HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Redmond

$150+ Cheap flights from Chicago (CHI) to Redmond (RDM)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/26. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RDM
nov. 29 — dic. 61
sáb. 11/29
sáb. 12/6
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Redmond with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Chicago to Bend/Redmond are usually found in January or June, booked 28 days in advance, depart on a Wednesday or Tuesday and return on a Tuesday

Cheap flight deals from Chicago to Redmond

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Redmond (RDM). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated octubre 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$298
(Alaska Airlines)

One-way from

$150
(Delta)

Popular in

December

Cheapest in

January

Average price

$416
Provider with most accurate pricing for Chicago (CHI)-Bend/Redmond flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Bend/Redmond flights.
Search Deals
From Chicago (CHI) to Bend/Redmond
Search Deals
One-way flight from Chicago (CHI) to Bend/Redmond
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($67 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($31 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

Find flight deals from Chicago to Redmond

Cheapest flights from Chicago to Redmond
Explore the most affordable flight options available from Chicago to Redmond. Find the lowest fares from popular airlines and budget airlines, with prices last updated on octubre 30, 2025.

This Alaska Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/2712:59 pmORD - RDM
1 stop6h 56mAlaska Airlines
mar. 12/21:30 pmRDM - ORD
1 stop8h 29mAlaska Airlines
Deal found 10/27$283
This Delta deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/272:12 pmORD - RDM
1 stop6h 42mDelta
mar. 12/27:34 pmRDM - ORD
2 stops11h 06mDelta
Deal found 10/27$288
This Alaska Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/2712:59 pmORD - RDM
1 stop6h 56mAlaska Airlines
lun. 12/18:54 pmRDM - ORD
1 stop25h 05mAlaska Airlines
Deal found 10/27$292
This Alaska Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/2712:59 pmORD - RDM
1 stop6h 56mAlaska Airlines
jue. 12/48:38 amRDM - ORD
1 stop11h 52mAlaska Airlines
Deal found 10/28$318
This Delta deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/1012:50 pmMDW - RDM
2 stops13h 09mDelta
dom. 12/147:34 pmRDM - MDW
2 stops11h 20mDelta
Deal found 10/29$319
This Delta deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/272:12 pmORD - RDM
1 stop6h 42mDelta
jue. 12/47:34 pmRDM - ORD
2 stops10h 30mDelta
Deal found 10/28$324
This Delta deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/201:38 pmORD - RDM
2 stops11h 15mDelta
lun. 11/247:34 pmRDM - ORD
2 stops10h 56mDelta
Deal found 10/28$329
This Alaska Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/256:00 amORD - RDM
1 stop20h 19mAlaska Airlines
lun. 12/18:54 pmRDM - ORD
1 stop25h 05mAlaska Airlines
Deal found 10/28$332
This Alaska Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/208:59 pmORD - RDM
1 stop16h 44mAlaska Airlines
lun. 11/243:56 pmRDM - ORD
1 stop11h 05mAlaska Airlines
Deal found 10/28$348
This Delta deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/1112:47 pmMDW - RDM
2 stops13h 09mDelta
vie. 11/147:34 pmRDM - MDW
2 stops11h 27mDelta
Deal found 10/28$526
This Delta deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/301:08 pmMDW - RDM
2 stops11h 27mDelta
dom. 11/25:55 amRDM - MDW
2 stops9h 48mDelta
Deal found 10/28$565
This Delta deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 11/121:15 pmMDW - RDM
2 stops11h 38mDelta
dom. 11/167:34 pmRDM - MDW
2 stops12h 18mDelta
Deal found 10/28$600

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Redmond that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated octubre 30, 2025.
Use the filters below to find and compare flights from Chicago to Redmond that are best for you.

Fly from

Chicago

Fly to

Redmond

Route

Depart

Return

Price

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

jue. 11/27

12:59 pm-5:55 pm

1 stop6h 56m

Bend/Redmond

mar. 12/2

1:30 pm-11:59 pm

1 stop8h 29m

$283

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

jue. 11/27

2:12 pm-6:54 pm

1 stop6h 42m

Bend/Redmond

mar. 12/2

7:34 pm-8:40 am

2 stops11h 06m

$288

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

jue. 11/27

12:59 pm-5:55 pm

1 stop6h 56m

Bend/Redmond

lun. 12/1

8:54 pm-11:59 pm

1 stop25h 05m

$292

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

mié. 1/14

8:00 am-12:54 pm

1 stop6h 54m

Bend/Redmond

dom. 1/18

5:52 am-2:38 pm

1 stop6h 46m

$308

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

jue. 11/27

7:00 am-12:11 pm

1 stop7h 11m

Bend/Redmond

jue. 12/4

3:51 pm-11:59 pm

1 stop6h 08m

$318

ChicagoRedmond

MDW - RDM

MDWRDM

Chicago Midway

mié. 12/10

12:50 pm-11:59 pm

2 stops13h 09m

Bend/Redmond

dom. 12/14

7:34 pm-8:54 am

2 stops11h 20m

$319

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

jue. 11/27

2:12 pm-6:54 pm

1 stop6h 42m

Bend/Redmond

jue. 12/4

7:34 pm-8:04 am

2 stops10h 30m

$324

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

jue. 11/20

1:38 pm-10:53 pm

2 stops11h 15m

Bend/Redmond

lun. 11/24

7:34 pm-8:30 am

2 stops10h 56m

$329

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

mar. 11/25

6:00 am-12:19 am

1 stop20h 19m

Bend/Redmond

lun. 12/1

8:54 pm-11:59 pm

1 stop25h 05m

$332

ChicagoRedmond

MDW - RDM

MDWRDM

Chicago Midway

mié. 11/12

1:15 pm-10:53 pm

2 stops11h 38m

Bend/Redmond

dom. 11/16

5:55 am-6:08 pm

2 stops10h 13m

$526

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 26 results
1
2
3

Compare providers for flights from Chicago to Redmond

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Redmond in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Redmond flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-Redmond flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago-Redmond flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Redmond flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Redmond flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Chicago to Redmond

Have a flexible travel schedule? Discover the best time to fly to Redmond from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

How far ahead should I book a flight from Chicago to Redmond?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Redmond. Price data was last updated on October 24, 2025.

The price you pay for your flight from Chicago to Redmond may vary depending on when you book. For the best chance of a lower fare, look to book 28 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Chicago to Redmond?

Currently, December is the cheapest month in which you can book a flight from Chicago to Redmond (average of $244). Flying from Chicago to Redmond in March is currently the most expensive (average of $463). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to RDM?

Find hourly flight availability from Chicago to Redmond. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated octubre 30, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago to Redmond at noon. If you’re flexible enough to do this you can expect to save up to 24% on your trip compared to booking a flight in the afternoon.

Reviews of airlines servicing Redmond

Get insights into the airlines that provide service to Redmond. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Redmond. Reviews last updated octubre 30, 2025.
Read reviews from past customers who have flown Alaska Airlines, Delta, and Hawaiian Airlines from Chicago to Redmond. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
11,214 reviews

Overall

8.0

Entertainment

7.0

Boarding

8.1

Food

7.1

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Alaska Airlines
8.0
Very good
11,214 reviews
Alaska Airlines
8.0
Very good
11,214 reviews

Overall

8.0

Entertainment

7.0

Boarding

8.1

Food

7.1

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Delta
7.9
Good
7,993 reviews
Alaska Airlines
8.0
Very good
11,214 reviews

Overall

8.0

Entertainment

7.0

Boarding

8.1

Food

7.1

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Hawaiian Airlines
7.8
Good
2,797 reviews
Alaska Airlines
8.0
Very good
11,214 reviews

Overall

8.0

Entertainment

7.0

Boarding

8.1

Food

7.1

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
United Airlines
7.4
Good
8,998 reviews
Alaska Airlines
8.0
Very good
11,214 reviews

Overall

8.0

Entertainment

7.0

Boarding

8.1

Food

7.1

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Redmond. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Redmond from Chicago?

    For a flight from Chicago to Redmond, you will be flying into Bend/Redmond. Bend/Redmond (RDM) is just 1.8 mi from the center of the city. Bend/Redmond is the only Redmond airport and it handles 0 inbound flights from Chicago per day. 5 airlines have flights to Bend/Redmond from Chicago on a regular basis.

  • How long is the flight from Chicago to Redmond?

    There are many flights that can get you from Chicago to Redmond in 6h 42m. Fly via Alaska Airlines or Delta to get the fastest option. Airlines will cover a distance of 1671 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines flying from Chicago to Redmond round-trip?

    According to our current data, Hawaiian Airlines ($246), American Airlines ($250), and Alaska Airlines ($278) offers the cheapest pricing from Chicago to Redmond. These flights start at 43% lower than the current average price 3 months from now.

  • Can I find deals for flights from Chicago to Redmond that include hotel bookings?

    Yes. In addition to deals on Chicago to Redmond flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Redmond?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Redmond.

  • Can I find deals for business class flights from Chicago to Redmond?

    Yes. Cheapflights offers flight deals from Chicago to Redmond by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Redmond?

    Currently, December is the cheapest month in which you can book a flight from Chicago to Redmond (average of $244). Flying from Chicago to Redmond in March is currently the most expensive (average of $463). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Redmond?

Book flights to Redmond if you plan to visit one of these locations
Bend
Madras

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Redmond

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Portland flights
Midway to Portland flights
O'Hare Intl to Boise flights
St. Louis to Portland flights
O'Hare Intl to Eugene flights
O'Hare Intl to Redmond flights
St. Louis to Boise flights
Midway to Boise flights
Midway to Redmond flights
Peoria to Portland flights
O'Hare Intl to Medford flights
St. Louis to Medford flights
Midway to Eugene flights
Moline to Portland flights
Peoria to Boise flights
St. Louis to Eugene flights
O'Hare Intl to North Bend flights
Evansville to Portland flights
Decatur to Portland flights
St. Louis to Redmond flights
Bloomington to Portland flights
Peoria to Medford flights
O'Hare Intl to Yakima flights
Peoria to Eugene flights
Springfield to Portland flights
Moline to Medford flights
Evansville to Boise flights
Midway to Medford flights
Bloomington to Boise flights
St. Louis to Yakima flights
Champaign to Portland flights
Moline to Eugene flights
Evansville to Medford flights
Champaign to Boise flights
Bloomington to Eugene flights
Peoria to North Bend flights
Springfield to Eugene flights
Springfield to Medford flights
Dubuque to Portland flights

Top 5 airlines flying from Chicago to Redmond

Discover the top 5 airlines that operate flights from Chicago to Redmond. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated octubre 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$246Average$413FlexibilityNo cancel feeOn-time85%
American AirlinesCheapest$250Average$286FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$278Average$457FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$278Average$463FlexibilityNo cancel feeOn-time69%
DeltaCheapest$278Average$398FlexibilityNo cancel feeOn-timeN/A

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.