RDM - CHI

$189 Find Cheap Flights from Redmond to Chicago - Compare and Save

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 9/7. 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

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Everything you should know

Cheapest round-trip
$362
Typical prices: $382-$601
Multiple Airlines
Mon 9/7Thu 9/10
RDM - ORD • 1 stop
Cheapest one-way
$189
Typical prices: $169-$186
Multiple Airlines
Mon 9/7
RDM - ORD • 1 stop
Top airlines
Cheapest • from $407 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
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Airline reviews
Airline reviews
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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 $346 (round-trip)
Shortest trip • 6h 07m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 27% price drop
Most popular
Good to know
Good to know
+1
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Good to know
Good to know
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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

Mon, Sep 7 - Thu, Sep 10
Multiple Airlines Logo
12:15 pm - 6:21 pmRDM  Bend/Redmond-ORD Chicago O'Hare Intl
28h 06m1 stop Las Vegas Harry Reid Intl
Multiple Airlines Logo
8:55 pm - 11:40 amORD  Chicago O'Hare Intl-RDM Bend/Redmond
16h 45m1 stop Las Vegas Harry Reid Intl
$362Multiple Airlines
Sat, Sep 5 - Tue, Sep 8
Delta Logo
12:31 pm - 9:33 pmRDM  Bend/Redmond-ORD Chicago O'Hare Intl
7h 02m1 stop Salt Lake City
Delta Logo
5:44 pm - 11:08 pmORD  Chicago O'Hare Intl-RDM Bend/Redmond
7h 24m1 stop Seattle/Tacoma Intl
$407Delta
Sat, Oct 31 - Tue, Nov 3
Alaska Airlines Logo
5:20 am - 1:18 pmRDM  Bend/Redmond-ORD Chicago O'Hare Intl
5h 58m1 stop Portland
Alaska Airlines Logo
2:07 pm - 6:23 pmORD  Chicago O'Hare Intl-RDM Bend/Redmond
6h 16m1 stop Portland
$407Alaska Airlines
Wed, Sep 2 - Wed, Sep 9
Alaska Airlines Logo
7:07 am - 7:21 pmRDM  Bend/Redmond-ORD Chicago O'Hare Intl
10h 14m1 stop San Diego
Alaska Airlines Logo
6:00 am - 12:40 pmORD  Chicago O'Hare Intl-RDM Bend/Redmond
8h 40m1 stop Seattle/Tacoma Intl
$407Alaska Airlines
Wed, Sep 16 - Sat, Sep 19
American Airlines Logo
2:46 pm - 11:43 pmRDM  Bend/Redmond-ORD Chicago O'Hare Intl
6h 57m1 stop Phoenix Sky Harbor Intl
American Airlines Logo
6:59 am - 2:14 pmORD  Chicago O'Hare Intl-RDM Bend/Redmond
9h 15m1 stop Phoenix Sky Harbor Intl
$407American Airlines
Wed, Sep 2 - Tue, Sep 8
Delta Logo
1:52 pm - 11:29 pmRDM  Bend/Redmond-ORD Chicago O'Hare Intl
7h 37m1 stop Seattle/Tacoma Intl
Delta Logo
7:00 am - 1:04 pmORD  Chicago O'Hare Intl-RDM Bend/Redmond
8h 04m1 stop Seattle/Tacoma Intl
$407Delta
Tue, Sep 1 - Sat, Sep 5
Delta Logo
1:52 pm - 11:29 pmRDM  Bend/Redmond-ORD Chicago O'Hare Intl
7h 37m1 stop Seattle/Tacoma Intl
Delta Logo
12:54 pm - 6:45 pmORD  Chicago O'Hare Intl-RDM Bend/Redmond
7h 51m1 stop Seattle/Tacoma Intl
$407Delta
Fri, Sep 11 - Tue, Sep 15
United Airlines Logo
1:52 pm - 11:00 pmRDM  Bend/Redmond-ORD Chicago O'Hare Intl
7h 08m1 stop San Francisco
United Airlines Logo
2:32 pm - 9:11 pmORD  Chicago O'Hare Intl-RDM Bend/Redmond
8h 39m1 stop Denver Intl
$421United Airlines
Fri, Sep 4 - Thu, Sep 10
Multiple Airlines Logo
12:15 pm - 1:36 pmRDM  Bend/Redmond-ORD Chicago O'Hare Intl
23h 21m2 stops Las Vegas Harry Reid Intl Denver Intl
Multiple Airlines Logo
8:55 pm - 11:40 amORD  Chicago O'Hare Intl-RDM Bend/Redmond
16h 45m1 stop Las Vegas Harry Reid Intl
$435Multiple Airlines
Thu, Sep 3 - Sun, Sep 6
United Airlines Logo
9:37 am - 9:30 pmRDM  Bend/Redmond-ORD Chicago O'Hare Intl
9h 53m1 stop Los Angeles Los Angeles
United Airlines Logo
8:40 am - 12:50 pmORD  Chicago O'Hare Intl-RDM Bend/Redmond
6h 10m1 stop Denver Intl
$441United 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 September.

