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$125+ 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 10/2. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RDM
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Bend/Redmond are usually found in January or June, booked 44 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 June 12, 2025.

Round-trip from

$222
(Alaska Airlines)

One-way from

$129
(Hawaiian Airlines)

Popular in

December

Cheapest in

January

Average price

$322
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. 13% potential increase in price ($72 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($32 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This Alaska Airlines deal was found by Cheapflights users on 6/10. 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 10/76:00 amORD - RDM
1 stop14h 56mAlaska Airlines
Sat 10/113:40 pmRDM - ORD
1 stop6h 19mAlaska Airlines
Deal found 6/10$222
This Trip.com deal was found by Cheapflights users on 6/12. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/86:00 amORD - RDM
1 stop8h 44mHawaiian Airlines
Mon 8/111:38 pmRDM - ORD
1 stop8h 21mHawaiian Airlines
Deal found 6/12$247
This Delta deal was found by Cheapflights users on 6/10. 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 7/146:15 pmORD - RDM
1 stop6h 39mDelta
Wed 7/2311:35 amRDM - ORD
2 stops8h 33mDelta
Deal found 6/10$284
This Delta deal was found by Cheapflights users on 6/11. 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 10/72:00 pmMDW - RDM
2 stops10h 44mDelta
Sat 10/117:25 pmRDM - MDW
2 stops11h 21mDelta
Deal found 6/11$289
This American Airlines deal was found by Cheapflights users on 6/12. 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.
Fri 7/184:39 pmORD - RDM
1 stop8h 29mAmerican Airlines
Fri 7/251:35 pmRDM - ORD
1 stop6h 58mAmerican Airlines
Deal found 6/12$319
This United Airlines deal was found by Cheapflights users on 6/10. 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 7/113:54 pmORD - RDM
1 stop8h 51mUnited Airlines
Thu 7/177:32 pmRDM - ORD
1 stop8h 43mUnited Airlines
Deal found 6/10$349

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 June 12, 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

Tue 10/7

6:00 am-6:56 pm

1 stop14h 56m

Bend/Redmond

Sat 10/11

3:40 pm-11:59 pm

1 stop6h 19m

$222

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Fri 8/8

6:00 am-12:44 pm

1 stop8h 44m

Bend/Redmond

Mon 8/11

1:38 pm-11:59 pm

1 stop8h 21m

$247

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Mon 7/14

6:15 pm-10:54 pm

1 stop6h 39m

Bend/Redmond

Wed 7/23

11:35 am-10:08 pm

2 stops8h 33m

$284

ChicagoRedmond

MDW - RDM

MDWRDM

Chicago Midway

Tue 10/7

2:00 pm-10:44 pm

2 stops10h 44m

Bend/Redmond

Sat 10/11

7:25 pm-8:46 am

2 stops11h 21m

$289

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Fri 7/18

4:39 pm-11:08 pm

1 stop8h 29m

Bend/Redmond

Fri 7/25

1:35 pm-10:33 pm

1 stop6h 58m

$319

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Fri 7/11

3:54 pm-10:45 pm

1 stop8h 51m

Bend/Redmond

Thu 7/17

7:32 pm-6:15 am

1 stop8h 43m

$349

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Thu 10/2

6:20 am-12:37 pm

1 stop8h 17m

$125

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Sat 7/12

4:50 pm-10:45 pm

1 stop7h 55m

$130

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Thu 9/11

2:07 pm-10:58 pm

1 stop10h 51m

$135

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Thu 9/11

6:00 pm-10:44 pm

1 stop6h 44m

$160

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Showing 1-10 of 12 results
1
2

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 June 9, 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 44 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 July is currently the most expensive (average of $495). 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 June 12, 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 June 12, 2025.
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

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
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

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
7,946 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

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
2,494 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

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
8,790 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

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
10,000 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

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. 5 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, Alaska Airlines ($222), Hawaiian Airlines ($247), and Delta ($284) offers the cheapest pricing from Chicago to Redmond. These flights start at 51% 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 ($129), United Airlines ($130), and Delta ($165).

  • 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 July is currently the most expensive (average of $495). 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 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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$246Average$413FlexibilityNo cancel feeOn-time85%
American AirlinesCheapest$250Average$288FlexibilityNo cancel feeOn-time71%
DeltaCheapest$285Average$439FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$312Average$517FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$372Average$531FlexibilityNo cancel feeOn-time69%

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