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$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 6/2. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RDM
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap 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 January 29, 2026.

This United Airlines deal was found by Cheapflights users on 1/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/87:00 am
ORD
-
RDM
1 stop7h 38m
United Airlines
Wed 4/151:55 pm
RDM
-
ORD
1 stop9h 04m
United Airlines
Deal found 1/28$233
This Delta deal was found by Cheapflights users on 1/28. 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.
Sat 4/117:20 am
ORD
-
RDM
1 stop6h 32m
Delta
Wed 4/1512:33 pm
RDM
-
ORD
1 stop6h 45m
Delta
Deal found 1/28$237
This Delta deal was found by Cheapflights users on 1/28. 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.
Tue 3/107:10 pm
ORD
-
RDM
1 stop6h 37m
Delta
Sat 3/1411:24 am
RDM
-
ORD
1 stop10h 27m
Delta
Deal found 1/28$270
This Delta deal was found by Cheapflights users on 1/28. 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.
Fri 3/66:45 pm
ORD
-
RDM
1 stop7h 00m
Delta
Tue 3/1011:24 am
RDM
-
ORD
2 stops8h 10m
Delta
Deal found 1/28$279
This Delta deal was found by Cheapflights users on 1/28. 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.
Tue 3/107:10 pm
ORD
-
RDM
1 stop6h 37m
Delta
Fri 3/134:55 pm
RDM
-
ORD
1 stop18h 29m
Delta
Deal found 1/28$280
This Delta deal was found by Cheapflights users on 1/28. 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.
Mon 3/97:25 am
ORD
-
RDM
1 stop29h 18m
Delta
Sat 3/1411:24 am
RDM
-
ORD
1 stop10h 27m
Delta
Deal found 1/28$303
This United Airlines deal was found by Cheapflights users on 1/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/126:17 am
ORD
-
RDM
1 stop7h 54m
United Airlines
Mon 3/161:54 pm
RDM
-
ORD
1 stop9h 05m
United Airlines
Deal found 1/28$306
This Delta deal was found by Cheapflights users on 1/27. 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 2/1012:46 pm
MDW
-
RDM
2 stops13h 06m
Delta
Wed 2/185:50 am
RDM
-
MDW
2 stops9h 47m
Delta
Deal found 1/27$380
This Delta deal was found by Cheapflights users on 1/28. 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.
Wed 2/251:49 pm
MDW
-
RDM
2 stops10h 56m
Delta
Sun 3/112:25 pm
RDM
-
MDW
2 stops22h 21m
Delta
Deal found 1/28$397
This Delta deal was found by Cheapflights users on 1/27. 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.
Fri 3/61:29 pm
MDW
-
RDM
2 stops11h 16m
Delta
Tue 3/106:20 am
RDM
-
MDW
2 stops9h 34m
Delta
Deal found 1/27$508
This Delta deal was found by Cheapflights users on 1/27. 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.
Sat 4/111:10 pm
MDW
-
RDM
2 stops11h 57m
Delta
Wed 4/156:05 am
RDM
-
MDW
2 stops10h 31m
Delta
Deal found 1/27$575
This Delta deal was found by Cheapflights users on 1/28. 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.
Thu 1/291:49 pm
MDW
-
RDM
2 stops12h 03m
Delta
Thu 2/55:50 am
RDM
-
MDW
2 stops10h 46m
Delta
Deal found 1/28$586

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$233
(United Airlines)

One-way from

$150
(Alaska Airlines)

Popular in

March

Cheapest in

June
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. 3% potential price decrease ($17 potential savings vs. average RT price).
Search Deals

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 January 29, 2026.
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

