Find flights
Deals
Insights
When to book
FAQs & Tips
Airlines

RDM - CHI

$139 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 9/18. 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
0 bags
Thu 7/4
Thu 7/11

Search 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
In the last 7 days travelers have searched 44,060,346 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

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

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

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

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.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
7:25 pm - 7:31 amRDM-ORD
10h 06m2 stops
7:15 am - 11:56 amORD-RDM
6h 41m1 stop
$283Delta
Find Deal
Tue, Sep 24 - Sat, Oct 19
1:53 pm - 12:23 amRDM-ORD
8h 30m1 stop
5:00 am - 1:04 pmORD-RDM
10h 04m1 stop
$288American Airlines
Find Deal
Thu, Aug 1 - Wed, Aug 7
6:50 pm - 4:37 amRDM-ORD
7h 47m1 stop
5:45 pm - 4:49 pmORD-RDM
25h 04m1 stop
$296Alaska Airlines
Find Deal
Tue, Sep 24 - Sat, Oct 19
2:05 pm - 4:15 pmRDM-ORD
24h 10m1 stop
6:00 am - 10:57 amORD-RDM
6h 57m1 stop
$308Alaska Airlines
Find Deal
Fri, Sep 20 - Mon, Sep 23
8:26 am - 4:37 amRDM-ORD
18h 11m1 stop
9:10 pm - 10:57 amORD-RDM
15h 47m1 stop
$316Alaska Airlines
Find Deal
Tue, Sep 10 - Sun, Sep 15
6:50 pm - 4:15 pmRDM-ORD
19h 25m2 stops
5:45 pm - 10:55 amORD-RDM
19h 10m2 stops
$321Alaska Airlines
Find Deal
Tue, Sep 24 - Sat, Oct 19
1:51 pm - 12:40 amRDM-ORD
8h 49m1 stop
7:10 am - 3:10 pmORD-RDM
10h 00m1 stop
$347United Airlines
Find Deal
Fri, Sep 20 - Sun, Sep 22
8:47 am - 9:57 pmRDM-ORD
11h 10m1 stop
11:53 pm - 12:36 pmORD-RDM
14h 43m1 stop
Sun, Sep 8 - Thu, Sep 12
8:47 am - 9:57 pmRDM-ORD
11h 10m1 stop
7:15 pm - 12:36 pmORD-RDM
19h 21m2 stops
Sun, Sep 8 - Thu, Sep 12
7:50 pm - 5:58 amRDM-ORD
8h 08m1 stop
6:30 pm - 12:24 amORD-RDM
7h 54m1 stop
$468United Airlines
Find Deal
Thu, Jul 11 - Sat, Jul 20

Flights from Redmond to Chicago - Travel Insights & Trends

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 flights from Redmond to Chicago clicked on KAYAK for each day over the last 12 months.
Your flight ticket price will generally be cheaper if you fly to Chicago on a Friday and more expensive on a Sunday. On your return trip to Redmond, you should consider flying back on a Saturday, and avoid Mondays for better deals.

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 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 April, where tickets cost $347 on average. On the other hand, the most expensive months are December and June, where the average cost of tickets is $640 and $621 respectively.

Which airlines provide the cheapest flights from Redmond to Chicago?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The cheapest return flight ticket from Redmond to Chicago found by KAYAK users in the last 72 hours was for $283 on Delta, followed by American Airlines ($288). One-way flight deals have also been found from as low as $139 on American Airlines and from $174 on Delta.

Good to know

Low season

January

High season

April

Cheapest flight

$139
Best time to beat the crowds but there is an average 12% increase in price.
Most popular time to fly and prices are also 26% 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 $139 for a one-way ticket and $283 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?

    oneworld, SkyTeam, 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, Delta or Alaska Airlines?

    The two airlines most popular with KAYAK users for flights from Redmond to Chicago are Delta and Alaska Airlines. With an average price for the route of $370 and an overall rating of 8.0, Delta is the most popular choice. Alaska Airlines is also a great choice for the route, with an average price of $534 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.

