORD
-
RDM
8h 38m
1 stop
$290United Airlines
Thu, May 7 - Tue, May 12
Delta Logo
12:20 pm - 11:57 pm
RDM
-
ORD
9h 37m
1 stop
Delta Logo
7:45 am - 6:40 pm
ORD
-
RDM
12h 55m
2 stops
$295Delta
Thu, May 7 - Tue, May 12
Delta Logo
7:20 pm - 8:36 am
RDM
-
ORD
11h 16m
2 stops
Delta Logo
7:45 am - 6:40 pm
ORD
-
RDM
12h 55m
2 stops
$300Delta
Thu, Apr 30 - Mon, May 4
Delta Logo
6:05 am - 4:39 pm
RDM
-
ORD
8h 34m
1 stop
Delta Logo
6:00 pm - 11:06 pm
ORD
-
RDM
7h 06m
1 stop
$303Delta
Tue, Jul 14 - Sun, Jul 19
Alaska Airlines Logo
7:49 pm - 5:02 am
RDM
-
ORD
7h 13m
1 stop
Alaska Airlines Logo
7:20 am - 11:47 am
ORD
-
RDM
6h 27m
1 stop
$309Alaska 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 February, where the average cost of round-trip tickets is $606 and $575 respectively.

Good to know

Low seasonJanuary
Cheapest flight$150
Best time to beat the crowds but there is an average 7% increase in price.
Most popular time to fly and prices are also 6% 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 $150 for a one-way ticket and $270 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 $427 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 $338 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 11950 reviews
8.1Boarding
7.1Food
7.0Entertainment
7.8Comfort
8.5Crew
Airline reviews

I'm not sure if you are going to ask me about the check in process. I could not get my boarding pass, so I had to stop at the American desk before security. I also had a difficult time downloading the app with the confirmation code for the two flights.

6.0 GoodAnonymous, Feb 2026
BNA - ORD
Read more Alaska Airlines reviews

I'm not sure if you are going to ask me about the check in process. I could not get my boarding pass, so I had to stop at the American desk before security. I also had a difficult time downloading the app with the confirmation code for the two flights.

Everything ran like it should. Staff was professional. Looking forward to flying with them again.

Boarding much smoother than previous United flights! The flight attendant helped monitor putting bags in overhead bins. On united no help resulted in bins in first class being filled before I boarded for first class. I had to search further down into economy. Then got stuck unable to return to my seat. People were putting backpacks that needed to go under seats in bins. It was a mess. This flight was a refreshing improvement. United also had so many categories of preboarding that first class could not board early. The pilot talked to us directly instead of using the intercom before flight.

Liked the attention and speed when getting wheelchair..........Was assured by phone that my needs would be taken care of and they were with my name.

The planes were in very nice condition. Comfortable enough leg room. I had a very quick connection on my return home I made it just fine and so did my luggage!!

Everything was fine. The snacks are a little on the tiny side.

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.

2+hrs delay without any reason provided and a cramped flight

We waited an hour on the runway to get a gate in Orlando

Flight was delayed by 3-hours and their fix was… complimentary pretzels.

Flight was delayed due to crew being not on time

Flight crew issues delayed my flight by 2 1/2 hours. Causing me to miss my connection.

The staff on board and gate was nice - a welcome change from the usual. We also arrived early, which was a great benefit, given that it takes 30 minutes plus to get bags at SRQ.

The staff was frielndly. The plane was terrible, it was too small and should be decommissioned. There were no back seat screens at all. The only beverages we had a choice from was coffee, tea or water. The only bathroom in the back was behind the flight attendant's jump seat and wasn't working. And I literally felt like I was sitting on top of the guy next to me. It was terribly hot in the plane and we had to sit on the tarmac in Chicago for 1/2 hour due to congestion in Mpls. Wouldn't they have know that before they even boarded us so that we could have sat in comfort in the terminal?

Never got on it. Was re-routed through Detroit and am still in airports 12 hours later waiting for my connecting plane to arrive.

Delta has too many delays now days. It is 1:06 am now. I was supposed to land in Norfolk at 10:30 pm. I got re-booked through Detroit and I’m still in Detroit. I hope to be landed in Norfolk by 3am. I’ve been in airports for 12 hours as of right now. There is a weather delay now but most delays lately have been maintenance.

Very Very late. Subsequent flights left an hour before ours

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!

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

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

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

Information on your arrival and departure airports