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$109+ Cheap flights from Redmond (RDM) to Chicago (CHI)

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 5/31. Fares are subject to change and may not be available on all flights or dates of travel.
RDM — CHI
Apr 2 — Apr 91
Wed 4/2
Wed 4/9
1 adult, Economy
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Cheap flight deals from Redmond to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Redmond (RDM) to Chicago (CHI). 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 March 28, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$248
(Hawaiian Airlines)

One-way from

$109
(Hawaiian Airlines)

Popular in

February

Cheapest in

April

Average price

$609
Provider with most accurate pricing for Bend/Redmond-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Bend/Redmond-Chicago (CHI) flights.
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From Bend/Redmond to Chicago (CHI)
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One-way flight from Bend/Redmond to Chicago (CHI)
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Highest demand for flights based on searches. 13% potential increase in price ($79 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($22 potential savings vs. average RT price).
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Average for round-trip flights in March 2025
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Find flight deals from Redmond to Chicago

Cheapest flights from Redmond to Chicago
Explore the most affordable flight options available from Redmond to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 28, 2025.

This Hawaiian Airlines deal was found by Cheapflights users on 3/25. 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 5/108:00 amRDM - ORD
1 stop9h 10mHawaiian Airlines
Sat 5/177:00 amORD - RDM
1 stop7h 22mHawaiian Airlines
Deal found 3/25$248
This United Airlines deal was found by Cheapflights users on 3/26. 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 5/201:19 pmRDM - ORD
1 stop5h 58mUnited Airlines
Tue 5/276:30 amORD - RDM
1 stop7h 41mUnited Airlines
Deal found 3/26$258
This Delta deal was found by Cheapflights users on 3/26. 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.
Tue 6/1711:20 amRDM - ORD
2 stops8h 50mDelta
Tue 6/247:00 amORD - RDM
2 stops13h 50mDelta
Deal found 3/26$259
This Alaska Airlines deal was found by Cheapflights users on 3/26. 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.
Sat 6/74:00 pmRDM - ORD
1 stop5h 56mAlaska Airlines
Sat 6/217:00 amORD - RDM
2 stops13h 51mAlaska Airlines
Deal found 3/26$322
This American Airlines deal was found by Cheapflights users on 3/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/172:11 pmRDM - ORD
1 stop8h 21mAmerican Airlines
Tue 6/245:00 amORD - RDM
1 stop10h 02mAmerican Airlines
Deal found 3/26$359
This Delta deal was found by Cheapflights users on 3/27. 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.
Mon 4/285:36 pmRDM - MDW
2 stops13h 04mDelta
Fri 5/21:16 pmMDW - RDM
2 stops12h 42mDelta
Deal found 3/27$359

Cheapflights Fare Finder

Customize your flight search to find flights from Redmond to Chicago 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 March 28, 2025.
Use the filters below to find and compare flights from Redmond to Chicago that are best for you.

