RDM - CHI

$180 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 9/23. 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
$357
Typical prices: $517-$326
Alaska Airlines
Wed 5/27Wed 6/3
RDM - ORD • 1 stop
Cheapest one-way
$180
Typical prices: $169-$214
American Airlines
Wed 9/23
RDM - ORD • 1 stop
Top airlines
Cheapest • from $357 (round-trip)
Best reviews • 7.9 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
Cheapest • Avg $288 (round-trip)
Shortest trip • 6h 05m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 55% price drop
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, May 27 - Wed, Jun 3
Alaska Airlines Logo
7:00 am - 6:50 pm
RDM
-
ORD
9h 50m
1 stop
Alaska Airlines Logo
9:00 am - 9:37 pm
ORD
-
RDM
14h 37m
1 stop
$357Alaska Airlines
Wed, Jun 17 - Tue, Jun 23
Delta Logo
1:25 pm - 11:39 pm
RDM
-
ORD
8h 14m
1 stop
Delta Logo
7:37 pm - 11:59 pm
ORD
-
RDM
6h 22m
1 stop
$359Delta
Wed, May 27 - Wed, Jun 3
Delta Logo
6:10 am - 6:50 pm
RDM
-
ORD
10h 40m
2 stops
Delta Logo
6:20 pm - 10:52 pm
ORD
-
RDM
6h 32m
1 stop
$362Delta
Wed, May 27 - Tue, Jun 2
Delta Logo
6:10 am - 4:49 pm
RDM
-
ORD
8h 39m
1 stop
Delta Logo
7:45 am - 6:38 pm
ORD
-
RDM
12h 53m
2 stops
$364Delta
Thu, May 28 - Tue, Jun 2
American Airlines Logo
1:59 pm - 12:30 am
RDM
-
ORD
8h 31m
1 stop
American Airlines Logo
3:22 pm - 10:56 pm
ORD
-
RDM
9h 34m
1 stop
$368American Airlines
Wed, Jun 17 - Mon, Jun 22
Delta Logo
1:25 pm - 11:39 pm
RDM
-
ORD
8h 14m
1 stop
Delta Logo
6:55 am - 12:45 pm
ORD
-
RDM
7h 50m
1 stop
$369Delta
Wed, May 27 - Tue, Jun 2
Delta Logo
7:20 pm - 8:36 am
RDM
-
ORD
11h 16m
2 stops
Delta Logo
2:11 pm - 10:52 pm
ORD
-
RDM
10h 41m
2 stops
$370Delta
Fri, May 29 - Tue, Jun 2
Delta Logo
6:10 am - 9:50 pm
RDM
-
ORD
13h 40m
2 stops
Delta Logo
7:45 pm - 11:44 pm
ORD
-
RDM
5h 59m
1 stop
$373Delta
Wed, Jun 17 - Tue, Jun 23
Delta Logo
6:26 am - 9:57 pm
RDM
-
ORD
13h 31m
2 stops
Delta Logo
7:37 pm - 11:59 pm
ORD
-
RDM
6h 22m
1 stop
$374Delta
Thu, May 28 - Mon, Jun 1
Alaska Airlines Logo
5:31 pm - 6:20 am
RDM
-
ORD
10h 49m
1 stop
Alaska Airlines Logo
7:49 pm - 9:14 am
ORD
-
RDM
15h 25m
1 stop
$379Alaska 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.

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 May.

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 $125 (return) on average. On the other hand, the most expensive months are September and March, where the average cost of round-trip tickets is $352 and $346 respectively.

Good to know

Low seasonJanuary
Cheapest flight$180
Best time to beat the crowds but there is an average 6% increase in price.
Most popular time to fly with an average 1% increase in price.
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 $180 for a one-way ticket and $357 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 $435 and an overall rating of 7.9, Alaska Airlines is the most popular choice. Delta is also a great choice for the route, with an average price of $358 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 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.
7.9
Alaska AirlinesOverall score based on 12319 reviews
7.0Entertainment
8.1Boarding
7.8Comfort
8.5Crew
7.1Food
Airline reviews

very nice blankets and comfortable seats. great service. Great flights.

10.0 ExcellentAnonymous, Apr 2026
PDX - SEA
Read more Alaska Airlines reviews

very nice blankets and comfortable seats. great service. Great flights.

great experience just at the end, we got in early and there wasn't anyone at the gate for 30 min so we had to just sit on the tarmac

Generally Good. Outbound flight was marred by a continuously s creaming baby. Fortunately the flight was only 90 mins long it would be nice if people traveling with small childres could be centered in one part of the plane. Also, you need to adapt your servey to include a "not applicable " option for things like food and entertainment, which are not offered on shorter flights. I fily Alaska by choice as given all the cirumstances, I fel\el you do a good job.

I was seating in 26A and the children in 27A and B were kicking me non-stop. They kicked me for hours nonstop and the parents refused to get off their phones or correct them. I kindly asked multiple times and got screamed at by the mom that her son is disabled. I told her I get it, but that I matter too and she is responsible for her child. He then kicked me so hard my drink spilled. Not one crew member or other passenger said or did a thing. It was so horrible.

My very first, first class flight! Loved the comfortable seats, foot rest and beverages. Did not have food due to short flight. Crew was very friendly!

Birding was slow. extremely slow; please do experiments on efficient plane boarding experiences; especially regarding passengers that pass their seat number…

This flight was all good. It was packed, but it took off on time and there were no problems. It would have been nice if they'd checked our bags for free, as they sometimes do.

There was an issue with the plane and it was late getting in. This caused me to miss my connecting flight from PDX to BOI. I had to ask if they would provide me with a food voucher and they did but didn’t seem to concerned about my delay.

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.

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.

The agent at check in and at the gate were less than thrilled to be at work. I'm not a fan of Kayak's placement on the plane. I got put in the middle seat and none of my preferences were used.

In ATL they have two sets of departure screens. Follow what is on your airline's departure board - the ATL Airport Authority departure board had completely incorrect details about the gate assignment for my flight, which would have made me miss boarding.

Flight was delayed it was hot while sitting on the plane, one engine was working on the plane until they had to do some jimmy rigging down the runway in order for the other engine to charge up. It was ridiculous

The flight was very good and the staff was very friendly and helpful!

The only thing I would say is we tried to get on a standby earlier flight, but with our fair we couldn’t. That seems senseless to leave with open seats..

Very easy to use and convenient, you can perform any action within the same portal

In a world of delays, Delta was on time both ways! Boarding was fast and efficient. Staff was friendly. AND wifi worked.

WiFi didn’t work. Flight delayed 3 hours Crew members were illiterate Seat lean back did not work.

Flight was delayed, we could have been notified earlier and in a consistent manner. App was not refreshing for another passenger to get the latest flight status. We could have stayed and waited at the hotel instead of waiting at the airport had we known the flight was going to delayed for more than 5 hours. The toilet is too tight, and needs to be cleaned more frequently (every hour). The entertainment screen froze, the touch screen not responding to touch. We were upgraded to comfort, it is more comfortable than regular economy seats.

This wasn't my experience with Delta. It was just the Pegasus flight. Seats were very hard. Staff was kinda rough. Not very nice. Charged me for snacks. For a 4 hour flight I would've expected more.

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

boarded early to only find out that flight would sit at gate for 45 min to an hour. Landed in chicago and sat on runway for over an hour before got to gate. Total delay was extensive for a 45 min flight door to door.

The flight was significantly delayed. The inbound flight from EWR was delayed departing because of mechanical problems. My original departure from CLT was 5:28 pm but due to the delay of the inbound flight, after arrival, deplaning, cleaning, boarding, we did not push back from the gate until 9:00 pm. Once in the air, the flight was smooth and what was originally supposed to be an arrival in ORD at 7:30 pm local time turned out to be 9:35 pm.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

newer aircraft, ability to connect my headset via blue tooth for entertainment.

Very comfortable flight, snacks and drinks were good, good communication from crew. Could have used a little more information on timing of boarding for group 5

Great flight. Got to watch a movie. Smooth flight and early arrival at ORD.

It was better than excellent. The staff in Mason City were great. The young woman that pushed my wheelchair did more than could be expected of her. She came from India 17 years ago. I don't remember her name.

After arriving in Chicago, we were taxiing for 1.5 hours with infrequent and untruthful updates about the amount of time it would take to arrive at the gate. Minimally, the team could have provided timing expectations that were more truthful, especially one their original expectations were not met.

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

Information on your arrival and departure airports