RDM - CHI

$159 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 10/31. 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

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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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, Nov 8 - Tue, Nov 11
Delta Logo
7:00 am - 5:18 pmRDM-ORD
8h 18m1 stop
Delta Logo
6:13 pm - 10:53 pmORD-RDM
6h 40m1 stop
$234Delta
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Sat, Nov 8 - Tue, Nov 11
Delta Logo
7:00 am - 4:50 pmRDM-ORD
7h 50m2 stops
Delta Logo
6:13 pm - 10:53 pmORD-RDM
6h 40m1 stop
$287Delta
Find Deal
Fri, Nov 7 - Tue, Nov 11
Delta Logo
12:29 pm - 9:43 pmRDM-ORD
7h 14m1 stop
Delta Logo
6:13 pm - 10:53 pmORD-RDM
6h 40m1 stop
$292Delta
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Fri, Nov 7 - Tue, Nov 11
Delta Logo
7:26 pm - 9:03 amRDM-ORD
11h 37m2 stops
Delta Logo
6:13 pm - 10:53 pmORD-RDM
6h 40m1 stop
$297Delta
Find Deal
Wed, Oct 8 - Tue, Oct 14
Hawaiian Airlines Logo
7:15 am - 6:59 pmRDM-ORD
9h 44m1 stop
Hawaiian Airlines Logo
3:50 pm - 10:26 pmORD-RDM
8h 36m1 stop
$298Hawaiian Airlines
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Sat, Nov 8 - Tue, Nov 11
United Airlines Logo
1:17 pm - 8:58 pmRDM-ORD
5h 41m1 stop
United Airlines Logo
6:15 am - 12:15 pmORD-RDM
8h 00m1 stop
$299United Airlines
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Sat, Nov 8 - Fri, Nov 14
Alaska Airlines Logo
12:43 pm - 5:01 amRDM-ORD
14h 18m1 stop
Alaska Airlines Logo
3:25 pm - 8:58 pmORD-RDM
7h 33m1 stop
$308Alaska Airlines
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Fri, Oct 31 - Mon, Nov 3
Alaska Airlines Logo
9:30 am - 6:59 pmRDM-ORD
7h 29m1 stop
Alaska Airlines Logo
6:00 am - 5:04 pmORD-RDM
13h 04m1 stop
$318Alaska Airlines
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Wed, Oct 1 - Mon, Oct 6
Hawaiian Airlines Logo
3:41 pm - 12:03 amRDM-ORD
6h 22m1 stop
Hawaiian Airlines Logo
3:50 pm - 10:26 pmORD-RDM
8h 36m1 stop
$372Hawaiian Airlines
Find Deal
Sun, Sep 28 - Thu, Oct 2
American Airlines Logo
5:30 am - 3:58 pmRDM-ORD
8h 28m1 stop
American Airlines Logo
3:59 pm - 11:08 pmORD-RDM
9h 09m1 stop
$545American Airlines
Find Deal

Everything you should know

Top airlines
Delta
Cheapest • from $234 (round-trip)
Alaska Airlines
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
May
Cheapest • 28% price drop
November
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$234
Overall average: $627
Delta
Sat 11/8Tue 11/11
RDM - ORD • 1 stop
Cheapest one-way
$159
Typical prices: $160-279
Alaska Airlines
Fri 10/31
RDM - ORD • 1 stop
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
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?

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 May, where tickets cost $337 (return) on average. On the other hand, the most expensive months are February and March, where the average cost of round-trip tickets is $749 and $609 respectively.

Good to know

Low seasonFebruary
Cheapest flight$159
Best time to beat the crowds but there is an average 60% increase in price.
Most popular time to fly and prices are also 7% 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 $159 for a one-way ticket and $234 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, 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 $474 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 $378 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 10000 reviews
8.5Crew
7.8Comfort
7.1Food
7.0Entertainment
8.1Boarding
Airline reviews

Website could be better with faster access to specific flight information and boarding pass once reservation is made. Not a fan of no seat selection on line. I had to consult gate agent each time to change seats on flights with lots of open seats. This cannot possibly be cost effective for airline. On plus side, Alaska seat legroom seemed larger than American. ns

10.0 ExcellentAnonymous, Sep 2025PDX - DFW
Read more Alaska Airlines reviews

Website could be better with faster access to specific flight information and boarding pass once reservation is made. Not a fan of no seat selection on line. I had to consult gate agent each time to change seats on flights with lots of open seats. This cannot possibly be cost effective for airline. On plus side, Alaska seat legroom seemed larger than American. ns

Staff inside Portland terminal were rude, made us fell rushed and not at all accommodating to seniors. For this alone I will probably never booked from them again.

It was fine—the seats are not very comfortable and the aisles are very narrow. Nothing different from other airlines

Why was I charged for a glass of wine on one flight and not on another? Why no movie or TVs? It was a long flight.

I booked a round trip. I ordered a lunch going and a lunch for the return but got both lunches going. Could have been my error. Both lunches were good.

5 1/2 hour trip. Nice plane. easy boarding. Could have used a bit more beverage service but it was a red eye flight and they didn't want to wake everyone.

Well the flight being delayed multiple time really was frustrating. But the crew and flight was good.

generally good. No snacks or drinks on the flight 3379 from Portland to San Jose, CA. Sad.

Everything except for the lack of a choice of the snack provided was great.

All went smoothly. Only one delay departing Seattle of around 30 minutes.

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

Crew was good. The reservation got mixed up and they didn't have my TSA number. I am also a Silver Medallion and wasn't able to use Sky Priority.

Delta made it easy, comfortable and timely. The crew was fantastic.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

Mechanic delay in addition to a 2 hour change in takeoff time was frustrating.

Delayed due to thunderstorms and no in-flight service due to rough weather — both of which are out of Delta’s control. Flight was good overall.

The flight attendants in SLC were rude. I arrived 40 minutes early to gate. Ticket said I needed check in for seat assignments and tried check in and attendants said they weren’t doing it. And proceeded to never call me to give me a ticket so when time to board I received the very last seat. Please relay to employees to do their job better..,

They we able to seat my companion and I next to each other. Plane’s temperature was very cool. Willl be more prepared on return trip.

All was good and they were able to seat my travel companion next to me. Thank you.

Like the ample leg room. May as well not bother with snacks if it's only a two ounce bag of pretzels. Didn't use the entertainment option. Was there one?

What an amazing flight. I haven’t experienced this level of service in a flight in years. This will be the only way to fly to Hawaii for me in the future.

Kayak sold me a ticket after check in time. Could not check in. Could not get on flight.

Love you guys are so friendly and kind and wonderful

Agents talk too fast over intercom. I know it’s memorized and we’ve all heard it before. Just slow down a little. Stop charging for checked bags. I was pleased to get my bags promptly at each end of my flight.

Everything was great except having to check in at Alaska. That was a surprise and took extra time and effort. Should have been explained somewhere maybe on the HA electronic ticket.

It was clean and the crew was great. I wish the chairs could recline just a little more and you would provide small pillows for people with bad backs. My back is fused and a little support would be great.

I accidentally made this purchase and they wouldn’t refund me even though I called immediately to cancel it.

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The first flight was better in terms of the aircraft.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

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

Information on your arrival and departure airports

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