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$109+ 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 5/28. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RDM
May 4 — May 111
Sun 5/4
Sun 5/11
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Bend/Redmond are usually found in January or May, booked 80 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 April 29, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$241
(United Airlines)

One-way from

$109
(Hawaiian Airlines)

Popular in

December

Cheapest in

January

Average price

$388
Provider with most accurate pricing for Chicago (CHI)-Bend/Redmond flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Bend/Redmond flights.
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From Chicago (CHI) to Bend/Redmond
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One-way flight from Chicago (CHI) to Bend/Redmond
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Highest demand for flights based on searches. 8% potential increase in price ($46 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($30 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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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 April 29, 2025.

This United Airlines deal was found by Cheapflights users on 4/28. 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.
Mon 5/127:00 amORD - RDM
1 stop9h 58mUnited Airlines
Tue 5/206:00 amRDM - ORD
1 stop6h 49mUnited Airlines
Deal found 4/28$241
This Delta deal was found by Cheapflights users on 4/29. 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.
Thu 8/287:15 amORD - RDM
1 stop6h 37mDelta
Sun 8/3112:35 pmRDM - ORD
1 stop7h 25mDelta
Deal found 4/29$259
This Alaska Airlines deal was found by Cheapflights users on 4/28. 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.
Tue 5/139:00 amORD - RDM
1 stop10h 00mAlaska Airlines
Sat 5/171:25 pmRDM - ORD
1 stop8h 34mAlaska Airlines
Deal found 4/28$262
This Delta deal was found by Cheapflights users on 4/28. 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 8/281:00 pmMDW - RDM
2 stops11h 47mDelta
Sun 8/315:55 amRDM - MDW
2 stops10h 08mDelta
Deal found 4/28$269
This Hawaiian Airlines deal was found by Cheapflights users on 4/28. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/106:00 amORD - RDM
1 stop8h 30mHawaiian Airlines
Tue 6/171:38 pmRDM - ORD
1 stop8h 21mHawaiian Airlines
Deal found 4/28$274
This American Airlines deal was found by Cheapflights users on 4/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/302:31 pmORD - RDM
1 stop7h 16mAmerican Airlines
Sat 9/133:23 pmRDM - ORD
1 stop7h 14mAmerican Airlines
Deal found 4/28$279

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 April 29, 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

Mon 5/12

7:00 am-2:58 pm

1 stop9h 58m

Bend/Redmond

Tue 5/20

6:00 am-2:49 pm

1 stop6h 49m

$241

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Tue 5/13

9:00 am-5:00 pm

1 stop10h 00m

Bend/Redmond

Sat 5/17

1:25 pm-11:59 pm

1 stop8h 34m

$262

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Tue 6/10

6:00 am-12:30 pm

1 stop8h 30m

Bend/Redmond

Tue 6/17

1:38 pm-11:59 pm

1 stop8h 21m

$274

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Tue 6/10

6:15 pm-10:57 pm

1 stop6h 42m

Bend/Redmond

Tue 6/17

7:00 am-6:25 pm

2 stops9h 25m

$282

ChicagoRedmond

MDW - RDM

MDWRDM

Chicago Midway

Sat 6/7

9:16 am-6:49 pm

2 stops11h 33m

Bend/Redmond

Fri 7/18

7:30 pm-8:39 am

2 stops11h 09m

$299

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Sat 6/21

7:00 am-12:18 pm

1 stop7h 18m

$139

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Sat 6/21

7:40 am-6:56 pm

2 stops13h 16m

$145

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Mon 5/12

7:10 am-12:55 pm

1 stop7h 45m

$177

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Thu 7/3

6:00 am-12:44 pm

1 stop8h 44m

$179

ChicagoRedmond

MDW - RDM

MDWRDM

Chicago Midway

Sat 7/12

1:46 pm-10:28 pm

2 stops10h 42m

$364

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/28

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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
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 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 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 April 25, 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 76 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, January is the cheapest month in which you can book a flight from Chicago to Redmond (average of $336). Flying from Chicago to Redmond in June is currently the most expensive (average of $539). 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 April 29, 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 16% on your trip compared to booking a flight in the evening.

Rainfall in Redmond by month

Plan your trip to Redmond by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Redmond ranges from 0.0 - 0.8 inches per month. January is typically the wettest month, when rainfall can reach 0.8 in. July is typically the driest time to visit Redmond when rainfall is around 0.0 in.

Temperature in Redmond by month

Plan your trip to Redmond by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Redmond, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 64.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 32.0 F).

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 April 29, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Delta and Hawaiian Airlines from Chicago to Redmond by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,961 reviews

Entertainment

7.1

Comfort

7.9

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
9,961 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Entertainment

7.1

Comfort

7.9

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,936 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Entertainment

7.1

Comfort

7.9

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Hawaiian Airlines
7.9
Good
2,406 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Entertainment

7.1

Comfort

7.9

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,696 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Entertainment

7.1

Comfort

7.9

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Entertainment

7.1

Comfort

7.9

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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.

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

    According to our current data, United Airlines ($241), Delta ($259), and Alaska Airlines ($262) offers the cheapest pricing from Chicago to Redmond. These flights start at 49% 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 Hawaiian Airlines ($109), Delta ($110), and Alaska Airlines ($131).

  • 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, January is the cheapest month in which you can book a flight from Chicago to Redmond (average of $336). Flying from Chicago to Redmond in June is currently the most expensive (average of $539). 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 Chicago?

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

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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 April 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$250Average$288FlexibilityNo cancel feeOn-time71%
DeltaCheapest$285Average$451FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$318Average$556FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$374Average$567FlexibilityNo cancel feeOn-time69%

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