Flight prices are below average for this route right now.

Flights to Chicago from Redmond usually cost between $406 and $478 in September.
The lowest price found in the past 5 days was $362 on Multiple Airlines (Sep 7-Sep 10).

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 February and June, where the average cost of round-trip tickets is $572 and $524 respectively.

Good to know

Low season

January

Cheapest flight

$189
Best time to beat the crowds but there is an average 23% 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 5 days, the lowest price for a flight from Redmond to Chicago was $189 for a one-way ticket and $362 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 $442 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 $378 and an overall rating of 7.8.

  • 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 12771 reviews
8.5Crew
7.8Comfort
7.0Food
7.0Entertainment
8.1Boarding
Airline reviews

Worst travel day of my life. First bumped from our 7am flight—that we booked to ensure enough time to get to Chicago and get ready to go to a concert. Ended up on a flight 5hours later only to arrive in Chicago and spend 2 hours sitting in the tarmac. Missed the concert ($650 in tickets) and was too late to cancel the hotel ($500). I did receive a $200 voucher for the next Alaska ticket—soooo generous 👎. Would LOVE if Alaska reimbursed the $1000+that I am out!

2.0 MediocreJerilynn, Aug 2026
Read more Alaska Airlines reviews

Worst travel day of my life. First bumped from our 7am flight—that we booked to ensure enough time to get to Chicago and get ready to go to a concert. Ended up on a flight 5hours later only to arrive in Chicago and spend 2 hours sitting in the tarmac. Missed the concert ($650 in tickets) and was too late to cancel the hotel ($500). I did receive a $200 voucher for the next Alaska ticket—soooo generous 👎. Would LOVE if Alaska reimbursed the $1000+that I am out!

They lost my bag and 24 hours later have yet to find it

3 of the 4 legs of our trip the crews were awesome! 1 leg the trip attendants were rude & dismissive, didn't even greet us when boarding even though both myself & my husband said hello directly to them when we boarded.

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 didn’t go, and can’t use a no refundable ticket.

I was able to upgrade easily on the way home to first class. No problems with luggage. Efficient time management getting us to our destination on time

The airline was great. What was annoying as hell were the inaccurate emails from KAYAK telling me the boarding gate changed and the date of my flight was 1 day later then the actual 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).

Quick easy boarding. Airport was unprepared for early landing and we were waiting in the plane for 20 minutes before getting a gate.

No complaints. One of the flight attendants was especially engaging and helpful. She was like a merging of nurse and teacher energy in one person.. The seats were very comfortable, and so nice to have extra legroom in the main cabin. Puts United and American to shame. Thanks

It was as good as it could be. Flying is not a pleasant experience these days.

There was an unruly family behind us that made the short flight miserable!!! The cabin crew did nothing to contain it.

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

Got on the plane and sat there for an hour before departure.

Cramped seating for me. Luckily it wasn’t a long flight

5 hour delay. They blamed the weather but it was the computer issues they had been dealing with for days.

I usually have a positive experience with Delta. Complimentary upgrades are always nice!

long flights are never truly comfortable but the airline did their best. crew was great and the flight was safe.

The captain was amazing and kept us informed throughout that there would be some rough air. The flight also got delayed but we were able to actually leave on time, which was great.

The staff did not do a good job of getting everyone boarded quickly, so we missed our take off window and had to sit on the tarmac for 20+ min waiting for our turn. The plan was old. Pockets on the back of seats were torn and tearing off. One of the attendants was rude-she would ask a question but he walking away before you finished answering so she kept getting our drink orders wrong.

The flight crew were very helpful. The seats were very close together. There was barely room to sit without touching the person next to you.

I’m an EP on AA every year for more than a decade but this was a very pleasant and surprising experience. Clean and sizable plane for HOU to CHI. 5 row first class. And excellent food in first class the steak option was really good. Your flight attendants even better. Seat 5A

Gluten free snack options and meals that offer both gluten free and dairy free.

Not a bad flight but a long delay boarding and taking off due to the pilot not arriving on time.

I would have preferred a flight voucher and to hop on a different flight. Delayed over 6 hours.

I almost missed my connection in Chicago due to having to wait on a gate to be open I am assuming. Having to run from E terminal to C terminal and I barely made it there before they closed the door. This may not be the actual airline's fault it's crazy how there is so little time between flight especially when they are placed so far apart in the airport.

The Wi-Fi did not work, so you weren't able to watch entertainment on your own device. They did not have wired headphones so you couldn't watch it on the in-seat entertainment screen either. There was plenty of time to do a drink and snag service but the flight attendants chose not to.

Great experience, boarding was fast and efficient, so much so that we arrived to Chicago very early

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.

I liked being upgraded to first class. The flight was a redeye, so I did sleep most of it.

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

Information on your arrival and departure airports