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$156+ 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 2/26. Fares are subject to change and may not be available on all flights or dates of travel.
RDM — CHI
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap 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 January 29, 2026.

This United Airlines deal was found by Cheapflights users on 1/29. 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.
Wed 4/291:55 pm
RDM
-
ORD
1 stop9h 04m
United Airlines
Tue 5/56:20 am
ORD
-
RDM
1 stop7h 33m
United Airlines
Deal found 1/29$232
This United Airlines deal was found by Cheapflights users on 1/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/285:10 am
RDM
-
ORD
1 stop7h 40m
United Airlines
Sat 3/72:45 pm
ORD
-
RDM
1 stop8h 05m
United Airlines
Deal found 1/28$237
This Delta deal was found by Cheapflights users on 1/29. 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 4/2912:33 pm
RDM
-
ORD
1 stop6h 45m
Delta
Tue 5/51:36 pm
ORD
-
RDM
2 stops12h 21m
Delta
Deal found 1/29$242
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2712:10 pm
RDM
-
ORD
1 stop15h 21m
Multiple Airlines
Thu 4/309:18 pm
ORD
-
RDM
1 stop16h 12m
Multiple Airlines
Deal found 1/27$268
This United Airlines deal was found by Cheapflights users on 1/29. 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.
Thu 2/191:13 pm
RDM
-
ORD
1 stop6h 16m
United Airlines
Tue 2/248:40 am
ORD
-
RDM
1 stop6h 18m
United Airlines
Deal found 1/29$274
This United Airlines deal was found by Cheapflights users on 1/29. 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.
Wed 4/11:55 pm
RDM
-
ORD
1 stop9h 04m
United Airlines
Mon 4/67:00 am
ORD
-
RDM
1 stop7h 38m
United Airlines
Deal found 1/29$281
This Alaska Airlines deal was found by Cheapflights users on 1/28. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/318:40 am
RDM
-
ORD
1 stop6h 21m
Alaska Airlines
Tue 11/36:00 am
ORD
-
RDM
1 stop8h 45m
Alaska Airlines
Deal found 1/28$299
This United Airlines deal was found by Cheapflights users on 1/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/61:54 pm
RDM
-
ORD
1 stop9h 05m
United Airlines
Sun 3/86:17 am
ORD
-
RDM
1 stop7h 54m
United Airlines
Deal found 1/28$307
This United Airlines deal was found by Cheapflights users on 1/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/181:13 pm
RDM
-
ORD
1 stop7h 40m
United Airlines
Fri 2/204:20 pm
ORD
-
RDM
1 stop8h 25m
United Airlines
Deal found 1/27$309
This Delta deal was found by Cheapflights users on 1/28. 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.
Sat 2/2811:23 am
RDM
-
ORD
2 stops8h 29m
Delta
Sat 3/75:15 pm
ORD
-
RDM
1 stop7h 08m
Delta
Deal found 1/28$310
This Delta deal was found by Cheapflights users on 1/27. 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.
Wed 2/185:50 am
RDM
-
MDW
2 stops9h 47m
Delta
Fri 2/201:26 pm
MDW
-
RDM
2 stops11h 19m
Delta
Deal found 1/27$390
This Delta deal was found by Cheapflights users on 1/28. 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.
Wed 2/115:50 am
RDM
-
MDW
2 stops10h 46m
Delta
Sat 2/141:29 pm
MDW
-
RDM
2 stops11h 16m
Delta
Deal found 1/28$450

Find 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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$232
(United Airlines)

One-way from

$156
(American Airlines)

Popular in

January

Cheapest in

December

Average price

$597
Provider with most accurate pricing for Bend/Redmond-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Bend/Redmond-Chicago (CHI) flights.
Search Deals
From Bend/Redmond to Chicago (CHI)
Search Deals
One-way flight from Bend/Redmond to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($20 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 January 29, 2026.
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

Wed 4/29

1:55 pm-12:59 am

1 stop9h 04m

Chicago O'Hare Intl

Tue 5/5

6:20 am-11:53 am

1 stop7h 33m

$232

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Sat 2/28

5:10 am-2:50 pm

1 stop7h 40m

Chicago O'Hare Intl

Sat 3/7

2:45 pm-8:50 pm

1 stop8h 05m

$237

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Wed 4/29

12:33 pm-9:18 pm

1 stop6h 45m

Chicago O'Hare Intl

Tue 5/5

1:36 pm-11:57 pm

2 stops12h 21m

$242

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Mon 4/27

12:10 pm-5:31 am

1 stop15h 21m

Chicago O'Hare Intl

Thu 4/30

9:18 pm-11:30 am

1 stop16h 12m

$268

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Sat 4/11

12:57 pm-10:58 pm

1 stop8h 01m

Chicago O'Hare Intl

Mon 4/13

2:35 pm-9:16 pm

1 stop8h 41m

$274

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Thu 2/19

1:13 pm-9:29 pm

1 stop6h 16m

Chicago O'Hare Intl

Tue 2/24

8:40 am-12:58 pm

1 stop6h 18m

$274

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Wed 4/1

1:55 pm-12:59 am

1 stop9h 04m

Chicago O'Hare Intl

Mon 4/6

7:00 am-12:38 pm

1 stop7h 38m

$281

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Fri 3/6

1:54 pm-12:59 am

1 stop9h 05m

Chicago O'Hare Intl

Sun 3/8

6:17 am-12:11 pm

1 stop7h 54m

$307

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Wed 2/18

1:13 pm-10:53 pm

1 stop7h 40m

Chicago O'Hare Intl

Fri 2/20

4:20 pm-10:45 pm

1 stop8h 25m

$309

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Sat 2/28

11:23 am-9:52 pm

2 stops8h 29m

Chicago O'Hare Intl

Sat 3/7

5:15 pm-10:23 pm

1 stop7h 08m

$310

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 44 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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy2 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, April is the cheapest month in which you can book a flight from Redmond to Chicago (average of $251). Flying from Redmond to Chicago in February is currently the most expensive (average of $531). 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.

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 January 29, 2026.
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
11,808 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Crew

8.5

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Alaska Airlines
8.0
Very good
11,808 reviews
Alaska Airlines
8.0
Very good
11,808 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Crew

8.5

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Delta
7.9
Good
8,127 reviews
Alaska Airlines
8.0
Very good
11,808 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Crew

8.5

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Hawaiian Airlines
7.8
Good
2,830 reviews
Alaska Airlines
8.0
Very good
11,808 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Crew

8.5

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
United Airlines
7.4
Good
9,215 reviews
Alaska Airlines
8.0
Very good
11,808 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Crew

8.5

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading

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?

    United Airlines and Delta can get you from Redmond to Chicago in just under 6h 45m. Your travel time can differ by up to 2h 19m. 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 United Airlines is currently your cheapest option to Chicago, with prices starting at $184. Additional round-trip tickets that might be worth considering are offered by Alaska Airlines and Delta, with the lowest prices starting at $262 and $288, respectively. United Airlines is priced at 55% 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 Delta. According to our data, you can fly for as low as $97. Users have also found prices from $139 and $159 on Alaska Airlines and United 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, April is the cheapest month in which you can book a flight from Redmond to Chicago (average of $251). Flying from Redmond to Chicago in February is currently the most expensive (average of $531). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$184Average$430FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$262Average$402FlexibilityNo cancel feeOn-time75%
DeltaCheapest$288Average$385FlexibilityNo cancel feeOn-timeN/A

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