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$127+ 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 9/30. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RDM
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
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 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 September 11, 2025.

Round-trip from

$233
(Hawaiian Airlines)

One-way from

$127
(Cheapflightsfares)

Popular in

December

Cheapest in

January

Average price

$347
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. 15% potential increase in price ($82 potential increase over avg. RT price).
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Cheapest flight prices on average. 8% potential price decrease ($33 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 11, 2025.

This Hawaiian Airlines deal was found by Cheapflights users on 9/10. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1810:00 amORD - RDM
1 stop9h 04mHawaiian Airlines
Sat 12/61:30 pmRDM - ORD
1 stop8h 29mHawaiian Airlines
Deal found 9/10$233
This Delta deal was found by Cheapflights users on 9/10. 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.
Sat 10/252:20 pmORD - RDM
1 stop6h 26mDelta
Wed 10/297:00 amRDM - ORD
1 stop8h 10mDelta
Deal found 9/10$234
This Delta deal was found by Cheapflights users on 9/9. 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 10/76:05 pmORD - RDM
1 stop6h 30mDelta
Sat 10/117:26 pmRDM - ORD
2 stops11h 04mDelta
Deal found 9/9$239
This Delta deal was found by Cheapflights users on 9/11. 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.
Sat 10/42:25 pmORD - RDM
1 stop6h 25mDelta
Sat 10/117:00 amRDM - ORD
1 stop8h 18mDelta
Deal found 9/11$243
This Delta deal was found by Cheapflights users on 9/10. 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.
Thu 10/26:10 pmORD - RDM
1 stop6h 46mDelta
Wed 10/87:00 amRDM - ORD
1 stop8h 10mDelta
Deal found 9/10$254
This Delta deal was found by Cheapflights users on 9/10. 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.
Sat 11/11:25 pmORD - RDM
2 stops11h 10mDelta
Tue 11/411:25 amRDM - ORD
1 stop10h 25mDelta
Deal found 9/10$267
This Hawaiian Airlines deal was found by Cheapflights users on 9/8. 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.
Sat 10/255:59 pmORD - RDM
1 stop8h 00mHawaiian Airlines
Wed 10/291:00 pmRDM - ORD
1 stop8h 59mHawaiian Airlines
Deal found 9/8$278
This Alaska Airlines deal was found by Cheapflights users on 9/8. 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.
Sat 11/13:25 pmORD - RDM
1 stop7h 33mAlaska Airlines
Tue 11/49:30 amRDM - ORD
1 stop8h 25mAlaska Airlines
Deal found 9/8$279
This Alaska Airlines deal was found by Cheapflights users on 9/9. 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 stop17h 25mAlaska Airlines
Sat 10/117:15 amRDM - ORD
1 stop14h 44mAlaska Airlines
Deal found 9/9$281
This Delta deal was found by Cheapflights users on 9/8. 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 10/2511:10 amMDW - RDM
2 stops13h 25mDelta
Wed 10/297:26 pmRDM - MDW
2 stops11h 14mDelta
Deal found 9/8$289
This Delta deal was found by Cheapflights users on 9/11. 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.
Sat 10/49:20 amMDW - RDM
2 stops11h 30mDelta
Sat 10/117:26 pmRDM - MDW
2 stops11h 29mDelta
Deal found 9/11$309
This Delta deal was found by Cheapflights users on 9/9. 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 10/71:08 pmMDW - RDM
2 stops12h 38mDelta
Sat 10/117:26 pmRDM - MDW
2 stops11h 29mDelta
Deal found 9/9$341

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 September 11, 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 11/18

10:00 am-5:04 pm

1 stop9h 04m

Bend/Redmond

Sat 12/6

1:30 pm-11:59 pm

1 stop8h 29m

$233

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Sat 10/25

2:20 pm-6:46 pm

1 stop6h 26m

Bend/Redmond

Wed 10/29

7:00 am-5:10 pm

1 stop8h 10m

$234

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Sat 11/1

7:37 am-10:35 pm

1 stop16h 58m

Bend/Redmond

Tue 11/4

7:26 pm-1:30 pm

1 stop16h 04m

$234

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Sat 10/4

2:25 pm-6:50 pm

1 stop6h 25m

Bend/Redmond

Sat 10/11

7:00 am-5:18 pm

1 stop8h 18m

$243

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Tue 10/7

2:10 pm-10:35 pm

2 stops10h 25m

Bend/Redmond

Sat 10/11

7:26 pm-8:30 am

2 stops11h 04m

$245

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Thu 10/2

6:10 pm-10:56 pm

1 stop6h 46m

Bend/Redmond

Wed 10/8

7:00 am-5:10 pm

1 stop8h 10m

$254

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Sat 10/25

5:59 pm-11:59 pm

1 stop8h 00m

Bend/Redmond

Wed 10/29

1:00 pm-11:59 pm

1 stop8h 59m

$278

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Sat 11/1

3:25 pm-8:58 pm

1 stop7h 33m

Bend/Redmond

Tue 11/4

9:30 am-7:55 pm

1 stop8h 25m

$279

ChicagoRedmond

MDW - RDM

MDWRDM

Chicago Midway

Sat 10/25

11:10 am-10:35 pm

2 stops13h 25m

Bend/Redmond

Wed 10/29

7:26 pm-8:40 am

2 stops11h 14m

$289

ChicagoRedmond

MDW - RDM

MDWRDM

Chicago Midway

Sat 10/4

9:20 am-6:50 pm

2 stops11h 30m

Bend/Redmond

Sat 10/11

7:26 pm-8:55 am

2 stops11h 29m

$309

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 36 results
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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 August 29, 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, 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 $475). 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 September 11, 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.

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 September 11, 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
10,000 reviews

Comfort

7.8

Entertainment

7.0

Overall

8.0

Food

7.1

Crew

8.5

Boarding

8.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Entertainment

7.0

Overall

8.0

Food

7.1

Crew

8.5

Boarding

8.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Delta
8.0
Very good
7,960 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Entertainment

7.0

Overall

8.0

Food

7.1

Crew

8.5

Boarding

8.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Hawaiian Airlines
7.8
Good
2,723 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Entertainment

7.0

Overall

8.0

Food

7.1

Crew

8.5

Boarding

8.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
United Airlines
7.4
Good
8,937 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Entertainment

7.0

Overall

8.0

Food

7.1

Crew

8.5

Boarding

8.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.

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 26m. Fly via Hawaiian 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 44% 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, 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 $475). 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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Alternative routes for Chicago to Redmond

See prices for flight routes from nearby airports that may be better suited for you.
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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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$246Average$413FlexibilityNo cancel feeOn-time85%
American AirlinesCheapest$250Average$286FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$278Average$461FlexibilityNo cancel feeOn-time75%
DeltaCheapest$278Average$439FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$348Average$581FlexibilityNo cancel feeOn-time69%

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