Fly from

Redmond

Fly to

Chicago

Route

Depart

Return

Price

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Sat 5/10

8:00 am-7:10 pm

1 stop9h 10m

Chicago O'Hare Intl

Sat 5/17

7:00 am-12:22 pm

1 stop7h 22m

$248

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Tue 5/20

1:19 pm-9:17 pm

1 stop5h 58m

Chicago O'Hare Intl

Tue 5/27

6:30 am-12:11 pm

1 stop7h 41m

$258

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Tue 6/17

11:20 am-10:10 pm

2 stops8h 50m

Chicago O'Hare Intl

Tue 6/24

7:00 am-6:50 pm

2 stops13h 50m

$259

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Fri 6/6

4:00 pm-11:56 pm

1 stop5h 56m

Chicago O'Hare Intl

Mon 6/9

7:59 pm-10:19 am

1 stop16h 20m

$298

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Tue 6/17

2:11 pm-12:32 am

1 stop8h 21m

Chicago O'Hare Intl

Tue 6/24

5:00 am-1:02 pm

1 stop10h 02m

$359

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Mon 4/28

5:36 pm-8:40 am

2 stops13h 04m

Chicago Midway

Fri 5/2

1:16 pm-11:58 pm

2 stops12h 42m

$359

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Sat 5/31

4:00 pm-11:56 pm

1 stop5h 56m

$109

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Wed 7/16

7:32 pm-5:18 am

1 stop7h 46m

$110

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Wed 7/16

7:28 pm-9:22 am

2 stops11h 54m

$115

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Sat 5/31

7:29 pm-8:40 am

2 stops11h 11m

$170

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/26

Showing 1-10 of 11 results
1
2

Compare providers for flights from Redmond to Chicago

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 Redmond to Chicago in March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 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 Redmond-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Redmond-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Redmond-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Redmond-Chicago 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 Redmond-Chicago 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 Redmond to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Redmond 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 Redmond to Chicago

What is the cheapest month to book a flight from Redmond to Chicago?

Currently, August is the cheapest month in which you can book a flight from Redmond to Chicago (average of $245). Flying from Redmond to Chicago in March is currently the most expensive (average of $323). 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 RDM to CHI?

Find hourly flight availability from Redmond to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated March 28, 2025.

One of the essential ways to save on airfare from Redmond to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the morning could potentially save you up to 14% on airfare.

Rainfall in Chicago by month

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

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

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

If weather is an important factor for your trip to Chicago, 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 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated March 28, 2025.
Read through reviews of airlines operating flights from Redmond to Chicago, such as Alaska Airlines, Delta and Hawaiian Airlines. 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
9,798 reviews

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Alaska Airlines
8.0
Very good
9,798 reviews
Alaska Airlines
8.0
Very good
9,798 reviews

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Delta
8.0
Very good
7,896 reviews
Alaska Airlines
8.0
Very good
9,798 reviews

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Hawaiian Airlines
7.9
Good
2,335 reviews
Alaska Airlines
8.0
Very good
9,798 reviews

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
United Airlines
7.4
Good
8,603 reviews
Alaska Airlines
8.0
Very good
9,798 reviews

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
9,798 reviews

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Related info for your journey

Find useful and relevant information for your journey from Redmond to Chicago. 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 from for flights from Redmond to Chicago?

    Bend/Redmond (RDM) is the airport you will fly out of if you book a flight from Redmond to Chicago. You should not have trouble finding flights to Chicago from Bend/Redmond; the airport handles an average of 0 outbound flights to Chicago per day. You should also have plenty of airline options to choose from since 3 airlines have flights from the Redmond airport to Chicago. It is only a 1.8 mi journey to Bend/Redmond (RDM) from Redmond’s city center.

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

    Flying on Hawaiian Airlines is currently your cheapest option to Chicago, with prices starting at $248. Additional round-trip tickets that might be worth considering are offered by United Airlines and Delta, with the lowest prices starting at $258 and $259, respectively. Hawaiian Airlines is priced at 52% lower than the current average price of a flight leaving 3 months from now.

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

    For one-way options, check prices for Hawaiian Airlines. According to our data, you can fly for as low as $109. Users have also found prices from $110 and $115 on United Airlines and Delta, respectively.

  • Can I find deals for flights from Redmond to Chicago that include hotel bookings?

    Yes. In addition to deals on Redmond to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Redmond to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Redmond to Chicago.

  • Can I find deals for business class flights from Redmond to Chicago?

    Yes. Cheapflights offers flight deals from Redmond to Chicago 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 Redmond to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Redmond to Chicago (average of $245). Flying from Redmond to Chicago in March is currently the most expensive (average of $323). 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
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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Alternative routes for Redmond to Chicago

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Top 3 airlines flying from Redmond to Chicago

Discover the top 3 airlines that operate flights from Redmond to Chicago. 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 March 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$263Average$457FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$337Average$576FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$350Average$584FlexibilityNo cancel feeOn-time75%
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