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$137+ 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 6/3. Fares are subject to change and may not be available on all flights or dates of travel.
RDM — CHI
May 5 — May 121
Mon 5/5
Mon 5/12
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 April 30, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$241
(United Airlines)

One-way from

$137
(Alaska Airlines)

Popular in

February

Cheapest in

May

Average price

$420
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. 12% potential increase in price ($74 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($20 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 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 April 30, 2025.

This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/191:51 pmRDM - ORD
1 stop7h 36mUnited Airlines
Wed 5/216:30 amORD - RDM
1 stop7h 47mUnited Airlines
Deal found 4/29$241
This Alaska Airlines 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/305:59 pmRDM - ORD
1 stop9h 41mAlaska Airlines
Wed 7/26:00 amORD - RDM
1 stop8h 44mAlaska Airlines
Deal found 4/29$280
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.
Wed 7/1612:35 pmRDM - ORD
1 stop7h 33mDelta
Sat 7/197:40 amORD - RDM
2 stops13h 10mDelta
Deal found 4/29$284
This Hawaiian Airlines 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/54:00 pmRDM - ORD
1 stop5h 56mHawaiian Airlines
Sun 6/86:00 amORD - RDM
1 stop8h 30mHawaiian Airlines
Deal found 4/29$298
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.
Wed 7/167:30 pmRDM - MDW
2 stops11h 15mDelta
Sat 7/199:19 amMDW - RDM
2 stops13h 48mDelta
Deal found 4/29$384

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 April 30, 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

Mon 5/19

1:51 pm-11:27 pm

1 stop7h 36m

Chicago O'Hare Intl

Wed 5/21

6:30 am-12:17 pm

1 stop7h 47m

$241

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Mon 6/30

5:59 pm-5:40 am

1 stop9h 41m

Chicago O'Hare Intl

Wed 7/2

6:00 am-12:44 pm

1 stop8h 44m

$280

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Wed 7/16

12:35 pm-10:08 pm

1 stop7h 33m

Chicago O'Hare Intl

Sat 7/19

7:40 am-6:50 pm

2 stops13h 10m

$284

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Thu 6/5

4:00 pm-11:56 pm

1 stop5h 56m

Chicago O'Hare Intl

Sun 6/8

6:00 am-12:30 pm

1 stop8h 30m

$298

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Wed 7/16

7:30 pm-8:45 am

2 stops11h 15m

Chicago Midway

Sat 7/19

9:19 am-9:07 pm

2 stops13h 48m

$384

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Tue 6/3

1:25 pm-11:59 pm

1 stop8h 34m

$137

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Tue 6/3

11:20 am-9:40 pm

2 stops8h 20m

$145

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Sun 8/10

3:51 pm-11:39 pm

1 stop5h 48m

$179

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Thu 6/19

7:36 pm-8:41 am

2 stops11h 05m

$245

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Tue 6/3

6:00 am-10:03 am

3 stops26h 03m

$359

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 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 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 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 $321). 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 April 30, 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 April 30, 2025.
Alaska Airlines
8.0
Very good
9,961 reviews

Boarding

8.2

Comfort

7.9

Food

7.1

Entertainment

7.1

Crew

8.5

Overall

8.0

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

Boarding

8.2

Comfort

7.9

Food

7.1

Entertainment

7.1

Crew

8.5

Overall

8.0

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
7,929 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Boarding

8.2

Comfort

7.9

Food

7.1

Entertainment

7.1

Crew

8.5

Overall

8.0

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
2,405 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Boarding

8.2

Comfort

7.9

Food

7.1

Entertainment

7.1

Crew

8.5

Overall

8.0

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

Boarding

8.2

Comfort

7.9

Food

7.1

Entertainment

7.1

Crew

8.5

Overall

8.0

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 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 United Airlines is currently your cheapest option to Chicago, with prices starting at $241. Additional round-trip tickets that might be worth considering are offered by Alaska Airlines and Delta, with the lowest prices starting at $280 and $284, respectively. United Airlines is priced at 53% 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 Alaska Airlines. According to our data, you can fly for as low as $137. Users have also found prices from $145 and $179 on Delta and Hawaiian Airlines, 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 $321). 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
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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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 April 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$263Average$454FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$327Average$547FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$337Average$576FlexibilityNo cancel feeOn-time69%

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