See more FAQs

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 9214 reviews
8.6Crew
7.3Food
7.3Entertainment
7.9Comfort
8.2Boarding
Airline reviews

When Alaska uses Sky west which it does on many flights in and out of PDX, The planes use " Gates" that are outside of the terminal and are a long walk to and from the planes. Also you must board and deplane using a ramp. I have difficulty walking so going into Portland was difficult. Going out was worse . We walked to nearly the emd of this "Tunnel " only to be told there was a problem with the plane so we had to take the long walk back to to the terminal and then back out again when the plane was fixed. I will look for a Southwest flight next time I go to Portland

2.0 MediocreAnonymous, Jun 2024PDX - OAK
Read more about Alaska Airlines reviews

When Alaska uses Sky west which it does on many flights in and out of PDX, The planes use " Gates" that are outside of the terminal and are a long walk to and from the planes. Also you must board and deplane using a ramp. I have difficulty walking so going into Portland was difficult. Going out was worse . We walked to nearly the emd of this "Tunnel " only to be told there was a problem with the plane so we had to take the long walk back to to the terminal and then back out again when the plane was fixed. I will look for a Southwest flight next time I go to Portland

Great! No issues at all. Friendly staff, on time flight, and smooth, comfortable flight.

The airline itself was extremely comfortable and the staff were wonderful. The communication was excellent amongst the pilots and flight attendants and the passengers. I was throughly impressed by the cleaning crew that came on the plane immediately to ready it for the next flight. I have flown a bunch of times post Covid pandemic and have never seen this! I gave the “okay” rating for the food and entertainment because I didn’t order food and there wasn’t entertainment offered through the plane (only your personal devices).

The flight both ways was pleasant and uneventful. The staff was friendly, accommodating, and overall very helpful.

1309 on May had some very bumpy segments that seem to take too long to get to smoother air. My initial flight out of GRR was delayed and missed connections. Sure glad I made a different one in ORD so I could be in Anchorage.

The one stewardess was rude about helping me put my bag in overhead….she said “ Is it heavy ?” (I am 73 yrs old)

That flight was a terrible experience. Flying to Portland was not much better. I will not ever fly Alaska Airlines again. I have a temporary disability due to recent neurocervical surgery. I cannot lift heavy things, I cannot walk long distances without vertigo and fainting, and I required wheelchair assistance. I showed up an hour and a half before my flight. The wheelchair queue assistance person was rude and chastised me for showing up so late. An older couple showed up almost an half an hour AFTER me, and she was sweet as pie to them. There was a long wait for wheelchair assistance as they were backed up. When I got to the gate, the gate attendants were rude and again, I got chastised for being late, even though it was not my fault they were backed up. When I asked for help with my bags and boarding the plane, they told me it was my fault and they were not obligated to help me. I was treated like a big inconvenience because I had a wheelchair and I couldn't "just walk." One of them literally rolled her eyes at me. I kept silent, because I just wanted to get home and I felt like they would not let me on if I complained, but I was practically crying. When I got down to the door to board, the wheelchair person left, and I asked the flight attendants for help. They said, well, you'll have to stand there and wait, even though I said I couldn't stand very long, and another passenger said, "Oh just let me do it" and helped me down. I tried not to bother the inflight attendants, because everytime you did, they acted exasperated and stressed out. I paid $7.50 for a bag of Pirate Booty and a tiny turkey beef stick for dinner. I needed wifi to work during the flight, and it kept crashing on me repeatedly and resetting my online work, costing me valuable time. I had to pay twice to get it on my laptop and phone, but I did get a refund when I returned. When I got to NY, the Portland agents had not arranged for a wheelchair to meet me and I had to stand for fifteen minutes waiting for the very nice young man who found an empty chair and had to wheel me and another passenger with carry on luggage to the front of JFK all by himself. Never, ever again. You all should be ashamed of how you treat people with disabilities. The other people who needed assistance to get on this flight did not fare much better than me, from what I could see.

