$166+ Cheap flights from Chicago (CHI) to Redmond (RDM)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/19. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RDM
Nov 30 — Dec 71
Round-trip
1 adult, Economy
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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.Cheap flight deals from Chicago to Redmond
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Best
Last-minute
One-way
Cheapest flights from Chicago to RedmondExplore 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 October 31, 2026.
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 October 31, 2026.
This Alaska Airlines deal was found by Cheapflights users on 10/30. 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.
Tue 12/16:00 am -
1 stop12h 51m
Sat 12/53:56 pm -
2 stops11h 41m
Deal found 10/30![Alaska Airlines logo]()
$468
This Alaska Airlines deal was found by Cheapflights users on 10/26. 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.
Fri 12/117:58 pm -
1 stop20h 19m
Sun 12/1312:25 pm -
1 stop22h 45m
Deal found 10/26![Alaska Airlines logo]()
$490
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/125:15 pm -
1 stop20h 25m
Mon 11/1612:20 pm -
2 stops25h 11m
Deal found 10/27![Multiple Airlines logo]()
$501
This American Airlines deal was found by Cheapflights users on 10/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/146:50 am -
1 stop8h 27m
Wed 11/1810:55 am -
1 stop8h 05m
Deal found 10/30![American Airlines logo]()
$551
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.
Fri 12/188:59 pm -
1 stop23h 54m
Mon 12/216:31 pm -
1 stop27h 28m
Deal found 10/27![Alaska Airlines logo]()
$554
This Delta deal was found by Cheapflights users on 10/30. 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.
Sat 11/1412:00 pm -
1 stop8h 47m
Wed 11/1812:19 pm -
2 stops9h 35m
Deal found 10/30![Delta logo]()
$556
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/244:35 pm -
1 stop8h 22m
Tue 12/11:51 pm -
1 stop7h 08m
Deal found 10/27![United Airlines logo]()
$563
Best flights from Chicago to RedmondDiscover carefully curated flight deals from Chicago to Redmond that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 31, 2026.
Discover carefully curated flight deals from Chicago to Redmond that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 31, 2026.
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.
Tue 1/266:57 pm -
1 stop6h 56m
Sat 1/302:41 pm -
1 stop7h 18m
Deal found 10/27![Alaska Airlines logo]()
$475
This Delta deal was found by Cheapflights users on 10/26. 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.
Sat 1/167:15 am -
1 stop6h 37m
Sat 1/2311:27 am -
2 stops8h 41m
Deal found 10/26![Delta logo]()
$480
This Alaska Airlines deal was found by Cheapflights users on 10/30. 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.
Tue 12/16:00 am -
1 stop12h 51m
Sat 12/57:40 am -
1 stop9h 30m
Deal found 10/30![Alaska Airlines logo]()
$483
This Alaska Airlines deal was found by Cheapflights users on 10/26. 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.
Fri 12/117:58 pm -
1 stop20h 19m
Sun 12/133:56 pm -
2 stops20h 25m
Deal found 10/26![Alaska Airlines logo]()
$494
This Alaska Airlines deal was found by Cheapflights users on 10/26. 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.
Thu 1/212:10 pm -
1 stop23h 45m
Mon 1/2512:35 pm -
1 stop22h 38m
Deal found 10/26![Alaska Airlines logo]()
$497
Last-minute flights from Chicago to RedmondDiscover last-minute flight deals from Chicago to Redmond. Data last updated October 31, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Redmond. Data last updated October 31, 2026 and is based on user searches.
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/297:20 am -
1 stop11h 06m
Sat 11/147:40 am -
1 stop7h 57m
Deal found 10/27![Alaska Airlines logo]()
$601
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.
Thu 10/2912:30 pm -
2 stops8h 20m
Sat 11/1412:19 pm -
1 stop7h 28m
Deal found 10/27![Delta logo]()
$606
This Priceline deal was found by Cheapflights users on 10/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/63:59 pm -
1 stop9h 50m
Sat 12/512:25 pm -
2 stops9h 34m
Deal found 10/30![Alaska Airlines logo]()
$552
This United Airlines deal was found by Cheapflights users on 10/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/66:00 am -
1 stop8h 06m
Sat 12/57:00 am -
1 stop7h 51m
Deal found 10/30![United Airlines logo]()
$563
This Delta deal was found by Cheapflights users on 10/30. 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.
Fri 11/61:55 pm -
2 stops10h 07m
Sat 12/55:15 am -
2 stops13h 38m
Deal found 10/30![Delta logo]()
$573
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/125:15 pm -
1 stop20h 25m
Mon 11/1612:20 pm -
2 stops25h 11m
Deal found 10/27![Multiple Airlines logo]()
$501
This American Airlines deal was found by Cheapflights users on 10/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/146:50 am -
1 stop8h 27m
Wed 11/1810:55 am -
1 stop8h 05m
Deal found 10/30![American Airlines logo]()
$551
This Delta deal was found by Cheapflights users on 10/30. 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.
Sat 11/1412:00 pm -
1 stop8h 47m
Wed 11/1812:19 pm -
2 stops9h 35m
Deal found 10/30![Delta logo]()
$556
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.
Tue 11/246:40 am -
1 stop8h 00m
Tue 12/16:21 am -
2 stops10h 05m
Deal found 10/27![Delta logo]()
$568
One-way flights from Chicago to RedmondSearch for one-way flight options from Chicago to Redmond. Find affordable one-way fares based on user searches. Data last updated October 31, 2026.
Search for one-way flight options from Chicago to Redmond. Find affordable one-way fares based on user searches. Data last updated October 31, 2026.
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/195:15 pm -
1 stop20h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Multiple Airlines logo]()
$166
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/184:36 pm -
3 stops45h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Multiple Airlines logo]()
$196
This Alaska Airlines deal was found by Cheapflights users on 10/26. 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.
Tue 12/156:00 am -
2 stops13h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Alaska Airlines logo]()
$237
This United Airlines deal was found by Cheapflights users on 10/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/158:40 am -
1 stop6h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![United Airlines logo]()
$238
This Travelocity deal was found by Cheapflights users on 10/26. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/176:00 am -
2 stops15h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Alaska Airlines logo]()
$250
Find 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 October 31, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $468 (Alaska Airlines) |
One-way from | $166 (Kiwi.com) |
Popular in | December |
Cheapest in | February |
Average price | $547 |
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 7,457,451 searches. Data last updated October 31, 2026.
Use the filters below to find and compare flights from Chicago to Redmond that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoRedmond
ORD Chicago O'Hare Intl - RDM Bend/Redmond
ORDRDM
Chicago O'Hare Intl
Thu 11/19
6:30 am-11:40 am
2 stops31h 10m
Bend/Redmond
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$193
ChicagoRedmond
ORD Chicago O'Hare Intl - RDM Bend/Redmond
ORDRDM
Chicago O'Hare Intl
Tue 12/15
6:00 am-5:55 pm
2 stops13h 55m
Bend/Redmond
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$237
ChicagoRedmond
ORD Chicago O'Hare Intl - RDM Bend/Redmond
ORDRDM
Chicago O'Hare Intl
Thu 11/26
6:00 am-11:55 am
2 stops31h 55m
Bend/Redmond
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$259
ChicagoRedmond
ORD Chicago O'Hare Intl - RDM Bend/Redmond
ORDRDM
Chicago O'Hare Intl
Wed 11/25
6:54 pm-11:47 am
2 stops18h 53m
Bend/Redmond
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$259
ChicagoRedmond
ORD Chicago O'Hare Intl - RDM Bend/Redmond
ORDRDM
Chicago O'Hare Intl
Thu 12/24
7:00 am-3:21 pm
2 stops10h 21m
Bend/Redmond
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$262
ChicagoRedmond
ORD Chicago O'Hare Intl - RDM Bend/Redmond
ORDRDM
Chicago O'Hare Intl
Wed 11/18
5:00 am-1:17 pm
1 stop10h 17m
Bend/Redmond
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$276
ChicagoRedmond
ORD Chicago O'Hare Intl - RDM Bend/Redmond
ORDRDM
Chicago O'Hare Intl
Wed 11/18
1:00 pm-6:46 pm
1 stop7h 46m
Bend/Redmond
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$276
Quickest round-trip
ChicagoRedmond
ORD Chicago O'Hare Intl - RDM Bend/Redmond
ORDRDM
Chicago O'Hare Intl
Thu 11/26
12:58 pm-5:23 pm
1 stop6h 25m
Bend/Redmond
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$278
ChicagoRedmond
ORD Chicago O'Hare Intl - RDM Bend/Redmond
ORDRDM
Chicago O'Hare Intl
Sat 11/21
3:47 pm-10:03 pm
2 stops8h 16m
Bend/Redmond
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$281
ChicagoRedmond
ORD Chicago O'Hare Intl - RDM Bend/Redmond
ORDRDM
Chicago O'Hare Intl
Tue 1/26
6:57 pm-11:53 pm
1 stop6h 56m
Bend/Redmond
Sat 1/30
2:41 pm-11:59 pm
1 stop7h 18m
$475
Showing 1-10 of 14 resultsSorted by cheapest first
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.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago-Redmond flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Redmond flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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.
CHI-RDM
ORD-RDM
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
CHI-RDM
ORD-RDM
What is the cheapest month to book a flight from Chicago to Redmond?
Currently, February is the cheapest month in which you can book a flight from Chicago to Redmond (average of $346). Flying from Chicago to Redmond in June is currently the most expensive (average of $628). 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.
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 October 31, 2026.
Read reviews from past customers who have flown Alaska Airlines,Delta, andUnited 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.
Entertainment
7.0
Boarding
8.1
Food
7.0
Comfort
7.8
Crew
8.5
Overall
7.9
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Entertainment
7.0
Boarding
8.1
Food
7.0
Comfort
7.8
Crew
8.5
Overall
7.9
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Entertainment
7.0
Boarding
8.1
Food
7.0
Comfort
7.8
Crew
8.5
Overall
7.9
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Entertainment
7.0
Boarding
8.1
Food
7.0
Comfort
7.8
Crew
8.5
Overall
7.9
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
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.
Traveling to a place near Redmond?
Book flights to Redmond if you plan to visit one of these locationsBend
Madras
Sunriver
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Chicago and Redmond flights
Browse other Chicago and Redmond flight options. Last updated on October 31, 2026.
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Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on October 31, 2026.
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Explore flights to Redmond departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on October 31, 2026.
Top 4 airlines flying from Chicago to Redmond
Discover the top 4 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 7,457,451 searches. Data last updated October 31, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$278 | Average$423 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$318 | Average$808 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$336 | Average$580 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$421 | Average$591 | FlexibilityNo cancel fee | On-time75% |