Wed 4/8

7:00 am-12:38 pm

1 stop7h 38m

Bend/Redmond

Wed 4/15

1:55 pm-12:59 am

1 stop9h 04m

$233

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Wed 3/11

7:20 am-11:52 am

1 stop6h 32m

Bend/Redmond

Sat 3/14

11:24 am-11:51 pm

1 stop10h 27m

$270

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Tue 3/10

1:19 pm-10:55 pm

2 stops11h 36m

Bend/Redmond

Sat 3/14

11:24 am-11:51 pm

1 stop10h 27m

$275

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Wed 4/8

6:00 am-12:10 pm

2 stops8h 10m

Bend/Redmond

Wed 4/15

8:14 pm-6:39 am

1 stop8h 25m

$285

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Tue 3/10

3:59 pm-11:47 pm

2 stops9h 48m

Bend/Redmond

Fri 3/13

4:55 pm-1:24 pm

1 stop18h 29m

$285

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Thu 3/12

6:17 am-12:11 pm

1 stop7h 54m

Bend/Redmond

Mon 3/16

1:54 pm-12:59 am

1 stop9h 05m

$306

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Fri 3/6

3:54 pm-9:32 pm

1 stop7h 38m

Bend/Redmond

Tue 3/10

9:02 am-11:56 pm

1 stop12h 54m

$308

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Wed 6/3

3:43 pm-9:20 pm

1 stop7h 37m

Bend/Redmond

Mon 6/8

6:00 am-6:46 pm

1 stop10h 46m

$309

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Fri 3/6

6:45 pm-11:45 pm

1 stop7h 00m

Bend/Redmond

Mon 3/9

6:20 am-6:05 pm

2 stops9h 45m

$316

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Mon 3/9

7:10 pm-11:47 pm

1 stop6h 37m

Bend/Redmond

Fri 3/13

4:55 pm-1:24 pm

1 stop18h 29m

$317

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 37 results
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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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 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.
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 January 23, 2026.

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 37 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, August is the cheapest month in which you can book a flight from Chicago to Redmond (average of $250). Flying from Chicago to Redmond in March is currently the most expensive (average of $398). 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.

How much does it cost to fly round-trip from Chicago to Redmond?

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 January 29, 2026.
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
11,808 reviews

Comfort

7.8

Crew

8.5

Boarding

8.1

Overall

8.0

Entertainment

7.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Alaska Airlines
8.0
Very good
11,808 reviews
Alaska Airlines
8.0
Very good
11,808 reviews

Comfort

7.8

Crew

8.5

Boarding

8.1

Overall

8.0

Entertainment

7.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Delta
7.9
Good
8,127 reviews
Alaska Airlines
8.0
Very good
11,808 reviews

Comfort

7.8

Crew

8.5

Boarding

8.1

Overall

8.0

Entertainment

7.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Hawaiian Airlines
7.8
Good
2,830 reviews
Alaska Airlines
8.0
Very good
11,808 reviews

Comfort

7.8

Crew

8.5

Boarding

8.1

Overall

8.0

Entertainment

7.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
United Airlines
7.4
Good
9,215 reviews
Alaska Airlines
8.0
Very good
11,808 reviews

Comfort

7.8

Crew

8.5

Boarding

8.1

Overall

8.0

Entertainment

7.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading

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. 4 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 32m. Fly via United Airlines, Delta, or Alaska Airlines 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, Delta ($139), Hawaiian Airlines ($246), and Alaska Airlines ($278) offers the cheapest pricing from Chicago to Redmond. These flights start at 68% lower than the current average price 3 months from now.

  • What are the cheapest airlines to fly from Chicago to Redmond one-way?

    The cheapest airlines for a one-way flight from Chicago to Redmond are United Airlines ($109), Delta ($125), and Alaska Airlines ($158).

  • 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, August is the cheapest month in which you can book a flight from Chicago to Redmond (average of $250). Flying from Chicago to Redmond in March is currently the most expensive (average of $398). 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

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See prices for flight routes from nearby airports that may be better suited for you.
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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 2,558,603 searches. Data last updated January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$139Average$378FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$246Average$413FlexibilityNo cancel feeOn-time85%
Alaska AirlinesCheapest$278Average$459FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$278Average$420FlexibilityNo cancel feeOn-time69%

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