My experience for a sort flight was perfect and hassle free.

It was warm on the plane. Perhaps the people who were coughing quite often should be encouraged to wear a mask?! It was a long 4 hours.

I didn’t like not knowing my seat till I got to the airport - and my boarding group was F (last).

It was good until there was a 3 hour delay because there was not any pilots to fly the plane.

There was plenty of overhead room but half of the passengers were told they had to check their carryon bags. My partner and I checked in as early as possible and our seats were split across the aisle.

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

I had a great flight. Everything went smoothly and the flight arrived early.

The flight and boarding were easy peasy. I was traveling with my 4-year-old, so a smooth boarding experience was especially appreciated. My only piece of feedback is really about where our gate was in O'Hare. They've shoved four gates into a tiny corner of the B terminal and there isn't early enough room or seating for everyone. Not United's problem, but did dent the overall experience.

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

The flight was delayed instead of leaving at 11 it left at 12.20

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

Good movies, iffy pay WiFi, food ok- on time though and that was great!

Awful…flight was delayed more than 12hrs, missed all connections to Fort Wayne, IN, had to get flight to another city 2 hours from my destination, flight was again delayed by 40 mins because they did not have enough fuel, again missed a connection, finally arrived in Indiana at 11pm…but before my 2 hour drive home, ay, no Five That Our Luggage Never Made On The plane and Still In Chicago

Boarding was friendly and quick. While the plane model was older with no live tv, the entertainment was full of movies and tv shows. All food was available. Pilots were very communicative with status of the flight. Flight landed on time.

The Palm Springs to Chicago O’Hare was on Time and Palm Springs airport is easier navigate. As our connection was only an approximately 50 minutes, we asked staff for insights for the Chicago airport in terms of transferring into the other terminal from which our flight left, and they were unhelpful. However, the United App was very helpful in terms of notifications and even providing directions. The Chicago to Detroit flight was significantly delayed which we all know does happen. However, there were very few updates or notifications as to why this was happening when we would actually arrive. It took nearly 30 minutes for bags to make it to baggage claim. We arrived nearly 1 hour late on a 40 minute flight.

Book cheap flights from Redmond to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Redmond to Chicago found on KAYAK in the last 72 hours.
9/18Wed
1 stopAmerican Airlines
8h 01mRDM-ORD
$139
9/12Thu
1 stopAmerican Airlines
8h 01mRDM-ORD
$149
9/18Wed
2 stopsDelta
10h 49mRDM-ORD
$174
9/12Thu
2 stops
18h 54mRDM-ORD
$178
9/12Thu
3 stops
29h 53mRDM-ORD
$208
7/25Thu
2 stops
18h 06mRDM-ORD
$216
9/18Wed
2 stopsDelta
11h 14mRDM-MDW
$224
7/25Thu
3 stops
29h 19mRDM-ORD
$239
7/25Thu
1 stopAlaska Airlines
11h 19mRDM-ORD
$263
7/28Sun
1 stopUnited Airlines
16h 44mRDM-ORD
$363

Search by stops

Search by airline

Search by price

Last minute flights from Redmond to Chicago

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Redmond to Chicago that are departing in the next 10 days.
6/6Thu
multi-stopUnited Airlines
21h 41mRDM-ORD
6/7Fri
multi-stopUnited Airlines
6h 29mORD-RDM
$699
6/6Thu
multi-stopDelta
7h 01mRDM-ORD
6/7Fri
multi-stopDelta
6h 22mORD-RDM
$860
6/6Thu
multi-stopDelta
9h 49mRDM-ORD
6/7Fri
multi-stopDelta
11h 10mORD-RDM
$870
6/6Thu
multi-stopDelta
11h 29mRDM-MDW
6/7Fri
multi-stopDelta
11h 26mMDW-RDM
$870

Search by stops

Search by airline

Search by price

Redmond - Chicago Flights

Departure:

Redmond (RDM)United States

Return flight deals:

Chicago - Redmond

Cabin classes: