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$150+ 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 11/25. Fares are subject to change and may not be available on all flights or dates of travel.
RDM — CHI
nov. 29 — dic. 61
sáb. 11/29
sáb. 12/6
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 octubre 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$283
(Alaska Airlines)

One-way from

$150
(United Airlines)

Popular in

March

Cheapest in

January

Average price

$426
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. 17% potential increase in price ($93 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in October 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 octubre 30, 2025.

This American Airlines deal was found by Cheapflights users on 10/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/102:57 pmRDM - ORD
1 stop7h 34mAmerican Airlines
sáb. 12/1312:10 pmORD - RDM
1 stop9h 23mAmerican Airlines
Deal found 10/29$298
This Delta deal was found by Cheapflights users on 10/29. 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.
mié. 12/107:34 pmRDM - ORD
2 stops10h 30mDelta
sáb. 12/135:29 pmORD - RDM
1 stop7h 21mDelta
Deal found 10/29$304
This Delta deal was found by Cheapflights users on 10/29. 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.
mié. 12/105:55 amRDM - MDW
2 stops10h 23mDelta
sáb. 12/131:14 pmMDW - RDM
2 stops11h 36mDelta
Deal found 10/29$309
This Alaska Airlines deal was found by Cheapflights users on 10/29. 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.
lun. 12/87:20 amRDM - ORD
1 stop10h 34mAlaska Airlines
vie. 12/128:59 pmORD - RDM
1 stop16h 53mAlaska Airlines
Deal found 10/29$318
This Delta deal was found by Cheapflights users on 10/29. 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.
lun. 12/87:00 amRDM - ORD
2 stops12h 21mDelta
vie. 12/127:40 pmORD - RDM
1 stop6h 19mDelta
Deal found 10/29$324
This Delta deal was found by Cheapflights users on 10/29. 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.
lun. 12/87:34 pmRDM - MDW
2 stops11h 45mDelta
vie. 12/1212:50 pmMDW - RDM
2 stops13h 09mDelta
Deal found 10/29$329
This Delta deal was found by Cheapflights users on 10/29. 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.
vie. 11/2112:25 pmRDM - ORD
1 stop7h 00mDelta
lun. 11/247:40 pmORD - RDM
1 stop6h 16mDelta
Deal found 10/29$349
This Alaska Airlines deal was found by Cheapflights users on 10/29. 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.
mar. 12/302:59 pmRDM - ORD
1 stop7h 00mAlaska Airlines
mar. 1/206:06 pmORD - RDM
1 stop7h 46mAlaska Airlines
Deal found 10/29$360
This Orbitz deal was found by Cheapflights users on 10/28. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 11/1712:43 pmRDM - ORD
2 stops15h 39mAlaska Airlines
mié. 11/198:00 amORD - RDM
1 stop11h 04mAlaska Airlines
Deal found 10/28$366
This Alaska Airlines deal was found by Cheapflights users on 10/29. 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.
mar. 12/302:59 pmRDM - ORD
1 stop7h 00mAlaska Airlines
mar. 1/62:12 pmORD - RDM
2 stops10h 25mAlaska Airlines
Deal found 10/29$368
This Delta deal was found by Cheapflights users on 10/28. 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.
lun. 11/177:34 pmRDM - MDW
2 stops11h 27mDelta
mié. 11/199:41 amMDW - RDM
2 stops11h 13mDelta
Deal found 10/28$447
This Delta deal was found by Cheapflights users on 10/29. 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.
lun. 12/157:34 pmRDM - MDW
2 stops11h 20mDelta
vie. 12/191:50 pmMDW - RDM
2 stops12h 09mDelta
Deal found 10/29$455

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 octubre 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

mié. 12/10

2:57 pm-12:31 am

1 stop7h 34m

Chicago O'Hare Intl

sáb. 12/13

12:10 pm-7:33 pm

1 stop9h 23m

$298

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

mié. 12/10

7:34 pm-8:04 am

2 stops10h 30m

Chicago O'Hare Intl

sáb. 12/13

5:29 pm-10:50 pm

1 stop7h 21m

$304

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

mié. 12/10

5:55 am-6:18 pm

2 stops10h 23m

Chicago Midway

sáb. 12/13

1:14 pm-10:50 pm

2 stops11h 36m

$309

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

lun. 1/5

5:54 am-5:12 pm

1 stop9h 18m

Chicago O'Hare Intl

lun. 1/12

6:06 pm-9:15 pm

1 stop29h 09m

$310

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

lun. 12/8

7:20 am-7:54 pm

1 stop10h 34m

Chicago O'Hare Intl

vie. 12/12

8:59 pm-11:52 am

1 stop16h 53m

$318

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

lun. 1/5

7:00 am-5:46 pm

2 stops8h 46m

Chicago O'Hare Intl

lun. 1/12

6:43 pm-10:50 pm

1 stop6h 07m

$324

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

lun. 12/8

7:00 am-9:21 pm

2 stops12h 21m

Chicago O'Hare Intl

vie. 12/12

7:40 pm-11:59 pm

1 stop6h 19m

$324

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

lun. 12/8

7:34 pm-9:19 am

2 stops11h 45m

Chicago Midway

vie. 12/12

12:50 pm-11:59 pm

2 stops13h 09m

$329

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

mar. 12/30

2:59 pm-11:59 pm

1 stop7h 00m

Chicago O'Hare Intl

mar. 1/13

6:06 pm-11:52 pm

1 stop7h 46m

$360

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

mar. 12/30

2:59 pm-11:59 pm

1 stop7h 00m

Chicago O'Hare Intl

mar. 1/20

6:06 pm-11:52 pm

1 stop7h 46m

$360

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 38 results
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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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Redmond-Chicago flight deals on Cheapflights vs. eDreams >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, May is the cheapest month in which you can book a flight from Redmond to Chicago (average of $258). Flying from Redmond to Chicago in March is currently the most expensive (average of $506). 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 octubre 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 in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 29% on airfare.

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 octubre 30, 2025.
Read reviews from past customers who have flown Alaska Airlines, Delta, and Hawaiian Airlines from Redmond to Chicago. 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
11,214 reviews

Comfort

7.8

Entertainment

7.0

Food

7.1

Overall

8.0

Crew

8.5

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Alaska Airlines
8.0
Very good
11,214 reviews
Alaska Airlines
8.0
Very good
11,214 reviews

Comfort

7.8

Entertainment

7.0

Food

7.1

Overall

8.0

Crew

8.5

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Delta
7.9
Good
7,993 reviews
Alaska Airlines
8.0
Very good
11,214 reviews

Comfort

7.8

Entertainment

7.0

Food

7.1

Overall

8.0

Crew

8.5

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Hawaiian Airlines
7.8
Good
2,797 reviews
Alaska Airlines
8.0
Very good
11,214 reviews

Comfort

7.8

Entertainment

7.0

Food

7.1

Overall

8.0

Crew

8.5

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
United Airlines
7.4
Good
8,998 reviews
Alaska Airlines
8.0
Very good
11,214 reviews

Comfort

7.8

Entertainment

7.0

Food

7.1

Overall

8.0

Crew

8.5

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.

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.

  • How long is the flight from Redmond to Chicago?

    American Airlines, Delta, and Alaska Airlines can get you from Redmond to Chicago in just under 7h 34m. Your travel time can differ by up to 2h 56m. Redmond and Chicago are separated by 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 Redmond to Chicago round-trip?

    Flying on Alaska Airlines is currently your cheapest option to Chicago, with prices starting at $262. Additional round-trip tickets that might be worth considering are offered by United Airlines and Delta, with the lowest prices starting at $278 and $288, respectively. Alaska Airlines is priced at 39% 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 United Airlines. According to our data, you can fly for as low as $150. Users have also found prices from $155 and $159 on Delta and Alaska 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, May is the cheapest month in which you can book a flight from Redmond to Chicago (average of $258). Flying from Redmond to Chicago in March is currently the most expensive (average of $506). 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
Merrillville
Lansing
Hammond
Porter
Benton Harbor

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Alternative routes for Redmond to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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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 octubre 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Alaska AirlinesCheapest$262Average$418FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$278Average$430FlexibilityNo cancel feeOn-time69%
DeltaCheapest$288Average$384FlexibilityNo cancel feeOn-timeN/A

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